ChatGPT answers, unedited

• 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.