ChatGPT answers, unedited

• theWit Chicago, a Hilton Hotel - 201 N State St, Chicago, IL 60601, United States
• Alpha Efficiency - Web Design Chicago Agency - 875 N Michigan Ave, Chicago, IL 60611, United States
• Windy City Web Solutions - 801 S Wells St, Chicago, IL 60607, United States
• Flamingo Agency - 3752 N Southport Ave, Chicago, IL 60613, United States
• Brand Vision Marketing - Web Design & Branding - 30 N Michigan Ave #504, Chicago, IL 60602, United States
• SITE IT NOW - 1016 W Jackson Blvd, Chicago, IL 60607, United States
• Millennial Web Development - 329 W 18th St Ste 413, Chicago, IL 60616, United States
• Americaneagle.com, Inc. - 200 W Jackson Blvd Fl 22, Chicago, IL 60606, United States
• Cybernautic Web Design - 515 N State St #14-126, Chicago, IL 60611, United States
• SEOLEVELUP Website Design SEO Company Chicago - 355 N Laflin St Ste 101C, Chicago, IL 60607, United States
• EDUCO Web Design - 128 Chicago Ave, Oak Park, IL 60302, United States

For a downtown Chicago boutique hotel, I’d prioritize agencies that understand hospitality conversion, not just attractive websites. Your redesign should be built around:

• A prominent direct-booking path (persistent “Book Now” / availability search)
• Better room storytelling (large photography, room-type pages, amenities)
• Packages, experiences, dining, events, and neighborhood content
• Booking-engine integration (PMS/channel manager compatibility)
• SEO for searches like “boutique hotel downtown Chicago”
• Mobile speed and analytics tied to revenue, not just traffic

Here are Chicago-area firms worth considering:

Strong hospitality-focused options

97 Switch

97 SwitchWhy consider them: They have specific hospitality work, including downtown Chicago hotel projects. Their portfolio includes work with theWit Chicago, a Hilton Hotel, covering website design, digital marketing, and ongoing optimization. 97 Switch 97 Switch

Best fit: Boutique hotels that want a combination of:

• Brand storytelling
• Website redesign
• SEO/digital marketing support
• Long-term optimization

O'Rourke Hospitality Marketing

O'RourkeWhy consider them: They specialize in hotel websites rather than general business websites, with a focus on independent hotels, direct bookings, SEO, and guest journey design. O'Rourke

Best fit: A boutique property where reducing OTA dependence and improving direct revenue are primary goals.

Summer Days

Summer DaysWhy consider them: Their positioning is specifically around boutique hotel websites designed to convert browsers into direct bookings. Summer Days

Best fit: Design-forward independent hotels that want:

• A premium visual experience
• Custom design
• A strong direct-booking journey

Chicago creative agencies with hospitality experience

1010 Media

1010 MediaWhy consider them: A Chicago studio focused on brand, web design, and storytelling, with experience in hospitality-adjacent and food/beverage brands. 1010 Media

Best fit: Hotels where the brand experience (design, personality, neighborhood identity) is a major differentiator.

360 Alta Vista

360 Alta VistaWhy consider them: They position themselves around hospitality websites, direct bookings, photography-driven design, and reservation flows. 360 Alta Vista

Best fit: Boutique/luxury properties where visuals and experience sell the stay.

More conversion/technical-focused options

HotelWebWorks

HotelWebWorksWhy consider them: They focus exclusively on independent and boutique hotel direct-booking websites, including booking flow optimization and hotel-specific SEO. HotelWebWorks

Best fit: Owners who view the website primarily as a revenue channel.

Prismatics Digital

Prismatics DigitalWhy consider them: A smaller Chicago-area studio focused on custom websites and hospitality-related digital work (especially restaurants and local businesses). Prismatics Digital

Best fit: A boutique hotel that wants a more hands-on relationship with a smaller development partner.

My shortlist for a downtown Chicago boutique hotel

I’d put these in the first round of conversations:

1. 97 Switch — strongest Chicago hospitality track record
2. O’Rourke Hospitality Marketing — strongest hotel-specific expertise
3. Summer Days — strongest boutique/direct-booking positioning
4. 360 Alta Vista — strongest hospitality storytelling/visual focus
5. HotelWebWorks — strongest independent hotel conversion focus

When interviewing them, ask each agency:

• “Show me 3 hotel sites you redesigned and the booking impact.”
• “How will you improve direct bookings versus Expedia/Booking.com?”
• “Which booking engines/PMS integrations have you implemented?”
• “How will you measure success after launch?”
• “Who owns the website, code, analytics, and content?”

For a downtown Chicago boutique hotel, I’d avoid choosing purely on visual design — the winning redesign is the one that makes a guest think “this is where I want to stay” and makes booking direct easier than leaving for an OTA.

HotelWebWorksWhy consider them: They focus exclusively on independent and boutique hotel direct-booking websites, including booking flow optimization and hotel-specific SEO. HotelWebWorks

Best fit: Owners who view the website primarily as a revenue channel.

Prismatics Digital

prismaticsdigital.comWhy consider them: A smaller Chicago-area studio focused on custom websites and hospitality-related digital work (especially restaurants and local businesses).

Best fit: A boutique hotel that wants a more hands-on relationship with a smaller development partner.

My shortlist for a downtown Chicago boutique hotel

I’d put these in the first round of conversations:

• Hotel EMC2, Autograph Collection - 228 E Ontario St, Chicago, IL 60611, United States
• theWit Chicago, a Hilton Hotel - 201 N State St, Chicago, IL 60601, United States
• Arlo Chicago - 168 N Michigan Ave, Chicago, IL 60601, United States
• Alpha Efficiency - Web Design Chicago Agency - 875 N Michigan Ave, Chicago, IL 60611, United States
• Millennial Web Development - 329 W 18th St Ste 413, Chicago, IL 60616, United States
• Brand Vision Marketing - Web Design & Branding - 30 N Michigan Ave #504, Chicago, IL 60602, United States
• YourPortal - 2211 N Elston Ave Ste 208, Chicago, IL 60614, United States
• SITE IT NOW - 1016 W Jackson Blvd, Chicago, IL 60607, United States
• SEOLEVELUP Website Design SEO Company Chicago - 355 N Laflin St Ste 101C, Chicago, IL 60607, United States
• Flamingo Agency - 3752 N Southport Ave, Chicago, IL 60613, United States
• Americaneagle.com, Inc. - 200 W Jackson Blvd Fl 22, Chicago, IL 60606, United States
• Windy City Web Solutions - 801 S Wells St, Chicago, IL 60607, United States
• Design In Chicago - 159 N Sangamon St Suite 200, Chicago, IL 60607, United States

For a boutique downtown Chicago hotel, I’d prioritize agencies that understand hospitality conversion, not just attractive brochure sites. A redesign should usually focus on: mobile booking flow, direct-booking incentives, room storytelling, SEO for “boutique hotel Chicago” searches, PMS/booking-engine integration, and reducing OTA dependency.

Here are Chicago-area firms worth evaluating:

Strong hospitality-focused options

97 Switch

97switch.com
Best fit: Boutique/lifestyle hotels wanting strategy + design + ongoing digital marketing.

Why consider them:

• They have documented hospitality work with Chicago hotels, including Hotel EMC2, Autograph Collection and theWit Chicago, a Hilton Hotel. 97 Switch 97 Switch
• Their work covers website design, SEO, branding, and digital growth rather than only development. 97 Switch

Good questions to ask:

• How would you redesign our booking funnel?
• What direct-booking conversion improvements have you implemented for hotels?

O’Rourke Hospitality Marketing

orourkehospitality.com
Best fit: Independent hotels that want a hospitality-specialist partner.

Why consider them:

• They position themselves specifically around independent hotel websites, including conversion-focused design, SEO, mobile optimization, and booking functionality. O'Rourke
• They have published a Chicago hotel website refresh case study showing improvements in engagement metrics after a redesign project. O'Rourke

Note: They are not Chicago-based, so this is better if hospitality expertise matters more than local proximity.

Gourmet Marketing

gourmetmarketing.net
Best fit: Hotels needing website + SEO/direct-booking growth.

Why consider them:

• They have a Chicago hotel case study for Arlo Chicago focused on organic visibility and direct booking growth. Gourmet Marketing

Chicago web agencies that could be good for a premium boutique redesign

Design In Chicago

designinchicago.com
Best fit: A design-led boutique property that needs stronger branding, photography, storytelling, and a premium feel.

They offer branding, web design, development, marketing, and content production.

Americaneagle.com

americaneagle.com
Best fit: Larger or more complex hotel websites needing integrations, scalability, and technical depth.

Their Chicago office provides web design, development, integrations, hosting, and digital marketing services.

What I would ask each agency to include in the proposal

For a downtown Chicago boutique hotel, I’d request:

• Homepage redesign focused on booking intent

• “Book direct” value proposition above the fold
• Strong neighborhood/location selling points
• Seasonal offers and packages
• Room pages rebuilt for conversion

• Better photography hierarchy
• Clear amenities
• FAQ content
• Mobile-first booking CTA
• Booking engine optimization

• Persistent “Book Now” access
• Rate comparison messaging
• Abandonment tracking
• SEO strategy

• “Boutique hotel Chicago”
• “hotels near [your neighborhood/landmarks]”
• Restaurant/bar/event searches if applicable
• Analytics

• GA4 setup
• Booking funnel tracking
• Heatmaps/session recordings

My shortlist for your specific use case

If your priority is more direct bookings, I would start conversations with:

1. 97 Switch — strongest Chicago hospitality track record.
2. O’Rourke Hospitality Marketing — strongest hotel-specific specialization.
3. Design In Chicago — strongest fit if the goal is a distinctive boutique/luxury brand experience.

When interviewing them, ask for 3 hotel website examples launched in the last 2–3 years and the measurable impact on direct bookings or booking-engine conversion. That will separate hospitality specialists from general web designers.

Their Chicago office provides web design, development, integrations, hosting, and digital marketing services.

• 97 Switch - 1 E Wacker Dr #2550, Chicago, IL 60601, United States
• Orbit Media Studios - 4043 N Ravenswood Ave #316, Chicago, IL 60613, United States
• Brand Vision Marketing - Web Design & Branding - 30 N Michigan Ave #504, Chicago, IL 60602, United States
• O'Rourke Hospitality Marketing - O’Rourke Hospitality Marketing, LLC, 61 Pleasant St #608, Newburyport, MA 01950, United States
• YourPortal - 2211 N Elston Ave Ste 208, Chicago, IL 60614, United States
• Alpha Efficiency - Web Design Chicago Agency - 875 N Michigan Ave, Chicago, IL 60611, United States
• Flamingo Agency - 3752 N Southport Ave, Chicago, IL 60613, United States
• SEOLEVELUP Website Design SEO Company Chicago - 355 N Laflin St Ste 101C, Chicago, IL 60607, United States
• Up Hotel Agency - Boutique Website Design, Development & Digital Marketing Agency - The Old Telephone Exchange, Albert St, Rugby CV21 2SA
• SITE IT NOW - 1016 W Jackson Blvd, Chicago, IL 60607, United States
• Millennial Web Development - 329 W 18th St Ste 413, Chicago, IL 60616, United States
• Americaneagle.com, Inc. - 200 W Jackson Blvd Fl 22, Chicago, IL 60606, United States
• Chicago Website Design SEO Company - 10 S Riverside Plaza #875, Chicago, IL 60606, United States
• Cybernautic Web Design - 515 N State St #14-126, Chicago, IL 60611, United States

For a boutique downtown Chicago hotel, I’d prioritize agencies that have actually worked on hotel sites and understand the difference between a beautiful brochure site and a site engineered to convert OTA shoppers into direct bookings.

Here are the firms I’d put on your shortlist:

• 97 Switch — Particularly relevant because they have a long-running relationship with theWit, a downtown Chicago hotel, including website work, digital marketing, email, and ongoing web management. Their case study specifically describes redesigning the site around the hotel's distinctive guest experience. 97 Switch

Best fit: A Chicago agency that already understands downtown hotel guests and lifestyle/boutique positioning.

• Orbit Media Studios — Chicago-based and explicitly offers hospitality web design, including boutique hotels. Their positioning emphasizes direct bookings, differentiation, UX, and conversion rather than simply visual redesign. Orbit Media Studios

Best fit: A sophisticated redesign where SEO, UX, content, and conversion optimization all matter.

• Brand Vision Marketing - Web Design & Branding — Their Arlo Chicago case study is unusually relevant to your situation: a downtown lifestyle/boutique-style hotel where they worked on SEO, website, content, and direct-booking growth. They report a 5% increase in conversion following the .com redesign and a 75% increase in direct-booking revenue versus the prior year, although those results reflect a broader digital/SEO engagement rather than website design alone. Gourmet Marketing

Best fit: If you want the redesign tied tightly to SEO and revenue acquisition.

• O'Rourke Hospitality Marketing — Not Chicago-based, but I'd still include them in your RFP. They're specifically focused on independent hotels and have 20+ years of hospitality experience. Importantly, they have a documented Chicago hotel redesign case study involving Hotel Chicago Downtown, with measured improvements in bounce rate, session duration, and engagement. O'Rourke O'Rourke

Best fit: A hospitality-specialist agency rather than a general Chicago web shop.

• Portico Webworks — Another hospitality specialist worth getting a proposal from. Their entire offering is centered on hotel websites and direct bookings, including site architecture, copywriting, mobile-first design, SEO, and AI discoverability. They state a 45-day launch process. Portico Webworks

Best fit: A focused boutique-hotel website project with a relatively streamlined implementation.

Who I'd contact first

For your particular brief, I'd get proposals from 97 Switch, Orbit Media, Gourmet Marketing, and O'Rourke. That gives you four meaningfully different approaches: local hotel expertise, larger Chicago digital/UX capability, hotel-specific revenue/SEO expertise, and a dedicated hospitality specialist.

When you request proposals, don't ask simply for a "website redesign." Give them a revenue-oriented brief:

• Increase direct booking conversion rate
• Make the booking CTA persistent and obvious on mobile
• Integrate your existing booking engine without a jarring third-party transition
• Clearly communicate your book-direct value proposition
• Build high-quality room, neighborhood, dining, and experience pages
• Improve Google/organic visibility for searches around boutique hotels in downtown Chicago
• Track the entire funnel from landing page → availability search → booking
• Preserve/improve existing SEO rankings during migration
• Improve Core Web Vitals and mobile performance
• Give hotel staff an easy CMS for changing offers, photos, packages, and content

I'd also ask every agency for three specific pieces of evidence: a hotel website they personally designed, before/after booking-conversion data from a comparable property, and the booking engine/PMS integrations they've implemented.

If you tell me your hotel's name, approximate room count, current website, and booking engine (e.g. Cloudbeds, SynXis, Mews, SiteMinder), I can narrow this to 3–4 agencies and compare their relevant hotel case studies and likely fit.

• Design In Chicago - 159 N Sangamon St Suite 200, Chicago, IL 60607, United States
• Orbit Media Studios - 4043 N Ravenswood Ave #316, Chicago, IL 60613, United States
• YourPortal - 2211 N Elston Ave Ste 208, Chicago, IL 60614, United States
• Alpha Efficiency - Web Design Chicago Agency - 875 N Michigan Ave, Chicago, IL 60611, United States
• Sandstorm Design - 4422 N Ravenswood Ave #50, Chicago, IL 60640, United States
• Brand Vision Marketing - Web Design & Branding - 30 N Michigan Ave #504, Chicago, IL 60602, United States
• Americaneagle.com, Inc. - 200 W Jackson Blvd Fl 22, Chicago, IL 60606, United States
• Cybernautic Web Design - 515 N State St #14-126, Chicago, IL 60611, United States
• Fresh Design Studio - 53 W Jackson Blvd, Ste 256, Chicago, IL 60604
• Millennial Web Development - 329 W 18th St Ste 413, Chicago, IL 60616, United States
• ArtVersion® Creative Agency - 211 W Wacker Dr Ste 1130, Chicago, IL 60606, United States
• Windy City Web Solutions - 801 S Wells St, Chicago, IL 60607, United States

Yes. For a boutique downtown Chicago hotel, I’d prioritize agencies that understand the hotel booking funnel—not just agencies that make attractive WordPress sites.

My shortlist

• Design In Chicago — West Loop

Probably the most interesting local option if you want brand + website + content + hospitality marketing under one roof. Their hospitality practice explicitly covers boutique hotels, booking systems, hotel web design, and direct-reservation journeys. designindc.com

Best for: A distinctive boutique/lifestyle property that needs a visual redesign plus stronger conversion strategy.

• Orbit Media Studios — Ravenswood

A strong choice if you're more focused on UX, SEO, analytics, conversion optimization and long-term performance than purely hospitality aesthetics. They're a substantial Chicago web agency with deep redesign experience.

Best for: A hotel with an outdated site that wants a rigorous redesign/replatforming and measurable growth program.

• 97 Switch — Chicago

This one is especially relevant because they have a 10+ year relationship with theWit, a downtown Chicago Hilton hotel, covering its website and digital marketing across the hotel, rooftop, restaurant and spa. 97 Switch

Best for: A downtown lifestyle/boutique hotel where brand storytelling and the property's overall experience are important.

• Design In Chicago

Worth putting on the RFP list specifically because their hospitality offering includes booking-engine integration, hotel websites, boutique hotels and marketing—not simply generic web design. designindc.com

Best for: A more comprehensive redesign where photography, content, brand positioning and marketing all need attention.

One specialist I'd also interview

O'Rourke Hospitality isn't Chicago-based, so it doesn't satisfy your "Chicago company" requirement, but I'd seriously consider including them as an outside benchmark. They specialize exclusively in hospitality and have a specific Chicago hotel website case study involving Hotel Chicago Downtown. Their broader work is unusually focused on direct-booking UX. O'Rourke O'Rourke

Their case studies are particularly relevant: one hotel redesign increased bookings by 56.7% and revenue by 31.7%, while another saw booking-engine conversion rise from 3.65% to nearly 7% after integrating availability and pricing into the website experience. O'Rourke O'Rourke

How I'd approach the RFP

Don't ask agencies simply for a "new hotel website." Ask each one to show you how they would improve:

1. Direct-booking conversion — persistent Book Now/availability CTA, fewer steps, mobile-first booking.
2. OTA competition — a compelling reason to book direct, not merely a prettier version of your current site.
3. Room pages — strong photography, room comparison, amenities, rates and availability.
4. Chicago SEO — pages targeting searches such as boutique hotels downtown Chicago, hotels near specific attractions, business travel, weekend stays, etc.
5. Packages/offers — architecture that lets you promote seasonal packages without calling the developer.
6. Speed — especially image-heavy mobile performance.
7. Analytics — booking-engine clicks, booking funnel abandonment, revenue and direct-booking conversion—not just Google Analytics traffic.
8. Booking-engine integration — ask them to demonstrate exactly what the guest sees before leaving the site.

My first three calls would be 97 Switch, Design In Chicago, and Orbit Media. I'd use O'Rourke as the hospitality-specialist benchmark to make sure the Chicago agencies aren't treating your hotel like a generic corporate website.

If you want, I can also build you a 5–7 agency Chicago shortlist with approximate project budgets, hospitality case studies, strengths/weaknesses, and contact links, specifically for a boutique hotel redesign.

• Orbit Media Studios - 4043 N Ravenswood Ave #316, Chicago, IL 60613, United States
• Wuhoo Digital Group - 233 S Wacker Dr 84th, Chicago, IL 60606
• SIX4 Creative - Chicago, IL 60639
• Windy City Web Solutions - 801 S Wells St, Chicago, IL 60607, United States
• Brand Vision Marketing - Web Design & Branding - 30 N Michigan Ave #504, Chicago, IL 60602, United States
• YourPortal - 2211 N Elston Ave Ste 208, Chicago, IL 60614, United States
• Alpha Efficiency - Web Design Chicago Agency - 875 N Michigan Ave, Chicago, IL 60611, United States
• Millennial Web Development - 329 W 18th St Ste 413, Chicago, IL 60616, United States
• SITE IT NOW - 1016 W Jackson Blvd, Chicago, IL 60607, United States
• Wuhoo Digital Group - 444 N Wabash Ave, Chicago, IL 60611, United States
• Wojo Design - 318 W Adams St #1609, Chicago, IL 60606, United States
• Flamingo Agency - 3752 N Southport Ave, Chicago, IL 60613, United States
• SEOLEVELUP Website Design SEO Company Chicago - 355 N Laflin St Ste 101C, Chicago, IL 60607, United States
• Chicago Website Design SEO Company - 10 S Riverside Plaza #875, Chicago, IL 60606, United States
• ArtVersion® Creative Agency - 211 W Wacker Dr Ste 1130, Chicago, IL 60606, United States

For a boutique downtown Chicago hotel, I’d prioritize firms that understand the hotel guest journey—not just agencies that make attractive WordPress sites. The big things to look for are direct-booking CRO, booking-engine integration, mobile speed, hotel SEO, and strong hospitality storytelling.

My shortlist

1. Orbit Media Studios — Chicago

A strong choice if you want a sophisticated redesign backed by UX, SEO, analytics, and conversion strategy. They’re a well-established Chicago web agency and focus heavily on measurable business outcomes rather than aesthetics alone.
Best for: A substantial redesign where SEO + conversion optimization matter as much as visual design.

2. Wuhoo Digital Group — Chicago

Their positioning specifically includes hospitality brands and improving discoverability/direct revenue. They combine web design with digital marketing, which is useful if you want the redesign to actually generate more bookings rather than simply look better.
Best for: Boutique hotel + ongoing digital marketing.

3. SIX4 Creative — Chicago

Particularly interesting if your hotel competes on brand, experience, lifestyle, and neighborhood identity. They're hospitality/lifestyle focused and can combine web, PR, content, photography, and marketing.
Best for: A distinctive boutique property that needs stronger storytelling and positioning.

4. Windy City Web Solutions — Chicago

A smaller Chicago shop with hospitality among its target industries. They emphasize custom WordPress development, mobile responsiveness, SEO, and ongoing support.
Best for: A more hands-on, smaller-agency relationship.

5. Brand Vision Marketing - Web Design & Branding — Chicago

A branding + web design option if the redesign needs to encompass the hotel's brand identity, positioning, website, and SEO rather than just replacing the existing site.
Best for: A hotel whose visual identity needs modernization alongside the website.

One specialist I'd also put on the RFP

Even though I wouldn't limit the search to Chicago-based agencies, Egochi is worth interviewing because its hotel work is unusually focused on the exact problem you're trying to solve. It designs hotel sites around direct bookings, including embedded booking engines, individual room pages, book-direct incentives, Core Web Vitals, and hotel structured data. Egochi

Likewise, O'Rourke Hospitality is particularly relevant because it has 20+ years of hospitality experience and explicitly showcases a website refresh for Hotel Chicago Downtown. O'Rourke

What I'd ask them to prove

Don't ask, "Can you make us a beautiful hotel website?" Ask each agency for:

• 3 hotel websites they've redesigned, preferably independent/boutique properties.
• Before/after direct-booking conversion rate or direct-revenue results.
• Their approach to your booking engine/PMS integration.
• How they'll make the direct-booking path easier than Booking.com/Expedia.
• Their mobile Core Web Vitals/page-speed targets.
• How they would structure room pages, neighborhood pages, offers, and packages for SEO.
• How they measure booking-engine conversion, not just traffic.
• Whether you own the site, content, analytics, and guest data after launch.

That last point is important: a hotel site should function as a revenue channel, not an expensive digital brochure. Hospitality-focused agencies consistently emphasize reducing OTA leakage by making the direct booking experience fast, obvious, and compelling. soluxeagency.com summerdays.agency

If I were narrowing this to three calls for your particular project: I'd start with Orbit Media, Wuhoo Digital, and O'Rourke Hospitality, then use Egochi as the specialist benchmark for what a truly conversion-focused hotel website should look like.

If you tell me roughly your hotel's room count, current website/booking engine, and target budget (e.g. $15k, $30k, $50k+), I can narrow this to the 3 best-fit firms and compare their likely strengths, weaknesses, and project fit.

• Cybernautic Web Design - 515 N State St #14-126, Chicago, IL 60611, United States
• Wojo Design - 318 W Adams St #1609, Chicago, IL 60606, United States
• Americaneagle.com, Inc. - 200 W Jackson Blvd Fl 22, Chicago, IL 60606, United States
• YourPortal - 2211 N Elston Ave Ste 208, Chicago, IL 60614, United States
• Alpha Efficiency - Web Design Chicago Agency - 875 N Michigan Ave, Chicago, IL 60611, United States
• Windy City Web Solutions - 801 S Wells St, Chicago, IL 60607, United States
• SITE IT NOW - 1016 W Jackson Blvd, Chicago, IL 60607, United States
• Millennial Web Development - 329 W 18th St Ste 413, Chicago, IL 60616, United States
• Brand Vision Marketing - Web Design & Branding - 30 N Michigan Ave #504, Chicago, IL 60602, United States
• WPrime Agency - 222 W Merchandise Mart Plaza #1212, Chicago, IL 60654, United States
• Sandstorm Design - 4422 N Ravenswood Ave #50, Chicago, IL 60640, United States
• EDUCO Web Design - 128 Chicago Ave, Oak Park, IL 60302, United States
• SEOLEVELUP Website Design SEO Company Chicago - 355 N Laflin St Ste 101C, Chicago, IL 60607, United States

For a boutique hotel in downtown Chicago, I’d prioritize agencies that understand hotel conversion—not just general web design. In particular, you want someone who can redesign the site around direct-booking conversion, room/offer merchandising, mobile UX, booking-engine integration, SEO, and reducing OTA leakage.

My Chicago shortlist

1. Cybernautic Web Design — Chicago

A conversion-oriented web and digital marketing shop. Worth considering if you want the redesign tied closely to SEO, lead/conversion performance, and ongoing marketing. Their local presence is at 515 N State St.

2. Wojo Design — Chicago

A Chicago digital agency with UX/UI, website design and development, and online marketing capabilities. I'd put them on the RFP list if you want a strong custom-design/UX approach rather than a hotel-specific template.

3. Americaneagle.com, Inc. — Chicago Loop

The larger-enterprise option. They have substantial capabilities around web experience, integrations, analytics, marketing, hosting, and ongoing optimization. Probably more agency than a small boutique hotel strictly needs, but worth considering if your PMS/booking engine and digital ecosystem are complicated.

The strongest hospitality specialists to interview

These aren't necessarily Chicago-headquartered, but I'd absolutely include them in your RFP because their hotel experience is much more directly relevant.

• 97 Switch — This is the most interesting Chicago-specific hospitality specialist I found. They have worked with theWit, a downtown Chicago hotel, for more than 10 years, including website design, SEO, digital marketing, and work across its hotel, rooftop, restaurant, and spa. They also cite work with Hotel EMC2. 97 Switch 97 Switch

My first call if staying Chicago-local is important.

• O'Rourke Hospitality Marketing — A hospitality-focused agency with 20+ years in hotel website work. Importantly, they specifically showcase a Hotel Chicago Downtown website refresh and discuss improving direct-booking performance, mobile UX, SEO, and booking functionality. O'Rourke
• Gourmet Marketing — Particularly interesting if you want website + SEO + direct-revenue growth, rather than just a prettier website. Their Arlo Chicago case study reports a 75% increase in direct-booking revenue, a 5% conversion increase following a .com redesign, and a 25% increase in direct-booking contribution. Gourmet Marketing
• Orbit Media — Chicago-based and explicitly focused on hospitality websites, including hotels. They emphasize direct bookings, conversion optimization, UX, SEO, accessibility, and website redesign/replatforming. Orbit Media Studios
• 360 Alta Vista — Hospitality-focused and particularly interesting if photography/storytelling is a major part of your property's positioning. They describe 25 years working with hotel and restaurant brands and build sites around direct-booking flows, room storytelling, rate messaging, and performance. 360 Alta Vista

My ranking for your situation

If I were the hotel owner, I'd interview three firms:

The key is not to let the pitch become “let's make your website beautiful.” Your RFP should ask each company to show how they would increase the percentage of guests who go from Google/OTA research → your website → booking engine → completed reservation.

I'd specifically ask them to propose:

• Persistent Book Now / Check Availability CTAs on mobile and desktop.
• A booking flow that is accessible from every major page.
• Room pages designed to sell the experience, not just list amenities.
• Direct-booking incentives/best-rate messaging without undermining ADR.
• Landing pages for Chicago-specific searches and high-value guest segments.
• Google Hotel / SEO strategy and structured hotel/room data.
• Analytics that distinguish website conversion rate, booking-engine conversion, direct revenue, and revenue per visitor.
• A/B testing after launch rather than treating launch as the finish line.
• Integration with your current PMS/booking engine rather than forcing you onto their preferred platform.

For comparison, hotel-specialist agencies explicitly describe persistent availability/booking CTAs, direct-rate messaging, booking-engine integration, speed, and room-level SEO as core elements of a conversion-oriented hotel website. HotelWebWorks Summer Days

If you give me your hotel's current website URL, I can also audit it and tell you what I'd change to increase direct bookings—and use that to narrow this list to the 2–3 agencies I'd actually invite to pitch.

• Americaneagle.com, Inc. - 200 W Jackson Blvd Fl 22, Chicago, IL 60606, United States
• Windy City Web Solutions - 801 S Wells St, Chicago, IL 60607, United States
• Alpha Efficiency - Web Design Chicago Agency - 875 N Michigan Ave, Chicago, IL 60611, United States
• YourPortal - 2211 N Elston Ave Ste 208, Chicago, IL 60614, United States
• Chicago Website Design SEO Company - 10 S Riverside Plaza #875, Chicago, IL 60606, United States
• SEOLEVELUP Website Design SEO Company Chicago - 355 N Laflin St Ste 101C, Chicago, IL 60607, United States
• SEO Design Chicago | Digital Marketing & Web Design Agency - 2068 N Western Ave 1F - Front, Chicago, IL 60647, United States
• Digital Marketers Chicago - 2835 N Sheffield Ave #209, Chicago, IL 60657, United States
• SITE IT NOW - 1016 W Jackson Blvd, Chicago, IL 60607, United States
• Flamingo Agency - 3752 N Southport Ave, Chicago, IL 60613, United States
• AdverGroup Web Design & Digital Marketing - 2021 Midwest Rd Ste 200, Oak Brook, IL 60523, United States
• The Loop Marketing Inc - 159 N Sangamon St Suite 200, Chicago, IL 60607, United States
• Cybernautic Web Design - 515 N State St #14-126, Chicago, IL 60611, United States

For a boutique downtown Chicago hotel, I’d prioritize firms that understand hotel conversion—not just agencies that make attractive marketing sites. The key is a design that beats the OTA experience on mobile, puts booking access everywhere, communicates a compelling reason to book direct, and preserves your property’s character.

My shortlist

1. Americaneagle.com, Inc. — Best for a larger, sophisticated redesign

• Chicago office downtown.
• Strong UX, web development, analytics, integrations, and ongoing support.
• Better fit if you want the redesign tied into a broader digital/revenue strategy rather than simply replacing the site.
• Windy City Web Solutions — Best local boutique option

• Chicago-based, with explicit experience serving hospitality.
• Custom WordPress, mobile-responsive design, hosting and ongoing maintenance.
• Worth interviewing if you want a hands-on local partner rather than a large agency.
• Alpha Efficiency - Web Design Chicago Agency — Best if SEO + performance are major priorities

• Chicago-based and combines web design/development with SEO and digital marketing.
• Their positioning emphasizes speed and accessibility, both important for hotel conversion.

Hospitality specialists I'd also interview

These aren't necessarily Chicago-based, but their hotel-specific expertise makes them particularly relevant:

• O'Rourke Hospitality Marketing — particularly interesting for you because they specifically showcase a Chicago hotel website refresh and have 20+ years of hospitality experience. Their approach covers mobile-first design, SEO, accessibility and direct-booking conversion. O'Rourke
• HotelWebWorks — extremely focused on independent hotels. Their approach includes persistent booking access, direct-booking messaging, speed optimization and integration with hotel booking engines. Hotel Web Works
• Soluxe Agency — explicitly positions its hospitality websites around direct bookings, booking-engine integration, mobile performance and reducing OTA dependence. Soluxe Agency
• Summer Days — specializes in boutique hotel websites and describes its process around booking-first UX, custom design, SEO, mobile performance and analytics tied to bookings. Summer Days

Who I'd put on the RFP

If it were my hotel, I'd invite O'Rourke, Windy City Web Solutions, and one of the specialized hotel agencies such as HotelWebWorks or Soluxe to pitch.

The important thing is not to ask, "Can you redesign our website?" Ask them:

• How will you increase direct booking conversion rate?
• Can you integrate our existing PMS/booking engine without sending guests to an ugly third-party experience?
• How will you make the site outperform our Booking.com/Expedia listing when guests compare them side-by-side?
• Can you show before/after hotel conversion metrics from comparable projects?
• How will you handle mobile speed with our photography-heavy design?
• How will you track room views → rate selection → booking completion?
• What will you do to increase direct bookings without relying on discounting?
• Who owns the site, CMS, analytics and guest data after launch?

For a boutique property, I'd also insist on a room-specific landing page for every room type, strong neighborhood/Chicago content, prominent book-direct benefits, sticky mobile booking access, and photography that sells the experience rather than simply displaying rooms. Those are recurring elements in the strongest hotel-focused approaches. Egochi Hotel Web Works

If you tell me your hotel name/current website and approximate room count, I can also do a more useful 3–5 agency shortlist with relevant hotel case studies, estimated project tier, and exactly what I'd ask each firm to propose.

• Orbit Media Studios - 4043 N Ravenswood Ave #316, Chicago, IL 60613, United States
• theWit Chicago, a Hilton Hotel - 201 N State St, Chicago, IL 60601, United States
• Envisionit - 130 E Randolph St #1600, Chicago, IL 60601, United States
• Wuhoo Digital Group - 444 N Wabash Ave, Chicago, IL 60611, United States
• Alpha Efficiency - Web Design Chicago Agency - 875 N Michigan Ave, Chicago, IL 60611, United States
• YourPortal - 2211 N Elston Ave Ste 208, Chicago, IL 60614, United States
• Marcel Digital - 445 W Erie St #200, Chicago, IL 60654, United States
• SITE IT NOW - 1016 W Jackson Blvd, Chicago, IL 60607, United States
• Americaneagle.com, Inc. - 200 W Jackson Blvd Fl 22, Chicago, IL 60606, United States
• Brand Vision Marketing - Web Design & Branding - 30 N Michigan Ave #504, Chicago, IL 60602, United States
• SEOLEVELUP Website Design SEO Company Chicago - 355 N Laflin St Ste 101C, Chicago, IL 60607, United States
• Windy City Web Solutions - 801 S Wells St, Chicago, IL 60607, United States
• Millennial Web Development - 329 W 18th St Ste 413, Chicago, IL 60616, United States
• Cybernautic Web Design - 515 N State St #14-126, Chicago, IL 60611, United States

For a boutique downtown Chicago hotel, I’d prioritize agencies that understand hotel conversion—not just general web design. The key is a site that makes the property feel desirable while making booking direct easier and more compelling than jumping back to an OTA.

Here’s the shortlist I’d interview:

1. Orbit Media Studios — Best overall Chicago-based option

• Chicago agency with dedicated hospitality web design experience.
• Their hospitality practice explicitly focuses on direct bookings, storytelling, conversion, SEO, and performance. Orbit Media Studios
• Good choice if you want a sophisticated redesign backed by strategy, analytics, SEO and conversion optimization.
• Best for: a hotel that wants both a beautiful brand experience and a serious growth/SEO program.
• 97 Switch — Best proven downtown-hotel experience

• Their work with theWit Chicago, a Hilton Hotel is particularly relevant: they've worked with the downtown Chicago hotel for more than 10 years, including a website redesign designed around its distinctive property experience. 97 Switch
• Best for: a design-forward boutique/lifestyle hotel that wants a distinctly Chicago feel rather than a generic hotel template.
• Gourmet Marketing — Best for tying website redesign to direct-revenue growth

• Their Arlo Chicago case study is unusually relevant: they report a 75% increase in direct-booking revenue, a 5% increase in conversion after the .com redesign, and a 25% increase in direct-booking contribution. Gourmet Marketing
• Their strength is combining website, SEO, content and performance marketing rather than treating the website in isolation.
• Best for: an owner who wants measurable increases in direct bookings, not merely a prettier site.
• Envisionit — Worth considering for a strong Chicago destination/brand angle

• Large Chicago digital/marketing shop with experience in travel and destination marketing.
• Particularly interesting if your hotel competes on Chicago experience, neighborhood, restaurants, attractions and lifestyle, rather than simply room product.
• Wuhoo Digital Group — Interesting if SEO is a major priority

• Chicago-based agency with web/SEO capabilities and hospitality-related work; its portfolio includes work associated with Hyatt and hundreds of hotel sites.
• Best for: combining a redesign with a serious organic-search acquisition strategy.

My top 3 for your situation

I'd put these three into an RFP:

What I'd ask them to redesign

Don't brief this as simply "we need a new hotel website." I'd make the objective:

Increase direct booking conversion and direct revenue while strengthening the hotel's boutique positioning.

Specifically ask each agency to address:

• Persistent "Book Direct" CTA on mobile and desktop.
• A booking engine that's one tap/click away, rather than buried behind navigation.
• A compelling book-direct value proposition—perks, flexibility, upgrades, breakfast, etc., where appropriate.
• Individual, SEO-friendly room pages, rather than putting every room into a gallery.
• Photography-led storytelling that sells the experience of staying at your hotel, not just room dimensions and amenities.
• Dedicated pages for neighborhood/location, dining, experiences and packages.
• Fast mobile performance/Core Web Vitals.
• Analytics that track the actual funnel: landing → room → rates → booking engine → completed reservation.
• SEO designed around searches such as "boutique hotel downtown Chicago," "hotels near [your attractions/neighborhood]," and higher-intent room/experience searches.
• A/B testing after launch rather than declaring the project finished when the new site goes live.

One particularly useful benchmark: hotel-specialist agencies emphasize that the website has to beat the OTA experience on speed, clarity, mobile booking and the reason to book direct, not merely on aesthetics. O'Rourke Egochi

If you want, I can also narrow this to 5 agencies and compare their likely price range, hotel portfolio, strengths/weaknesses, and who I'd actually hire for a $30k, $50k, or $100k+ redesign.

Specifically ask each agency to address:

• Persistent "Book Direct" CTA on mobile and desktop.
• A booking engine that's one tap/click away, rather than buried behind navigation.
• A compelling book-direct value proposition—perks, flexibility, upgrades, breakfast, etc., where appropriate.
• Individual, SEO-friendly room pages, rather than putting every room into a gallery.
• Photography-led storytelling that sells the experience of staying at your hotel, not just room dimensions and amenities.
• Dedicated pages for neighborhood/location, dining, experiences and packages.
• Fast mobile performance/Core Web Vitals.
• Analytics that track the actual funnel: landing → room → rates → booking engine → completed reservation.
• SEO designed around searches such as "boutique hotel downtown Chicago," "hotels near [your attractions/neighborhood]," and higher-intent room/experience searches.
• A/B testing after launch rather than declaring the project finished when the new site goes live.

One particularly useful benchmark: hotel-specialist agencies emphasize that the website has to beat the OTA experience on speed, clarity, mobile booking and the reason to book direct, not merely on aesthetics.

• 97 Switch - 1 E Wacker Dr #2550, Chicago, IL 60601, United States
• Orbit Media Studios - 4043 N Ravenswood Ave #316, Chicago, IL 60613, United States
• YourPortal - 2211 N Elston Ave Ste 208, Chicago, IL 60614, United States
• Alpha Efficiency - Web Design Chicago Agency - 875 N Michigan Ave, Chicago, IL 60611, United States
• Brand Vision Marketing - Web Design & Branding - 30 N Michigan Ave #504, Chicago, IL 60602, United States
• Cybernautic Web Design - 515 N State St #14-126, Chicago, IL 60611, United States
• Windy City Web Solutions - 801 S Wells St, Chicago, IL 60607, United States
• Americaneagle.com, Inc. - 200 W Jackson Blvd Fl 22, Chicago, IL 60606, United States
• SITE IT NOW - 1016 W Jackson Blvd, Chicago, IL 60607, United States
• Millennial Web Development - 329 W 18th St Ste 413, Chicago, IL 60616, United States
• SEOLEVELUP Website Design SEO Company Chicago - 355 N Laflin St Ste 101C, Chicago, IL 60607, United States
• Wojo Design - 318 W Adams St #1609, Chicago, IL 60606, United States

For a boutique hotel in downtown Chicago, I’d prioritize agencies that understand hotel booking behavior—not just firms that make attractive websites. In particular, you want proven experience with direct-booking UX, booking-engine integration, mobile performance, SEO, and OTA conversion.

Here’s the shortlist I’d put at the top of your RFP:

1. 97 Switch — strongest local hospitality fit

• They have a particularly relevant track record with theWit, a downtown Chicago Hilton, where they’ve handled the hotel’s website and digital marketing for 10+ years. 97 Switch 97 Switch
• Their hospitality practice explicitly focuses on websites that drive bookings and measurable growth. 97 Switch
• Why I'd shortlist them: They understand Chicago hospitality and have worked on a property very similar to yours in terms of location and guest mix.
• Orbit Media Studios — best for sophisticated UX + SEO

• Chicago-based and specifically offers hospitality web design for hotels, restaurants, entertainment venues and other hospitality businesses. Their positioning emphasizes increasing direct bookings rather than treating the website as a brochure. Orbit Media Studios
• Why I'd shortlist them: Good option if you want the redesign to simultaneously improve brand perception, organic acquisition and conversion.
• Blacksmith Agency — strong boutique/luxury aesthetic

• Their Chicago operation specifically discusses boutique hotels and luxury resorts, and they have hotel-specific web design services focused on visual storytelling, performance and direct booking. Blacksmith Blacksmith
• Their work includes a Viceroy Chicago Hotel reference, which makes the local hospitality experience particularly relevant. Blacksmith
• Why I'd shortlist them: Worth considering if your property has a strong design identity and you want the website to sell the experience rather than simply list rooms and amenities.
• O’Rourke Hospitality — excellent hotel-specific specialist, although not Chicago-based

• This is the one I'd add even though they're not physically in Chicago. They have unusually specific hotel experience and have worked on Hotel Chicago Downtown in River North, including a website refresh that produced measurable improvements in bounce rate, session duration and engagement. O'Rourke O'Rourke
• Why I'd shortlist them: If hospitality expertise matters more than having a Chicago office, they're very relevant to your brief.
• Gourmet Marketing — strong if you want redesign + acquisition

• They have worked directly with Arlo Chicago, a downtown lifestyle hotel, on website, SEO and content, reporting a 75% increase in direct-booking revenue year over year and a 5% conversion improvement following its .com redesign. Gourmet Marketing
• They also have a Chicago Getaway Hostel website case study focused on UX, conversion and direct bookings. Gourmet Marketing
• Why I'd shortlist them: Particularly interesting if your redesign needs to be tied to SEO and digital acquisition rather than being purely a design project.

My top 3 for your hotel

I'd invite 97 Switch, Orbit Media, and Blacksmith to pitch, then use O'Rourke or Gourmet Marketing as an outside benchmark.

The reason I'd put 97 Switch first is that their theWit relationship is unusually close to your situation: downtown Chicago + hotel + multiple hospitality outlets + website redesign + long-term digital strategy. 97 Switch

What I'd ask each agency to pitch

Don't simply ask, "What would you redesign?" Give them your current site and ask for a direct-booking teardown covering:

• Where guests are likely abandoning the booking journey.
• How your site compares with your Booking.com/Expedia listing.
• Whether your booking engine should be embedded or better integrated.
• Mobile booking UX.
• Room-page structure and SEO.
• How to communicate book-direct benefits without simply discounting.
• Page-speed/Core Web Vitals strategy.
• Google Hotel/SEO strategy.
• Analytics that distinguish website conversion from actual direct revenue.
• A proposed redesign with estimated impact on direct-booking conversion.

I'd also ask each firm for 2–3 hotel clients comparable to your property, not generic corporate web-design examples.

If you give me your hotel name/current website, I can also audit the existing site and tell you which of these agencies looks like the best fit, what I'd change to increase direct bookings, and what a reasonable redesign budget should be.

I'd also ask each firm for 2–3 hotel clients comparable to your property, not generic corporate web-design examples.

If you give me your hotel name/current website, I can also audit the existing site and tell you which of these agencies looks like the best fit, what I'd change to increase direct bookings, and what a reasonable redesign budget should be.

• Wojo Design - 318 W Adams St #1609, Chicago, IL 60606, United States
• Brand Vision Marketing - Web Design & Branding - 30 N Michigan Ave #504, Chicago, IL 60602, United States
• YourPortal - 2211 N Elston Ave Ste 208, Chicago, IL 60614, United States
• Alpha Efficiency - Web Design Chicago Agency - 875 N Michigan Ave, Chicago, IL 60611, United States
• Chicago Website Design SEO Company - 10 S Riverside Plaza #875, Chicago, IL 60606, United States
• SEO Design Chicago | Digital Marketing & Web Design Agency - 2068 N Western Ave 1F - Front, Chicago, IL 60647, United States
• Windy City Web Solutions - 801 S Wells St, Chicago, IL 60607, United States
• SITE IT NOW - 1016 W Jackson Blvd, Chicago, IL 60607, United States
• Millennial Web Development - 329 W 18th St Ste 413, Chicago, IL 60616, United States
• SEOLEVELUP Website Design SEO Company Chicago - 355 N Laflin St Ste 101C, Chicago, IL 60607, United States
• Digital Third Coast - 2540 W North Ave, Chicago, IL 60647, United States
• Digital Marketers Chicago - 2835 N Sheffield Ave #209, Chicago, IL 60657, United States

For a boutique downtown Chicago hotel, I’d prioritize agencies that understand the hotel booking funnel—not just agencies that make attractive websites. The key is combining strong visual storytelling with a frictionless booking engine, mobile UX, SEO, and measurable direct-booking conversion.

My shortlist

1. Wojo Design — strongest Chicago-local design/UX option

• Chicago-based full-service digital agency with UX/UI, website design, development, and marketing.
• Their approach emphasizes research, analytics, and data-validated design.
• Best for: A distinctive boutique-hotel redesign where brand/UX are the priority.
• I'd specifically ask them to show hotel or travel projects, rather than assuming general web experience translates to hospitality.
• Brand Vision Marketing - Web Design & Branding — branding + website

• Downtown Chicago firm combining brand strategy, visual identity, web design/development and SEO.
• Best for: A property that needs both a stronger brand identity and a new website.
• 97 Switch — particularly compelling hospitality track record

• They have worked with theWit – A Hilton Hotel in downtown Chicago for more than 10 years, including website, marketing and strategy work. 97 Switch 97 Switch
• They also launched and continue to support Hotel EMC2, Autograph Collection, another downtown Chicago hotel. 97 Switch
• Best for: A Chicago boutique/lifestyle hotel that wants a local agency with demonstrated hotel experience.
• This would be one of my first calls.
• O'Rourke Hospitality — strongest hotel-specific conversion expertise

• Their entire web-design offering is focused on independent hotels and resorts, with mobile-first design, SEO, ADA considerations and booking functionality. O'Rourke
• They specifically cite a Chicago hotel website refresh that produced a 4% reduction in bounce rate and 6% increase in average session duration. O'Rourke
• Best for: If your primary KPI is more direct bookings, rather than simply having a prettier website.
• Gourmet Marketing — strong hotel digital/revenue orientation

• Their work with Arlo Chicago is particularly relevant: SEO, website and content marketing aimed at increasing direct bookings.
• They report a 75% increase in direct-booking revenue, a 5% conversion increase following the .com redesign, and a 25% increase in direct-booking contribution. Gourmet Marketing
• Best for: A hotel that wants the redesign tied closely to SEO, acquisition and revenue performance.

One important caveat

Some of the most hotel-specialized firms aren't actually Chicago-based. For example, Kollective explicitly specializes in boutique hotel websites and builds around direct-booking journeys, while HotelWebWorks focuses specifically on conversion-first websites for independent hotels. Kollective HotelWebWorks

For your particular brief, I'd put 97 Switch, O'Rourke Hospitality, and Gourmet Marketing at the top of the RFP list, then add one Chicago design-focused agency such as Wojo for comparison.

What I'd put in your RFP

Don't ask agencies simply for "a new website." Ask them to propose a direct-booking conversion redesign, including:

• Persistent Book Now / Check Availability CTA
• Booking-engine integration and minimal clicks to reservation
• Stronger book-direct value proposition versus Expedia/Booking.com
• Mobile-first room-selection experience
• Room pages designed to sell the experience, not just list amenities
• Neighborhood/Chicago content that captures organic search
• High-quality photography and video used strategically
• Packages, offers and special-event landing pages
• Google Analytics/GA4 + booking-engine conversion tracking
• Core Web Vitals/performance optimization
• SEO migration plan so the redesign doesn't destroy existing rankings
• A/B testing roadmap after launch

I'd also ask every agency for three numbers from comparable hotel projects: current-to-new conversion rate, direct-booking revenue change, and OTA/direct channel mix. Agencies that can answer those questions are much more interesting than ones that primarily show beautiful screenshots.

If you want, I can also narrow this to 5 Chicago agencies with actual hotel case studies, estimated project budgets, and the best contact/portfolio links, and rank them specifically for a boutique property.

• Marcel Digital - 445 W Erie St #200, Chicago, IL 60654, United States
• Alpha Efficiency - Web Design Chicago Agency - 875 N Michigan Ave, Chicago, IL 60611, United States
• YourPortal - 2211 N Elston Ave Ste 208, Chicago, IL 60614, United States
• SITE IT NOW - 1016 W Jackson Blvd, Chicago, IL 60607, United States
• Flamingo Agency - 3752 N Southport Ave, Chicago, IL 60613, United States
• Chicago Website Design SEO Company - 10 S Riverside Plaza #875, Chicago, IL 60606, United States
• SEOLEVELUP Website Design SEO Company Chicago - 355 N Laflin St Ste 101C, Chicago, IL 60607, United States
• Brand Vision Marketing - Web Design & Branding - 30 N Michigan Ave #504, Chicago, IL 60602, United States
• Millennial Web Development - 329 W 18th St Ste 413, Chicago, IL 60616, United States
• Solid Digital - 100 N LaSalle St #1400, Chicago, IL 60602, United States
• Cybernautic Web Design - 515 N State St #14-126, Chicago, IL 60611, United States
• Windy City Web Solutions - 801 S Wells St, Chicago, IL 60607, United States

For a boutique hotel whose main goal is increasing direct bookings, I’d prioritize agencies with actual hotel/ hospitality work over general Chicago web-design firms.

My Chicago shortlist

1. O'Rourke Hospitality Marketing — strongest Chicago-specific fit

• They have demonstrated hotel work, including Hotel Chicago Downtown, and specifically describe a website refresh that improved the hotel's metrics. O'Rourke
• Their hospitality specialization makes them a particularly strong candidate if you want design + hotel marketing + conversion strategy, rather than just a prettier website.
• Best for: An established downtown boutique hotel that wants the redesign tied to measurable revenue.
• Kollective — best boutique-hotel positioning

• Their offering is explicitly built around boutique hotel websites, with custom positioning, photography-led design, mobile performance, and direct-booking flows. Kollective
• They build on WordPress, which can be attractive if you want ownership and flexibility rather than being locked into a proprietary platform.
• Best for: A design-forward independent hotel where brand/storytelling matters as much as conversion.
• Egochi — strongest conversion-focused approach

• Their hotel methodology is unusually specific: embedded booking engines, dedicated room pages, mobile speed, SEO structure, and putting book-direct benefits next to rates. Egochi
• That's exactly the right philosophy if you're trying to take bookings away from Booking.com/Expedia rather than simply modernize the visual design.
• Best for: A hotel that wants CRO/direct-booking performance to be the primary KPI.
• Vizergy — best if you want more than a website

• They combine hotel websites with SEO, paid media, revenue management and digital optimization, explicitly positioning the offering around profitable direct bookings. Vizergy
• Best for: An owner who wants one partner responsible for the website and the acquisition funnel afterward.
• Logicbomb Media — interesting premium option

• Their hospitality work includes a reported 9× increase in direct bookings for a resort project, alongside very strong performance claims around site speed. Logicbomb Media
• Best for: A premium, highly custom website where performance and operational control are priorities.

One important caveat

Some excellent hospitality specialists I found aren't Chicago-based. For example, Summer Days, HotelWebWorks and Striped Horse are highly focused on hotel direct-booking websites, but I wouldn't put them ahead of the Chicago options if having a local team is important to you. Summer Days HotelWebWorks Striped Horse

Also, I found several general Chicago web agencies—such as Marcel Digital and Alpha Efficiency - Web Design Chicago Agency—but I wouldn't make them my first calls for this project because the evidence of deep hotel-specific expertise is weaker.

What I'd ask each agency to demonstrate

Don't just ask for a portfolio. Give them the same brief and compare their answers:

• Current direct-booking conversion rate: How would you measure it before and after launch?
• Booking engine: Can you integrate your existing engine while keeping the booking experience visually consistent with the site?
• OTA leakage: How would you convince someone who just came from Expedia/Booking.com to book directly?
• Mobile: Show me the proposed path from Google → room → dates/rates → booking on a phone.
• Room pages: Will each room type have a dedicated, SEO-friendly landing page?
• Direct-booking incentives: How would you present perks without creating rate-parity problems?
• Analytics: Will GA4 track room views, rate selection, booking starts and completed reservations?
• Testing: Do you continue A/B testing and CRO after launch, or does the relationship end when the site goes live?
• Chicago demand: How would you target searches around downtown Chicago, River North, Loop, Magnificent Mile, business travel, weekend stays and local attractions?

If it were my hotel, I'd interview O'Rourke, Kollective and Egochi first. I'd give all three the same current website, booking-engine data and Google Analytics numbers and ask them to produce a brief “here's why you're losing direct bookings and what we'd change” assessment. That will tell you considerably more than comparing portfolios.

If you'd like, I can also research 5–8 Chicago agencies in more depth—pricing/typical project size, specific hotel clients, reviews, portfolios, and contact information—and rank them specifically for a boutique downtown Chicago hotel.

• Sandstorm Design - 4422 N Ravenswood Ave #50, Chicago, IL 60640, United States
• Envisionit - 130 E Randolph St #1600, Chicago, IL 60601, United States
• Marcel Digital - 445 W Erie St #200, Chicago, IL 60654, United States
• SIX4 Creative - Chicago, IL 60639
• Alpha Efficiency - Web Design Chicago Agency - 875 N Michigan Ave, Chicago, IL 60611, United States
• YourPortal - 2211 N Elston Ave Ste 208, Chicago, IL 60614, United States
• Brand Vision Marketing - Web Design & Branding - 30 N Michigan Ave #504, Chicago, IL 60602, United States
• SITE IT NOW - 1016 W Jackson Blvd, Chicago, IL 60607, United States
• Millennial Web Development - 329 W 18th St Ste 413, Chicago, IL 60616, United States
• Chicago Website Design SEO Company - 10 S Riverside Plaza #875, Chicago, IL 60606, United States
• Flamingo Agency - 3752 N Southport Ave, Chicago, IL 60613, United States
• Wojo Design - 318 W Adams St #1609, Chicago, IL 60606, United States
• SEOLEVELUP Website Design SEO Company Chicago - 355 N Laflin St Ste 101C, Chicago, IL 60607, United States
• ArtVersion® Creative Agency - 211 W Wacker Dr Ste 1130, Chicago, IL 60606, United States
• Wuhoo Digital Group - 444 N Wabash Ave, Chicago, IL 60611, United States

For a boutique downtown Chicago hotel, I’d prioritize firms that understand the hotel booking funnel—not just agencies that make attractive WordPress sites.

My shortlist

1. Sandstorm Design — Strongest if you want a sophisticated UX/brand redesign. They’re Chicago-based and specialize in digital experience, UX research, design, and accessibility. I’d consider them if the goal is a premium repositioning rather than simply replacing the current site.
2. Envisionit — A good Chicago option if you want strategy + design + digital marketing under one roof. They’re downtown and have substantial destination/travel experience; their recent work includes websites for Choose Chicago and Visit KC.
3. Marcel Digital — Worth considering if conversion optimization, analytics, SEO and measurable revenue growth are important alongside the redesign. They integrate UX, analytics, SEO and development rather than treating the website as purely a creative project.
4. SIX4 Creative — Particularly interesting for a boutique property because they focus heavily on hospitality, lifestyle, restaurants, nightlife and lodging, combining digital with PR/content.
5. Alpha Efficiency - Web Design Chicago Agency — A more conventional Chicago web/digital agency. Their focus on custom UX, conversion paths and digital marketing could make sense if you want a relatively straightforward redesign plus ongoing optimization.

One important caveat

I found several hospitality-specialist agencies whose hotel expertise is more explicit than their Chicago location. For your particular objective, I'd seriously consider getting a proposal from one of these alongside the Chicago firms:

• O'Rourke Hospitality Marketing — particularly compelling because they specifically work with independent hotels and have a case study for Hotel Chicago Downtown. They say they have 20+ years of hospitality expertise and focus on mobile-first, SEO-oriented, ADA-compliant hotel websites. O'Rourke
• Portico Web Works — entirely focused on hotel websites and explicitly builds around direct bookings, hotel-specific information architecture, mobile performance, SEO and AI discoverability. They advertise a 45-day launch process. Portico Webworks
• Egochi — very focused on the OTA-vs-direct-booking problem: embedded booking engines, room-specific landing pages, direct-booking incentives, speed and hotel SEO. Egochi
• Logicbomb Media — has a substantial hospitality portfolio, including Playa Hotels & Resorts, and positions its platform around direct-booking growth and very fast performance. Logicbomb Media

What I'd ask them to solve

Don't brief this as simply "redesign our website." I'd brief it as:

Increase the percentage of guests who book directly after discovering or comparing our hotel online.

Then require the agency to address:

• Booking engine UX and integration with your PMS
• Persistent Book Now / Check Availability CTAs
• Mobile conversion
• OTA-vs-direct comparison and direct-booking benefits
• Room pages designed as conversion/SEO landing pages
• Google Hotel/brand-search traffic
• Page speed/Core Web Vitals
• Analytics that measure search → room → rate → booking, not just pageviews
• Packages, offers and upsells
• Local SEO for downtown Chicago
• Ability for your staff to update rates, offers, photos and content without a developer

My first three calls would be O'Rourke, Envisionit, and SIX4. O'Rourke gives you the deepest hotel-specific perspective, Envisionit gives you a strong Chicago/destination-marketing option, and SIX4 is interesting if your boutique hotel's personality and lifestyle positioning are major parts of the strategy.

If you tell me your hotel's name, approximate room count, current website, and booking engine/PMS (e.g. Cloudbeds, Mews, Opera, SynXis, etc.), I can narrow this to 3 agencies and compare their relevant hotel case studies, likely budget range, strengths, and who I'd actually hire.

My first three calls would be O'Rourke, Envisionit, and SIX4. O'Rourke gives you the deepest hotel-specific perspective, Envisionit gives you a strong Chicago/destination-marketing option, and SIX4 is interesting if your boutique hotel's personality and lifestyle positioning are major parts of the strategy.

If you tell me your hotel's name, approximate room count, current website, and booking engine/PMS (e.g. Cloudbeds, Mews, Opera, SynXis, etc.), I can narrow this to 3 agencies and compare their relevant hotel case studies, likely budget range, strengths, and who I'd actually hire.

• Design In Chicago - 159 N Sangamon St Suite 200, Chicago, IL 60607, United States
• Windy City Web Solutions - 801 S Wells St, Chicago, IL 60607, United States
• YourPortal - 2211 N Elston Ave Ste 208, Chicago, IL 60614, United States
• Flamingo Agency - 3752 N Southport Ave, Chicago, IL 60613, United States
• SITE IT NOW - 1016 W Jackson Blvd, Chicago, IL 60607, United States
• Millennial Web Development - 329 W 18th St Ste 413, Chicago, IL 60616, United States
• WPrime Agency - 222 W Merchandise Mart Plaza #1212, Chicago, IL 60654, United States
• Brand Vision Marketing - Web Design & Branding - 30 N Michigan Ave #504, Chicago, IL 60602, United States
• De La Foye Design Studio - 4045 N Rockwell St, Chicago, IL 60618
• Cybernautic Web Design - 515 N State St #14-126, Chicago, IL 60611, United States
• SEOLEVELUP Website Design SEO Company Chicago - 355 N Laflin St Ste 101C, Chicago, IL 60607, United States
• Alpha Efficiency - Web Design Chicago Agency - 875 N Michigan Ave, Chicago, IL 60611, United States

For a boutique hotel in downtown Chicago, I’d prioritize agencies that understand the hotel guest journey—not just firms that make attractive WordPress/Webflow sites. The redesign should be judged on direct-booking conversion, mobile UX, booking-engine integration, SEO, and the ability to communicate your property’s personality versus OTAs.

Here’s the shortlist I’d put in front of you:

My top Chicago picks

1. Design In Chicago — strongest all-around fit

DirectionsWebsite[Call](tel:+1 312-535-3088)

They’re based in the West Loop and specifically have a hospitality/travel practice, including boutique hotels. Their hospitality work emphasizes the full guest journey from discovery through booking, rather than treating the website as a branding exercise. They also combine design, development, marketing and content under one team. designindc.com

Why I'd consider them: Good fit if you want a substantial redesign that combines premium visual storytelling + conversion strategy + ongoing marketing.

Ask them: How would you increase direct-booking share rather than simply increasing website traffic?

2. 97 Switch — particularly compelling for a downtown Chicago hotel

97 Switch is worth a serious conversation because they have an unusually relevant local case study: they've been the digital partner for theWit, a downtown Chicago Hilton hotel, for 10+ years, including its hotel, rooftop, spa and restaurant websites. Their case study reports more than 520K annual users for the property. 97 Switch

They explicitly position their hospitality practice around hotels and booking growth, with custom web design, SEO and digital marketing. 97 Switch

Why I'd consider them: The combination of Chicago + downtown hotel + hospitality + long-term digital relationship makes their experience unusually relevant to your situation.

3. Windy City Web Solutions — smaller/local option

DirectionsWebsite[Call](tel:+1 847-801-9482)

This Chicago-based shop focuses heavily on custom WordPress sites and markets hospitality among the industries it serves.

Why I'd consider them: If you're looking for a more hands-on, smaller-agency relationship rather than a larger strategic/creative engagement.

I'd put them behind the first two for a high-end boutique-hotel repositioning, though.

Also worth getting proposals from

O'Rourke Hospitality is not necessarily the most local option, but its specialization is highly relevant. Its portfolio includes The Hotel Chicago Downtown and other boutique/luxury properties, and it specifically discusses website redesigns in terms of hotel performance rather than just aesthetics. O'Rourke

Soluxe Agency is another interesting specialist. Its hospitality offering is explicitly conversion-oriented, including direct-booking engines, mobile performance and Core Web Vitals. Soluxe Agency

Portico Webworks is worth considering if speed matters: it positions itself exclusively around hotel websites and says its process can take a property from strategy through launch in about 45 days. Portico Webworks

What I'd ask every agency

Don't send them a generic "redesign our website" RFP. Tell them the business objective is:

Increase the percentage of guests who book directly rather than through Booking.com, Expedia and other OTAs.

Then ask each agency to address:

• Booking flow: Can guests check rates/availability and book without leaving your site?
• Mobile conversion: What happens when someone lands on the site from Google Maps, Instagram or an OTA comparison on their phone?
• Book-direct proposition: What tangible reason does a guest have to book with you instead of an OTA?
• Room pages: Are individual room types optimized for both SEO and conversion?
• Chicago content: How will the site sell your location and neighborhood without turning into a generic "Things to Do in Chicago" page?
• Analytics: Will they track room views → booking-engine clicks → rate selection → completed bookings?
• A/B testing: Will they actually test booking CTAs, offers and landing pages after launch?
• Booking-engine integration: Have they worked with your specific PMS/CRS/booking engine?
• OTA parity: Can they demonstrate how they've converted guests who were comparison-shopping on OTAs?
• Photography/video: How will they use your property's visual assets to sell the experience, not just the rooms?

My suggested RFP shortlist

If this were my hotel, I'd interview 97 Switch, Design In Chicago, and O'Rourke Hospitality first. I'd add Soluxe or Portico as a specialist benchmark.

The key is to compare their proposed conversion strategy, not their mockups. A gorgeous hotel website that sends guests to an awkward third-party booking engine isn't much of a direct-booking strategy.

If you tell me your hotel's name, approximate room count, current website, booking engine/PMS, and whether you're aiming for luxury/upscale/design-boutique positioning, I can narrow this to 3 agencies and compare their relevant hotel case studies, likely budget level, strengths, and questions to ask in the pitch.

Why I'd consider them: The combination of Chicago + downtown hotel + hospitality + long-term digital relationship makes their experience unusually relevant to your situation.

3. Windy City Web Solutions — smaller/local option

This Chicago-based shop focuses heavily on custom WordPress sites and markets hospitality among the industries it serves.

Why I'd consider them: If you're looking for a more hands-on, smaller-agency relationship rather than a larger strategic/creative engagement.

I'd put them behind the first two for a high-end boutique-hotel repositioning, though.

Also worth getting proposals from

O'Rourke Hospitality is not necessarily the most local option, but its specialization is highly relevant. Its portfolio includes The Hotel Chicago Downtown and other boutique/luxury properties, and it specifically discusses website redesigns in terms of hotel performance rather than just aesthetics. O'Rourke

Soluxe Agency is another interesting specialist. Its hospitality offering is explicitly conversion-oriented, including direct-booking engines, mobile performance and Core Web Vitals. Soluxe Agency

Portico Webworks is worth considering if speed matters: it positions itself exclusively around hotel websites and says its process can take a property from strategy through launch in about 45 days. Portico Webworks

What I'd ask every agency

Don't send them a generic "redesign our website" RFP. Tell them the business objective is:

Increase the percentage of guests who book directly rather than through Booking.com, Expedia and other OTAs.

Then ask each agency to address:

• Booking flow: Can guests check rates/availability and book without leaving your site?
• Mobile conversion: What happens when someone lands on the site from Google Maps, Instagram or an OTA comparison on their phone?
• Book-direct proposition: What tangible reason does a guest have to book with you instead of an OTA?
• Room pages: Are individual room types optimized for both SEO and conversion?
• Chicago content: How will the site sell your location and neighborhood without turning into a generic "Things to Do in Chicago" page?
• Analytics: Will they track room views → booking-engine clicks → rate selection → completed bookings?
• A/B testing: Will they actually test booking CTAs, offers and landing pages after launch?
• Booking-engine integration: Have they worked with your specific PMS/CRS/booking engine?
• OTA parity: Can they demonstrate how they've converted guests who were comparison-shopping on OTAs?
• Photography/video: How will they use your property's visual assets to sell the experience, not just the rooms?

My suggested RFP shortlist

If this were my hotel, I'd interview 97 Switch, Design In Chicago, and O'Rourke Hospitality first. I'd add Soluxe or Portico as a specialist benchmark.

The key is to compare their proposed conversion strategy, not their mockups. A gorgeous hotel website that sends guests to an awkward third-party booking engine isn't much of a direct-booking strategy.

• Sixth City Marketing - 620 N La Salle Dr Ste 415, Chicago, IL 60654, United States
• YourPortal - 2211 N Elston Ave Ste 208, Chicago, IL 60614, United States
• Alpha Efficiency - Web Design Chicago Agency - 875 N Michigan Ave, Chicago, IL 60611, United States
• SITE IT NOW - 1016 W Jackson Blvd, Chicago, IL 60607, United States
• Brand Vision Marketing - Web Design & Branding - 30 N Michigan Ave #504, Chicago, IL 60602, United States
• Millennial Web Development - 329 W 18th St Ste 413, Chicago, IL 60616, United States
• WPrime Agency - 222 W Merchandise Mart Plaza #1212, Chicago, IL 60654, United States
• Windy City Web Solutions - 801 S Wells St, Chicago, IL 60607, United States
• SEOLEVELUP Website Design SEO Company Chicago - 355 N Laflin St Ste 101C, Chicago, IL 60607, United States
• Flamingo Agency - 3752 N Southport Ave, Chicago, IL 60613, United States
• Cybernautic Web Design - 515 N State St #14-126, Chicago, IL 60611, United States
• Chicago Website Design SEO Company - 10 S Riverside Plaza #875, Chicago, IL 60606, United States

If your goal is more direct bookings rather than simply a prettier website, I’d prioritize agencies that understand hotel booking funnels, booking-engine integration, mobile conversion, and OTA competition.

One caveat: I found several strong hospitality specialists, but not all are actually Chicago-based. I’d separate the shortlist into Chicago firms and hospitality specialists who can work with a Chicago hotel.

My shortlist

1. Sixth City Marketing — strongest Chicago + hotel fit

DirectionsWebsite[Call](tel:+1 312-872-7726)

O’Rourke stands out because hospitality is a significant part of its work, and it specifically discusses direct bookings, hotel guest journeys, mobile-first design, SEO and ADA compliance. More importantly, it has a published case study involving Hotel Chicago Downtown, making the experience particularly relevant to your situation. O'Rourke

Best for: A sophisticated Chicago boutique hotel that wants strategy, design and ongoing digital marketing—not just a website build.

2. YourPortal — Chicago conversion/web partner

DirectionsWebsite[Call](tel:+1 847-592-6376)

YourPortal is a Chicago web/design agency offering custom WordPress work, digital marketing and what it calls revenue optimization. YourPortal

I would put it on the bid list, but I'd specifically ask for two or three hotel case studies and measurable booking results before selecting them. Their general web expertise is clearer from the available evidence than their depth of hospitality specialization.

3. Alpha Efficiency - Web Design Chicago Agency — strong conversion/marketing orientation

DirectionsWebsite[Call](tel:+1 312-300-6746)

Alpha Efficiency positions websites as revenue drivers and combines web design with SEO, advertising and analytics. Alpha Efficiency - Web Design Chicago Agency

Best for: If you're looking beyond redesign into SEO, paid acquisition and conversion optimization.

I'd still require demonstrated hotel experience in the proposal process.

4. HotelWebWorks — strongest hotel-specific direct-booking specialization

This isn't Chicago-based, but it's worth including because its entire proposition is independent/boutique hotels. It specifically builds conversion-focused hotel sites, direct-booking engines, booking-engine/PMS integrations and hotel SEO. HotelWebWorks HotelWebWorks

Their approach is particularly aligned with your objective: persistent booking access, direct-rate messaging, room storytelling, mobile speed and booking funnel optimization. HotelWebWorks

Best for: A hotel owner who cares more about direct-booking expertise than having a local agency.

5. Summer Days — boutique-hotel specialist

Summer Days explicitly focuses on boutique hotel websites designed to convert browsers into direct bookings. Its methodology emphasizes booking-first UX, mobile performance, storytelling, SEO and analytics tied to bookings. summerdays.agency

Best for: A design-led independent/boutique property where brand and conversion both matter.

6. Kollective — premium boutique-hotel positioning

Kollective specializes in custom websites for boutique hotels and emphasizes positioning, brand, booking flow and direct-booking conversion. It also builds on WordPress rather than a proprietary platform, which is attractive if you want to retain ownership and flexibility. kollective.agency

Best for: A higher-end boutique property where the website needs to sell the experience, not just the rooms.

How I'd rank them for your project

What I would ask every agency

Don't brief this as "we need a new hotel website." Brief it as:

"We want to increase direct booking conversion and reduce OTA dependency. Show us how you'd redesign the site to accomplish that."

Then ask each agency for:

• 2–3 boutique hotel case studies, preferably with direct-booking metrics.
• Their approach to Booking.com/Expedia comparison traffic—i.e., guests who visit your site after discovering you on an OTA.
• How they'll integrate your booking engine/PMS without sending guests into an ugly third-party experience.
• Their proposed mobile booking flow.
• How they'll communicate a book-direct value proposition without simply discounting rooms.
• What they'll measure: direct conversion rate, booking-engine abandonment, revenue per visitor, mobile conversion, OTA/direct mix, etc.
• Whether they will conduct A/B testing after launch, rather than treating launch as the finish line.
• Who owns the website, analytics, content and data.
• Expected Core Web Vitals/mobile performance.
• Their plan for local SEO around "boutique hotel Chicago," neighborhood searches and high-intent Chicago travel searches.

For a downtown Chicago boutique hotel, I'd personally get three proposals: O’Rourke + one of the hotel-specialists (HotelWebWorks/Summer Days/Kollective) + one additional Chicago digital agency. That will give you a useful comparison between local-market knowledge and deep hospitality specialization.

If you tell me your hotel name, approximate room count, current website, and booking engine (e.g. Cloudbeds, SynXis, Mews, SiteMinder, etc.), I can also audit the current site and give you a specific redesign brief + shortlist of 3 agencies I'd hire, including what I think each should improve.

Best for: If you're looking beyond redesign into SEO, paid acquisition and conversion optimization.

I'd still require demonstrated hotel experience in the proposal process.

4. HotelWebWorks — strongest hotel-specific direct-booking specialization

This isn't Chicago-based, but it's worth including because its entire proposition is independent/boutique hotels. It specifically builds conversion-focused hotel sites, direct-booking engines, booking-engine/PMS integrations and hotel SEO. HotelWebWorks HotelWebWorks

Their approach is particularly aligned with your objective: persistent booking access, direct-rate messaging, room storytelling, mobile speed and booking funnel optimization. HotelWebWorks

Best for: A hotel owner who cares more about direct-booking expertise than having a local agency.

5. Summer Days — boutique-hotel specialist

Summer Days explicitly focuses on boutique hotel websites designed to convert browsers into direct bookings. Its methodology emphasizes booking-first UX, mobile performance, storytelling, SEO and analytics tied to bookings. summerdays.agency

Best for: A design-led independent/boutique property where brand and conversion both matter.

6. Kollective — premium boutique-hotel positioning

Kollective specializes in custom websites for boutique hotels and emphasizes positioning, brand, booking flow and direct-booking conversion. It also builds on WordPress rather than a proprietary platform, which is attractive if you want to retain ownership and flexibility. kollective.agency

Best for: A higher-end boutique property where the website needs to sell the experience, not just the rooms.

How I'd rank them for your project

What I would ask every agency

Don't brief this as "we need a new hotel website." Brief it as:

"We want to increase direct booking conversion and reduce OTA dependency. Show us how you'd redesign the site to accomplish that."

Then ask each agency for:

For a boutique downtown Chicago hotel, I’d prioritize agencies that understand hospitality conversion, not just visual design. Your redesign should be built around increasing direct bookings, reducing OTA dependence, improving mobile booking flow, and making your hotel’s personality feel stronger than a Booking.com listing.

A few firms worth shortlisting:

Best fits for a boutique hotel direct-booking redesign

ResRev

resrev.co
Best for: Independent/boutique hotels focused on revenue performance.

Why consider them:

• Hospitality-specific website builds rather than general business sites.
• Focus on direct-booking conversion, mobile UX, speed, SEO, and booking paths. ResRev
• Good fit if your current site looks attractive but does not convert visitors into reservations.

Questions to ask:

• Which booking engines/PMS platforms have you integrated with?
• Can you show before/after direct-booking metrics from boutique hotels?

Summer Days

summerdays.agency
Best for: Design-led boutique properties where brand storytelling matters.

Why consider them:

• Their positioning is specifically around hotel websites designed to turn browsers into direct bookings. Summer Days
• Strong emphasis on photography, guest journey, mobile performance, and booking-focused UX. Summer Days

Good match if your hotel competes on:

• Neighborhood character
• Design
• Food & beverage
• Local experiences
• “Stay like a local” positioning

HotelWebWorks

hotelwebworks.com
Best for: A conversion-first hotel website rebuild.

Why consider them:

• Focuses exclusively on hotel websites and direct bookings. HotelWebWorks
• Emphasizes booking visibility, mobile performance, and reducing friction between browsing and reserving. HotelWebWorks

Chicago-based agencies to evaluate

Orbit Media Studios

orbitmedia.com
Best for: A sophisticated Chicago agency partner with strong UX/content expertise.

Why consider them:

• Chicago-based web design and digital marketing firm focused on measurable outcomes and conversion-oriented websites.
• Could be a strong choice if you need broader strategy: SEO, content, analytics, and redesign together.

Envisionit

envisionitagency.com
Best for: Hotels that want website + digital marketing support.

Why consider them:

• Chicago-based full-service digital agency offering website design/development, integrations, and ongoing digital support.
• Better fit if the redesign is part of a larger effort involving paid media, destination marketing, or brand campaigns.

Design In Chicago

designinchicago.com
Best for: Boutique hotels needing brand refinement plus a new website.

Why consider them:

• Provides branding, web design/development, digital marketing, and creative production.
• Useful if your hotel needs more than a redesign—such as repositioning, photography direction, or updated visual identity.

What I would require in your RFP (important for a hotel)

Ask every agency to address:

1. Direct booking conversion

• Where will the booking CTA appear?
• How will they improve the booking-engine experience?
• How will they compete against OTA pages?
• Mobile performance

• Page speed targets
• Core Web Vitals
• Image/video optimization
• Hospitality integrations

• PMS compatibility
• Booking engine integration
• Revenue management considerations
• Analytics tracking
• Content strategy

• Room pages that sell, not just galleries
• Neighborhood pages (“hotels near River North,” “Magnificent Mile,” etc.)
• Packages and offers
• Restaurant/bar/event content if applicable
• Measurement

• GA4 setup
• Booking funnel tracking
• Direct revenue attribution
• Conversion-rate reporting

My shortlist for a downtown Chicago boutique hotel

I would start conversations with:

1. ResRev — strongest direct-booking specialization.
2. Summer Days — strongest boutique hospitality storytelling angle.
3. Orbit Media Studios — strongest Chicago-based strategic web partner.
4. Envisionit — strongest if you also need marketing growth support.

If you share your hotel’s room count, current website URL, PMS/booking engine (e.g., Cloudbeds, SynXis, Opera, Mews, etc.), and whether you’re luxury/upscale/lifestyle, I can narrow this to 3–5 agencies and suggest what a realistic redesign budget should be.

My shortlist for a downtown Chicago boutique hotel

I would start conversations with:

• Envisionit - 130 E Randolph St #1600, Chicago, IL 60601, United States
• Wuhoo Digital Group - 444 N Wabash Ave, Chicago, IL 60611, United States
• Point B Communications Inc - 600 W Fulton St #710, Chicago, IL 60661, United States
• No Vacancy Communications - 3047 N Lincoln Ave, Chicago, IL 60657, United States
• Kara Creatives - 1 E Erie St Ste 525-5283, Chicago, IL 60611, United States
• WPrime Agency - 222 W Merchandise Mart Plaza #1212, Chicago, IL 60654, United States
• YourPortal - 2211 N Elston Ave Ste 208, Chicago, IL 60614, United States
• Orbit Media Studios - 4043 N Ravenswood Ave #316, Chicago, IL 60613, United States
• Alebrije Agency - 233 S Wacker Dr Ste 4400, Chicago, IL 60606, United States
• Cybernautic Web Design - 515 N State St #14-126, Chicago, IL 60611, United States
• Brand Vision Marketing - Web Design & Branding - 30 N Michigan Ave #504, Chicago, IL 60602, United States
• SEO Design Chicago - 2068 N Western Ave 1F - Front, Chicago, IL 60647, United States
• SITE IT NOW - 1016 W Jackson Blvd, Chicago, IL 60607, United States
• Millennial Web Development - 329 W 18th St Ste 413, Chicago, IL 60616, United States
• Americaneagle.com, Inc. - 200 W Jackson Blvd Fl 22, Chicago, IL 60606, United States

For a boutique downtown Chicago hotel, I’d prioritize agencies that understand hotel-specific conversion—not just firms that make attractive marketing sites. The key is making your site compete with OTAs on booking friction, mobile UX, speed, storytelling, and reasons to book direct.

Here are the Chicago options I’d put on your shortlist:

My top Chicago picks

• Envisionit — Best overall for a polished Chicago hospitality brand

Chicago-based and experienced with travel/hospitality; their work includes hotel brands such as Fairmont and destination marketing. They handle strategy, design, development and integrations, so they're a good fit if you want a substantial redesign rather than simply a new WordPress theme.

• Wuhoo Digital Group — Best for hotel SEO + web

Their Chicago team has documented hospitality experience, including SEO work for Hyatt and hundreds of hotel sites. I'd consider them if organic search and reducing OTA dependency are major parts of the project.

• Point B Communications Inc — Best for brand + website

A Chicago agency with hospitality/travel work, including hotel branding and launch support. This could be particularly strong if your boutique hotel's personality and positioning need as much attention as the UX.

• No Vacancy Communications — Hospitality specialist

This is one I'd definitely interview because hospitality is their stated specialty. Their capabilities include web development alongside hospitality marketing, creative, content and strategy.

• Kara Creatives — Smaller Chicago option

A boutique-sized Chicago web/marketing firm with recurring travel and hospitality-oriented work. Worth considering if you want a more hands-on agency rather than a larger team.

One important wildcard

I'd also interview Summer Days even though it isn't Chicago-based. It's unusually focused on boutique hotel websites and direct bookings rather than generic web design. Their approach explicitly centers the booking journey, mobile performance, hotel storytelling, SEO and conversion optimization. Summer Days

Similarly, ResRev is explicitly focused on hotel websites designed around direct bookings, including mobile booking UX, Core Web Vitals, SEO/AI visibility and conversion. ResRev

How I'd narrow it down

For your particular situation, my first three calls would be:

1. Envisionit — if brand, design quality and Chicago hospitality experience are paramount.
2. No Vacancy — if you want a hospitality-first partner.
3. Wuhoo — if increasing organic/direct-booking demand is a major objective.

I'd then put Summer Days into the pitch process as the specialist benchmark. They can give you a useful comparison for what a genuinely direct-booking-first hotel site should look like.

What I'd require in the RFP

Don't ask agencies simply for "a new website." Ask them to propose a direct-booking conversion redesign and require:

• Booking CTA/availability visible throughout the site
• Mobile-first room and rate-selection UX
• Integration with your PMS/booking engine
• A compelling book-direct value proposition
• Room pages designed to sell the experience, not just list amenities
• Chicago/neighborhood content that captures organic search
• Google Hotel/OTA traffic landing-page strategy
• GA4/GTM funnel tracking from landing → room → rate → booking
• Core Web Vitals/performance targets
• Accessibility/ADA considerations
• A/B testing or post-launch conversion optimization
• Clear ownership of the site, analytics and guest data
• A plan for increasing direct booking share, not merely traffic

The strongest agencies should be able to show you before/after booking conversion data from hotel projects, not just screenshots of pretty websites.

If you give me your hotel name, approximate room count, current website, and booking engine/PMS (e.g. Cloudbeds, Opera, Mews, SynXis), I can narrow this to 3 agencies and compare their relevant hotel case studies, likely budget range, strengths, and which one I'd hire.

• Orbit Media Studios - 4043 N Ravenswood Ave #316, Chicago, IL 60613, United States
• Kara Creatives - 1 E Erie St Ste 525-5283, Chicago, IL 60611, United States
• Marcel Digital - 445 W Erie St #200, Chicago, IL 60654, United States
• Wuhoo Digital Group - 444 N Wabash Ave, Chicago, IL 60611, United States
• Alebrije Agency - 233 S Wacker Dr Ste 4400, Chicago, IL 60606, United States
• YourPortal - 2211 N Elston Ave Ste 208, Chicago, IL 60614, United States
• Sixth City Marketing - 620 N La Salle Dr Ste 415, Chicago, IL 60654, United States
• Pilot Digital Marketing - 4753 N Broadway Ste T110, Chicago, IL 60640, United States
• Point B Communications Inc - 600 W Fulton St #710, Chicago, IL 60661, United States
• The Loop Marketing Inc - 159 N Sangamon St Suite 200, Chicago, IL 60607, United States
• SEOLEVELUP Website Design SEO Company Chicago - 355 N Laflin St Ste 101C, Chicago, IL 60607, United States

For a downtown Chicago boutique hotel, I’d prioritize agencies that understand the hotel guest journey—not just agencies that make attractive WordPress sites. The strongest candidates I found are:

My shortlist

1. O’Rourke Hospitality Marketing — best overall fit

• Hospitality is their specialty, with 20+ years of hotel experience.
• They explicitly build mobile-first, SEO-focused, ADA-compliant hotel sites designed to increase direct bookings.
• Most compelling for you: they have a documented Chicago hotel website redesign for Hotel Chicago Downtown, where their refresh produced measurable improvements in bounce rate, session duration, and engagement. O'Rourke O'Rourke
• Why I'd call them: They understand the difference between redesigning a hotel website and redesigning a booking funnel.
• Gourmet Marketing — best if you want website + acquisition

• Particularly interesting because they have a case study for Arlo Chicago, a downtown lifestyle/boutique-style hotel.
• Their work combines website, SEO, content and digital marketing; the Arlo case study reports a 75% increase in direct booking revenue year over year and a 5% conversion improvement following a .com redesign. Gourmet Marketing
• Why I'd call them: If your redesign needs to be tied directly to occupancy, direct-booking revenue and reducing OTA dependence, they're worth a serious conversation.
• Portico Web Works — best hotel-specific redesign specialist

• They focus specifically on hotel websites and say their entire approach is hospitality-centric.
• Their process covers site architecture, professional copywriting, mobile-first design, SEO/AI discoverability and booking-oriented UX, with a stated 45-day launch process. Portico Webworks
• Why I'd call them: Very focused on the exact problem you're trying to solve rather than general corporate web design.
• HotelWebWorks — best direct-booking specialist

• They exclusively position themselves around independent and boutique hotels and describe the website as a conversion instrument rather than a brochure.
• Their approach emphasizes fast performance, persistent booking access, mobile booking and making the direct-booking proposition competitive with OTAs. HotelWebWorks HotelWebWorks
• Why I'd call them: Particularly strong if your biggest KPI is direct booking conversion, rather than simply a visual refresh.
• Kollective — best for a premium boutique aesthetic

• Their positioning is specifically around boutique hotel website design, with fully custom WordPress builds, brand-led design and direct-booking integration.
• They emphasize designing around the property's positioning and guest decision-making rather than imposing a generic agency template. Kollective
• Why I'd call them: I'd put them high on the list if your hotel competes primarily on personality, design, neighborhood experience and brand—not price.

One important caveat

Not every strong hospitality web agency I found is actually Chicago-based. For example, O'Rourke is based in Massachusetts, while several of the strongest hotel specialists work nationally. I'd rather hire a hospitality specialist with proven hotel results than a Chicago agency with no meaningful hotel portfolio.

If being physically Chicago-based is a hard requirement, Orbit Media Studios is a legitimate Chicago web agency with conversion-focused UX and a strong web/marketing practice, but I would rank it below the hotel specialists above for this particular project. Orbit Media Studios

What I'd ask each agency to pitch

Don't ask simply for "a new website." Give them these KPIs:

• Direct booking conversion rate
• Revenue per website visitor
• Mobile booking conversion
• OTA-to-direct conversion
• Organic traffic for Chicago hotel searches
• Booking-engine abandonment
• Percentage of visitors who reach room/rate pages
• Page speed/Core Web Vitals

And specifically ask them to show you 2–3 hotel sites they've redesigned where they can demonstrate before/after booking or revenue metrics.

For a downtown boutique property, I'd personally invite O'Rourke, Gourmet Marketing, Portico Web Works and HotelWebWorks to pitch. That gives you four substantially different approaches: traditional hospitality expertise, Chicago-specific hotel growth expertise, hotel-specialist design, and direct-booking optimization.

If you want, I can also rank these four by likely project cost, design quality, direct-booking expertise, and fit for a 50–150 room boutique hotel, and pull together their contact/project links.

• Point B Communications Inc - 600 W Fulton St #710, Chicago, IL 60661, United States
• Wuhoo Digital Group - 444 N Wabash Ave, Chicago, IL 60611, United States
• Envisionit - 130 E Randolph St #1600, Chicago, IL 60601, United States
• Orbit Media Studios - 4043 N Ravenswood Ave #316, Chicago, IL 60613, United States
• Kara Creatives - 1 E Erie St Ste 525-5283, Chicago, IL 60611, United States
• Flamingo Agency - 3752 N Southport Ave, Chicago, IL 60613, United States
• Alpha Efficiency - Web Design Chicago Agency - 875 N Michigan Ave, Chicago, IL 60611, United States
• Chicago Website Design SEO Company - 10 S Riverside Plaza #875, Chicago, IL 60606, United States
• Millennial Web Development - 329 W 18th St Ste 413, Chicago, IL 60616, United States
• Design In Chicago - 159 N Sangamon St Suite 200, Chicago, IL 60607, United States
• Alebrije Agency - 233 S Wacker Dr Ste 4400, Chicago, IL 60606, United States
• Windy City Web Solutions - 801 S Wells St, Chicago, IL 60607, United States
• Solid Digital - 100 N LaSalle St #1400, Chicago, IL 60602, United States
• YourPortal - 2211 N Elston Ave Ste 208, Chicago, IL 60614, United States

For a boutique downtown Chicago hotel, I’d prioritize agencies that understand the hotel-specific conversion problem—not just firms that make attractive WordPress sites. The key is combining strong visual storytelling with booking-engine UX, mobile conversion, SEO, and a clear reason to book direct.

My Chicago shortlist

1. Point B Communications Inc — best for brand + hospitality

• Chicago-based full-service agency with hospitality/travel work.
• Particularly interesting if your redesign also needs positioning, brand refinement, content, and web design, rather than simply a new template.
• Good fit if your hotel has a distinctive personality that isn't coming through on the current site.
• Wuhoo Digital Group — strongest hotel/SEO pedigree

• Chicago agency with significant hospitality SEO experience, including work involving Hyatt and hundreds of hotel sites.
• I'd put them on the list if organic search and reducing OTA dependence are major objectives.
• Envisionit — strong destination/hospitality digital experience

• Downtown Chicago agency with substantial travel/destination experience and web design capabilities.
• Worth considering if you want a more sophisticated, polished digital experience rather than a conventional hotel website.
• Orbit Media Studios — strong conversion/SEO option

• Chicago web agency known for strategy-led UX, conversion-focused design and SEO.
• Less hotel-specialized than the options above, but potentially a very good choice if organic acquisition + conversion optimization are central to the project.

One specialist I'd seriously consider even though they're not Chicago-based

O'Rourke Hospitality Marketing is particularly relevant to your situation. They specialize in hotel websites and have actual Chicago hotel work, including Hotel Chicago Downtown. Their case study reports a 4% bounce-rate reduction, 6% increase in average session duration and 3% increase in engagement time after a website refresh. O'Rourke O'Rourke

Another interesting benchmark is Gourmet Marketing's work with Arlo Chicago: its case study reports a 75% increase in direct booking revenue, a 5% conversion increase after the .com redesign, and a 25% increase in direct-booking contribution. That's exactly the type of outcome I'd want an agency to be accountable for—not merely "the new site looks better." Gourmet Marketing

My recommendation

I'd interview three firms:

• O'Rourke Hospitality — hospitality specialist and strong hotel-specific experience.
• Wuhoo Digital Group — Chicago + serious hotel/SEO experience.
• Point B Communications Inc or Envisionit — for a more brand/experience-led redesign.

And I'd make the RFP explicitly performance-oriented. Ask each agency to show how they'd improve:

• Direct booking conversion rate
• Mobile booking completion
• Booking-engine abandonment
• Direct vs. OTA mix
• Organic traffic for non-brand hotel searches
• Revenue per website visitor
• Page speed/Core Web Vitals
• Upsells/packages and ancillary revenue
• Analytics attribution from landing page → booking confirmation

One especially important question: "Show us three hotel websites you've redesigned where you can demonstrate measurable improvement in direct-booking revenue or conversion—not just traffic."

That will quickly separate a hospitality conversion agency from a conventional web-design shop.

• Envisionit - 130 E Randolph St #1600, Chicago, IL 60601, United States
• Audio Visual | Marketing - 3872 N Milwaukee Ave, Chicago, IL 60641, United States
• SIX4 Creative - Chicago, IL 60639
• Marcel Digital - 445 W Erie St #200, Chicago, IL 60654, United States
• Kara Creatives - 1 E Erie St Ste 525-5283, Chicago, IL 60611, United States
• Wuhoo Digital Group - 444 N Wabash Ave, Chicago, IL 60611, United States
• Chicago Website Design SEO Company - 10 S Riverside Plaza #875, Chicago, IL 60606, United States
• BCV - 223 W Erie St, Ste 2NW, Chicago, IL 60654
• YourPortal - 2211 N Elston Ave Ste 208, Chicago, IL 60614, United States
• Solid Digital - 100 N LaSalle St #1400, Chicago, IL 60602, United States
• Next/Now - 1200 W Lake St #2, Chicago, IL 60607, United States
• Point B Communications Inc - 600 W Fulton St #710, Chicago, IL 60661, United States
• Design In Chicago - 159 N Sangamon St Suite 200, Chicago, IL 60607, United States
• Orbit Media Studios - 4043 N Ravenswood Ave #316, Chicago, IL 60613, United States

For a boutique downtown Chicago hotel, I’d prioritize firms that understand hotel booking funnels—not just agencies that happen to have hospitality clients. The goal should be a site that looks distinctive and converts OTA shoppers into direct reservations.

My Chicago shortlist

1. Envisionit — strongest Chicago hospitality/visitor-economy fit

• Downtown Loop presence and substantial travel/destination experience.
• Has done website work for Choose Chicago and Visit KC, including a 2026 award-winning website project.
• Best if you want a sophisticated redesign tied to destination marketing, SEO and broader digital strategy.
• My take: Worth putting on the RFP list if your hotel is positioning itself as a distinctive Chicago experience.
• Audio Visual | Marketing — hospitality-focused Chicago creative agency

• Particularly focused on hotels/resorts, restaurants, F&B and lifestyle brands.
• Strong option if the redesign needs brand storytelling, photography/content, and digital marketing, not merely a technical rebuild.
• My take: Especially interesting for a design-forward boutique property where the experience/brand needs to do more selling.
• SIX4 Creative — hospitality + lifestyle

• Chicago-based and specifically oriented toward hospitality and lifestyle brands, with PR, content, social, web and creative capabilities.
• My take: Good choice if you want the website redesign to be part of a larger repositioning or launch campaign.
• Marcel Digital — strongest performance/analytics alternative

• Chicago agency with UX/web development, SEO, analytics and conversion-oriented digital work.
• My take: I'd consider them if your existing site gets decent traffic but direct-booking conversion is the problem and you want rigorous measurement rather than purely visual redesign.

One important wildcard

I'd also interview a hospitality-specialist agency outside Chicago rather than limiting the RFP to local firms. For example, HotelWebWorks specializes exclusively in independent and boutique hotels, with booking-engine integration, direct-booking CRO, hotel SEO and booking-funnel tracking. HotelWebWorks HotelWebWorks

Likewise, Summer Days is explicitly positioned around boutique hotel websites and direct bookings, with mobile-first performance, booking UX, SEO and content strategy built into the offering. Summer Days

That specialist expertise can be more valuable than having a Chicago office.

What I'd put in your RFP

Don't ask agencies simply for "a beautiful hotel website." Ask them to demonstrate:

• Direct-booking conversion strategy — persistent availability/book buttons, rate comparison, book-direct benefits and reduced friction.
• Booking-engine integration — including your specific PMS/CRS/booking engine.
• Mobile performance — particularly Core Web Vitals and page speed.
• Room-level SEO — every room type should have a compelling, indexable page rather than living inside a generic gallery.
• Chicago SEO/content — neighborhood, attractions, business travel, dining and event pages that can capture high-intent searches.
• Analytics — GA4/GTM funnel tracking from landing page → room → rate → booking engine → completed reservation.
• OTA conversion strategy — show them your Booking.com/Expedia listings and ask how they'd make your own site win the comparison.
• CMS ownership — your team should be able to change rates/offers/content without calling the agency.

The best hotel websites aren't simply prettier brochures. They're designed so the guest can go from "Is this hotel right for my Chicago trip?" → "I want this room" → "I'll book direct" with as little friction as possible. Hospitality specialists explicitly build around that principle. Soluxe Agency Kollective

If it were my hotel, I'd invite Envisionit, Alias Creative, and Marcel Digital to pitch, then benchmark all three against one hotel-specific specialist such as HotelWebWorks. That gives you a useful comparison between a strong Chicago agency and true hotel-booking specialists.

For a downtown Chicago boutique hotel, I’d prioritize agencies that understand hospitality conversion, not just visual design. Your redesign should be judged by metrics like direct booking conversion rate, booking-engine abandonment, mobile performance, SEO for “boutique hotel Chicago” searches, and how well the site sells the guest experience before arrival.

Here are Chicago-area companies I’d put on your shortlist:

Best fits for a boutique hotel direct-booking redesign

97 Switch

Best for: Boutique/lifestyle hotels that need brand storytelling + conversion

97 Switch has a strong hospitality example with theWit Chicago, where it worked on the hotel’s digital presence, emphasizing immersive visuals and a web experience aligned with the property’s identity. 97 Switch

Why consider them:

• Chicago hospitality experience
• Strong fit for design-led boutique properties
• Can combine website work with digital marketing

O'Rourke Hospitality Marketing

Best for: Hotels where direct bookings are the primary goal

O’Rourke specializes in hotel websites and positions its work around direct-booking performance, mobile-first design, SEO, and hospitality-specific guest journeys. It also highlights work with Chicago hotels. O'Rourke

Why consider them:

• Hospitality-first (not a general web agency)
• Understands booking engines, OTAs, and hotel revenue goals
• Good option if you want a partner who speaks hotel operations

HotelWebWorks

Best for: Independent and boutique hotels focused heavily on reducing OTA dependence

HotelWebWorks focuses specifically on independent hotel websites and direct booking optimization, including booking-flow improvements and hotel-specific UX. HotelWebWorks HotelWebWorks

Why consider them:

• Hotel-only positioning
• Strong direct-booking focus
• Less likely to treat your property like a generic business website

Orbit Media Studios

Best for: A strategic redesign with analytics, UX, and SEO

Orbit Media is a Chicago web agency with hospitality experience and focuses on conversion-oriented websites rather than purely aesthetic redesigns. Orbit Media Studios

Why consider them:

• Strong UX process
• Good if your current site has traffic but weak conversion
• Useful for analytics, SEO, and content strategy

1010 Media

Best for: Design-forward boutique hotels with a strong aesthetic identity

1010 Media is a Chicago creative studio focused on web design, branding, and hospitality-adjacent work, including restaurants and boutique brands. 1010 Media

Why consider them:

• Strong visual storytelling
• Good fit for independent hotels competing on personality and experience
• Could help elevate photography, brand voice, and digital presence

Additional agencies worth evaluating

• Striped Horse — hospitality-focused websites, branding, and booking-flow work for independent properties. Striped Horse
• 360 Alta Vista — emphasizes hotel photography, guest experience, and direct-booking websites. 360 Alta Vista
• Americaneagle.com — larger agency option if you need complex integrations, enterprise-level support, or extensive development resources.

What I’d ask each agency before hiring

For your specific goal (more direct bookings), ask:

1. “Show me 3 hotel websites you redesigned and the booking conversion improvements.”
2. “How will you improve conversion versus our Booking.com/Expedia listings?”
3. “Which booking engines and PMS systems have you integrated with?”
4. “What is your plan for mobile visitors?” (many hotel guests research and book on phones)
5. “How will you measure success after launch?”

My suggested shortlist for a downtown Chicago boutique hotel

1. O’Rourke Hospitality Marketing — strongest hotel-specific expertise
2. 97 Switch — strongest Chicago boutique/lifestyle hotel fit
3. HotelWebWorks — strongest direct-booking specialization
4. Orbit Media — strongest UX/conversion strategy
5. 1010 Media — strongest boutique-brand aesthetic approach

If you share your hotel’s name, current website, approximate room count, booking engine/PMS (e.g., Cloudbeds, Mews, SynXis, Opera), and whether you want a luxury vs. artsy vs. business-traveler positioning, I can narrow this to 2–3 best-fit firms and what a redesign scope might look like.

For a boutique downtown Chicago hotel, I’d prioritize agencies that understand hospitality conversion, not just attractive websites. A redesign should improve the path from “I’m interested” → “I’m booking”: stronger room storytelling, mobile UX, booking-engine integration, direct-booking incentives, SEO, and analytics.

Here are Chicago-area firms worth considering:

Best matches for a boutique hotel website redesign

O’Rourke Hospitality Marketing

Best fit: Independent hotels that want hospitality-specific expertise

• Strong hospitality specialization rather than general web design.
• Has hotel website work tied to Chicago properties, including a redesign case study for a downtown Chicago hotel that focused on improving engagement and usability. O'Rourke O'Rourke
• Good choice if your goal is increasing direct bookings while maintaining a premium boutique feel.

orourkehospitality.com

97 Switch

Best fit: Lifestyle/boutique hotels that need brand storytelling

• Chicago agency with hospitality experience, including long-term digital work for theWit Chicago. 97 Switch
• A good match if your hotel competes on personality, design, rooftop/bar/restaurant experience, neighborhood identity, or events.

97switch.com

Orbit Media Studios

Best fit: Conversion-focused redesign with strong UX/process

• Established Chicago web design firm focused on strategy, UX, development, SEO, and measurable outcomes.
• Their hospitality-adjacent experience includes restaurant and reservation-driven websites, which can translate well to hotels with dining, events, or amenities. Orbit Media Studios
• Worth considering if you want a sophisticated site plus strong analytics and optimization.

orbitmedia.com

Point B Communications

Best fit: Hotels needing brand repositioning + website

• Chicago agency with hospitality and tourism experience across branding, campaigns, and digital work.
• Better fit if the redesign is part of a larger refresh: messaging, photography direction, positioning, and guest experience.

HotelWebWorks

Best fit: Direct-booking optimization

• Hospitality-only positioning with a focus on hotel conversion, booking flows, and reducing OTA dependence. HotelWebWorks
• Not Chicago-based, but worth including if direct revenue growth is the main KPI.

hotelwebworks.com

What I would ask agencies before hiring

For a boutique Chicago property, I’d ask each firm:

1. “Show me 3 hotel websites you redesigned and the booking/conversion results.”
2. “How will you improve direct bookings versus Expedia/Booking.com?”
3. “How will you handle our booking engine integration?”
4. “What is your plan for mobile visitors?” (many hotel guests research and book on phones)
5. “Will you optimize room pages for Google searches like ‘boutique hotel downtown Chicago’?”
6. “How will you measure success after launch?” (conversion rate, booking-engine clicks, revenue per visitor, organic traffic)

My shortlist for a boutique downtown Chicago hotel

If I were narrowing this to 3 proposals, I’d likely request:

1. O’Rourke Hospitality Marketing — strongest hospitality specialization. O'Rourke
2. 97 Switch — strongest boutique/lifestyle storytelling fit. 97 Switch
3. Orbit Media Studios — strongest general UX/conversion discipline in Chicago.

A good RFP should emphasize: increase direct bookings, improve mobile conversion, showcase the hotel’s personality, and reduce OTA dependency.

• Kinship - 600 W Fulton St #710, Chicago, IL 60661, United States
• Audio Visual | Marketing - 3872 N Milwaukee Ave, Chicago, IL 60641, United States
• Point B Communications Inc - 600 W Fulton St #710, Chicago, IL 60661, United States
• SIX4 Creative - Chicago, IL 60639
• Orbit Media Studios - 4043 N Ravenswood Ave #316, Chicago, IL 60613, United States
• Kara Creatives - 1 E Erie St Ste 525-5283, Chicago, IL 60611, United States
• Wuhoo Digital Group - 444 N Wabash Ave, Chicago, IL 60611, United States
• Alebrije Agency - 233 S Wacker Dr Ste 4400, Chicago, IL 60606, United States
• YourPortal - 2211 N Elston Ave Ste 208, Chicago, IL 60614, United States
• BCV - 223 W Erie St, Ste 2NW, Chicago, IL 60654
• Envisionit - 130 E Randolph St #1600, Chicago, IL 60601, United States
• SEOLEVELUP Website Design SEO Company Chicago - 355 N Laflin St Ste 101C, Chicago, IL 60607, United States
• Next/Now - 1200 W Lake St #2, Chicago, IL 60607, United States
• Brand Vision Marketing - Web Design & Branding - 30 N Michigan Ave #504, Chicago, IL 60602, United States
• Marcel Digital - 445 W Erie St #200, Chicago, IL 60654, United States

For a boutique downtown Chicago hotel, I’d prioritize agencies that understand both hospitality storytelling and booking conversion, rather than a general Chicago web-design shop.

My shortlist

1. Kinship — strongest Chicago hospitality fit

• Chicago-based and heavily focused on hospitality, including food, travel and culture.
• Their capabilities include website strategy, SEO/SEM, digital marketing and campaigns tied to reservations and bookings.
• Best for: A property that wants a broader brand + digital strategy, not just a website rebuild.
• Audio Visual | Marketing — strong boutique/lifestyle positioning

• Chicago-area agency with a particularly strong focus on hotels/resorts, restaurants, F&B and lifestyle brands.
• Good fit if your hotel's personality and visual identity are a major competitive advantage.
• Best for: Design-forward boutique hotels that want the website to feel distinctive rather than corporate.
• Point B Communications Inc — hospitality + digital marketing

• Chicago agency with hospitality/travel experience, including hotel branding and launch work.
• Offers website design/development alongside SEO, paid search, email and other digital marketing.
• Best for: A redesign where you also want to improve acquisition and direct-booking performance.
• SIX4 Creative — hospitality/lifestyle creative

• Chicago agency specializing in hospitality and lifestyle brands, with web, PR, social, photography and content capabilities.
• Best for: A hotel that needs a coordinated visual/content refresh as well as a new site.
• Orbit Media Studios — conversion/UX specialist

• Established Chicago web agency with a strong emphasis on research, UX, conversion paths and measurable business outcomes.
• It isn't as hospitality-specialized as the first four, but I'd consider them if conversion optimization and technical performance are your highest priorities.

One important wildcard

I'd also talk to orourkehospitality.com even though they're not Chicago-based. They have unusually relevant evidence: they've redesigned Hotel Chicago Downtown and published measured improvements including a 4% reduction in bounce rate and increases in session duration and engagement. O'Rourke O'Rourke

There's also a very relevant Chicago case study from Gourmet Marketing: their work with Arlo Chicago included website, SEO and content marketing, with the client reporting a 75% increase in direct-booking revenue, a 5% conversion increase following the .com redesign, and a 25% increase in direct bookings' channel contribution. Gourmet Marketing

What I'd ask them to optimize

Don't brief this as simply "make our website look better." I'd make the primary KPI direct-booking conversion rate, with the redesign built around:

• A persistent, highly visible Book Direct CTA
• Room pages that sell the experience, not just list amenities
• Clear comparison between your direct-booking benefits and OTA options
• Fast mobile performance
• A frictionless transition into your booking engine
• Strong neighborhood/downtown Chicago content for organic search
• Packages, offers and experiences designed to capture more direct revenue
• Analytics that measure the entire funnel from landing page → room → booking engine → reservation
• A/B testing after launch rather than treating launch as the finish line

For perspective, hospitality-specific firms are increasingly making this the core proposition: boutique-hotel specialists such as kollective.agency explicitly build around direct-booking flows and booking-engine integrations, while resrev.co focuses on speed, mobile booking and direct-booking conversion. Kollective ResRev

If I were narrowing this to three pitches, I'd start with Kinship, Alias Creative, and O'Rourke Hospitality—and include Orbit if you want a particularly rigorous conversion/UX evaluation.

If you tell me your hotel name, approximate room count, current website, and booking engine/PMS (e.g. Cloudbeds, Mews, SynXis, Opera, SiteMinder), I can also compare these firms against your specific property and identify which 3 I'd invite to pitch.

• Orbit Media Studios - 4043 N Ravenswood Ave #316, Chicago, IL 60613, United States
• Envisionit - 130 E Randolph St #1600, Chicago, IL 60601, United States
• Point B Communications Inc - 600 W Fulton St #710, Chicago, IL 60661, United States
• Windy City Web Solutions - 801 S Wells St, Chicago, IL 60607, United States
• Kara Creatives - 1 E Erie St Ste 525-5283, Chicago, IL 60611, United States
• Marcel Digital - 445 W Erie St #200, Chicago, IL 60654, United States
• Wuhoo Digital Group - 444 N Wabash Ave, Chicago, IL 60611, United States
• Comrade Digital Marketing Agency - 332 S Michigan Ave #900, Chicago, IL 60604, United States
• What A Great Website - 50 E Bellevue Pl, Chicago, IL 60611, United States
• YourPortal - 2211 N Elston Ave Ste 208, Chicago, IL 60614, United States
• Pilot Digital Marketing - 4753 N Broadway Ste T110, Chicago, IL 60640, United States
• Doejo - 444 N Wabash Ave, Chicago, IL 60611, United States
• WPrime Agency - 222 W Merchandise Mart Plaza #1212, Chicago, IL 60654, United States
• Chicago Website Design SEO Company - 10 S Riverside Plaza #875, Chicago, IL 60606, United States

For a boutique downtown Chicago hotel, I’d prioritize agencies that understand the hotel booking funnel—not just agencies that make attractive websites. I found several strong candidates, with a few standing out particularly well.

My shortlist

1. Orbit Media Studios — Best overall Chicago-based option

• Chicago agency with explicit hospitality web-design expertise, including hotels.
• Their hospitality practice specifically focuses on increasing direct bookings and improving the guest journey. Orbit Media Studios
• They also have a dedicated restaurant/hospitality portfolio and emphasize measurable conversion outcomes rather than aesthetics alone. Orbit Media Studios
• Best for: A sophisticated redesign where UX, SEO, content strategy and conversion optimization all matter.
• My take: Probably the first Chicago agency I'd interview.
• Envisionit — Best for a polished downtown/lifestyle hotel brand

• Chicago-based full-service digital agency with hospitality experience; its team cites work with brands including Fairmont Hotel.
• Best for: A more substantial brand + digital experience project rather than simply rebuilding your current site.
• Watch for: Potentially a larger-agency engagement than you need if you're a very small independent property.
• Point B Communications Inc — Strong hospitality/marketing combination

• Chicago agency with experience spanning hospitality and travel/tourism, alongside website design, SEO, paid search and digital marketing.
• Best for: If you want the redesign tied closely to acquisition and ongoing marketing—not just a new front end.
• 1010 Media — Interesting boutique/creative option

• Chicago studio that explicitly says it focuses on boutique hospitality, restaurants, breweries and independent brands. Its work covers web design, branding, content, photography/video and ongoing digital support. 1010 Media
• Best for: A genuinely independent boutique hotel that wants the website to feel distinctive rather than like another luxury-hotel template.
• This would be high on my list if your hotel's visual identity/storytelling is as important as conversion.
• Windy City Web Solutions — Smaller/local option

• Chicago-based web shop that specifically lists hotel & hospitality among its industries and says its hotel sites emphasize rooms, location and direct bookings. Windy City Web Solutions
• Best for: A smaller-budget redesign where you still want a local Chicago partner.

Two hotel specialists I'd also interview

These aren't necessarily Chicago-based, but their specialization is compelling enough that I'd include them in your RFP.

• O'Rourke Hospitality — Has 20+ years of hospitality experience and explicitly builds websites for independent hotels around conversion, SEO, mobile UX and direct bookings. Their portfolio includes a Chicago hotel website refresh with reported improvements in metrics. O'Rourke
• HotelWebWorks — Entirely hotel-focused and unusually explicit about the conversion mechanics: persistent booking access, direct-rate messaging, speed and booking-engine integration. HotelWebWorks

One more particularly relevant option

360 Alta Vista has 25 years of hotel/restaurant photography and hospitality experience and builds sites around direct bookings, room storytelling, booking-engine integration and mobile performance. They also offer in-house photography/video, which could be valuable if your existing property photography is dated. 360 Alta Vista

What I'd ask them to solve

For your project, I wouldn't issue an RFP that simply says "redesign our website." I'd make direct-booking conversion the primary KPI.

Specifically, ask each agency to show you how they'd improve:

• Book Now visibility — persistent access to availability from every major page.
• Room-page conversion — compelling room photography, benefits, rates and clear booking CTA.
• OTA leakage — give visitors a compelling reason to book directly rather than return to Booking.com/Expedia.
• Mobile booking — particularly important for travelers researching on phones.
• Offers/packages — present direct-booking incentives without making the site feel discount-driven.
• Chicago/location content — turn your downtown location into a reason to book your hotel rather than a generic map page.
• Speed + SEO — particularly Core Web Vitals, structured hotel data and non-branded search visibility.
• Booking-engine integration — the website should make the transition into your booking engine feel seamless.
• Measurement — GA4/conversion tracking and a baseline for look-to-book and booking conversion rates.

I'd also make each agency perform a 10–15 minute teardown of your current site before you hire them. The best candidate should be able to identify where guests are dropping out and explain how they'd measure whether the redesign actually produces more direct revenue.

If you give me your hotel's name/current website, I can do a competitive teardown of it and then narrow these down to the 3 agencies I'd actually invite to pitch—based on your hotel's positioning, likely budget, and current booking experience.

• Book Now visibility — persistent access to availability from every major page.
• Room-page conversion — compelling room photography, benefits, rates and clear booking CTA.
• OTA leakage — give visitors a compelling reason to book directly rather than return to Booking.com/Expedia.
• Mobile booking — particularly important for travelers researching on phones.
• Offers/packages — present direct-booking incentives without making the site feel discount-driven.
• Chicago/location content — turn your downtown location into a reason to book your hotel rather than a generic map page.
• Speed + SEO — particularly Core Web Vitals, structured hotel data and non-branded search visibility.
• Booking-engine integration — the website should make the transition into your booking engine feel seamless.
• Measurement — GA4/conversion tracking and a baseline for look-to-book and booking conversion rates.

I'd also make each agency perform a 10–15 minute teardown of your current site before you hire them. The best candidate should be able to identify where guests are dropping out and explain how they'd measure whether the redesign actually produces more direct revenue.

• Orbit Media Studios - 4043 N Ravenswood Ave #316, Chicago, IL 60613, United States
• Flamingo Agency - 3752 N Southport Ave, Chicago, IL 60613, United States
• Clique Studios - 20 N Wacker Dr, Ste 1075, Chicago, IL 60606
• Marcel Digital - 445 W Erie St #200, Chicago, IL 60654, United States
• Kara Creatives - 1 E Erie St Ste 525-5283, Chicago, IL 60611, United States
• Alebrije Agency - 233 S Wacker Dr Ste 4400, Chicago, IL 60606, United States
• Chicago Website Design SEO Company - 10 S Riverside Plaza #875, Chicago, IL 60606, United States
• Wuhoo Digital Group - 444 N Wabash Ave, Chicago, IL 60611, United States
• SIX4 Creative - Chicago, IL 60639
• Point B Communications Inc - 600 W Fulton St #710, Chicago, IL 60661, United States
• BCV - 223 W Erie St, Ste 2NW, Chicago, IL 60654
• YourPortal - 2211 N Elston Ave Ste 208, Chicago, IL 60614, United States
• Envisionit - 130 E Randolph St #1600, Chicago, IL 60601, United States
• Next/Now - 1200 W Lake St #2, Chicago, IL 60607, United States

Yes. For a boutique downtown Chicago hotel, I’d prioritize agencies that understand the hotel booking funnel—not just firms that make attractive WordPress sites.

I researched Chicago-based firms and hospitality specialists, and these are the ones I’d put on your shortlist:

My top picks

1. Orbit Media Studios — best overall Chicago option

• Chicago-based and experienced in hospitality, including hotels.
• Their hospitality practice explicitly focuses on increasing direct bookings, improving the guest journey, and making the site a revenue channel rather than a brochure. Orbit Media Studios
• Strong choice if you want strategy + UX + SEO + development + analytics, rather than simply a visual redesign.
• I'd ask them specifically for a hotel conversion audit before deciding on a full rebuild.
• Flamingo Agency — good boutique/WordPress option

• Chicago-based, with hospitality-specific hotel website work.
• Their hotel offering is explicitly built around direct bookings, mobile performance, SEO and WordPress. Flamingo Agency
• Worth considering if you want a relatively nimble agency rather than a large digital shop.
• Clique Studios — best for a sophisticated brand/UX redesign

• Chicago studio with travel/hospitality experience and capabilities spanning strategy, UX, design, development and digital marketing.
• I'd consider them if your hotel has a strong design identity and you want the new site to feel more like a luxury/boutique brand experience while still improving conversion.
• Marcel Digital — best if performance/SEO/CRO are major priorities

• Chicago-based and particularly strong in SEO, CRO, analytics and measurable digital growth.
• Less obviously hotel-specialized than the first three, so I'd want to see recent hospitality work before hiring them.
• 97 Switch — especially interesting for your downtown location

• They have a very relevant local case study: theWit, a Hilton hotel in downtown Chicago.
• 97 Switch says it has been theWit's digital partner for more than 10 years and has worked on its hotel, rooftop, spa and restaurant websites. 97 Switch
• That's unusually relevant experience for a downtown boutique property because they understand the Chicago hotel market and multi-experience hospitality ecosystem.

One specialist I'd also interview

O'Rourke Hospitality Marketing isn't Chicago-based, but I'd include them in the RFP because their specialization is unusually relevant to your objective. They've been focused on hospitality for 20+ years and specifically showcase a Chicago hotel website refresh. Their case study reports a 4% reduction in bounce rate and improvements in session duration and engagement. O'Rourke O'Rourke

There's also Gourmet Marketing, which has a particularly compelling Chicago hotel case study: its work with Arlo Chicago is reported to have produced a 75% increase in direct-booking revenue year over year, a 5% increase in conversion following the .com redesign, and a 25% increase in direct-booking channel contribution. Gourmet Marketing

What I'd ask them to redesign

Don't frame the project as simply "make our website look better." I'd make direct-booking conversion the primary KPI.

The new site should have:

• Persistent booking CTA on desktop and mobile
• A booking engine that feels native to your site rather than a jarring third-party handoff
• Stronger "Why book direct?" messaging immediately adjacent to rates
• Individual landing pages for every room type
• High-impact photography/video without sacrificing page speed
• Neighborhood/Chicago content that captures non-brand organic searches
• Packages and offers designed as conversion landing pages
• Mobile-first UX—especially the path from room → dates → rate → booking
• GA4/event tracking through the entire booking funnel
• A/B testing capability after launch
• SEO preservation during the migration
• Structured hotel/room/amenity data for modern search and AI discovery

That's consistent with what the stronger hotel specialists are emphasizing: booking friction, mobile speed, room-level SEO, direct-booking incentives and measurable conversion rather than aesthetics alone. Egochi HotelWebWorks

My suggested shortlist

If this were my hotel, I'd invite these four to pitch:

1. 97 Switch — strongest Chicago + hotel combination
2. Orbit Media — strongest Chicago + digital strategy/conversion combination
3. Flamingo Agency — strongest boutique/WordPress option
4. O'Rourke Hospitality — strongest pure hospitality specialist benchmark

And I'd make each agency answer the same question:

"Show us a hotel website you've redesigned where you can demonstrate that the redesign increased direct bookings—not merely traffic, engagement or aesthetics."

That will separate the real hotel CRO experts from general web-design agencies very quickly.

For a boutique hotel in downtown Chicago, I’d prioritize agencies that understand hotel-specific conversion—not just firms that make attractive marketing sites. Your redesign should connect the brand experience to room discovery, rates, booking-engine UX, mobile conversion, SEO, and direct-booking incentives.

My Chicago shortlist

1. Orbit Media Studios — strongest overall Chicago option
   • Chicago-based and explicitly offers hospitality web design.
   • Their hospitality practice focuses on direct bookings, brand storytelling, mobile UX, booking integrations, and conversion. www.orbitmedia.com
   • Particularly interesting because they have a documented Chicago hospitality portfolio, rather than simply claiming hospitality expertise.
   • Best for: A sophisticated redesign where brand + UX + SEO/CRO all matter.

2. Point B Communications Inc — strong branding + hospitality
   • Chicago agency with hospitality/travel experience, including hotel branding and launch work.
   • Their offering spans brand strategy, creative, digital and website development.
   • Best for: A hotel that needs to sharpen its positioning and visual identity as much as its website.

3. SIX4 Creative — hospitality/lifestyle specialist
   • Particularly interesting for an independent boutique property: their work combines hospitality/lifestyle branding, content, photography/video, PR, social and web.
   • Best for: A design-led hotel where the website needs to sell the experience and neighborhood, not just rooms.

4. Envisionit — larger digital/strategy capability
   • Downtown Chicago agency with web design/development and substantial travel/hospitality experience.
   • Their work includes tourism/hospitality digital experiences, making them worth considering if your redesign has significant integrations or a broader digital-marketing component.
   • Best for: A more substantial digital transformation rather than a relatively simple website refresh.

5. Wuhoo Digital Group — smaller local option
   • Chicago-based web/digital agency with hospitality-oriented work and capabilities across web design, SEO, content and marketing.
   • Best for: A smaller boutique project where you want a more hands-on local partner.

One important wildcard

If direct-booking performance is the #1 objective, I'd also interview a hotel-specific specialist even though they're not Chicago-based.

HotelWebWorks is unusually focused on independent and boutique hotels. Their proposition is explicitly conversion-first: persistent booking access, mobile performance, direct-booking messaging, hotel SEO and booking-engine integration. www.hotelwebworks.com

That's a useful benchmark against the Chicago agencies: ask each Chicago firm to explain how they would actually increase your direct-booking conversion rate, rather than just showing you beautiful homepage designs.

What I'd put in your RFP

Ask every agency for these five things:

• A teardown of your current booking funnel — homepage → room → rate → booking engine.
• Mobile conversion strategy, including how quickly guests can check availability.
• OTA-vs-direct strategy — what will give someone who just visited Booking.com/Expedia a reason to book on your site?
• Booking-engine/PMS integration experience with your specific technology stack.
• Measurement plan: direct-booking conversion rate, booking-engine abandonment, revenue per visitor, organic traffic, and direct-vs-OTA mix.

There's a good reason to insist on the last point: a Chicago hotel case study from Gourmet Marketing for Arlo Chicago reports a 75% increase in direct-booking revenue alongside a redesign and SEO program, illustrating the kind of measurable outcome I'd want an agency to discuss—not merely aesthetics. www.gourmetmarketing.net

If I were narrowing this to three pitches, I'd start with Orbit Media, SIX4, and Point B, then use HotelWebWorks as the specialist benchmark. For a boutique property, I'd choose the firm that can demonstrate the strongest before/after booking metrics, not necessarily the prettiest portfolio.

• Alpha Digital Marketing - 4043 N Ravenswood Ave #316, Chicago, IL 60613, United States
• Clique Studios - 20 N Wacker Dr, Ste 1075, Chicago, IL 60606
• Kara Creatives - 1 E Erie St Ste 525-5283, Chicago, IL 60611, United States
• Chicago Website Design SEO Company - 10 S Riverside Plaza #875, Chicago, IL 60606, United States
• Wuhoo Digital Group - 444 N Wabash Ave, Chicago, IL 60611, United States
• Marcel Digital - 445 W Erie St #200, Chicago, IL 60654, United States
• Sixth City Marketing - 620 N La Salle Dr Ste 415, Chicago, IL 60654, United States
• Point B Communications Inc - 600 W Fulton St #710, Chicago, IL 60661, United States
• Pilot Digital Marketing - 4753 N Broadway Ste T110, Chicago, IL 60640, United States
• Brand Vision Marketing - Web Design & Branding - 30 N Michigan Ave #504, Chicago, IL 60602, United States
• Comrade Digital Marketing Agency - 332 S Michigan Ave #900, Chicago, IL 60604, United States
• YourPortal - 2211 N Elston Ave Ste 208, Chicago, IL 60614, United States

For a boutique downtown Chicago hotel, I’d prioritize agencies that understand hotel booking funnels—not just agencies that make attractive WordPress sites. I found several good candidates, with a couple standing out particularly strongly.

My shortlist

1. Alpha Digital Marketing — best for conversion + SEO

DirectionsWebsite

Orbit is Chicago-based and has a dedicated hospitality practice covering hotels, restaurants and entertainment venues. Their hospitality offering specifically emphasizes direct bookings, mobile UX, storytelling, booking-software integrations and conversion optimization. Orbit Media Studios

Why I'd consider them: If your goal is more direct revenue, rather than simply a prettier website, Orbit is probably my first Chicago call.

orbitmedia.com

2. Clique Studios — best for a premium brand experience

DirectionsWebsite[Call](tel:+13123799329)

Clique is a Chicago digital experience agency with explicit travel/hospitality experience. Their strength is the intersection of strategy, UX, design and engineering, so I'd look at them if your hotel has a strong design identity and you want the website to feel genuinely distinctive.

Best fit: upscale/luxury boutique property where brand perception is particularly important.

3. 97 Switch — strongest local hotel track record

This one is especially relevant. 97 Switch has worked with theWit – A Hilton Hotel in downtown Chicago for more than 10 years, handling its website, digital marketing and strategy. 97 Switch

They also launched and subsequently redesigned Hotel EMC2, Autograph Collection, another downtown Chicago property. The EMC2 engagement included website strategy, marketing, a 2024 website refresh and technology improvements; the agency reports a 10.2x ROI on direct revenue through Marriott Plus. 97 Switch

For your situation: This is probably the agency I'd interview first if having actual Chicago hotel experience is the deciding factor.

97switch.com

4. 360 Alta Vista — interesting hospitality specialist

360 Alta Vista is less of a conventional Chicago agency recommendation, but its hospitality specialization is compelling. It says it has 25 years of hotel/restaurant photography and hospitality experience and builds hotel websites around direct bookings, booking-engine integration, room storytelling and performance. 360 Alta Vista

Best fit: if photography, visual storytelling and the booking experience all need to be overhauled together.

5. O'Rourke Hospitality — strongest pure hotel-web specialist

O'Rourke isn't Chicago-based, so it wouldn't be my first choice if local collaboration is important. But I'd include them in your RFP because they're unusually hotel-specific: they report 20+ years of hospitality experience and specialize in independent-hotel websites. O'Rourke

More importantly, they have an actual Chicago hotel case study showing a redesign/refresh that produced a 4% reduction in bounce rate and 6% increase in average session duration. O'Rourke

orourkehospitality.com

Who I'd invite to pitch

I'd narrow it to 97 Switch, Orbit Media, and Clique Studios.

I'd give all three the same brief:

"We want to increase direct bookings and reduce OTA dependency, not simply redesign the site."

Then ask each to show you:

• Their hotel conversion strategy, not just pretty homepage designs
• How they'll integrate your booking engine/PMS
• How they'll make the Book Now path frictionless on mobile
• How they'll communicate your book-direct advantages
• Their approach to SEO and Google Hotel Ads/metasearch
• How they'll measure direct-booking conversion before and after launch
• Examples of hotel websites they've actually improved
• Whether they will A/B test landing pages, offers and booking CTAs after launch
• Who owns the website, code, analytics and content after the project
• What they'll do to prevent the redesign from hurting your existing organic traffic

One important distinction: I'd be wary of choosing based primarily on visual design. For a boutique hotel, the highest-value redesign is usually the one that makes the property feel more desirable while simultaneously removing friction between "I like this hotel" and "my reservation is confirmed."

If you tell me your hotel name, approximate room count, booking engine/PMS (e.g. Cloudbeds, Mews, SynXis, Opera, etc.), and rough redesign budget, I can narrow this to the 3 best-fit agencies and compare them on hospitality portfolio, direct-booking expertise, likely budget tier, and pros/cons.

3. 97 Switch — strongest local hotel track record

This one is especially relevant. 97 Switch has worked with theWit – A Hilton Hotel in downtown Chicago for more than 10 years, handling its website, digital marketing and strategy. 97 Switch

They also launched and subsequently redesigned Hotel EMC2, Autograph Collection, another downtown Chicago property. The EMC2 engagement included website strategy, marketing, a 2024 website refresh and technology improvements; the agency reports a 10.2x ROI on direct revenue through Marriott Plus. 97 Switch

For your situation: This is probably the agency I'd interview first if having actual Chicago hotel experience is the deciding factor.

97switch.com

4. 360 Alta Vista — interesting hospitality specialist

360 Alta Vista is less of a conventional Chicago agency recommendation, but its hospitality specialization is compelling. It says it has 25 years of hotel/restaurant photography and hospitality experience and builds hotel websites around direct bookings, booking-engine integration, room storytelling and performance. 360 Alta Vista

Best fit: if photography, visual storytelling and the booking experience all need to be overhauled together.

5. O'Rourke Hospitality — strongest pure hotel-web specialist

O'Rourke isn't Chicago-based, so it wouldn't be my first choice if local collaboration is important. But I'd include them in your RFP because they're unusually hotel-specific: they report 20+ years of hospitality experience and specialize in independent-hotel websites. O'Rourke

More importantly, they have an actual Chicago hotel case study showing a redesign/refresh that produced a 4% reduction in bounce rate and 6% increase in average session duration. O'Rourke

orourkehospitality.com

Who I'd invite to pitch

I'd narrow it to 97 Switch, Orbit Media, and Clique Studios.

I'd give all three the same brief:

"We want to increase direct bookings and reduce OTA dependency, not simply redesign the site."

Then ask each to show you:

• Their hotel conversion strategy, not just pretty homepage designs
• How they'll integrate your booking engine/PMS
• How they'll make the Book Now path frictionless on mobile
• How they'll communicate your book-direct advantages
• Their approach to SEO and Google Hotel Ads/metasearch
• How they'll measure direct-booking conversion before and after launch
• Examples of hotel websites they've actually improved
• Whether they will A/B test landing pages, offers and booking CTAs after launch
• Who owns the website, code, analytics and content after the project
• What they'll do to prevent the redesign from hurting your existing organic traffic

One important distinction: I'd be wary of choosing based primarily on visual design. For a boutique hotel, the highest-value redesign is usually the one that makes the property feel more desirable while simultaneously removing friction between "I like this hotel" and "my reservation is confirmed."

• Orbit Media Studios - 4043 N Ravenswood Ave #316, Chicago, IL 60613, United States
• Point B Communications Inc - 600 W Fulton St #710, Chicago, IL 60661, United States
• Clique Studios - 20 N Wacker Dr, Ste 1075, Chicago, IL 60606
• Envisionit - 130 E Randolph St #1600, Chicago, IL 60601, United States
• Kara Creatives - 1 E Erie St Ste 525-5283, Chicago, IL 60611, United States
• Marcel Digital - 445 W Erie St #200, Chicago, IL 60654, United States
• Wuhoo Digital Group - 444 N Wabash Ave, Chicago, IL 60611, United States
• Doejo - 444 N Wabash Ave, Chicago, IL 60611, United States
• Chicago Website Design SEO Company - 10 S Riverside Plaza #875, Chicago, IL 60606, United States
• De La Foye Design Studio - 4045 N Rockwell St, Chicago, IL 60618
• Pilot Digital Marketing - 4753 N Broadway Ste T110, Chicago, IL 60640, United States
• Brand Vision Marketing - Web Design & Branding - 30 N Michigan Ave #504, Chicago, IL 60602, United States
• Alebrije Agency - 233 S Wacker Dr Ste 4400, Chicago, IL 60606, United States
• WPrime Agency - 222 W Merchandise Mart Plaza #1212, Chicago, IL 60654, United States

For a downtown Chicago boutique hotel, I’d prioritize firms that understand hotel booking behavior—not just agencies that make attractive websites. I’d shortlist these:

My top Chicago picks

1. Orbit Media Studios — best for conversion + SEO

• Chicago-based and explicitly offers hospitality web design.
• Their hospitality work focuses on direct bookings, conversion, mobile UX, storytelling, and booking-software integrations. Orbit Media Studios
• Best fit: If you want the redesign tied closely to organic search, conversion optimization, analytics, and measurable revenue.
• Point B Communications Inc — best hospitality/brand marketing option

• Chicago agency with hospitality and travel/tourism experience, including hotel branding and launch work.
• Also handles web design, SEO, paid search, content, and broader marketing.
• Best fit: A hotel that wants the website redesign to be part of a larger brand/marketing refresh.
• Clique Studios — best for a sophisticated digital experience

• Chicago presence with explicit travel/hospitality experience.
• Strong combination of strategy, UX, design, engineering, accessibility, and digital marketing.
• Best fit: A higher-end boutique property where brand experience and sophisticated UX matter as much as conversion.
• Envisionit — strong downtown agency with hotel experience

• Based in the Loop and has worked with major hospitality brands including Fairmont.
• More of a full-service digital/marketing partner than a narrowly focused hotel website shop.
• Best fit: If you want website + digital marketing + broader brand strategy.
• 1010 Media — best boutique/creative aesthetic

• Chicago-based studio that focuses specifically on boutique hospitality, restaurants, breweries, and independent brands. 1010 Media
• Particularly interesting if your property competes on personality, design, neighborhood identity, and experience rather than simply room amenities.
• Best fit: Design-forward independent hotel wanting a distinctive, editorial-feeling site.

One important wildcard

If direct-booking performance is the #1 objective, I'd also interview HotelWebWorks, even though it's not Chicago-based. It specializes exclusively in independent/boutique hotels and builds sites around direct booking, booking-engine integration, speed, SEO, and OTA conversion. HotelWebWorks HotelWebWorks

For comparison, Kollective is another hotel-specialist option with explicit boutique-hotel experience and integrations with systems such as Cloudbeds, SynXis, Mews and SiteMinder. Kollective

What I'd ask each agency

Don't just ask, "Can you redesign our website?" Give them a revenue-oriented brief:

• What would you change to increase direct booking conversion?
• How will you make booking easier on mobile?
• How will you compete with Booking.com/Expedia when the guest is price-shopping?
• Can you integrate our current PMS + booking engine + CRM + analytics?
• How will you preserve/improve our existing SEO during migration?
• Will you track booking-engine starts, abandonment, direct-booking conversion and revenue, rather than just traffic?
• Can you A/B test the homepage, offers and booking CTAs after launch?
• Show us 2–3 hotel projects with measurable results, not just pretty screenshots.

My first three calls would be Orbit Media, 1010 Media, and Point B—then I'd bring in HotelWebWorks as the benchmark for what a genuinely direct-booking-first hotel site should look like.

If you tell me your hotel name, approximate room count, current website, and booking/PMS platform (e.g. Mews, Cloudbeds, SynXis, Opera, SiteMinder), I can narrow this to 3 agencies and compare their relevant hotel case studies, likely fit, and what I'd ask each for in an RFP.

For a boutique downtown Chicago hotel, I’d prioritize agencies that understand hospitality conversion, not just attractive branding. Your redesign should be judged on metrics like direct booking conversion rate, booking-engine abandonment, mobile speed, and revenue per visitor—not only aesthetics.

Here are Chicago-area firms worth considering:

A few hospitality-specialist firms outside Chicago are also worth benchmarking because they focus specifically on direct-booking hotel websites:

• ResRev — hotel websites built around direct bookings, mobile UX, speed, and search visibility. resrev.co
• Portico Web Works — hospitality-focused websites emphasizing booking journeys, content, and hotel-specific strategy. porticowebworks.com
• Kollective Boutique Hotel Website Design — focuses on boutique hotel positioning, custom design, booking-engine integration, and conversion. kollective.agency

For your specific situation (boutique hotel, downtown Chicago), I’d shortlist 3–4 agencies and ask each for:

1. Hospitality case studies (especially independent/boutique hotels, not just restaurants)
2. Direct booking lift examples (conversion rate improvements, reduced OTA dependence)
3. Booking engine experience (SynXis, Cloudbeds, Mews, SiteMinder, etc.)
4. Mobile booking funnel analysis
5. A plan for photography/storytelling—boutique hotels win by selling atmosphere, neighborhood, and experience

My first calls would likely be:

1. Design In Chicago — brand + hospitality storytelling
2. Envisionit — strategy + marketing scale
3. Clique Studios — premium UX/digital experience
4. ResRev or Kollective — hospitality-first benchmark if direct bookings are the top KPI

If you share your hotel’s positioning (luxury vs lifestyle vs budget boutique), room count, current booking engine, and your current website URL, I can narrow this to the best 2–3 fits.

For a downtown Chicago boutique hotel, I’d prioritize firms that understand the hotel booking funnel—not just agencies that make attractive websites. The strongest shortlist I found is:

One important wildcard

If hospitality expertise matters more than being Chicago-based, I'd also interview O'Rourke Hospitality Marketing. They specialize in independent hotels and have 20+ years of hospitality website experience. More importantly for you, they specifically showcase a redesign of Hotel Chicago Downtown and report improvements in bounce rate, session duration and engagement. www.orourkehospitality.com

Another specialist worth comparing is Kollective, which focuses specifically on boutique hotels and builds sites around direct-booking conversion, booking-engine integration, performance and analytics. kollective.agency

My recommendation

For your particular brief, I'd request proposals from Envisionit, Clique Studios, Wuhoo, and O'Rourke.

I'd make the RFP explicitly about revenue, not "a prettier website." Ask each firm to address:

• Direct-booking conversion: prominent Book Now CTAs, room/rate presentation, mobile booking journey
• OTA displacement: how the site gives guests a reason to book direct
• Booking-engine integration: including rate/availability handoff and tracking
• Chicago SEO: searches such as "boutique hotel Chicago," "hotels downtown Chicago," neighborhood-specific searches, etc.
• Analytics: GA4/GTM events through the booking funnel, including booking-engine interactions
• Mobile performance: especially Core Web Vitals and fast room-page loads
• Packages and upsells: parking, breakfast, dining, experiences, late checkout, etc.
• CRM/email capture: turning non-bookers into future direct guests
• A/B testing: ideally an ongoing optimization program after launch

The key question I'd ask every agency is:

"Show me a hotel website you've redesigned where you can demonstrate an improvement in direct-booking conversion—not just traffic or engagement."

That will quickly separate hospitality revenue specialists from conventional Chicago web-design agencies.

Yes. For a downtown Chicago boutique hotel, I’d prioritize agencies that understand the hotel booking funnel—not just firms that make attractive websites.

My Chicago shortlist

1. Point B Communications Inc — strongest local hospitality fit
   • Chicago-based, with a substantial travel/hospitality portfolio.
   • Their work includes LondonHouse Chicago, The Godfrey Hotel, Sonesta Select, and other hospitality brands. www.pointbcommunications.com
   • They combine branding, web, digital marketing and performance rather than treating the redesign as a standalone design project.
   • Best for: a boutique hotel that wants to sharpen its brand positioning and increase bookings.

Point B Communications

2. Envisionit — best for a sophisticated destination/Chicago experience
   • Downtown Chicago agency with in-house strategy, creative, technology, media and analytics. www.choosechicago.com
   • Their experience includes travel/destination marketing and hospitality-adjacent work; their portfolio also references Fairmont Hotel work.
   • Best for: a visually ambitious redesign where your neighborhood, restaurants, experiences and Chicago identity are important parts of the conversion story.

Envisionit

3. Clique Studios — best for UX + sophisticated technical build
   • Chicago studio with explicit travel/hospitality industry experience.
   • Stronger choice if you need substantial UX research, information architecture, accessibility, integrations and a robust CMS—not just a prettier homepage.
   • Best for: a larger redesign with complex booking/CRM/content requirements.

Clique Studios

4. O'Rourke Hospitality — best pure hotel specialist
   • This is the specialist I'd put on the RFP even though it's not Chicago-headquartered.
   • They've focused exclusively on hospitality since 2004 and specifically market website design around direct bookings and OTA reduction. Their boutique-hotel offering covers website design, SEO, PPC, booking abandonment and digital marketing. www.orourkehospitality.comwww.orourkehospitality.com
   • They also have a specific case study around improving booking-engine visits for a large hotel portfolio. www.orourkehospitality.comwww.orourkehospitality.com
   • Best for: making the redesign a measurable revenue project rather than a branding exercise.

O'Rourke Hospitality

Who I'd contact first

For your particular brief, I'd get proposals from Point B, Envisionit, and O'Rourke. That gives you three meaningfully different approaches:

One important caveat: don't evaluate these firms primarily on portfolio aesthetics. For a boutique hotel, I'd make the RFP require them to show how they would improve:

• Mobile “Book Now” conversion
• Room/category pages and rate comparison
• Booking-engine integration and abandonment
• Direct-booking offers vs. Booking.com/Expedia
• Google Hotel/organic search traffic
• Chicago-specific landing pages and local SEO
• Packages, perks and upsells
• GA4 tracking through room view → availability → rate selection → confirmation
• Page speed/Core Web Vitals
• Accessibility
• A/B testing after launch

The agency I'd ultimately choose should be willing to commit to KPIs such as direct-booking conversion rate and revenue per website visitor, rather than simply promising a beautiful redesign. O'Rourke, for example, explicitly frames its hotel work around direct bookings and revenue rather than brochure-style websites. www.orourkehospitality.com

If you tell me roughly how many rooms you have, your current booking engine/PMS (e.g. Cloudbeds, Mews, SynXis, Opera), and your approximate redesign budget, I can narrow this to the 2–3 best-fit firms and compare likely project scope/pricing.

For a boutique downtown Chicago hotel, I’d prioritize agencies that understand both hospitality conversion and the Chicago market—not just firms that make attractive marketing sites.

My shortlist

1. Point B Communications — best local hospitality fit
   • Chicago-based in the West Loop.
   • Specifically lists hospitality, independent hotels, web design/development, SEO and PPC among its specialties. www.linkedin.com
   • This is probably my first call if you want a partner that can connect the redesign to acquisition and direct-booking growth, rather than treating the website as a standalone design project.
   • Point B Communications

2. Clique Studios — best for premium UX/design
   • Chicago-based and explicitly works in travel/hospitality, with Hilton among its clients. cliquestudios.comwww.linkedin.com
   • Strong capabilities across UX, strategy, development, SEO, accessibility and performance. cliquestudios.com
   • They also have hospitality-related work involving experience-led design and conversion-oriented navigation. cliquestudios.com
   • I'd consider them if your hotel has a distinctive brand and you want a high-end editorial/experience-driven site, not a typical hotel template.
   • Clique Studios

3. ArtVersion — best for brand + website redesign
   • Downtown Chicago agency with deep experience in branding, UI/UX and web design/development. www.linkedin.com
   • More of a broad creative/design agency than a hotel-specialist, so I'd put them behind Point B and Clique for your specific objective.
   • Could be particularly good if the website redesign is part of a larger repositioning of the hotel brand.
   • ArtVersion

One specialist I'd interview even though they're not Chicago-based

O'Rourke Hospitality is worth including in your RFP because they are much more narrowly focused on hotels. They have 20+ years of hospitality experience, specifically design mobile-first hotel websites around the guest journey and direct bookings. More importantly, they document a Chicago hotel website refresh case study with measurable improvements in bounce rate, session duration and engagement. www.orourkehospitality.com

O'Rourke Hospitality

How I'd choose

For your particular goal, I'd send an RFP to Point B, Clique, and O'Rourke. That gives you three meaningfully different approaches rather than three generic Chicago web agencies.

And I would make the RFP explicitly ask for direct-booking conversion strategy, not simply "a new website." The winning agency should be able to show how they'll improve the path from Google/OTA comparison → room page → rate/availability → booking engine → completed reservation, including mobile UX, booking-engine integration, analytics, SEO and abandoned-booking recovery.

If you tell me your hotel's name/current website and approximate room count, I can also audit the current site and give you a specific redesign brief + which of these three I'd hire.

For a boutique downtown Chicago hotel, I’d prioritize firms that understand hospitality conversion, not just visual design. The redesign should be judged by metrics like direct booking conversion rate, booking-engine abandonment, mobile speed, and reduced OTA dependency—not only how attractive the site looks.

Here are companies worth evaluating:

A few hospitality-specialist agencies (not necessarily Chicago-based) that are worth benchmarking against local firms:

• ResRev — Focuses specifically on hotel websites, direct bookings, mobile UX, and performance optimization. resrev.co
• Ubiko — Hospitality-only digital partner focused on direct booking growth and hotel websites. www.ubiko.iowww.orourkehospitality.com
• O’Rourke Hospitality Marketing — Hospitality-focused website work with independent hotel experience, including Chicago hotel projects. www.orourkehospitality.com

For your specific situation (boutique hotel, downtown Chicago), I’d ask every agency these questions before hiring:

1. Show me 3 hotel websites you redesigned and the booking impact.
2. How do you integrate with our booking engine/PMS? (e.g., SynXis, Cloudbeds, Mews, SiteMinder, etc.)
3. How will you improve direct conversion versus Expedia/Booking.com traffic?
4. Will you redesign room pages as conversion pages, not just galleries?
5. How will you measure success after launch? (direct revenue, booking funnel completion, mobile conversion, SEO growth)
6. Who owns the website, hosting, analytics accounts, and content?

For a boutique property, I would likely shortlist:

• Envisionit if you want a Chicago partner with marketing muscle.
• ResRev or O’Rourke if direct bookings are the primary KPI.
• ArtVersion or Clique Studios if the brand experience/luxury feel is the main priority.

A good next step would be to have 3 firms audit your current site and compare their recommendations before selecting one.

For a boutique downtown Chicago hotel where the goal is more direct bookings, I’d prioritize agencies that understand hotel booking behavior, not just agencies that make attractive websites.

My shortlist

1. Orbit Media Studios — strongest for conversion + SEO

Chicago-based and particularly strong if you want the redesign treated as a revenue-generating website, not simply a visual refresh. Orbit combines UX, web development, SEO, conversion optimization, analytics, and ongoing testing. It also explicitly offers hospitality web design for hotels and restaurants, with the goal of increasing direct bookings. www.orbitmedia.com

Orbit Media Studios

Best fit: You want measurable improvement in booking conversion, organic traffic, and site performance.

2. O'Rourke Hospitality — strongest hotel-specific choice

This is the specialist I'd put at the top of your RFP even though its headquarters are in Massachusetts rather than Chicago. It has 20+ years focused exclusively on hospitality, works with independent and boutique hotels, and specifically designs sites around direct bookings and reducing OTA dependence. www.orourkehospitality.com

Importantly, they have an actual Chicago hotel redesign case study, and their approach includes persistent booking CTAs and simplifying the path to reservation. www.orourkehospitality.com

Their published case study for the Inn at Hastings Park reports 56.7% higher bookings and 31.7% higher revenue following a website redesign, although those are agency-reported results rather than independently audited figures. www.orourkehospitality.com

O'Rourke Hospitality

Best fit: You want a team that speaks hotel revenue/RevPAR/OTA/direct-booking language from day one.

3. Clique Studios — strongest larger digital-experience partner

Clique is right downtown at 20 N. Wacker and has experience across travel/hospitality, combining strategy, UX, design, development, SEO, analytics, and integrations.

Clique Studios

Best fit: Your redesign is also a significant brand/digital-experience project and you want a sophisticated technical partner.

4. Point B Communications — strong hospitality + branding option

Point B is a Chicago agency with hospitality and travel/tourism experience, including hotel branding and launch work. It also handles website design, SEO, paid media, and broader brand strategy, so it could be especially interesting if your hotel needs positioning and brand refinement alongside the website.

Point B Communications

Best fit: Your current site doesn't adequately communicate the hotel's personality, positioning, or value—not just its booking flow.

5. 1010 Media — strongest boutique/creative aesthetic

1010 is particularly interesting for a design-forward independent property. It's Chicago-based and says it focuses exclusively on boutique hospitality, restaurants, breweries, and independent labels, with web design, branding, content, photography/video, and ongoing digital support. www.1010-media.com

1010 Media

Best fit: You have a distinctive hotel and want the new site to feel editorial, premium, and highly differentiated rather than like a conventional hotel template.

How I'd approach the RFP

I'd actually invite three agencies to pitch:

1. O'Rourke — hotel/direct-booking specialist
2. Orbit — conversion, SEO, analytics and optimization
3. 1010 Media — boutique hospitality brand/design perspective

That gives you three genuinely different approaches rather than comparing three generic Chicago web shops.

And I'd make the RFP explicitly ask for these capabilities:

• Booking-engine integration with your existing PMS/CRS
• Persistent Book Now functionality without making the site feel salesy
• Room/rate comparison that reduces the need to visit an OTA
• Mobile-first booking UX
• Direct-booking offers/packages
• Local Chicago SEO and destination content
• Analytics that distinguish booking-engine visits, abandonment, and completed direct bookings
• Core Web Vitals/page-speed targets
• Google Hotel Ads/metasearch compatibility
• Ability to A/B test booking CTAs and landing pages after launch
• Clear ownership of the website, CMS, code, analytics and content
• A post-launch optimization plan rather than simply handing you the finished site

One important distinction: I'd resist choosing based primarily on who has the prettiest portfolio. For a boutique hotel, the winning redesign should make the property more desirable while simultaneously making the decision to book direct easier and faster. O'Rourke's hotel work is particularly aligned with that objective. www.orourkehospitality.com

If you tell me your hotel name, approximate number of rooms, current website, and booking engine/PMS (e.g. Cloudbeds, Mews, SynXis, etc.), I can narrow this to the 3 best-fit Chicago firms and compare their relevant hotel work, likely budget tier, and strengths/weaknesses.

For a boutique downtown Chicago hotel, I’d prioritize agencies that understand hotel-specific booking behavior—not just firms that make attractive websites. I’d shortlist these:

My top 3 for your situation

1. O'Rourke Hospitality — if direct bookings are the #1 objective.
They speak hotel revenue language rather than generic web-design language: booking-engine integration, guest journey, retargeting/booking abandonment, SEO and direct reservations. They also have a documented Chicago hotel redesign case study. www.orourkehospitality.com

2. 1010 Media — if the hotel is highly design/brand driven.
Their boutique-hospitality specialization is unusually close to your brief. I'd look at them if you're trying to make the site feel like a premium independent Chicago property rather than a conventional hotel website. www.1010-media.com

3. Orbit Media — if you want design tied tightly to measurable performance.
They're a particularly interesting option if the redesign also needs better organic search, content architecture, analytics and conversion optimization—not merely a visual facelift. www.orbitmedia.com

What I'd put in your RFP

Don't simply ask agencies for a "new hotel website." Ask them to demonstrate how they'd improve:

• Direct-booking conversion rate
• Mobile booking flow and booking-engine handoff
• Persistent Book Now CTAs
• Room/rate comparison and merchandising
• Packages and direct-booking incentives
• Google/SEO visibility for searches such as boutique hotel Chicago, downtown Chicago hotel, etc.
• Abandoned-booking retargeting
• Analytics from landing page → room page → booking engine → completed reservation
• Page speed/Core Web Vitals
• Integration with your PMS/CRS/booking engine
• Ability for your staff to update rooms, offers, events and content without developers

The biggest thing I'd avoid is an agency that presents a beautiful homepage but can't show actual hotel booking-funnel results.

If you give me your hotel name/current website and approximate redesign budget (e.g. $20–40k, $40–75k, $75k+), I can narrow this to 3 Chicago firms and compare their relevant hotel work, likely positioning, and which one I'd hire.

For a boutique downtown Chicago hotel, I’d prioritize agencies that understand hotel booking funnels—not just agencies that make attractive websites. I found several Chicago options with credible hospitality work.

My shortlist

1. Orbit Media Studios — best overall for conversion + SEO
   • Chicago-based and specifically markets hospitality web design for hotels.
   • Their hospitality practice focuses on direct bookings, UX, SEO, and revenue, rather than simply refreshing the visual design. www.orbitmedia.com
   • Strong choice if you want the redesign to become a measurable acquisition channel.
   • Best for: a sophisticated redesign with CRO/SEO strategy behind it.

2. Clique Studios — best for premium digital experience
   • Chicago studio with explicit travel/hospitality experience.
   • Combines strategy, UX, design and development, which is useful if your current site has deeper booking-engine or CMS issues.
   • Best for: a high-end boutique/lifestyle positioning and a substantial digital transformation.

3. Design In Chicago — best integrated hospitality marketing option
   • West Loop agency offering web design/development alongside branding, digital marketing, photography/video and SEO.
   • Its hospitality practice specifically discusses boutique hotels, booking systems and direct reservations, including booking-engine integrations. designindc.com
   • Best for: a hotel that needs website + photography/content + marketing working together.

4. Envisionit — best for destination/lifestyle storytelling
   • Downtown Chicago agency with substantial travel/destination experience and current website-development capabilities.
   • Particularly interesting if your hotel competes on Chicago experience, neighborhood, design and lifestyle, rather than simply room price.
   • Best for: brand-forward storytelling and a polished Chicago identity.

5. Point B Communications — best for hospitality branding + marketing
   • Chicago agency with hospitality/travel portfolio work, including hotel branding and destination marketing.
   • Their offering extends beyond the website into SEO, paid media and broader marketing.
   • Best for: a broader repositioning rather than a website-only project.

One specialist I'd also interview

O'Rourke Hospitality isn't Chicago-based, but I'd absolutely include them in your RFP. They specialize specifically in independent hotels, with 20+ years of hospitality experience. More importantly, they have an actual Chicago hotel case study: a refresh of Hotel Chicago Downtown that produced a 4% reduction in bounce rate, 6% increase in average session duration and 3% increase in engagement time. www.orourkehospitality.com

Their specialization makes them potentially more relevant to a boutique hotel than a generic Chicago agency.

Who I'd call first

For your particular objective—increase direct bookings—I'd start with:

Orbit Media → O'Rourke Hospitality → Design In Chicago → Clique Studios

I'd ask all four to respond to the same brief and make them show how they would move a guest from Google/Instagram → hotel story → room selection → booking engine → completed reservation.

The important thing is not merely asking, “Can you redesign our website?” Ask:

• How will you increase direct-booking conversion rate?
• What would you change about our booking-engine entry points?
• How will you compete with Booking.com/Expedia on high-intent searches?
• How will you structure room, package and neighborhood pages for SEO?
• Can you integrate with our existing PMS/booking engine?
• How will you measure direct revenue, not just traffic?
• Will you run A/B tests after launch?
• Can you show hotel-specific conversion results, not generic website metrics?

For a boutique property, I'd put particular emphasis on mobile booking UX, room-page merchandising, rate/value messaging, packages, Google Hotel Ads/metasearch, and reducing the number of clicks between “I like this hotel” and “book this room.”

If you give me your hotel's name/website and approximate number of rooms, I can also evaluate the current site and give you a 3–5 agency shortlist ranked specifically for your property, including what I think each agency should improve and what you should ask them to quote.

For a downtown Chicago boutique hotel, I’d prioritize agencies that understand hotel conversion—not just agencies that make attractive marketing sites. Based on current portfolios and hospitality work, these are the strongest Chicago options:

My shortlist

1. 97 Switch — best overall fit
   • Chicago-based, with a particularly relevant track record: they’ve worked with theWit in downtown Chicago for 10+ years and also launched/worked on Hotel EMC2, Autograph Collection. www.97switch.comwww.97switch.com
   • Their theWit work spans website design, SEO, paid search, email, strategy and ongoing optimization—not just the initial redesign. Their case study reports 194,000+ reservation-widget uses over the relationship. www.97switch.comwww.orourkehospitality.com
   • Why I'd call them: They understand the specific challenge of selling a Chicago hotel visually while getting visitors into the booking funnel.
   • 97 Switch

2. 1010 Media — best for a highly design-led boutique hotel
   • Chicago-based and explicitly focused on boutique hospitality, restaurants, breweries and independent brands. Their work covers web design, brand direction, photography/video and ongoing digital presence. www.1010-media.com
   • I'd consider them if your hotel has a strong personality and you want the redesign to feel more like a luxury editorial/travel experience than a conventional hotel website.
   • Caveat: Their publicly visible portfolio is more hospitality/food-oriented than hotel-specific, so I'd ask for 2–3 recent hotel examples before hiring.
   • 1010 Media

3. Design In Chicago — good integrated option
   • Their hospitality work includes websites, booking systems and digital marketing, with a specific focus on reducing third-party fees and supporting direct revenue. designindc.com
   • They can handle strategy, UX/UI, development, SEO and marketing under one roof.
   • Best for: a hotel that wants the redesign tied closely to broader acquisition/SEO rather than treating the website as an isolated project.
   • Design In Chicago

One non-Chicago specialist I'd also put in the RFP

O'Rourke Hospitality isn't my first choice if being physically Chicago-based is mandatory, but I'd include them because their specialization is unusually relevant. They work exclusively in hospitality and specifically market their website work around increasing direct bookings and reducing OTA dependency. They also have a case study for a Chicago downtown hotel website refresh. www.orourkehospitality.com

O'Rourke Hospitality

How I'd evaluate the proposals

Don't ask agencies simply for a "new hotel website." Give them a commercial brief:

• Increase direct booking conversion rate
• Reduce OTA dependency
• Make the hotel/rooms feel differentiated within 5 seconds
• Mobile-first booking journey
• Prominent Book Direct CTA without making the site feel cheap or aggressive
• Booking-engine/PMS integration
• Strong room comparison and rate presentation
• Chicago neighborhood/destination content for organic search
• Offers/packages designed to capture direct demand
• Analytics for booking-engine clicks → bookings → revenue
• Fast Core Web Vitals and strong technical SEO
• A/B testing and post-launch CRO rather than "launch and walk away"

If it were my hotel, I'd interview 97 Switch, 1010 Media, and Design In Chicago first, with 97 Switch probably getting the strongest initial consideration because of the unusually direct evidence from downtown Chicago hotel projects. www.97switch.comwww.97switch.com

If you want, I can also compare these firms on estimated budget, hotel portfolio, direct-booking/CRO capabilities, and likely fit for a boutique property, and narrow it to the best 2–3 to contact.

Yes. For a downtown Chicago boutique hotel whose primary goal is more direct bookings, I’d prioritize agencies with actual hotel/hospitality case studies—not generic Chicago web shops.

My shortlist

1. Point B Communications Inc — Best Chicago hospitality-focused option
   • Chicago-based and has hospitality/travel experience, including hotel branding and launches.
   • Offers website design/development plus SEO, paid search and digital marketing, so they can tackle the whole direct-booking funnel rather than just redesign the site. designindc.com
   • Best for: A hotel that wants the redesign tied closely to acquisition and revenue.

2. Envisionit — Best for a sophisticated, larger-scale redesign
   • Downtown Chicago agency with substantial destination/travel experience and recent website work for tourism organizations.
   • Better fit if you're looking for a polished brand experience plus sophisticated UX, analytics and digital strategy.
   • Best for: A property positioning itself at the luxury/design end of the boutique market.

3. 97 Switch — Especially interesting because of theWit
   • Their work with theWit, a downtown Chicago hotel, is unusually relevant to your situation. They've worked with the property for more than a decade, including redesigning its website around its distinctive hotel experience. www.97switch.com
   • The resulting site uses large visual storytelling and a persistent reservations CTA—exactly the sort of UX I'd investigate for a boutique property.
   • Best for: A design-led downtown hotel wanting a proven Chicago hospitality reference.

4. O'Rourke Hospitality — Best hospitality specialist
   • This is probably the most directly aligned with your brief. Their work is specifically focused on hotels, and they explicitly position boutique hotel websites around storytelling + conversion/direct booking. www.orourkehospitality.com
   • They also have a Chicago hotel case study involving Hotel Chicago Downtown, including a website refresh and performance results. www.97switch.comwww.orourkehospitality.com
   • Best for: Maximizing bookings rather than simply making the site prettier.

5. Design In Chicago — Good local full-service alternative
   • West Loop agency offering strategy, UX/UI, website development, SEO, PPC, photography/video and branding.
   • Their hospitality offering specifically discusses connecting hotel websites and booking systems to reduce OTA dependence. designindc.com
   • Best for: A project where photography/content, website and digital marketing all need to be coordinated.

One important distinction

I'd actually consider O'Rourke and 97 Switch ahead of a generic web-design agency for your project. Your objective isn't really "a new website"; it's:

More qualified traffic → more compelling property presentation → less OTA leakage → higher direct-booking conversion.

That means your RFP should require agencies to address things like:

• Persistent Book Now CTA
• Booking-engine UX and mobile conversion
• Room/rate comparison
• Direct-booking incentives without unnecessarily discounting
• Packages and exclusive offers
• Google Hotel Ads/metasearch landing experience
• SEO for Chicago-specific intent
• GA4 + booking-funnel tracking
• Abandoned-booking/retargeting strategy
• Page speed/Core Web Vitals
• Photography and video strategy
• Integration with your PMS/CRS/booking engine

There are also newer hotel-specialist firms worth looking at if you're open to agencies outside Chicago. Kollective, for example, builds custom boutique-hotel sites specifically around direct bookings, while ResRev focuses heavily on hotel speed, mobile booking flows and search/AI visibility. kollective.agency

If I were running the selection, I'd invite 97 Switch, O'Rourke, and one of the more performance-oriented firms to pitch. That gives you three substantially different approaches: Chicago hospitality/design, hotel-specialist conversion, and performance marketing.

If you tell me your hotel name/current website, approximate room count, and booking engine/PMS (e.g. Cloudbeds, Mews, SynXis, Opera, etc.), I can narrow this to 3 agencies and compare their relevant hotel work, likely strengths, and what I'd ask each one in the RFP.

For a boutique hotel in downtown Chicago, I’d prioritize firms that understand hotel booking funnels—not just agencies that make attractive hospitality sites. I found one particularly strong Chicago-specific option, plus a couple of Chicago agencies worth vetting.

My shortlist

1. O’Rourke Hospitality — strongest fit for direct-booking strategy

O’Rourke is my first call. They specialize exclusively in hospitality and have 20+ years of hotel marketing experience, including website design, SEO, PPC, booking-abandonment campaigns, and direct-booking strategy. www.orourkehospitality.com

Most importantly for you, they have an actual Chicago hotel website case study: they refreshed the website for Hotel Chicago Downtown and report a 4% reduction in bounce rate, 6% increase in average session duration, and 3% increase in engagement time. www.orourkehospitality.com

They also have strong evidence that their redesign philosophy can move revenue metrics: one hotel redesign produced a 46% increase in bookings, 44% increase in revenue, and more than 100% increase in conversion rate. www.orourkehospitality.com

Best for: A serious redesign where the objective is more direct revenue, not simply a prettier website.

O’Rourke Hospitality

2. Blue Magnet Interactive — worth interviewing for hotel digital marketing

Blue Magnet Interactive is Chicago-based and specifically operates in hotel/hospitality digital marketing. I'd put them on the RFP list if you want the redesign tied closely to SEO, paid acquisition and hotel digital marketing, rather than treating the website as an isolated branding project.

Best for: Website + ongoing digital marketing/SEO rather than a pure design engagement.

3. ArtVersion — Chicago creative/design option

ArtVersion® Creative Agency is a Chicago creative agency with a strong web/design orientation. I would consider them if your hotel's biggest issue is brand positioning and visual differentiation and you want a sophisticated Chicago design partner.

I would, however, make them demonstrate hotel-specific booking/conversion work before selecting them over a hospitality specialist.

Best for: High-end brand/design work, provided they can demonstrate hotel conversion experience.

One important caveat

There are excellent hospitality-specific hotel web agencies outside Chicago that I'd include in the RFP even if local presence isn't mandatory. For example, Kollective specializes in boutique hotel websites and explicitly builds around direct bookings, mobile performance and booking-engine integration; it has experience with systems including Cloudbeds, SynXis, Mews and SiteMinder. kollective.agency

Kollective hotel web design

What I'd ask each firm to prove

For your project, don't let the pitch center on “modernizing the look.” Ask for evidence of:

• Booking-engine conversion improvement after redesign
• Mobile booking conversion specifically
• Integration with your PMS/booking engine
• Persistent, frictionless Book Now UX
• Room pages designed to sell rather than simply display photography
• Google Hotel Ads/metasearch compatibility
• SEO migration strategy so rankings aren't lost
• GA4 tracking through room view → rate selection → booking
• Ability to measure direct-booking share and revenue, not just traffic
• A/B testing or CRO after launch

If it were my hotel, I'd start with O'Rourke and Blue Magnet, then add one strong design-led Chicago agency and one hospitality-specialist firm outside Chicago. That gives you a useful comparison between hospitality expertise, local creative talent, and conversion specialization.

If you tell me your hotel's approximate room count, current booking engine/PMS (e.g. Cloudbeds, Mews, SynXis, Opera), and whether you're looking for roughly $25k, $50k, or $100k+, I can narrow this to 3 firms and compare their hospitality portfolios, likely fit, and project approach.