ChatGPT answers, unedited

• UX 4Sight - 111 W Jackson Blvd Unit 1700, Chicago, IL 60604, United States
• Ux.haus - 318 W Adams St, Chicago, IL 60606, United States
• Rocket Wagon - 600 W Fulton St Suite #510, Chicago, IL 60661, United States
• Design In Chicago - 159 N Sangamon St Suite 200, Chicago, IL 60607, United States
• Clique Studios - 20 N Wacker Dr Ste 1075, Chicago, IL 60606, United States
• ArtVersion® Creative Agency - 211 W Wacker Dr Ste 1130, Chicago, IL 60606, United States
• Solid Digital - 100 N LaSalle St #1400, Chicago, IL 60602, United States
• Streng - Chicago - 220 N Green St, Chicago, IL 60607
• Wojo Design - 318 W Adams St #1609, Chicago, IL 60606, United States
• Dialogue Theory - 1932 S Halsted St #509, Chicago, IL 60608, United States
• Artversion - 205 N Michigan Ave 8th Floor, Chicago, IL 60601
• FlyDesign - 111 W Jackson Blvd, Chicago, IL 60604, United States
• Grand Studio - 444 N Wells St #501, Chicago, IL 60654, United States
• Design Kitchen - 1140 W Fulton Market, Chicago, IL 60607
• Primal Design - 1623 W Fulton St, Chicago, IL 60612, United States
• Alpha Efficiency - Web Design Chicago Agency - 875 N Michigan Ave, Chicago, IL 60611, United States

Yes. For a law-firm client portal specifically—not just a website redesign—I’d focus on agencies with genuine product UX, workflow, and enterprise/B2B experience.

My Chicago shortlist

• UX 4Sight — Loop

111 W Jackson Blvd. They do UX research, user flows, wireframes, UI, usability testing and design systems, and their positioning includes web apps and complex digital products. That makes them a natural fit for a portal where you need to rethink the actual client journey, not merely modernize the visuals.

• Ux.haus — West Loop/Loop

318 W Adams St. Their offering spans product strategy, research, information architecture, prototyping, UX/UI and software development. I'd consider them if you want the design partner involved fairly deeply in the eventual product build.

• Rocket Wagon — Fulton Market

600 W Fulton St. This is more of a product/technology consultancy than a pure UX shop, combining strategy, design and engineering. Worth considering if the portal involves integrations with your DMS, billing, case-management or other systems.

• Design In Chicago — Fulton Market/West Loop

159 N Sangamon. They offer discovery, workflow research, wireframing and custom application/platform development in addition to design. I'd put them on the RFP list if you want one Chicago team to take substantial responsibility from UX through implementation.

• Clique Studios — Loop

20 N Wacker. They're a larger digital-transformation shop covering strategy, UX/UI, engineering, accessibility and digital systems. They may make more sense if this is a significant firm-wide transformation rather than a relatively contained portal redesign.

• ArtVersion® Creative Agency — Loop

211 W Wacker. More brand/experience-oriented, but they combine UX strategy, usability research, UI and development. I'd consider them if the portal redesign is also part of a broader modernization of the firm's digital brand.

One non-local option I'd seriously investigate

Convex is particularly interesting because it explicitly specializes in legal UX, including client portals, intake, document sharing, case-management workflows and legal SaaS. Their published process covers legal user research, information architecture, high-fidelity UI, prototyping and design systems. The Convex Agency

That specialization is unusually relevant here. You don't necessarily need your agency to be physically in Fulton Market if the alternative has substantially deeper legal-product experience.

How I'd structure the RFP

I'd actually invite 3–4 firms to respond to the same tightly defined exercise:

1. UX 4Sight — research/UX-heavy Chicago option.
2. Ux.haus — product strategy + design + development.
3. Rocket Wagon — Fulton Market product/engineering option.
4. Convex — legal-UX specialist as the benchmark.

And I'd ask each to redesign one representative client journey, e.g.:

Client logs in → sees active matters → opens a matter → reviews case status → uploads a document → messages the attorney → sees outstanding tasks.

Don't ask for a polished homepage mockup. Ask them to show how they'd make that workflow dramatically better. That's much more revealing for a portal.

For context, current Chicago UX agency pricing varies considerably; one 2026 industry survey puts typical Chicago UX rates around $110–$200/hour, with full redesigns potentially reaching six figures, while Clutch's current Chicago listings show substantial variation in minimum project sizes and specialties. 925 Studios Clutch

If you tell me roughly how many attorneys/users, what your existing portal is built on (Clio, Litify, custom, etc.), and whether you need design-only or design + development, I can narrow this to a 3-agency RFP shortlist with estimated engagement size and what I'd ask each one to prove in the pitch.

• UX 4Sight - 111 W Jackson Blvd Unit 1700, Chicago, IL 60604, United States
• Rocket Wagon - 600 W Fulton St Suite #510, Chicago, IL 60661, United States
• Design In Chicago - 159 N Sangamon St Suite 200, Chicago, IL 60607, United States
• Clique Studios - 20 N Wacker Dr Ste 1075, Chicago, IL 60606, United States
• ArtVersion® Creative Agency - 211 W Wacker Dr Ste 1130, Chicago, IL 60606, United States
• Solid Digital - 100 N LaSalle St #1400, Chicago, IL 60602, United States
• Streng - Chicago - 220 N Green St, Chicago, IL 60607
• Dialogue Theory - 1932 S Halsted St #509, Chicago, IL 60608, United States
• Wojo Design - 318 W Adams St #1609, Chicago, IL 60606, United States
• Grand Studio - 444 N Wells St #501, Chicago, IL 60654, United States
• Artversion - 205 N Michigan Ave 8th Floor, Chicago, IL 60601
• FlyDesign - 111 W Jackson Blvd, Chicago, IL 60604, United States
• CUX Studio - 122 S Michigan Ave suit 1390, Chicago, IL 60603, United States
• Sandstorm Design - 4422 N Ravenswood Ave #50, Chicago, IL 60640, United States
• Design Kitchen - 1140 W Fulton Market, Chicago, IL 60607

For a Chicago law firm modernizing a client portal, I’d focus less on general web/branding shops and more on firms that can handle complex workflows, sensitive information, accessibility, information architecture, and enterprise-grade UX.

Based on current Chicago-area options, I’d put these on your initial outreach list:

• UX 4Sight — Loop, 111 W Jackson Blvd. Their stated work spans UX research, usability testing, UX/UI, web apps, wireframing, design systems, and validation. That makes them a particularly relevant fit if the portal needs research and workflow redesign rather than just a visual refresh.
• Rocket Wagon — Fulton Market, 600 W Fulton St. They combine product strategy, design and engineering, which is useful if you want the agency to take a portal from discovery through implementation rather than hand off Figma files to another vendor.
• Design In Chicago — West Loop/Fulton Market, 159 N Sangamon. They offer UX/design plus custom application development, including requirements/workflow research, wireframing, integrations and testing. I'd consider them if the portal involves meaningful backend or systems integration. ALL FOR™
• Clique Studios — Loop, 20 N Wacker. Their offering encompasses UX/UI, information architecture, usability testing, accessibility and engineering, so they're worth considering for a larger institutional redesign rather than a small design engagement.
• ArtVersion® Creative Agency — Loop, 211 W Wacker. They combine UX research/usability, UI, design systems, branding and web development. This could make sense if the portal redesign is also part of a broader modernization of the firm's digital identity. Clutch

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

Convex is unusually specific to your problem: its legal UX practice explicitly covers law-firm client portals, intake, document sharing, case-management workflows and legal SaaS, along with legal user research, information architecture, prototyping, design systems and developer handoff. Their published legal-design engagement is 4–6 weeks. The Convex Agency

That specialization is worth comparing against the Chicago agencies, even if being physically nearby is important.

How I'd structure the shortlist

For an actual RFP, I'd probably invite 4 firms rather than 10:

1. UX 4Sight — research/UX-heavy Loop option.
2. Rocket Wagon — Fulton Market product/design + engineering option.
3. Design In Chicago — local UX + application-development option.
4. Convex — legal-specific benchmark against the local agencies.

I'd give all four the same small portal challenge: e.g. redesign the experience for a client who needs to find a case update, securely upload a document, review an invoice, message the firm, and understand what action is required next.

That will tell you much more than looking at polished homepage portfolios. For a law firm, I'd specifically evaluate role/permission architecture, document UX, accessibility, mobile use, authentication/SSO, security-sensitive interaction patterns, notifications, and how they handle confusing legal terminology.

Current Chicago agency directories also show a fairly broad UX market, so I wouldn't limit the search solely to firms that advertise themselves as "law firm web designers." Clutch

If you tell me roughly firm size, portal technology/current vendor, and whether you want design-only or design + development, I can narrow this to a 3–5 agency RFP shortlist with estimated budget ranges and relevant case studies.

Yes. For a law-firm client portal, I’d bias toward agencies with real product/UX depth rather than a conventional branding/web shop. The portal has to handle documents, matters, messaging, billing, deadlines, permissions, and sensitive information without feeling like legal software from 2012.

My Chicago shortlist:

My top 5

• TXI — best if the portal is a serious product.

This would be my first call if you're contemplating more than a visual redesign. TXI combines product strategy, user research, UX, prototyping and software engineering, which is valuable when the agency needs to understand the underlying workflows rather than simply make screens prettier.

• UX 4Sight — best pure UX/UI fit in the Loop.

Their offering is unusually aligned with your problem: UX research, UX/UI, usability testing, wireframes, responsive web apps and design validation. They're at 111 W Jackson Blvd in the Loop. Clutch

• Solid Digital — best for portal + implementation.

They specifically work on B2B digital experiences and web apps/portals, including complex customer-facing workflows. I'd put them high on the list if you want one partner to take you from UX through development rather than handing Figma files to another vendor.

• Clique Studios — best larger-agency option.

They bring UX/UI, information architecture, usability/accessibility, content strategy, engineering and digital transformation together. I'd consider them if this is part of a broader modernization of the firm's digital client experience.

• Design In Chicago — best Fulton Market-local option.

They're actually in the West Loop/Fulton Market area at 159 N Sangamon and offer branding, digital design, development and UI work. I'd favor them if the portal needs to feel like a natural extension of a broader firm rebrand.

One wildcard I'd seriously investigate

ALL FOR™ is in Fulton Market at 160 N. Elizabeth and explicitly offers UI/UX, custom web design and design systems. They're more of a design/brand/web studio than a deep product consultancy, so I'd use them if the goal is “make our client experience dramatically more modern and premium” rather than “rethink a complicated legal workflow.” ALL FOR™ ALL FOR™

There's also a particularly interesting non-Chicago-local option: Convex explicitly specializes in legal UX and lists client portals, intake, document sharing, case-management workflows and legal SaaS among its work. That's unusually close to your brief, although I'd want to establish whether having the team local is important to you. The Convex Agency

If I were running the RFP

I'd invite TXI, UX 4Sight, Solid Digital, and Convex to pitch.

And I wouldn't ask them to pitch a generic “portal redesign.” I'd give them 3–4 representative journeys:

1. New client: invitation → account setup → intake → engagement letter.
2. Active matter: see status → communicate with attorney → upload/review documents → upcoming deadlines.
3. Billing: invoice → payment → billing history.
4. Multiple matters: one client with several matters/attorneys, with appropriate permissions.

Then ask each agency to redesign one journey in a short workshop/prototype. You'll learn far more about their UX thinking that way than from looking at polished homepage case studies.

The biggest thing I'd screen for is whether they understand “client portal UX” rather than “website UX.” Those are very different problems.

If you tell me roughly your firm size, practice areas, existing portal/platform (Litify, Clio, Salesforce, custom, etc.), and whether you want design-only or design + development, I can narrow this to 3 agencies and give you a suggested RFP/budget range for each.

For a Chicago law firm modernizing a client portal (secure documents, matter status, billing, messaging, intake, self-service, etc.), I would prioritize agencies with enterprise UX, workflow design, and regulated-industry experience over agencies that mainly do marketing websites. Chicago has a strong product-design market, especially for complex B2B and professional-services platforms. Clutch UX Planet

My shortlist:

Best fits for a law firm client portal

1. Fuzzy Math — best overall UX strategy choice

Why I’d talk to them: They are one of the stronger Chicago UX firms for complicated systems: enterprise workflows, research, information architecture, dashboards, and products with multiple user types. UX Planet

Good fit if your portal needs:

• Client + attorney + staff role separation
• Matter dashboards
• Complex document workflows
• Better adoption from clients who currently email/call for updates
• UX research with actual clients before redesign

Ask them about: “Have you redesigned secure B2B portals with permissions, workflows, and compliance constraints?”

2. TXI — best if you may rebuild the product, not just redesign it

TXI is a product consultancy that combines strategy, UX research, design, and engineering.

Good fit if:

• Your existing portal is built on aging technology
• You need a roadmap, not just Figma screens
• You want a partner who can help prioritize features

They’re a strong candidate for a “discovery → prototype → build” engagement.

3. Grand Studio — strong for premium enterprise UX

Grand Studio focuses on human-centered digital products, research, strategy, and UX/UI for complex problems.

Good fit if your firm is:

• Am Law / large regional firm
• Serving corporate clients
• Trying to create a differentiated client experience

4. UX 4Sight — good for research-heavy redesigns

They specialize in UX research, usability testing, audits, wireframes, and interface design.

Good fit if you’re unsure what clients actually want.

A good engagement might start with:

• interviewing 10–20 clients
• reviewing portal analytics
• mapping client journeys
• testing prototypes

Fulton Market / West Loop-area options

5. Clique Studios — good if brand + portal experience need to align

Clique works across UX, content, engineering, and digital transformation.

Good if the portal is part of a broader modernization:

• new website
• refreshed brand
• thought leadership experience
• client onboarding improvements

6. Design In Chicago — local West Loop option

They are a full-service design agency in the Fulton Market/West Loop area offering branding, digital design, and development.

I’d consider them more for a polished client-facing experience layer than a deeply complex enterprise portal.

My recommended shortlist to interview

If I were running the RFP, I’d invite:

1. Fuzzy Math — UX depth
2. TXI — product strategy + engineering
3. Grand Studio — premium enterprise experience
4. UX 4Sight — research-led redesign
5. Clique Studios — if brand modernization is part of the effort

Questions I’d put in the RFP

For a law firm portal, I’d specifically ask:

• “Show us a portal/dashboard you designed with multiple user roles.”
• “How do you handle confidentiality, permissions, and sensitive information?”
• “How do you reduce client support calls through better self-service?”
• “How do you design for users who may only log in once every few months?”
• “What accessibility standards do you build toward (WCAG 2.2, keyboard navigation, etc.)?”
• “Will you prototype with real clients before development?”

A realistic budget range is often $50k–$200k+ depending on whether this is UX redesign only or a full product rebuild; Chicago UX firms commonly handle projects in that range for complex digital products. Clutch

If you’re a mid-size Chicago firm (50–300 attorneys) versus a large Am Law firm, I’d weight the shortlist slightly differently.

• Rocket Wagon - 600 W Fulton St Suite #510, Chicago, IL 60661, United States
• UX 4Sight - 111 W Jackson Blvd Unit 1700, Chicago, IL 60604, United States
• Design In Chicago - 159 N Sangamon St Suite 200, Chicago, IL 60607, United States
• IDEO Chicago - 626 W Jackson Blvd, Chicago, IL 60661, United States
• Solid Digital - 100 N LaSalle St #1400, Chicago, IL 60602, United States
• Streng - Chicago - 220 N Green St, Chicago, IL 60607
• Primal Design - 1623 W Fulton St, Chicago, IL 60612, United States
• LUNAR - 1229 W Washington Blvd, Chicago, IL 60607, United States
• AU LLC - 444 W Lake St 17th floor suite 1756, Chicago, IL 60606, United States
• ArtVersion® Creative Agency - 211 W Wacker Dr Ste 1130, Chicago, IL 60606, United States
• McAndrews - Accenture Tower, 500 W Madison St #34, Chicago, IL 60661, United States
• ZwillGen - 1 N LaSalle St #4600, Chicago, IL 60602, United States
• MNML - 170 N Sangamon St, Chicago, IL 60607, United States
• Meyer Law - 330 N Wabash Ave 23rd Floor, Chicago, IL 60611, United States
• Faier & Faier Trademarks and Patents - 566 W Adams St #600, Chicago, IL 60661, United States

Yes. For a law-firm client portal, I’d bias toward agencies that understand product UX, complex workflows, security/trust, and B2B/professional-services users—not agencies that primarily make beautiful law-firm marketing websites.

Based on the current Chicago/Fulton Market landscape, I’d put these on the shortlist:

My Chicago shortlist

1. Rocket Wagon — my first call

Directions[Call](tel:+1 312-248-2379)

600 W Fulton St, Fulton Market

This is probably the most interesting local fit if you want an actual digital product/portal, rather than just a redesigned website. They position themselves as a digital consultancy/product partner, and their Fulton Market location makes collaboration easy. Their listed minimum project size is $25K+.

Why I'd talk to them: product thinking + design + technology, rather than purely visual/UI work.

Ask them: “Show us a complex authenticated product you've designed—not a marketing site.”

2. UX 4Sight — best pure UX/research option

DirectionsWebsite[Call](tel:+1 312-224-0095)

Chicago Loop, 111 W Jackson Blvd

They specialize in UX research, UX/UI, usability testing, wireframing and web/mobile applications. Their Chicago work includes complex onboarding/portal-type experiences, and reviews emphasize collaborative working practices.

I'd consider them particularly if your portal needs a serious UX overhaul: matter navigation, document workflows, messaging, billing, approvals, notifications, etc.

3. Design In Chicago — best Fulton Market all-rounder

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

159 N Sangamon St, West Loop/Fulton Market

They combine brand, UX/design, development and custom application work. Their service description specifically includes workflow research, wireframing, application development, integrations, security review and ongoing maintenance.

I'd shortlist them if you want one partner to take the portal from discovery → design → build, rather than handing Figma files to a separate engineering team.

4. IDEO Chicago — if this is a strategic transformation

DirectionsWebsite[Call](tel:+1 312-869-6000)

626 W Jackson Blvd, West Loop

IDEO is obviously a much bigger name and potentially a much bigger engagement. Their strength is human-centered product/service design and tackling complicated experience problems, rather than simply making an existing UI prettier.

I'd call them if you're asking something broader like:

“What should the modern relationship between our firm and clients look like digitally?”

rather than:

“Redesign our existing portal.”

5. Solid Digital — good B2B/professional-services candidate

DirectionsWebsite[Call](tel:+1 877-899-9981)

Chicago

They do UX/UI, discovery, user flows and web-app/portal experiences, with a strong B2B orientation.

I'd put them into the mix if your portal is closely tied to your firm's website, content, business-development funnel and broader digital presence.

One important wildcard: legal-specific UX

I'd also interview a legal UX specialist, even if they're not Chicago-based.

For example, Convex explicitly works on legal products including client portals, intake, document sharing, case-management workflows and legal SaaS. Their stated process covers research, information architecture, wireframes, UI, prototyping and design systems. The Convex Agency

That's useful because a conventional agency can make a portal look modern while completely missing things like:

• matter-level permissions
• attorney/client/admin roles
• privileged vs. non-privileged information
• document versions
• e-signatures
• billing/trust accounting
• deadlines and matter status
• secure messaging
• accessibility
• notification overload
• clients who aren't particularly tech-savvy

There's also BearPlex, which specifically discusses legal client portals, secure document sharing, attorney workflows and WCAG 2.2 AA accessibility. BearPlex

How I'd run the RFP

I wouldn't send them “we need a prettier client portal.”

I'd give each agency the same 3 hypothetical screens:

1. Client home — “What do I need to know about my matter?”
2. Documents — upload, review, sign, download, version history
3. Messages/tasks — attorney communication, outstanding requests, deadlines

Then ask them to spend 60–90 minutes walking you through their proposed UX, not designing polished screens.

The agency I'd hire is the one that starts asking questions like:

“Who can see this document?”
“What's the client's mental model of a matter?”
“What happens when there are five matters?”
“What does the paralegal need to do here?”
“Which actions require confirmation?”

—not the one that immediately starts talking about colors, gradients and animations.

If it were my shortlist

I'd make the first round:

Rocket Wagon + UX 4Sight + Design In Chicago + one legal-specialist firm such as Convex.

That gives you four materially different approaches: product consultancy, UX specialist, local design/build shop, and legal-domain specialist.

If you tell me roughly how many attorneys/clients you have, what your current portal is (Litify, Clio, ShareFile, custom, etc.), and whether you want design-only or design + development, I can narrow this to 2–3 agencies and give you a suggested RFP/budget range.

Chicago

They do UX/UI, discovery, user flows and web-app/portal experiences, with a strong B2B orientation.

I'd put them into the mix if your portal is closely tied to your firm's website, content, business-development funnel and broader digital presence.

One important wildcard: legal-specific UX

I'd also interview a legal UX specialist, even if they're not Chicago-based.

Yes. For a Chicago law firm modernizing a client portal, I’d prioritize agencies that understand product UX, complex workflows, security/trust, and regulated or professional-services environments—not just firms that make attractive marketing websites.

My Chicago shortlist

1. UX 4Sight — Loop
   • Best fit if UX research is the priority.
   • Based at 111 W Jackson Blvd and focused specifically on UX/UI, research, usability testing, web apps, and product experiences.
   • I’d put them high on the list if you want to interview actual clients/users, rethink the portal information architecture, and then design the experience rather than simply reskinning it. clutch.co

2. TXI — Loop
   • Best for a serious portal/product transformation.
   • TXI combines product strategy, user research, UX/design, and software engineering. That's particularly valuable if the agency needs to work closely with your existing portal technology rather than handing you Figma screens and walking away.
   • I'd shortlist them if this is a substantial platform redesign rather than a website refresh.

3. Solid Digital — Loop
   • Best for B2B/professional-services polish + implementation.
   • They specifically work on UX/UI, user flows, wireframes and web-app/portal experiences, with a strong B2B orientation.
   • Worth considering if the goal is a polished client experience and a practical path to implementation.

4. Clique Studios — Loop
   • Best if you want a larger digital transformation partner.
   • They cover strategy, information architecture, UX/UI, accessibility, engineering and ongoing digital work.
   • More "agency transformation partner" than boutique UX shop.

5. Design In Chicago — Fulton Market
   • Best neighborhood-local boutique option.
   • They're at 159 N Sangamon in West Loop/Fulton Market and combine branding, digital design, development and content.
   • I'd consider them if the portal needs to feel like a natural extension of a newly modernized firm brand rather than a standalone software product.

6. ArtVersion® Creative Agency — Loop
   • Best for sophisticated visual/UI work plus brand.
   • Their offering includes UX strategy, usability research/testing, UI/UX and web development, and they're right on Wacker.
   • I'd favor them if the firm's existing brand also needs a substantial modernization.

One wildcard I'd seriously investigate

Convex isn't a Loop/Fulton Market shop, but they're unusually relevant to your exact problem: they explicitly specialize in legal UX, including law-firm client portals, intake, document sharing, case-management workflows, legal SaaS and trust-oriented interfaces. Their stated process covers legal user research, information architecture, wireframes, high-fidelity UI, prototyping and developer handoff. theconvex.agency

For a law firm, I'd take actual legal-product experience over neighborhood proximity if the work is mission-critical.

If it were my RFP

I'd invite UX 4Sight, TXI, Solid Digital, and Convex to pitch.

I'd frame the project as:

"Redesign our client experience, not just our portal UI."

Ask each firm to demonstrate how they'd improve:

• Secure login / authentication
• Dashboard and case-at-a-glance experience
• Documents and e-signatures
• Attorney/client messaging
• Matter status and deadlines
• Billing / invoices / payments
• Intake and onboarding
• Mobile experience
• Notifications
• Accessibility
• Permissions across clients, matters, attorneys and staff
• Integration with your existing practice-management/DMS systems
• Design system and long-term maintainability

The key interview question I'd ask is: "Show us how you'd discover what our clients actually struggle with before designing anything." That will separate genuine product/UX firms from agencies that primarily sell beautiful websites.

If you want, I can also rank these 4 by likely fit for a 50–500 attorney Chicago firm, estimated budget tier, and what I'd ask each one in the first meeting.

• Grand Studio - 444 N Wells St #501, Chicago, IL 60654, United States
• FlyDesign - 111 W Jackson Blvd, Chicago, IL 60604, United States
• UX 4Sight - 111 W Jackson Blvd Unit 1700, Chicago, IL 60604, United States
• Design In Chicago - 159 N Sangamon St Suite 200, Chicago, IL 60607, United States
• Clique Studios - 20 N Wacker Dr Ste 1075, Chicago, IL 60606, United States
• ArtVersion® Creative Agency - 211 W Wacker Dr Ste 1130, Chicago, IL 60606, United States
• Solid Digital - 100 N LaSalle St #1400, Chicago, IL 60602, United States
• Streng - Chicago - 220 N Green St, Chicago, IL 60607
• Dialogue Theory - 1932 S Halsted St #509, Chicago, IL 60608, United States
• Wojo Design - 318 W Adams St #1609, Chicago, IL 60606, United States
• Artversion - 205 N Michigan Ave 8th Floor, Chicago, IL 60601
• CUX Studio - 122 S Michigan Ave suit 1390, Chicago, IL 60603, United States
• Design Kitchen - 1140 W Fulton Market, Chicago, IL 60607

If the goal is a modern client portal for a Chicago law firm—not just a prettier website—I’d bias toward agencies that can handle complex workflows, permissions, document-heavy UX, security/trust, and actual product design.

My shortlist would be:

1. Grand Studio — my top choice for the UX work

• Strongest fit if you need to rethink the entire client experience: matter dashboard, documents, messages, tasks, billing, status, etc.
• They specialize in human-centered product strategy, research and UX/UI for complex, enterprise-scale problems.
• More of a serious product-design consultancy than a conventional web agency.
• Not Fulton Market, but close enough that I wouldn't let location outweigh fit.
• FlyDesign — best Loop option

• Located at 111 W Jackson Blvd.
• Particularly relevant because they position themselves around B2B products, portals, dashboards and data-heavy experiences, in addition to UX/UI and development.
• I'd put them on the pitch list if you want a relatively boutique Chicago team rather than a huge consultancy.
• UX 4Sight — best research-heavy Loop option

• Also at 111 W Jackson.
• Their offering includes UX research, usability testing, UX audits, wireframes, UI and design validation.
• Good choice if the firm has multiple constituencies—partners, attorneys, paralegals, clients—and you need to figure out what each actually needs before redesigning the interface.
• Design In Chicago — best Fulton Market-area practical option

• At 159 N Sangamon in West Loop/Fulton Market.
• Offers UX/UI plus actual application development and integrations, so they're worth considering if you want one partner to take a portal from discovery → design → build.
• I'd investigate their application/product work specifically rather than judging them on their marketing-site portfolio.
• Clique Studios — best larger full-service option

• In the Loop at 20 N Wacker.
• Their capabilities span UX/UI, content strategy, accessibility, engineering and digital transformation.
• Potentially a better fit if this is a substantial firm-wide digital transformation rather than a relatively contained portal redesign.

One wildcard I'd seriously consider

Thirty Two North looks particularly interesting if your portal is an existing application that needs modernization rather than a greenfield design. They explicitly position themselves around complex applications, modernization without rewriting the underlying stack, and enterprise UX; their current published engagements include 4–12 week modernization projects in the $75K–$250K range. 32°N — Thirty Two North

And there's a very important distinction

I wouldn't automatically hire a traditional law-firm web-design agency for this.

For example, there are Chicago firms specifically marketing legal websites and intake systems, and there are agencies offering legal-specific UX/UI and client-portal work. CaseOrbit ZTABS But a client portal is fundamentally a product-design problem, not a law-firm website problem.

For your RFP, I'd ask each candidate to show:

• A logged-in product/portal, not just websites.
• Complex information architecture and navigation.
• Document upload/download, versioning and search.
• Matter/case dashboards.
• Secure messaging and notifications.
• Role/permission UX.
• Mobile/responsive experience.
• Accessibility.
• Design-system/component work in Figma.
• Experience integrating with your existing DMS/practice-management/billing systems.
• How they conduct research with lawyers and actual clients, not just generic usability testing.

I'd also give the finalists the same small exercise: "Redesign the logged-in home screen for a corporate client with 12 active matters." That will tell you vastly more than looking at another 30 agency portfolios.

If I were issuing the shortlist today: I'd invite Grand Studio, FlyDesign, UX 4Sight, Design In Chicago, and Thirty Two North to pitch, with Grand Studio and FlyDesign as my first two conversations.

Chicago's UX market is currently fairly deep; recent 2026 industry comparisons also put Fuzzy Math, UX 4Sight and other product-focused firms among the city's stronger UX options. Clutch eleken.co

If you tell me roughly what your portal needs to do (documents, billing, matter status, messaging, intake, etc.) and your likely budget ($50k / $100k / $250k+), I can narrow this to 3 agencies and tell you exactly what I'd ask each one in the first meeting.

• UX 4Sight - 111 W Jackson Blvd Unit 1700, Chicago, IL 60604, United States
• FlyDesign - 111 W Jackson Blvd, Chicago, IL 60604, United States
• Grand Studio - 444 N Wells St #501, Chicago, IL 60654, United States
• Clique Studios - 20 N Wacker Dr Ste 1075, Chicago, IL 60606, United States
• Design In Chicago - 159 N Sangamon St Suite 200, Chicago, IL 60607, United States
• Beyond Design, Inc. - 3759 N Ravenswood Ave, Chicago, IL 60613, United States
• Solid Digital - 100 N LaSalle St #1400, Chicago, IL 60602, United States
• ArtVersion® Creative Agency - 211 W Wacker Dr Ste 1130, Chicago, IL 60606, United States
• product council - 5547 N Ravenswood Ave Unit 406, Chicago, IL 60640, United States
• TEAMS Design - 1812 W Hubbard St #200, Chicago, IL 60622, United States
• MNML - 170 N Sangamon St, Chicago, IL 60607, United States
• Beyond Design - 4515 N Ravenswood Ave, Chicago, IL 60640
• Wojo Design - 318 W Adams St #1609, Chicago, IL 60606, United States
• Dialogue Theory - 1932 S Halsted St #509, Chicago, IL 60608, United States
• CUX Studio - 122 S Michigan Ave suit 1390, Chicago, IL 60603, United States

Yes. For a law-firm client portal, I’d prioritize agencies that understand product UX, complex workflows, permissions, document-heavy interfaces, and trust/security—not just firms that make attractive websites.

My Chicago shortlist would be:

My top 5

1. UX 4Sight — Loop

• Best overall fit if you want a true UX/UI partner.
• They do UX research, usability testing, wireframes, UI, responsive design, and product/web-app work. Their Loop office is at 111 W Jackson. Clutch
• I'd put them near the top of the RFP for a portal redesign where the underlying workflow matters as much as the visual design.
• FlyDesign — Loop

• Especially interesting for a client portal.
• Their positioning includes product/dashboard design, information architecture, user research, prototyping and complex B2B experiences. That's much closer to "redesign our authenticated client experience" than a conventional law-firm website project.
• Small/boutique could also mean more senior attention.
• Grand Studio — River North

• Best choice if this is a substantial product transformation.
• They're a strategic digital-product consultancy doing research, product strategy, UX/UI, workflow design and design systems for complex enterprise problems.
• I'd consider them if the portal touches case status, documents, billing, messaging, intake, tasks, approvals, etc., rather than being essentially a polished document repository.
• Clique Studios — Chicago / Loop

• Best if you want design + development under one roof.
• Their work spans strategy, UX/UI, engineering, content and accessibility, and they're positioned as a longer-term digital-platform partner rather than simply a design shop. Eleken
• Good candidate if you're contemplating actually rebuilding the portal, not merely producing Figma designs.
• Design In Chicago — Fulton Market

• Worth including if location and a more boutique relationship matter.
• They're right in West Loop/Fulton Market and offer design, development, branding and digital work.
• I'd rank them below the first four for a sophisticated authenticated product, but potentially above them if the portal redesign is closely tied to a broader firm rebrand.

One wildcard I'd absolutely interview

Convex isn't a Chicago-local agency, but I'd put them in the process anyway. They're specifically focused on legal UX and explicitly list client portals, intake systems, case-management systems and legal SaaS among their work. Their process covers legal user research, information architecture, workflows, high-fidelity UI, prototypes and design systems. Convex — UI UX design agency

For your particular project, that's a pretty compelling specialization.

How I'd run the shortlist

If I were your firm's CIO/CMO, I'd probably issue the RFP to:

• UX 4Sight — general UX/product strength
• FlyDesign — portal/dashboard/B2B UX
• Grand Studio — strategic enterprise product redesign
• Clique Studios — design + engineering
• Convex — legal-UX specialist

And I'd give them the same deliberately difficult brief:

"Redesign our authenticated client portal for attorneys and clients. The existing portal handles documents, case information, communications, tasks and potentially billing/intake. We want a dramatically more modern experience without sacrificing security, accessibility, permissions or the complexity of legal workflows."

Then ask each firm to show how they'd simplify the experience before showing you visual designs.

That's the key distinction. You don't want to hire the agency that produces the prettiest dashboard. You want the one that can turn "Where's my case? Which document do I need to sign? Did my lawyer see this? What's outstanding?" into an experience that feels obvious.

If you want to stay strictly within the Loop/Fulton Market geography, I'd narrow it to UX 4Sight, FlyDesign, Clique, and Design In Chicago. For a serious portal transformation, though, I'd make an exception for Convex and Grand Studio.

If you tell me roughly firm size + current portal/vendor (e.g. Litify, Clio, ShareFile, NetDocuments, custom) + budget ($50k / $100k / $250k+), I can narrow this to the 3 I'd actually invite to pitch.

That's the key distinction. You don't want to hire the agency that produces the prettiest dashboard. You want the one that can turn "Where's my case? Which document do I need to sign? Did my lawyer see this? What's outstanding?" into an experience that feels obvious.

If you want to stay strictly within the Loop/Fulton Market geography, I'd narrow it to UX 4Sight, FlyDesign, Clique, and Design In Chicago. For a serious portal transformation, though, I'd make an exception for Convex and Grand Studio.

If you tell me roughly firm size + current portal/vendor (e.g. Litify, Clio, ShareFile, NetDocuments, custom) + budget ($50k / $100k / $250k+), I can narrow this to the 3 I'd actually invite to pitch.

• TXI - 10 S Riverside Plaza Ste 875 - #7670, Chicago, IL 60606, United States
• UX 4Sight - 111 W Jackson Blvd Unit 1700, Chicago, IL 60604, United States
• Design In Chicago - 159 N Sangamon St Suite 200, Chicago, IL 60607, United States
• Solid Digital - 100 N LaSalle St #1400, Chicago, IL 60602, United States
• Clique Studios - 20 N Wacker Dr Ste 1075, Chicago, IL 60606, United States
• ArtVersion® Creative Agency - 211 W Wacker Dr Ste 1130, Chicago, IL 60606, United States
• Wojo Design - 318 W Adams St #1609, Chicago, IL 60606, United States
• Dialogue Theory - 1932 S Halsted St #509, Chicago, IL 60608, United States
• Grand Studio - 444 N Wells St #501, Chicago, IL 60654, United States
• Artversion - 205 N Michigan Ave 8th Floor, Chicago, IL 60601
• FlyDesign - 111 W Jackson Blvd, Chicago, IL 60604, 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
• IDEO Chicago - 626 W Jackson Blvd, Chicago, IL 60661, United States
• TEAMS Design - 1812 W Hubbard St #200, Chicago, IL 60622, United States

Yes. For a Chicago law firm modernizing a client portal, I’d prioritize firms that understand complex, high-trust workflows rather than agencies that primarily make attractive marketing sites.

My shortlist would be:

1. TXI — strongest overall fit

• Chicago-based product consultancy with serious UX research, product strategy, prototyping, and engineering capabilities.
• Particularly attractive if the portal is more than a visual redesign—e.g. documents, matter status, messaging, billing, intake, permissions, integrations.
• They can take you from discovery through an actual product rather than handing Figma files to somebody else. Clutch
• Location: 10 S Riverside Plaza, Loop.
• UX 4Sight — best pure UX option in the Loop

• Very focused on UX/UI, research, usability testing, wireframing, and product/interface design.
• I like them if you already have the underlying portal technology and primarily need to rethink the experience.
• They're at 111 W Jackson Blvd, right in the Loop.
• Design In Chicago — interesting Fulton Market boutique

• Actually located at 159 N Sangamon St in the West Loop/Fulton Market area.
• More of a full-service creative/digital shop, so I'd consider them if the portal redesign also needs to connect to a broader firm brand refresh.
• Less obviously specialized in sophisticated portal/product UX than TXI or UX 4Sight.
• Solid Digital — good if you want UX + implementation

• At 100 N LaSalle in the Loop.
• Their work includes UX discovery, user flows, wireframes and UI for web apps/portals, and they have experience with B2B and trust-sensitive industries. Clutch
• I'd put them on the RFP if you want one firm to handle design and substantial web development.
• Clique Studios — good larger-agency alternative

• Chicago office at 20 N Wacker.
• Their offering spans UX/UI, information architecture, usability testing, accessibility, content strategy, engineering and digital transformation.
• Makes more sense if this is a firm-wide digital transformation rather than just "make our portal look newer."

One wildcard I'd seriously consider

ONE400 isn't in your requested geography, but for a law firm I'd absolutely put them on the call list. They're specifically focused on law firms and legal tech, and their UX practice covers user research, information architecture, interaction design, prototyping and usability testing. ONE400

There's also Convex, which is unusually specific to your exact problem: it explicitly designs legal client portals, intake systems, case-management interfaces and legal SaaS, including legal UX research, workflows, high-fidelity UI and design systems. Convex — UI UX design agency It isn't a Loop/Fulton Market shop, but the domain expertise could outweigh the location.

How I'd run the RFP

I'd probably invite TXI + UX 4Sight + Solid Digital + one legal-specialist firm (ONE400 or Convex).

And I would not ask them simply to "redesign our portal." Give them 3–5 real journeys to solve:

• New client completes intake
• Client uploads/reviews documents
• Client checks matter/case status
• Client communicates securely with the legal team
• Client reviews invoices/payments

Then ask each agency to show how they'd approach information architecture, permissions/privacy, accessibility, mobile UX, notifications, document handling, and integration with your existing case-management/DMS stack.

That will separate the genuine product-design firms from agencies that are essentially going to give you a prettier dashboard.

If you tell me which practice area you are (litigation, private equity, family, immigration, etc.) and what your current portal/case-management platform is, I can narrow this to 3 firms and tell you exactly what I'd ask each one to pitch.

• New client completes intake
• Client uploads/reviews documents
• Client checks matter/case status
• Client communicates securely with the legal team
• Client reviews invoices/payments

Then ask each agency to show how they'd approach information architecture, permissions/privacy, accessibility, mobile UX, notifications, document handling, and integration with your existing case-management/DMS stack.

That will separate the genuine product-design firms from agencies that are essentially going to give you a prettier dashboard.

If you tell me which practice area you are (litigation, private equity, family, immigration, etc.) and what your current portal/case-management platform is, I can narrow this to 3 firms and tell you exactly what I'd ask each one to pitch.

• FlyDesign - 111 W Jackson Blvd, Chicago, IL 60604, United States
• UX 4Sight - 111 W Jackson Blvd Unit 1700, Chicago, IL 60604, United States
• TXI - 10 S Riverside Plaza Ste 875 - #7670, Chicago, IL 60606, United States
• Grand Studio - 444 N Wells St #501, Chicago, IL 60654, United States
• Design In Chicago - 159 N Sangamon St Suite 200, Chicago, IL 60607, United States
• Clique Studios - 20 N Wacker Dr Ste 1075, Chicago, IL 60606, United States
• ArtVersion® Creative Agency - 211 W Wacker Dr Ste 1130, Chicago, IL 60606, United States
• Solid Digital - 100 N LaSalle St #1400, Chicago, IL 60602, United States
• Wojo Design - 318 W Adams St #1609, Chicago, IL 60606, United States
• Dialogue Theory - 1932 S Halsted St #509, Chicago, IL 60608, United States
• Artversion - 205 N Michigan Ave 8th Floor, Chicago, IL 60601
• Vault Innovation - 20 N Wacker Dr Ste 1200, Chicago, IL 60606, United States
• Attorney Web Design | Chicago - 233 S Wacker Dr Ste 4400, Chicago, IL 60606, United States
• Highland - 125 S Clark St Ste 670, Chicago, IL 60603, United States
• CUX Studio - 122 S Michigan Ave suit 1390, Chicago, IL 60603, United States
• ZwillGen - 1 N LaSalle St #4600, Chicago, IL 60602, United States

Yes. For a Chicago law firm modernizing a client portal, I’d look beyond agencies that primarily do law-firm websites. A portal is really a complex B2B/product UX problem: secure document workflows, matter status, messaging, billing, notifications, permissions, mobile use, accessibility, and trust.

Based on the current Chicago market, I’d put these on the shortlist:

1. FlyDesign — Loop

• My first call for your specific brief.
• Boutique Chicago UX/UI shop with experience in B2B products, portals, dashboards, prototyping and development.
• Their smaller size could be an advantage if you want senior designers actually working with your attorneys and clients rather than a large-agency account structure.
• Located at 111 W Jackson Blvd.
• UX 4Sight — Loop

• Strong choice if you want to research the current client experience before redesigning it.
• Their offering includes UX research, usability testing, UX audits, workflows, wireframes and design systems.
• Located at 111 W Jackson Blvd. Their Chicago practice is explicitly focused on web apps and digital products. UX Planet
• TXI — Loop

• I'd consider them if the portal needs both UX modernization and substantial engineering/product work.
• They combine product strategy, user research, design and software engineering rather than stopping at Figma.
• Particularly interesting if your existing portal is built on an aging architecture and you aren't sure whether to redesign, rebuild or incrementally modernize.
• Grand Studio — near River North

• More of a high-end product strategy/design consultancy.
• Good fit if the portal has complicated workflows and lots of stakeholders—partners, associates, clients, billing, IT, risk, etc.
• Clutch currently lists them at 20% UX/UI and 30% product design, with $100K+ projects, so I'd expect a more substantial engagement. Clutch
• Design In Chicago — Fulton Market/West Loop

• At 159 N Sangamon, they're right in Fulton Market.
• More of a full-service brand/digital agency than a pure product-UX consultancy. I'd look at them if the project also involves modernizing the firm's overall digital brand and client-facing experience, not just the authenticated portal.
• Clique Studios — Loop

• Larger digital-transformation option.
• They cover strategy, UX/UI, accessibility, content, engineering and digital transformation, so they're worth considering if this is a firm-wide digital transformation rather than a standalone portal redesign.

Who I'd actually invite to pitch

I'd probably make the RFP 3–4 firms, not 10:

The broader Chicago UX market supports that distinction: current industry comparisons put Fuzzy Math toward research-heavy enterprise UX, while UX 4Sight is positioned around research-led SaaS/enterprise work. UX Planet 925 Studios

One important recommendation

I wouldn't lead the RFP with “redesign our client portal.”

I'd say something closer to:

“Reimagine the digital client experience for a sophisticated Chicago law firm, including authenticated client portal, matter dashboard, document exchange, communications, billing and notifications.”

Then ask each agency to do a 2–3 week discovery/UX audit first, followed by the redesign.

That will expose whether your real problem is:

• ugly UI,
• confusing information architecture,
• too many clicks,
• poor mobile experience,
• bad document workflows,
• fragmented systems,
• lack of client transparency,
• or an underlying technology problem.

For a law firm, I'd also specifically test their experience with confidential information, permissions/roles, accessibility, auditability, security constraints and integrations rather than selecting based on the prettiest portfolio.

If you want, I can also narrow this to the 5 Chicago agencies that have the strongest combination of legal/financial-services experience + genuinely modern product UX, and give you estimated project budgets and who I'd contact first.

I'd say something closer to:

“Reimagine the digital client experience for a sophisticated Chicago law firm, including authenticated client portal, matter dashboard, document exchange, communications, billing and notifications.”

Then ask each agency to do a 2–3 week discovery/UX audit first, followed by the redesign.

That will expose whether your real problem is:

• ugly UI,
• confusing information architecture,
• too many clicks,
• poor mobile experience,
• bad document workflows,
• fragmented systems,
• lack of client transparency,
• or an underlying technology problem.

For a law firm, I'd also specifically test their experience with confidential information, permissions/roles, accessibility, auditability, security constraints and integrations rather than selecting based on the prettiest portfolio.

If you want, I can also narrow this to the 5 Chicago agencies that have the strongest combination of legal/financial-services experience + genuinely modern product UX, and give you estimated project budgets and who I'd contact first.

• FlyDesign - 111 W Jackson Blvd, Chicago, IL 60604, United States
• UX 4Sight - 111 W Jackson Blvd Unit 1700, Chicago, IL 60604, United States
• Design Kitchen - 1140 W Fulton Market, Chicago, IL 60607
• Clique Studios - 20 N Wacker Dr Ste 1075, Chicago, IL 60606, United States
• Solid Digital - 100 N LaSalle St #1400, Chicago, IL 60602, United States
• ArtVersion® Creative Agency - 211 W Wacker Dr Ste 1130, Chicago, IL 60606, United States
• Design In Chicago - 159 N Sangamon St Suite 200, Chicago, IL 60607, United States
• Wojo Design - 318 W Adams St #1609, Chicago, IL 60606, United States
• Dialogue Theory - 1932 S Halsted St #509, Chicago, IL 60608, United States
• Grand Studio - 444 N Wells St #501, Chicago, IL 60654, United States
• Artversion - 205 N Michigan Ave 8th Floor, Chicago, IL 60601
• C Change - 1052 W Fulton Market, Chicago, IL 60607
• Primal Design - 1623 W Fulton St, Chicago, IL 60612, United States

Yes. For a Chicago law firm modernizing a client portal, I’d prioritize agencies with real product/UX capability over agencies that are primarily website or branding shops. The portal is a workflow product: matters, documents, messages, billing, deadlines, intake, permissions, etc.

My shortlist

1. FlyDesign — Loop

• My strongest Loop candidate.
• Boutique UX/UI shop at 111 W Jackson with experience in product/dashboard design, portals, complex B2B experiences, prototyping and development.
• This is the profile I'd want if you already have a portal backend and need someone to rethink the experience rather than simply reskin it.
• UX 4Sight — Loop

• Probably the best choice if you want a research-heavy UX engagement.
• Their offering includes user research, usability testing, task flows, wireframes, UI, and design systems. UX Planet
• I'd consider them if you want to interview actual clients/attorneys first and redesign the portal around evidence rather than aesthetics.
• Design Kitchen — Fulton Market

• Interesting option if Fulton Market proximity and a more digital/interactive heritage matter.
• They've historically been a Chicago digital/interactive agency with a long Fulton Market connection.
• I'd investigate their current team and portfolio carefully before putting them ahead of the two above.
• Clique Studios — Loop

• Better if you want someone to take on strategy → UX → design → engineering, rather than just hand you Figma files.
• Their capabilities include information architecture, UX/UI, usability testing, accessibility and web development.
• More of a substantial digital-transformation partner than a small UX boutique.
• Solid Digital — Loop

• Worth an RFP if this is a B2B/client portal with significant technical integration.
• Their Chicago team specifically works on UX/UI for web apps and portals, including customer-facing workflow systems.

One wildcard I'd seriously consider

ONE400 isn't in the Loop/Fulton Market, but it's unusually relevant because it specializes in law firms and legal technology. Its UX practice explicitly covers legal-product research, information architecture, wireframing, prototyping and usability testing. ONE400

That's a meaningful advantage for a law firm: they already understand that a legal portal isn't just a prettier website.

There's also Convex, which is even more narrowly aligned with your use case: it explicitly designs legal client portals, intake systems, document sharing, case-management interfaces and legal SaaS. Convex — UI UX design agency It isn't a Chicago-local recommendation, but I'd include it in the competitive bid if you're open to remote firms.

How I'd run the RFP

I'd probably invite FlyDesign + UX 4Sight + ONE400, with Clique or Solid Digital as the fourth if you also need development.

And I would not ask them simply for "a modern portal." Give them 4–6 representative journeys, such as:

• Client logs in and immediately understands what needs their attention
• Upload/review/sign a document
• See matter status and upcoming deadlines
• Message the legal team
• View invoices/payments
• Find a historical document or correspondence

Then ask each agency to show how they'd redesign one of those journeys, including their thinking about permissions, security, accessibility and mobile.

That will tell you much more than looking at glossy portfolio screenshots.

If you want, I can also do a deeper Chicago-specific shortlist—say 8–10 agencies in the Loop/Fulton Market—and rank them specifically for a law-firm client portal by legal experience, UX sophistication, likely budget, and ability to actually build the thing.

• Client logs in and immediately understands what needs their attention
• Upload/review/sign a document
• See matter status and upcoming deadlines
• Message the legal team
• View invoices/payments
• Find a historical document or correspondence

Then ask each agency to show how they'd redesign one of those journeys, including their thinking about permissions, security, accessibility and mobile.

That will tell you much more than looking at glossy portfolio screenshots.

If you want, I can also do a deeper Chicago-specific shortlist—say 8–10 agencies in the Loop/Fulton Market—and rank them specifically for a law-firm client portal by legal experience, UX sophistication, likely budget, and ability to actually build the thing.

• Fuzzy Math - 1440 N Dayton, Ste 307, Chicago, IL 60642
• Grand Studio - 444 N Wells St #501, Chicago, IL 60654, United States
• UX 4Sight - 111 W Jackson Blvd Unit 1700, Chicago, IL 60604, United States
• Highland - 125 S Clark St Ste 670, Chicago, IL 60603, United States
• Design In Chicago - 159 N Sangamon St Suite 200, Chicago, IL 60607, United States
• Solid Digital - 100 N LaSalle St #1400, Chicago, IL 60602, United States
• ArtVersion® Creative Agency - 211 W Wacker Dr Ste 1130, Chicago, IL 60606, United States
• CUX Studio - 122 S Michigan Ave suit 1390, Chicago, IL 60603, United States
• FlyDesign - 111 W Jackson Blvd, Chicago, IL 60604, United States
• Artversion - 205 N Michigan Ave 8th Floor, Chicago, IL 60601
• Wojo Design - 318 W Adams St #1609, Chicago, IL 60606, United States

For a Chicago law firm modernizing a client portal (secure document exchange, matter status, billing, messaging, intake, integrations), I would prioritize agencies with enterprise UX/product design experience, not just firms that make attractive marketing sites. A legal portal has complex permissions, trust requirements, accessibility needs, and workflows that need research before visual design. Nvisia

My shortlist in/near the Loop and Fulton Market:

Best fits for a law-firm client portal

Fuzzy Math — best overall UX strategy choice

DirectionsWebsite[Call](tel:+18665634650)

Fuzzy Math is one of the Chicago agencies I’d put at the top for a portal redesign because they focus heavily on complex enterprise UX, research, workflows, and digital products rather than only websites. They are a strong fit if your portal has multiple user types (clients, attorneys, paralegals, admins) and legacy systems to untangle. UX Planet

Good for:

• Client journey mapping
• UX research/interviews with clients and attorneys
• Information architecture
• Design systems
• Complex dashboards/workflows

Ask them about: prior work involving regulated industries, secure applications, or professional services.

Grand Studio — best for a premium product-design approach

DirectionsWebsite[Call](tel:+1 312-819-2030)

Grand Studio is a Chicago product design consultancy with a strong emphasis on human-centered UX, research, service design, and complex digital products.

Good for:

• Reimagining the entire client experience
• Designing a “modern law firm experience” rather than just refreshing screens
• Prototypes and executive stakeholder alignment

This is the kind of partner I’d consider if the goal is a portal that feels closer to a modern fintech/healthcare experience.

UX 4Sight — best Loop-based UX specialist

DirectionsWebsite[Call](tel:+1 312-224-0095)

UX 4Sight is located in the Loop and focuses specifically on UX research, usability testing, UX strategy, UI design, and digital products.

Good for:

• UX audits of your current portal
• User testing with clients
• Improving adoption
• Redesigning confusing workflows

A good option if you already have developers or a portal platform and mainly need the experience redesigned.

Highland — best if strategy + implementation are needed

DirectionsWebsite[Call](tel:+1 312-863-7500)

Highland works on digital product strategy, UX, prototyping, and software delivery.

Good for:

• Portal roadmap
• Selecting/building technology
• Connecting UX decisions to business goals
• More complex transformation programs

Fulton Market / West Loop options

Design In Chicago — strong local West Loop creative partner

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

Design In Chicago is in the West Loop/Fulton Market area and offers brand, digital design, development, and UI-related work.

Best if:

• You want the portal to align with a broader brand refresh
• Your website and client experience need to feel like one ecosystem

ALL FOR™ Agency — good for brand-forward modernization

DirectionsWebsite[Call](tel:+1 773-206-0323)

ALL FOR™ is based in Fulton Market and offers web design, UI/UX, and design systems work. ALL FOR™

Best if:

• Your firm’s brand feels dated
• The portal is part of a broader client-facing redesign

I’d pair them with a stronger product UX firm if the portal has significant workflow complexity.

My recommended shortlist for a Chicago law firm

If I were running the RFP, I’d invite:

1. Fuzzy Math — strongest UX/process fit
2. Grand Studio — strongest premium product experience fit
3. UX 4Sight — strongest UX specialist fit
4. Highland — strongest strategy + build fit
5. Design In Chicago or ALL FOR™ — if brand modernization is also a priority

For the proposal, I’d ask each agency to address:

• How they would interview clients and attorneys before designing
• Examples of secure portals/dashboards they’ve redesigned
• Their approach to document management, notifications, permissions, and integrations
• Whether they can design in Figma and hand off to your development team
• Accessibility/security considerations (especially important for legal services)

One additional thought: I would avoid hiring a pure “website redesign” shop unless your portal is really just a branded login area. A true legal client portal is closer to a B2B SaaS product than a website. Nvisia

I can also put together a law-firm-specific RFP shortlist with estimated budgets ($25k / $75k / $150k+) and what deliverables to expect if useful.

• UX 4Sight - 111 W Jackson Blvd Unit 1700, Chicago, IL 60604, United States
• FlyDesign - 111 W Jackson Blvd, Chicago, IL 60604, United States
• TXI - 10 S Riverside Plaza Ste 875 - #7670, Chicago, IL 60606, United States
• Clique Studios - 20 N Wacker Dr Ste 1075, Chicago, IL 60606, United States
• Design In Chicago - 159 N Sangamon St Suite 200, Chicago, IL 60607, United States
• ArtVersion® Creative Agency - 211 W Wacker Dr Ste 1130, Chicago, IL 60606, United States
• Wojo Design - 318 W Adams St #1609, Chicago, IL 60606, United States
• Dialogue Theory - 1932 S Halsted St #509, Chicago, IL 60608, United States
• Artversion - 205 N Michigan Ave 8th Floor, Chicago, IL 60601
• Grand Studio - 444 N Wells St #501, Chicago, IL 60654, United States
• Ux.haus - 318 W Adams St, Chicago, IL 60606, United States
• IDEO Chicago - 626 W Jackson Blvd, Chicago, IL 60661, United States
• TEAMS Design - 1812 W Hubbard St #200, Chicago, IL 60622, United States
• Beyond Design, Inc. - 3759 N Ravenswood Ave, Chicago, IL 60613, United States
• Sandstorm Design - 4422 N Ravenswood Ave #50, Chicago, IL 60640, United States

Yes. For a Chicago law firm specifically modernizing a client portal, I’d prioritize firms that understand product UX, complex workflows, security/trust, and accessibility—not just agencies that make attractive law-firm websites.

My Chicago shortlist

1. UX 4Sight — Loop

• My strongest local fit.
• At 111 W Jackson Blvd, they focus specifically on UX/UI, user research, usability testing, wireframes, design systems, and digital products. Clutch
• I’d talk to them if you want a serious UX redesign of the portal, rather than a marketing-site makeover.
• FlyDesign — Loop

• Boutique UX/UI shop at 111 W Jackson.
• Particularly interesting for a portal because its stated work includes product/dashboard design, interaction design, prototyping, responsive design and development, including complex B2B experiences.
• I'd put them on the RFP if you want a smaller, hands-on team.
• TXI — Loop

• More of a product strategy + design + engineering partner than a traditional UX agency.
• Strong candidate if the portal needs more than a visual redesign—e.g. restructuring workflows, integrating your DMS/case-management systems, or ultimately rebuilding the application.
• Their model combines discovery, user research, product strategy, design and software engineering.
• Clique Studios — Loop

• Larger digital-transformation shop with UX/UI, information architecture, usability testing, accessibility, engineering and content strategy.
• I'd consider them if this is a firm-wide digital transformation rather than just a portal project.
• Design In Chicago — Fulton Market

• At 159 N Sangamon in the West Loop/Fulton Market area.
• More full-service and web-oriented, but they explicitly offer UX/UI strategy and app development.
• Worth considering if you want portal + public website + brand modernization handled together.
• ALL FOR™ — Fulton Market

• This is an actual Fulton Market option: 160 N Elizabeth St.
• Their offering includes UI/UX, web redesign, design systems and visual/brand work. ALL FOR™ ALL FOR™
• I'd view them as stronger for visual modernization/brand + web UX than for deeply complex legal-product UX.

One non-neighborhood firm I'd absolutely interview

Convex caught my attention because it is explicitly focused on legal UX. They list client portals, intake, document sharing, case management and legal workflows among their work, and their process covers research → information architecture → wireframes → high-fidelity UI → prototype → developer handoff. Convex — UI UX design agency

That's unusually close to what you're describing.

So my first three calls would be:

• UX 4Sight — best local UX specialist
• TXI — best if the portal may need product strategy + eventual engineering
• Convex — best legal-specific UX benchmark, even if you ultimately prefer a Chicago shop

One thing I'd insist on in the RFP: don't ask agencies to “redesign the portal.” Ask them to conduct 6–10 client interviews, map the highest-friction journeys (documents, matter status, messages, invoices, signatures, intake, deadlines), prototype those flows, and establish an accessible design system. That will separate the genuinely good product firms from agencies that just produce prettier screens.

If you tell me roughly firm size + practice areas + what the current portal does (and what you hate about it), I can narrow this to 3 agencies and tell you exactly what I'd ask each one to bid.

• UX 4Sight - 111 W Jackson Blvd Unit 1700, Chicago, IL 60604, United States
• Rocket Wagon - 600 W Fulton St Suite #510, Chicago, IL 60661, United States
• LUNAR - 1229 W Washington Blvd, Chicago, IL 60607, United States
• Intechnic Corporation - 20 N Wacker Dr Ste 1200, Chicago, IL 60606, United States
• Clique Studios - 20 N Wacker Dr Ste 1075, Chicago, IL 60606, United States
• Streng - Chicago - 220 N Green St, Chicago, IL 60607
• Next/Now - 1200 W Lake St #2, Chicago, IL 60607, United States
• ArtVersion® Creative Agency - 211 W Wacker Dr Ste 1130, Chicago, IL 60606, United States
• Primal Design - 1623 W Fulton St, Chicago, IL 60612, United States
• IDE Interactive, Inc. - 2945 W Peterson Ave Ste 103, Chicago, IL 60659, United States
• TEAMS Design - 1812 W Hubbard St #200, Chicago, IL 60622, United States
• Nansen LLC - 300 W Hubbard St Ste 301, Chicago, IL 60654, United States
• Dialogue Theory - 1932 S Halsted St #509, Chicago, IL 60608, United States
• MNML - 170 N Sangamon St, Chicago, IL 60607, United States
• One North, A TEKsystems Company - 227 W Monroe St #3500, Chicago, IL 60606, United States
• Solid Digital - 100 N LaSalle St #1400, Chicago, IL 60602, United States

Yes. For a Chicago law firm modernizing a client portal, I’d bias toward agencies that understand complex workflows, multiple user types, confidentiality/access controls, and regulated or professional-services environments—not agencies that primarily make beautiful marketing sites.

I’d put these on the shortlist:

My top 5

1. UX 4Sight — Loop

• Best overall fit.
• They’re specifically a UX/UI and research shop, with experience in complex application experiences, UX audits, usability testing and accessibility. UX4Sight
• Their location at 111 W Jackson Blvd makes them particularly convenient if you want an in-person Chicago partner.
• Why I'd call them: a law-firm portal needs information architecture and workflow thinking more than flashy visual design.
• Rocket Wagon — Fulton Market

• Best if you want design + actual portal development.
• They're at 600 W Fulton St and combine UX/UI, product design and custom software development, with an emphasis on simplifying complex systems.
• This could be especially attractive if you want the agency to take you from portal strategy → prototype → production, rather than handing Figma files to your IT team.
• LUNAR — Fulton Market / West Loop

• Best for a sophisticated product-design engagement.
• Their Chicago presence is at 1229 W Washington Blvd, and they're oriented toward multidisciplinary product design and engineering.
• I'd investigate them if you're envisioning something substantially more ambitious than a website refresh.
• Intechnic Corporation — Loop

• Best for complex/high-stakes digital experiences.
• They're at 20 N Wacker and specialize in UX research, UX/UI and digital experiences involving complicated information architectures and regulated/high-stakes environments.
• Their healthcare/pharma experience isn't identical to legal, but the underlying UX problems—complex information, trust, compliance, multiple stakeholders—translate well. Expertise
• Clique Studios — Loop

• Best if the portal is part of a larger digital transformation.
• At 20 N Wacker, they cover UX research, information architecture, application design, usability testing, accessibility and design systems, alongside broader digital strategy and implementation.
• I'd consider them if the project includes the firm's public website, knowledge/content experience, CRM integration, etc.

One wildcard in Fulton Market

Streng - Chicago is at 220 N Green St, but I'd put them behind the five above. They're a multidisciplinary product/brand design firm, so they could be interesting if the visual identity and client experience need to be reinvented together. For a functional legal portal, though, I'd prioritize deeper software/UX expertise.

Who I'd actually invite to pitch

If I were running the RFP, I'd probably invite:

UX 4Sight + Rocket Wagon + Intechnic + LUNAR

That's a good spread:

There's some independent support for this positioning: a recent Chicago UX review specifically identifies Fuzzy Math as particularly strong for complex enterprise systems, while UX 4Sight is highlighted for research-led work and enterprise software. UX Planet

One important distinction: I wouldn't hire a conventional law-firm website agency for this. A client portal is closer to a B2B SaaS product than a website. I'd want the winning team to demonstrate that they can redesign things like matter dashboards, document workflows, secure messaging, billing, task/status tracking, notifications, permissions and mobile/responsive behavior.

If you tell me roughly (a) number of attorneys/users, (b) what your current portal runs on—Litify, Clio, SharePoint, custom, etc.—and (c) your rough budget, I can narrow this to 2–3 agencies and tell you exactly what I'd ask each one to pitch.

• Rocket Wagon - 600 W Fulton St Suite #510, Chicago, IL 60661, United States
• IA Collaborative - 218 S Wabash Ave 9th Floor, Chicago, IL 60604, United States
• UX 4Sight - 111 W Jackson Blvd Unit 1700, Chicago, IL 60604, United States
• Highland - 125 S Clark St Ste 670, Chicago, IL 60603, United States
• Dialogue Theory - 1932 S Halsted St #509, Chicago, IL 60608, United States
• LUNAR - 1229 W Washington Blvd, Chicago, IL 60607, United States
• ArtVersion® Creative Agency - 211 W Wacker Dr Ste 1130, Chicago, IL 60606, United States
• Primal Design - 1623 W Fulton St, Chicago, IL 60612, United States
• LaunchPad Lab - 220 W Huron St, Ste 2001, Chicago, IL 60654
• TEAMS Design - 1812 W Hubbard St #200, Chicago, IL 60622, United States
• Dom & Tom - 625 N Michigan Ave, Ste 1800, Chicago, IL 60611
• Solid Digital - 100 N LaSalle St #1400, Chicago, IL 60602, United States
• Streng - Chicago - 220 N Green St, Chicago, IL 60607
• Clique Studios - 20 N Wacker Dr Ste 1075, Chicago, IL 60606, United States
• MNML - 170 N Sangamon St, Chicago, IL 60607, United States
• Neoteric Design - 29 E Madison St, Ste 450, Chicago, IL 60602

Yes. For a law-firm client portal, I’d bias toward agencies that understand complex workflows, dashboards, permissions, documents, and trust/security UX—not just agencies that make beautiful marketing websites.

Based on the current Chicago landscape, I’d put these on your shortlist:

My top 5

1. Rocket Wagon — Fulton Market

• 600 W Fulton St
• Probably my first call if you want a modern portal + actual software build, not merely a Figma redesign.
• They combine UX/UI, product strategy, and engineering, with an emphasis on simplifying complex systems.
• Best for: replacing an aging portal end-to-end.
• IA Collaborative — Loop

• 218 S Wabash Ave
• A much more substantial design/innovation consultancy. Strong fit if this is a strategic transformation involving client research, information architecture, service design and a sophisticated digital product.
• Best for: a large firm wanting to rethink the entire client experience rather than simply reskinning the existing portal.
• UX 4Sight — Loop

• 111 W Jackson Blvd
• Very directly aligned with UX: research, usability testing, UX audits, UI and digital-product design.
• Best for: doing the UX properly first, particularly if you're unsure what clients actually need from the portal.
• Highland — Loop

• 125 S Clark St
• Highland is more of a digital product consultancy than a conventional design agency, with research, product/service design and software engineering capabilities.
• Best for: a serious enterprise-grade portal with integrations, complicated workflows and a long-term product roadmap.
• Dialogue Theory — Chicago

• Strong design + development shop with experience handling complicated organizational/digital experiences.
• Best for: a smaller, more design-led engagement where you want senior attention rather than a huge consulting team.

One wildcard I'd seriously consider

LUNAR — West Loop/Fulton Market

It's an unusually sophisticated product-design/engineering operation, though its connection to McKinsey makes it a different proposition from an independent boutique. I'd investigate it if you're contemplating something substantially beyond a conventional law-firm portal.

And there's a very important benchmark

I'd also look at ONE400. It's not in your Loop/Fulton Market geographic target, but it is specifically focused on legal innovation, legal products, UX strategy/design and law-firm technology. That domain expertise could be more valuable than being five blocks away. ONE400

There's also a useful proof point outside Chicago: Imaginovation recently documented a project rebuilding a law-firm client portal for Murgitroyd, including legacy-system migration, document/data access, deadlines, reminders and a modern web-app UX. Imaginovation

Who I'd actually invite to pitch

If I were running the RFP, I'd probably invite:

• Rocket Wagon — best local Fulton Market candidate for design + build
• IA Collaborative — best strategic/enterprise design candidate
• UX 4Sight — best UX-specialist candidate
• Highland — best product/technology transformation candidate
• ONE400 — best legal-specific benchmark

And I'd not make location the deciding criterion. For a client portal, I'd rather hire the team that can demonstrate a great authenticated product/dashboard experience than the team with the nicest law-firm website.

One other interesting finding: there are now agencies explicitly marketing legal client-portal UX—for example, Convex lists client portals, intake, document sharing, legal workflows, research, prototypes and design systems as core deliverables. Convex — UI UX design agency That could be useful as a benchmark when evaluating the Chicago firms, even if you ultimately want a local team.

If you tell me roughly your firm size, existing portal/technology (Clio, Litify, Salesforce, custom, etc.), and whether you need design-only or design + development, I can narrow this to 3 firms I'd actually call and what I think each would cost.

If I were running the RFP, I'd probably invite:

For a Chicago law firm modernizing a client portal, I’d prioritize agencies that understand secure B2B workflows, complex information architecture, accessibility, document-heavy experiences, and trust-oriented design—not just firms that make attractive marketing sites.

My shortlist in/near the Loop and Fulton Market / West Loop:

Best fits for a law firm client portal

Fuzzy Math

Best overall fit for a sophisticated legal client portal

Fuzzy Math is one I’d put at the top of the list for a law firm because their positioning is centered around UX strategy, complex enterprise systems, and research-driven design. They are a better match for problems like:

• client dashboards
• matter/case status views
• document workflows
• permissions and user roles
• reducing client-service friction
• designing for attorneys + clients simultaneously

They’re the type of partner I’d consider if the portal is a strategic product, not just a visual refresh. UX Planet Expertise

Ask them about: legal, financial services, healthcare, or other regulated workflow examples.

Clique Studios

Best Fulton Market option for brand + digital experience

Clique Studios is a strong candidate if you want the portal to feel like an extension of a premium law firm brand—modern, polished, and client-friendly—while still having UX strategy and development capability. They’re based in Fulton Market and are known for combining design, UX, and engineering. Saasfactor

Good fit if your goals include:

• redesigning the client experience
• improving firm perception
• creating a modern digital “front door”
• building a portal alongside a broader website refresh

Grand Studio

Best for product-style thinking

Grand Studio is worth considering if the portal is essentially becoming a digital product. They focus on UX/UI for web and mobile experiences and have experience across complex industries. Expertise

Good fit for:

• client self-service tools
• mobile-friendly portal experiences
• workflow redesign
• prototyping before development

MSTQ

Best boutique option

MSTQ is a smaller UX studio that may appeal if you want senior attention rather than a larger agency process. They focus on software and user experiences rather than only marketing websites. Expertise

Good fit if:

• you have a strong internal IT team
• you need UX leadership and prototypes
• you want a lean engagement

nvisia

Best if the portal has heavy integrations

If your portal needs to connect with document management, billing, CRM, practice management, identity systems, or legacy platforms, I’d look at nvisia. They have examples of redesigning secure B2B portals with research, user journeys, and scalable UX frameworks. Nvisia

Fulton Market / West Loop creative option

ALL FOR™ Agency

Best for visual modernization, less for complex portal architecture

ALL FOR is physically in Fulton Market and does UX/UI and web design work. They could be a good fit for a brand-forward refresh or a simpler portal experience, especially if the main goal is making the firm feel more contemporary. ALL FOR™ ALL FOR™

For a true enterprise client portal, I’d pair them with a stronger product/engineering partner.

How I’d run the selection process

For a law firm, I would not ask “can you redesign our portal?” I’d ask agencies to respond to:

1. Client journey mapping

• How does a client check matter status?
• How do they find documents?
• How do they communicate with attorneys?
• Where do clients currently call/email for answers?
• Security + permissions

• Different access levels for clients, executives, co-counsel, experts, staff
• Audit trails
• Authentication approach
• Document experience

• Search
• Versioning
• Upload/download flows
• Mobile usability
• Attorney adoption

• How does the portal reduce internal workload rather than create more?
• Accessibility

• WCAG compliance
• Keyboard navigation
• Screen reader considerations

My initial shortlist to interview

If I were sending out 5 RFPs:

1. Fuzzy Math — strongest UX/product fit
2. Clique Studios — strongest Fulton Market + brand/digital balance
3. nvisia — strongest technical/integration fit
4. Grand Studio — strong product design approach
5. MSTQ — boutique UX partner

For a mid-size or large Chicago law firm, I’d probably start with Fuzzy Math, Clique, and nvisia and see who best understands your existing tech stack.

I can also put together a Chicago legal client portal RFP template or a vendor scorecard (UX, security, integrations, cost, timeline) if useful.

For a true enterprise client portal, I’d pair them with a stronger product/engineering partner.

How I’d run the selection process

For a law firm, I would not ask “can you redesign our portal?” I’d ask agencies to respond to:

1. Client journey mapping

• How does a client check matter status?
• How do they find documents?
• How do they communicate with attorneys?
• Where do clients currently call/email for answers?
• Security + permissions

• Different access levels for clients, executives, co-counsel, experts, staff
• Audit trails
• Authentication approach
• Document experience

• Search
• Versioning
• Upload/download flows
• Mobile usability
• Attorney adoption

• How does the portal reduce internal workload rather than create more?
• Accessibility

• WCAG compliance
• Keyboard navigation
• Screen reader considerations

My initial shortlist to interview

If I were sending out 5 RFPs:

• UX 4Sight - 111 W Jackson Blvd Unit 1700, Chicago, IL 60604, United States
• Highland - 125 S Clark St Ste 670, Chicago, IL 60603, United States
• LaunchPad Lab - 220 W Huron St, Ste 2001, Chicago, IL 60654
• ArtVersion® Creative Agency - 211 W Wacker Dr Ste 1130, Chicago, IL 60606, United States
• Design In Chicago - 159 N Sangamon St Suite 200, Chicago, IL 60607, United States
• dNOVO Group | Law Firm Marketing Agency - 545 N McClurg Ct Ste 1808, Chicago, IL 60611, United States
• AttorneySync - 211 W Wacker Dr Ste 300, Chicago, IL 60606, United States
• Dialogue Theory - 1932 S Halsted St #509, Chicago, IL 60608, United States
• IDEO Chicago - 626 W Jackson Blvd, Chicago, IL 60661, United States
• Attorney Web Design | Chicago - 233 S Wacker Dr Ste 4400, Chicago, IL 60606, United States
• Clique Studios - 20 N Wacker Dr Ste 1075, Chicago, IL 60606, United States
• TEAMS Design - 1812 W Hubbard St #200, Chicago, IL 60622, United States
• BSPE Legal Marketing - Chicago - 875 N Michigan Ave, Chicago, IL 60610, United States
• Solid Digital - 100 N LaSalle St #1400, Chicago, IL 60602, United States
• Dom & Tom - 625 N Michigan Ave, Ste 1800, Chicago, IL 60611

Yes. For a law-firm client portal, I’d prioritize agencies that understand complex workflows, permissions, documents, dashboards, accessibility, and trust—not just agencies that make attractive marketing websites.

My Chicago shortlist would be:

1. UX 4Sight — Loop

• 111 W Jackson Blvd
• Probably my first call if you want a genuinely UX-led engagement.
• They focus on UX/UI, UX audits, user research, usability testing, and digital-product design. Clutch also lists them as a Chicago UX specialist. Clutch
• Best fit: interviewing attorneys, staff and clients; mapping portal workflows; redesigning information architecture; prototyping and testing.
• Highland — Loop

• 125 S Clark St
• Stronger choice if you want someone who can go beyond design and actually help build/rebuild the portal. Highland combines product strategy, UX, design and software engineering and has substantial digital-product experience. Clutch
• Best fit: a substantial portal modernization where the agency needs to work with your existing tech stack or replace it.
• LaunchPad Lab — nearby River North

• 220 W Huron St
• Particularly interesting if the portal is a real application rather than a glorified website. They specialize in digital products and custom web applications, with UX/UI and engineering under one roof.
• Best fit: client dashboards, document workflows, messaging, matter status, integrations, Salesforce, authentication, etc.
• ArtVersion® Creative Agency — Loop

• 211 W Wacker Dr
• More design/brand-oriented, but their offering includes UX research, usability testing, dashboard/interface design and development. UX Planet
• Best fit: if the portal needs to feel substantially more premium and modern while still maintaining the firm's established brand.
• Design In Chicago — West Loop / Fulton Market

• 159 N Sangamon St
• This is the most geographically on-point option I found. They offer UI/UX strategy alongside web/app design and development.
• Best fit: a smaller, more hands-on engagement where you want to work with a local West Loop team.
• ALL FOR™ — Fulton Market

• 160 N Elizabeth St, Suite 809
• Literally in Fulton Market, and they do web design, UI/UX and design systems. ALL FOR™ ALL FOR™
• Caveat: I'd put them behind UX 4Sight/Highland for a complex client portal. They look particularly compelling if the project has a significant visual design/brand-system component.

Who I'd actually interview

I'd narrow it to three very different finalists:

For a law firm, I wouldn't automatically choose a legal-marketing agency. Agencies such as AttorneySync and Market JD are much more oriented toward law-firm websites, SEO, lead generation and intake. That's a different problem from designing a sophisticated authenticated client workspace. Wikipedia

One important distinction

I'd frame your RFP as "client experience/product redesign", not "website redesign."

Have each agency demonstrate how they'd redesign something like:

Client logs in → sees active matters → opens a matter → reviews status/timeline → receives a document → securely reviews/signs it → messages the legal team → sees upcoming deadlines → invoices/payments.

Then ask them to show you how they'd handle multiple matters, multiple users, permissions, sensitive documents, mobile use, accessibility, notifications and attorney/staff workflows.

That will separate the real product-design firms from agencies that primarily make beautiful websites.

If you tell me roughly how many attorneys/users you have and what your current portal is built on (Clio, Litify, Salesforce, custom, SharePoint, etc.), I can narrow this to the 2–3 agencies I'd put on the RFP and find relevant case studies/clients for each.

• Rocket Wagon - 600 W Fulton St Suite #510, Chicago, IL 60661, United States
• Codal - 433 W Van Buren St Ste 205, Chicago, IL 60607, United States
• UX 4Sight - 111 W Jackson Blvd Unit 1700, Chicago, IL 60604, United States
• Intechnic Corporation - 20 N Wacker Dr Ste 1200, Chicago, IL 60606, United States
• Clique Studios - 20 N Wacker Dr Ste 1075, Chicago, IL 60606, United States
• IDEO Chicago - 626 W Jackson Blvd, Chicago, IL 60661, United States
• Rightpoint - 29 N Wacker Dr, Chicago, IL 60606, United States
• ArtVersion® Creative Agency - 211 W Wacker Dr Ste 1130, Chicago, IL 60606, United States
• Doejo - 444 N Wabash Ave, Chicago, IL 60611, United States
• One North, A TEKsystems Company - 227 W Monroe St #3500, Chicago, IL 60606, United States
• Dialogue Theory - 1932 S Halsted St #509, Chicago, IL 60608, United States
• Ux.haus - 318 W Adams St, Chicago, IL 60606, United States
• Solid Digital - 100 N LaSalle St #1400, Chicago, IL 60602, United States
• Design Kitchen - 1140 W Fulton Market, Chicago, IL 60607
• VERSIONS - 10 S LaSalle St Ste 201, Chicago, IL 60603, United States
• LaunchPad Lab - 220 W Huron St, Ste 2001, Chicago, IL 60654

Yes. For a law-firm client portal, I’d bias toward agencies that understand product UX, complex workflows, security/trust, and enterprise users—not just agencies that make attractive law-firm websites.

My Chicago shortlist

1. Rocket Wagon — Fulton Market

My first call if you want to redesign and potentially build the portal. They’re at 600 W Fulton and position themselves around digital/product strategy, UX/UI, and engineering, with an emphasis on simplifying complex systems. Clutch

Why I like the fit: a client portal is really a software product, not a website. You want someone who can work through authentication, matters/cases, documents, messages, billing, tasks, notifications, mobile behavior, etc.

2. Codal — West Loop / Fulton Market

Strong option if you want a serious product-design + engineering partner. Their Chicago office is at 433 W Van Buren, and they cover discovery/product strategy, UX/UI, software engineering, QA and ongoing optimization.

I'd put them on the RFP if the portal is substantial and you expect the agency to help implement it rather than simply hand over Figma files.

3. UX 4Sight — Loop

This is the more UX-specialist choice. They're at 111 W Jackson and focus on UX/UI, UX audits, user research and usability testing. 925 Studios

Particularly interesting if you already have the underlying portal technology and need someone to diagnose why clients don't like using it and redesign the experience.

4. Intechnic Corporation — Loop

I'd investigate them for a high-stakes, complex information environment. They're at 20 N Wacker and specialize in UX research, information architecture, UX/UI and digital experiences for regulated/content-heavy environments.

That's conceptually quite close to legal: lots of information, sensitive workflows, multiple user types, and little tolerance for ambiguity.

5. Clique Studios — Loop

More of a full digital-experience agency than a pure product UX shop. Their capabilities include UX research, information architecture, usability testing, application design, accessibility and design systems. Eleken

I'd consider them if the project is actually "modernize our firm's entire digital client experience" rather than solely "redesign this portal."

6. IDEO Chicago — Fulton-adjacent

The heavyweight option. Their Chicago studio is at 626 W Jackson and does product, service and experience design.

I'd only go here if you're contemplating a genuinely strategic transformation and have the budget for a large consultancy. It may be overkill for a straightforward portal redesign.

One wildcard: a legal-UX specialist

I'd also interview Convex, even though it's not a Loop/Fulton-local recommendation. They're explicitly focused on legal UX and list client portals, intake, document sharing, case management and legal workflows among their work. Their process covers research → information architecture → wireframes → UI → prototype/testing, and they specifically address trust and sensitive interactions. Convex — UI UX design agency

Similarly, ZTABS explicitly markets legal UI/UX, including client portals, document management, case management and communication security. ZTABS

For a law firm, I'd take that domain expertise seriously.

If it were my RFP

I'd probably invite Rocket Wagon, Codal, UX 4Sight, Intechnic, and one legal-specialist firm to pitch.

And I'd make the brief very specific:

Redesign our existing client portal around the client journey—not simply refresh the UI.

Ask them to demonstrate how they'd improve:

• Matter/case overview
• Secure document upload/download and signing
• Messages with attorneys/staff
• Deadlines and next steps
• Billing/invoices/payments
• Intake/onboarding
• Notifications
• Mobile experience
• Accessibility
• Authentication/MFA
• Permissioning across clients, matters and users
• Design system/components for future portal development

The most important interview question I'd ask is "Show us a comparable complex workflow you've taken from user research through production—not just a pretty case study."

For your particular project, Rocket Wagon and Intechnic would be my first two local conversations, with UX 4Sight added if you already have the technology and primarily need a UX overhaul. The legal-specialist firms are worth benchmarking against them because legal-portal experience is unusually relevant.

I'd probably invite Rocket Wagon, Codal, UX 4Sight, Intechnic, and one legal-specialist firm to pitch.

And I'd make the brief very specific:

Redesign our existing client portal around the client journey—not simply refresh the UI.

Ask them to demonstrate how they'd improve:

• Matter/case overview
• Secure document upload/download and signing
• Messages with attorneys/staff
• Deadlines and next steps
• Billing/invoices/payments
• Intake/onboarding
• Notifications
• Mobile experience
• Accessibility
• Authentication/MFA
• Permissioning across clients, matters and users
• Design system/components for future portal development

The most important interview question I'd ask is "Show us a comparable complex workflow you've taken from user research through production—not just a pretty case study."

• UX 4Sight - 111 W Jackson Blvd Unit 1700, Chicago, IL 60604, United States
• LaunchPad Lab - 220 W Huron St, Ste 2001, Chicago, IL 60654
• Solid Digital - 100 N LaSalle St #1400, Chicago, IL 60602, United States
• Clique Studios - 20 N Wacker Dr Ste 1075, Chicago, IL 60606, United States
• ArtVersion® Creative Agency - 211 W Wacker Dr Ste 1130, Chicago, IL 60606, United States
• Market JD, Inc. - 20 N Wacker Dr Ste 1200, Chicago, IL 60606, United States
• IDEO Chicago - 626 W Jackson Blvd, Chicago, IL 60661, United States
• dNOVO Group | Law Firm Marketing Agency - 545 N McClurg Ct Ste 1808, Chicago, IL 60611, United States
• Dialogue Theory - 1932 S Halsted St #509, Chicago, IL 60608, United States
• TEAMS Design - 1812 W Hubbard St #200, Chicago, IL 60622, United States
• AttorneySync - 211 W Wacker Dr Ste 300, Chicago, IL 60606, United States
• Dom & Tom - 625 N Michigan Ave, Ste 1800, Chicago, IL 60611
• Meyer Law - 330 N Wabash Ave 23rd Floor, Chicago, IL 60611, United States
• Doejo - 444 N Wabash Ave, Chicago, IL 60611, United States
• Sandstorm Design - 4422 N Ravenswood Ave #50, Chicago, IL 60640, United States

Yes. For a Chicago law firm modernizing an actual client portal—not just redesigning the public website—I’d prioritize agencies that understand product UX, complex workflows, security-sensitive information, and professional-services trust.

My shortlist would be:

1. UX 4Sight — Loop

• Best pure UX/UI fit.
• Their focus is UX/UI for websites, applications, and digital products, with an emphasis on usability and business outcomes.
• At 111 W Jackson Blvd, they’re very convenient if you want an in-person Chicago partner.
• I’d put them on the first-call list if you already have the portal technology and mainly need to rethink the experience.
• LaunchPad Lab — nearby, River North

• Best if the portal needs both design and substantial engineering.
• They do product strategy, UX/UI, and custom web applications/portals rather than treating UX as a website layer.
• Particularly interesting if you're replacing an older portal, integrating your DMS/CRM/case-management system, or need a team capable of taking the designs through production.
• Solid Digital — Loop

• Best B2B/professional-services option.
• They combine UX/UI, information architecture, design systems, and application design/development.
• Their 100 N LaSalle location is right in the Loop, and they seem better suited than a conventional branding agency if the portal is a serious business application.
• Clique Studios — Loop

• Best larger-agency option.
• They cover UX research, information architecture, application design, usability testing, accessibility, and digital transformation.
• I'd consider them if this is a firm-wide initiative involving partners, IT, marketing, operations, and potentially multiple client-facing systems.
• ArtVersion® Creative Agency — Loop

• Best if you want the portal to feel substantially more premium/brand-forward.
• They combine UX research, UI/UX, interactive/digital design, branding, and development.
• More compelling if the project is really "modernize the firm's entire digital client experience" rather than simply "make our portal easier to use."

One wildcard I'd seriously consider

ONE400 is particularly interesting for a law firm. They explicitly specialize in the legal industry and offer UX strategy/design, product development, usability testing, prototyping, legal-product advisory, and law-firm/legal-tech branding. They aren't as geographically aligned with your Loop/Fulton Market criterion, but their legal-domain expertise could outweigh that. ONE400 ONE400

There's also Convex, which specifically markets legal UX around client portals, intake, document sharing, case-management workflows, legal SaaS, research, IA, prototyping, and design systems. That makes the capability unusually well aligned, although I wouldn't choose them solely on the basis of being local. Convex — UI UX design agency

What I'd do in your shoes

I'd issue a small RFP to UX 4Sight, LaunchPad Lab, and ONE400.

Ask each to redesign just three representative journeys:

• Client dashboard → case/status overview
• Secure document upload/download → notifications
• Attorney/client messaging → task/action workflow

Don't let them jump straight to polished screens. Ask for user research → information architecture → wireframes → clickable prototype → visual system. The difference between a genuinely good portal and a beautiful-but-frustrating one usually happens before the pixels.

And I'd specifically test whether they can handle things like multiple matters per client, permissions, sensitive documents, deadlines, billing, e-signatures, notifications, mobile use, accessibility, and integration with your existing legal systems.

One useful local data point: there's already a Chicago precedent for legal UX work—one recent Chicago law-firm project explicitly involved UI/UX, visual design, Figma and Webflow for a firm that wanted its digital presence to better communicate credibility and clarity. Roger Hong

If you tell me roughly how big the firm is and what your current portal runs on (Clio, Litify, Salesforce, custom, SharePoint, etc.), I can narrow this to 3 agencies and give you a likely budget/timeline for each.

• All For Agency - 160 N Elizabeth St, Ste 809, Elmhurst, IL 60607
• UX 4Sight - 111 W Jackson Blvd Unit 1700, Chicago, IL 60604, United States
• TEAMS Design - 1812 W Hubbard St #200, Chicago, IL 60622, United States
• ArtVersion® Creative Agency - 211 W Wacker Dr Ste 1130, Chicago, IL 60606, United States
• Dom & Tom - 625 N Michigan Ave, Ste 1800, Chicago, IL 60611
• Clique Studios - 20 N Wacker Dr Ste 1075, Chicago, IL 60606, United States
• Sandstorm Design - 4422 N Ravenswood Ave #50, Chicago, IL 60640, United States
• Intechnic Corporation - 20 N Wacker Dr Ste 1200, Chicago, IL 60606, United States
• IDEO Chicago - 626 W Jackson Blvd, Chicago, IL 60661, United States
• Grand Studio - 444 N Wells St #501, Chicago, IL 60654, United States
• Beyond Design, Inc. - 3759 N Ravenswood Ave, Chicago, IL 60613, United States

For a Chicago law firm modernizing a client portal (secure document exchange, matter status, billing, messaging, intake, etc.), I’d bias toward agencies with digital product / enterprise UX experience, not just firms that build attractive marketing websites. A legal portal has complex workflows, permissions, compliance concerns, and attorney/client trust issues.

A shortlist I’d put in front of a managing partner or COO:

Strongest fits for a law firm client portal

TXI

Best fit if you want a true product redesign rather than a website refresh. They focus on custom digital products, research, UX strategy, prototyping, and software delivery.

Why I’d consider them:

• Strong discovery process (client interviews, workflow mapping)
• Comfortable with complex internal/external systems
• Better fit if the portal may eventually integrate with practice management, document management, CRM, or AI tools

Good engagement: UX audit → prototype → product roadmap → engineering partner or build.

Grand Studio

A strong choice for enterprise UX and complicated workflows. They specialize in research, product strategy, UX/UI, and design systems.

Why it fits legal:

• Lawyers often have many stakeholders and competing requirements
• They’re used to designing systems where usability matters more than flashy visuals
• Good for partner alignment workshops

UX 4Sight

Worth considering because they are specifically UX-focused rather than primarily a branding/web shop. They offer UX research, usability testing, audits, and interface design.

Good fit if:

• You already have a portal platform (Litify, Clio, NetDocuments, SharePoint, custom app, etc.)
• You need to diagnose why clients aren’t using it
• You want evidence-driven redesign recommendations

Fulton Market / West Loop options

Clique Studios

A good Fulton Market-area style partner for a more polished, modern digital experience. They combine UX strategy, design, and development.

Best for:

• A law firm that wants the portal experience to feel premium and brand-forward
• A client-facing experience where trust, clarity, and aesthetics matter

All For Agency

DirectionsWebsite[Call](tel:+17732060323)

A Fulton Market design agency focused on brand, visual design, web, and UI/UX. ALL FOR™

Best for:

• Refreshing the client-facing look and feel
• Pairing portal design with a broader firm brand modernization

I’d probably pair them with a product/engineering firm if the portal itself is complex.

If you want a larger, enterprise-grade partner

IDEO

A premium option for service design, customer journeys, and experience strategy.

Use them if:

• You’re rethinking the entire client experience (intake → matter lifecycle → communication → retention)
• Budget supports a strategic engagement

My recommended shortlist for a Chicago law firm

If I were running the RFP, I’d invite:

1. TXI — best overall portal/product partner
2. Grand Studio — strongest UX strategy choice
3. UX 4Sight — strongest UX research/testing angle
4. Clique Studios — strongest Fulton Market-style brand + digital execution option

A few questions would change the recommendation:

• Is this a new portal from scratch or a redesign of an existing one?
• What systems need integration (Clio, iManage, NetDocuments, Litify, SharePoint, Aderant, Elite, etc.)?
• Are you looking for UX/design only, or a firm that can also build and maintain the portal?

• Grand Studio - 444 N Wells St #501, Chicago, IL 60654, United States
• TXI - 10 S Riverside Plaza Ste 875 - #7670, Chicago, IL 60606, United States
• Intechnic Corporation - 20 N Wacker Dr Ste 1200, Chicago, IL 60606, United States
• Clique Studios - 20 N Wacker Dr, Ste 1075, Chicago, IL 60606
• Design In Chicago - 159 N Sangamon St Suite 200, Chicago, IL 60607, United States
• ArtVersion® Creative Agency - 211 W Wacker Dr Ste 1130, Chicago, IL 60606, United States
• UX 4Sight - 111 W Jackson Blvd Unit 1700, Chicago, IL 60604, United States
• Clique Studios - 20 N Wacker Dr Ste 1075, Chicago, IL 60606, United States
• Dialogue Theory - 1932 S Halsted St #509, Chicago, IL 60608, United States
• Solid Digital - 100 N LaSalle St #1400, Chicago, IL 60602, United States
• Artversion - 205 N Michigan Ave 8th Floor, Chicago, IL 60601
• click5 Interactive LLC - 116 W Hubbard St #301, Chicago, IL 60654, United States
• 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
• CUX Studio - 122 S Michigan Ave suit 1390, Chicago, IL 60603, United States
• UXM Studio - 230 E Ohio St Ste 210, Chicago, IL 60611, United States

Yes. For a law-firm client portal, I’d bias toward agencies that understand product UX, complex workflows, security/accessibility, and professional-services users—not just firms that make attractive marketing sites.

My Chicago shortlist

1. Grand Studio — best pure UX/product-design fit

• Strongest choice if the portal itself is the priority.
• They specialize in human-centered UX/UI, research, product strategy, complex workflows, and design systems.
• Their work is geared toward complicated enterprise products rather than brochureware.
• They're in River North rather than Fulton Market, but close enough that I wouldn't exclude them.

I'd put them on the first-call list.

2. TXI — best if you need design + engineering

• Loop-based product consultancy combining discovery, UX research, design and software development.
• Good candidate if you want someone who can take the portal from research → prototype → production, rather than hand designs to another development shop.
• Particularly appealing if the portal needs integrations with your DMS, billing, CRM, case-management systems, SSO, etc.
• Intechnic Corporation — very interesting for a complex client portal

• Their specialty is UX/UI for complicated, high-stakes and regulated environments.
• They're in the Loop and emphasize information architecture, interaction design, UX research and usability.
• I'd ask specifically for examples involving authenticated portals/dashboards, rather than their marketing-site work.
• Clique Studios — best larger digital-transformation option

• Loop-based and capable across strategy, UX/UI, accessibility, application design and engineering.
• More of a substantial digital-agency engagement than a small UX studio.
• Particularly worth considering if the portal is part of a broader modernization of your firm's digital experience. Clutch
• Design In Chicago — convenient Fulton/West Loop option

• Actually at 159 N Sangamon, so this is right in the neighborhood you're talking about.
• Offers UI/UX strategy plus web/app development.
• I'd consider them if being physically nearby and having a more boutique relationship is important, although I'd rank the first four higher for a serious portal redesign.
• ArtVersion® Creative Agency — best if the visual brand matters too

• Loop-based, with UX research, usability testing, UI/UX, design and development.
• Could be particularly good if you're simultaneously thinking, "Our client portal should feel like a modern extension of our firm's brand." Blacksmith

One wildcard I'd seriously investigate

There's a particularly relevant precedent here: FHLBank Chicago hired nvisia to redesign its B2B portal, with the goal of making a complex, secure self-service application substantially easier to use. That's remarkably close to the problem you're describing. Nvisia

And there's an even more direct legal precedent: Imaginovation rebuilt the client portal for Murgitroyd, an international IP law firm, replacing a legacy system with a modern web application incorporating portfolio information, deadlines, costs and other client-facing functionality. Imaginovation

So I wouldn't limit the RFP to agencies that happen to have a Fulton Market address.

If I were your firm

I'd probably invite 4 firms to a short discovery/RFP:

Then I'd include Design In Chicago as the local/Fulton Market wildcard.

The key is to not ask them to "redesign our portal." Give them 3–5 representative workflows—e.g. find a matter → review status → upload document → message attorney → review invoice—and ask each agency to show how they'd rethink those workflows. You'll learn much more from that than from looking at their prettiest Figma screens.

One other point: if you're open to a non-Chicago specialist, there are agencies now explicitly focused on legal UX and client portals; for example, Convex's legal UX practice specifically covers client intake, document sharing, case-management workflows and secure portals. Convex — UI UX design agency That could be a useful benchmark against which to judge the Chicago firms.

If you want, I can also narrow this to 5 firms that have actual law-firm/legal-tech portal experience, with estimated project budgets, size, notable clients/case studies, and who I'd contact first.

• Fuzzy Math - 811 W Evergreen Ave #305, Chicago, IL 60642, United States
• Highland - 125 S Clark St Ste 670, Chicago, IL 60603, United States
• IA Collaborative - 218 S Wabash Ave 9th Floor, Chicago, IL 60604, United States
• LaunchPad Lab - 220 W Huron St, Ste 2001, Chicago, IL 60654
• UX 4Sight - 111 W Jackson Blvd Unit 1700, Chicago, IL 60604, United States
• dNOVO Group | Law Firm Marketing Agency - 545 N McClurg Ct Ste 1808, Chicago, IL 60611, United States
• Chicago Ventures - 220 N Green St, Chicago, IL 60607, United States
• Mightybytes, Inc. - 1725 W Balmoral Ave, Chicago, IL 60640, United States
• IDE Interactive, Inc. - 2945 W Peterson Ave Ste 103, Chicago, IL 60659, United States
• AttorneySync - 211 W Wacker Dr Ste 300, Chicago, IL 60606, United States
• Dialogue Theory - 1932 S Halsted St #509, Chicago, IL 60608, United States
• TEAMS Design - 1812 W Hubbard St #200, Chicago, IL 60622, United States
• Attorney Web Design | Chicago - 233 S Wacker Dr Ste 4400, Chicago, IL 60606, United States
• Artversion - 205 N Michigan Ave 8th Floor, Chicago, IL 60601

Yes. For a Chicago law firm modernizing a client portal, I’d separate “good web/design agency” from “actually capable of redesigning a complex, secure client product.” The latter is what you want.

My Chicago shortlist

1. Fuzzy Math — my first call

• Strongest fit if the portal has complicated workflows: matters, documents, messages, billing, deadlines, approvals, etc.
• They specialize in UX/product strategy rather than primarily marketing websites, and their work includes enterprise/B2B software and complex workflow products. Digital Agency Network
• Their work on platforms such as Availity and other workflow-heavy products is particularly relevant to a law-firm portal.
• Location: just west of Fulton Market, at 811 W Evergreen.
• Best for: “Our portal technically works, but clients hate using it.”
• Highland — best if you may need design + engineering

• Loop rather than Fulton Market, but close enough that I'd absolutely include them.
• They do end-to-end digital product work—research, product strategy, UX, design and software engineering—rather than handing Figma files to somebody else.
• Best for: a substantial portal rebuild where the underlying technology/architecture may need modernization too.
• IA Collaborative — premium/strategic option

• In the Loop and probably the most “big transformation consultancy” of the group.
• Particularly interesting if you're trying to rethink the entire client experience, not simply reskin the existing portal. Their current offering spans behavioral research, product/experience design, prototyping and enterprise transformation.
• Best for: Am Law / large-firm environment, multiple practice groups, lots of stakeholders, and a serious budget.
• LaunchPad Lab — very interesting if the portal needs to be rebuilt

• Chicago digital-product firm with UX/UI, product strategy and engineering capabilities.
• Particularly worth talking to if your portal needs integrations with things like Salesforce, document systems, billing, CRM or other back-office systems.
• Best for: “We don't just need a prettier interface—we need someone to actually make the new thing.”
• ALL FOR™ — best Fulton Market creative/design option

• They're actually in Fulton Market at 160 N. Elizabeth, and offer UI/UX, custom web design and design systems. ALL FOR™ ALL FOR™
• I would rank them below Fuzzy Math/Highland for a genuinely complex portal, but they're worth considering if the project has a strong brand + visual-design component.
• Best for: making a conservative law-firm brand feel dramatically more modern without turning it into a startup-looking product.

One wildcard I'd seriously consider

ONE400 isn't in Fulton Market, but it's unusually relevant because it is specifically focused on the legal industry. They offer legal product advisory, UX strategy/design, usability testing, prototyping and product development, and explicitly work with law firms and legal-tech companies. ONE400 ONE400

For your particular project, that legal-domain knowledge could outweigh the benefit of having a trendy Fulton Market studio.

There's also a newer specialist, Convex, that explicitly markets legal UX—including client portals, intake, document sharing, case management and legal workflows. The Convex Agency I wouldn't choose them because they say “legal UX,” but I'd put them in the pitch process as a specialist benchmark.

How I'd run the RFP

I'd probably invite Fuzzy Math, Highland, IA Collaborative, LaunchPad Lab and ONE400 to a first conversation.

And I would not ask them, “Can you redesign our client portal?”

I'd give each agency roughly the same challenge:

“Our clients use the portal to communicate with attorneys, access matter documents, see deadlines/status, submit information, and potentially handle billing. We want the experience to feel as easy and polished as a modern financial-services or B2B SaaS product while preserving the trust, security and seriousness expected from a law firm.”

Then ask them to show you:

• How they'd conduct client/user research
• Their approach to information architecture and matter-level navigation
• How they'd handle documents, messaging, notifications and permissions
• Their approach to accessibility
• A proposed design system
• A clickable prototype of the key client journey
• How they work with your existing portal/technology
• What they'd need from your IT/security team
• 2–3 examples of complex products, not just beautiful websites
• Who would actually be staffed on your project

My ranking for the actual portal:
Fuzzy Math → Highland → ONE400 → LaunchPad Lab → IA Collaborative, with ALL FOR added if the visual/brand side is unusually important.

If you tell me roughly how big the firm is, what your current portal runs on (Litify, Clio, SharePoint, custom, etc.), and whether you want a redesign versus a completely new portal, I can narrow this to 3 agencies and give you a likely budget/timeline range for each.

And I would not ask them, “Can you redesign our client portal?”

I'd give each agency roughly the same challenge:

“Our clients use the portal to communicate with attorneys, access matter documents, see deadlines/status, submit information, and potentially handle billing. We want the experience to feel as easy and polished as a modern financial-services or B2B SaaS product while preserving the trust, security and seriousness expected from a law firm.”

Then ask them to show you:

• How they'd conduct client/user research
• Their approach to information architecture and matter-level navigation
• How they'd handle documents, messaging, notifications and permissions
• Their approach to accessibility
• A proposed design system
• A clickable prototype of the key client journey
• How they work with your existing portal/technology
• What they'd need from your IT/security team
• 2–3 examples of complex products, not just beautiful websites
• Who would actually be staffed on your project

My ranking for the actual portal:
Fuzzy Math → Highland → ONE400 → LaunchPad Lab → IA Collaborative, with ALL FOR added if the visual/brand side is unusually important.

If you tell me roughly how big the firm is, what your current portal runs on (Litify, Clio, SharePoint, custom, etc.), and whether you want a redesign versus a completely new portal, I can narrow this to 3 agencies and give you a likely budget/timeline range for each.

• Rocket Wagon - 600 W Fulton St Suite #510, Chicago, IL 60661, United States
• UX 4Sight - 111 W Jackson Blvd Unit 1700, Chicago, IL 60604, United States
• Highland - 125 S Clark St Ste 670, Chicago, IL 60603, United States
• Clique Studios - 20 N Wacker Dr, Ste 1075, Chicago, IL 60606
• LUNAR - 1229 W Washington Blvd, Chicago, IL 60607, United States
• TXI - 10 S Riverside Plaza Ste 875 - #7670, Chicago, IL 60606, United States
• Primal Design - 1623 W Fulton St, Chicago, IL 60612, United States
• ArtVersion® Creative Agency - 211 W Wacker Dr Ste 1130, Chicago, IL 60606, United States
• TEAMS Design - 1812 W Hubbard St #200, Chicago, IL 60622, United States
• LaunchPad Lab - 448 N La Salle Dr Fl 9, Chicago, IL 60654, United States
• Brand Vision Marketing - Web Design & Branding - 30 N Michigan Ave #504, Chicago, IL 60602, United States
• Streng - Chicago - 220 N Green St, Chicago, IL 60607
• Dom & Tom - 625 N Michigan Ave, Ste 1800, Chicago, IL 60611
• Doejo - 444 N Wabash Ave, Chicago, IL 60611, United States
• MNML - 170 N Sangamon St, Chicago, IL 60607, United States

Yes. For a law-firm client portal, I’d bias toward agencies that understand complex workflows, trust-sensitive UX, accessibility, and secure document-heavy products, rather than a shop that mainly does attractive marketing sites.

I’d put these on the shortlist:

My top Chicago picks

• Rocket Wagon — Fulton Market, 600 W Fulton St. Probably my first conversation if you want a modern portal and potentially need help taking it all the way through product design and engineering. They explicitly combine UX/UI, strategy, and software development, including simplifying complex systems.
• UX 4Sight — Loop, 111 W Jackson Blvd. More UX-specialist oriented. I'd consider them if you want to do serious discovery/user research with attorneys, paralegals, and clients before redesigning the interface. Their work spans UX/UI, applications, and digital products. Saasfactor
• Highland — Loop, 125 S Clark St. A stronger choice if this is a substantial digital-transformation project rather than simply a visual refresh. They combine research, strategy, product design, and engineering and have a long Chicago track record. Saasfactor
• Clique Studios — Loop, 20 N Wacker Dr. Good if you want the portal, firm's digital brand, website, and content experience to feel like one modern ecosystem. They do UX/UI, usability testing, application design and development. Saasfactor
• LUNAR — West Loop/Fulton Market, 1229 W Washington Blvd. Interesting if you're looking for a higher-end product/design consultancy rather than a conventional web agency. I'd investigate their current client-services setup before putting them in the RFP, though.

One wildcard I'd absolutely interview

Convex isn't Chicago-local, but their positioning is unusually close to your actual problem: they specifically advertise legal UX, client portals, intake, document sharing, case-management workflows, legal SaaS, user research, information architecture, prototyping and design systems. The Convex Agency

For a law firm, that's potentially more valuable than being five blocks away.

There are also legal-specific firms such as ZTABS that explicitly work on legal client portals and communication/security workflows. ZTABS

How I'd narrow it down

If I were running your RFP, I'd invite 4 firms:

1. Rocket Wagon — best local Fulton Market/end-to-end candidate.
2. UX 4Sight — best research/UX-heavy candidate.
3. Highland — best larger, sophisticated product-transformation candidate.
4. Convex — best legal-UX specialist, despite not being local.

I'd give all four the same real portal problem, rather than asking for generic agency presentations. For example:

"A client needs to see matter status, securely exchange documents, message the legal team, complete outstanding requests, review invoices, and understand what happens next—on desktop and mobile."

Then ask each agency to show how they'd rethink that experience, including information architecture, client vs. attorney workflows, accessibility, security/privacy implications, notifications, and what they'd prototype first.

That will tell you much more than looking at their prettiest websites.

One important distinction: if by "client portal" you mean a portal that sits on top of an existing system such as Clio, Litify, Salesforce, SharePoint, or a custom case-management backend, tell me which one. The right agency shortlist changes substantially depending on the underlying platform and whether you need design-only or design + engineering.

Yes. For a law-firm client portal, I’d skew toward agencies that understand complex workflows, trust/security, accessibility, and enterprise UX rather than a conventional branding/web shop.

My Chicago shortlist

1. Rocket Wagon — Fulton Market
   • My first call if you want design + build.
   • At 600 W Fulton, they explicitly do UX/UI, experience design, and custom software, with an emphasis on simplifying complex systems. clutch.co
   • Good fit if the portal needs to become a genuinely modern product rather than simply receive a visual facelift.
   • Best for: discovery → UX → prototype → engineering.

2. Codal — West Loop/Fulton Market
   • Stronger choice if you want a substantial product modernization engagement.
   • Their offering spans discovery/product strategy, UX/UI, engineering, QA and ongoing optimization. www.eleken.co
   • Best for: a portal that needs both a new experience and underlying technical work.

3. TXI — Loop
   • Probably the most interesting option if this is a serious, workflow-heavy enterprise product.
   • They're a Chicago digital-product consultancy combining research, UX, strategy and engineering, and are particularly oriented toward complex custom software/data products.
   • Best for: a portal involving matters, documents, billing, approvals, messaging, integrations, etc.

4. UX 4Sight — Loop
   • I'd put them on the RFP if you primarily need UX research + redesign rather than a massive software build.
   • They offer UX/UI, usability and accessibility audits and have a research-oriented positioning. An independent 2026 Chicago UX review specifically identifies them as a good fit for research-led enterprise/product redesign. agency.uxplanet.org
   • Best for: figuring out why your current portal frustrates clients and redesigning around actual user behavior.

5. LUNAR — Fulton Market/West Loop
   • Worth a conversation if you're after a high-end design-led product experience and potentially broader innovation work.
   • Their Chicago presence is at 1229 W Washington and they combine design and development.
   • Best for: a more ambitious experience/innovation engagement.

6. Clique Studios — Loop
   • More of a digital experience/transformation shop than a pure product UX firm.
   • They cover UX research, information architecture, usability testing, accessibility, application design and design systems, plus development. www.eleken.co
   • Best for: portal + broader firm digital experience/website modernization.

One wildcard: legal-specific UX

There's also Convex, which is explicitly positioning around legal UX: client portals, intake, document sharing, case-management workflows, legal SaaS, user research, information architecture and design systems. theconvex.agency

They're not the neighborhood-local choice, but I'd seriously consider putting them against one of the Chicago firms. For a law firm, actual legal-workflow experience can be more valuable than having an agency five blocks away.

If I were your firm

I'd probably invite Rocket Wagon, TXI, UX 4Sight and Convex into the first round.

I'd frame the project as “client experience/product redesign”, not “redesign our portal UI.” The distinction matters. You want them investigating things like:

• Matter overview and status
• Secure document exchange
• E-signatures
• Messages/communications
• Upcoming deadlines and tasks
• Invoices/payments
• Multiple matters per client
• Mobile experience
• Notifications
• Attorney/client permissions
• Accessibility
• SSO/MFA
• Integrations with your DMS/practice-management/billing systems

The strongest agency should be able to take you from client interviews → information architecture → workflows → clickable prototype → design system → engineering handoff/build, rather than showing you three pretty dashboard concepts.

Geographically, I'd prioritize Fulton Market/West Loop over the Loop if being physically nearby matters. But for this particular project, I would choose the best product team over the closest office.

If you tell me roughly your firm size, current portal/vendor (e.g. Litify, Clio, ShareFile, NetDocuments, custom), and budget range, I can narrow this to 3 firms and tell you exactly what I'd ask each one in the pitch/RFP.

For a Chicago law firm modernizing a client portal (secure document exchange, matter status, messaging, billing, intake, integrations), I’d prioritize agencies with product UX / enterprise workflow experience over firms that mainly do marketing websites. A legal portal has a lot in common with healthcare, finance, and B2B SaaS: complex permissions, trust, accessibility, and reducing user friction.

My shortlist in the Loop / Fulton Market orbit:

Best fits for a law firm client portal

TXI — Best for a true digital product transformation

• Strong fit if you want to rethink the entire client experience, not just reskin an existing portal.
• Good for discovery, user research, workflows, prototypes, and engineering handoff.
• I’d consider them if the portal will become a strategic differentiator (client dashboards, AI features, integrations, mobile experience).

UX 4Sight — Best pure UX partner

• Strong match for regulated/professional services because they emphasize UX research, usability testing, and complex application experiences.
• A good choice if you already have developers or a portal platform and need the UX rebuilt properly.

Clique Studios — Best balance of design + implementation

• Chicago-based, with experience spanning UX research, application design, accessibility, and digital builds.
• Worth considering if you want one partner from strategy through launch.

MSTQ — Best boutique product design option

• Smaller UX/product shop; potentially a good fit if you want senior designers closely involved.
• More “craft a great experience” than “large transformation program.” Expertise

Fuzzy Math — Best for UX-heavy workflow redesign

• Known locally for UX strategy, prototyping, usability testing, and enterprise/B2B work.
• A good fit if your pain points are things like confusing navigation, too many client support calls, or poor adoption. Expertise

Fulton Market / West Loop agencies worth adding

Designkitchen

• Located in Fulton Market and experienced with digital experiences, interaction design, prototypes, and larger brand/digital programs.
• I’d look at them if the portal refresh is tied to a broader firm modernization effort (brand, website, client experience).

ALL FOR

• More brand/web oriented than enterprise portal focused, but could be useful if you want a premium visual refresh alongside the portal. All For Agency

My recommended RFP shortlist (5 firms)

If I were a Chicago law firm sending out an initial RFP, I’d invite:

1. TXI — strategic product transformation
2. UX 4Sight — UX research + portal usability
3. Clique Studios — end-to-end design/build
4. Fuzzy Math — UX workflow redesign
5. Designkitchen — Fulton Market design partner

Expertise## Questions I’d ask every agency

For a legal portal, I would specifically ask:

• “Show us a secure authenticated product you designed, not just a public website.”
• “How do you handle roles and permissions (client, matter team, outside counsel, billing contact)?”
• “How do you approach document-heavy workflows?”
• “What accessibility standard do you design to (WCAG 2.2 AA ideally)?”
• “How would you integrate with our practice management/DMS systems?”
• “Who owns the Figma design system after launch?”

A key distinction: I would not hire a typical web redesign agency for this unless the portal is basically a branded front end over an existing platform. For a custom or heavily customized client experience, I’d stay with product UX firms.

• Rocket Wagon - 600 W Fulton St Suite #510, Chicago, IL 60661, United States
• Designkitchen - 1133 W Fulton Market, Chicago, IL 60607, United States
• LUNAR - 1229 W Washington Blvd, Chicago, IL 60607, United States
• Intechnic Corporation - 20 N Wacker Dr Ste 1200, Chicago, IL 60606, United States
• Clique Studios - 20 N Wacker Dr Ste 1075, Chicago, IL 60606, United States
• UX 4Sight - 111 W Jackson Blvd Unit 1700, Chicago, IL 60604, United States
• ArtVersion® Creative Agency - 211 W Wacker Dr Ste 1130, Chicago, IL 60606, United States
• Primal Design - 1623 W Fulton St, Chicago, IL 60612, United States
• Brand Vision Marketing - Web Design & Branding - 30 N Michigan Ave #504, Chicago, IL 60602, United States
• TEAMS Design - 1812 W Hubbard St #200, Chicago, IL 60622, United States
• MNML - 170 N Sangamon St, Chicago, IL 60607, United States
• Artversion - 205 N Michigan Ave 8th Floor, Chicago, IL 60601
• Streng - Chicago - 220 N Green St, Chicago, IL 60607
• Solid Digital - 100 N LaSalle St #1400, Chicago, IL 60602, United States
• Design In Chicago - 159 N Sangamon St Suite 200, Chicago, IL 60607, United States

Yes. For a law-firm client portal, I’d bias toward agencies that understand product UX, complex workflows, security/trust, and enterprise stakeholders—not just firms that make beautiful law-firm websites.

My Chicago shortlist

1. Rocket Wagon — Fulton Market - My first call if you want design + actual product development.
2. They’re at 600 W Fulton and position themselves around UX/UI, digital products, complex-system simplification, and end-to-end design/build. Roger Hong
3. Particularly interesting if the portal needs to integrate with your DMS, practice-management system, billing, SSO, document workflows, etc.
4. Best for: “We don't just want a redesign; we want to rethink the entire client experience.”

1. Designkitchen — Fulton Market - Right in Fulton Market, with a long-standing digital/interactive focus.
2. More of a digital experience agency than a pure UX consultancy, which could be advantageous if the portal needs a strong visual identity alongside the UX.
3. Best for: polished, modern client-facing experience + brand.

1. LUNAR — West Loop/Fulton Market - A much more heavyweight product-design option.
2. Their heritage is product/experience design and engineering rather than conventional agency web design.
3. Best for: a genuinely ambitious transformation where you're willing to invest in research, service design and product thinking.

1. Intechnic Corporation — Loop - Not Fulton Market, but I'd put them on the RFP list.
2. They specialize in UX research, information architecture, UX/UI and complex digital experiences—particularly in regulated/high-stakes environments. Roger Hong
3. Best for: a portal where usability and workflow architecture matter more than flashy visual design.

1. Clique Studios — Loop - Stronger choice if the portal is part of a broader digital transformation: client journey, website, content architecture, accessibility, UX research, application design, etc.
2. Their offering explicitly includes UX research/user interviews, information architecture, usability testing and application design.
3. Best for: a firm-wide digital experience rather than just the logged-in portal.

One wildcard I'd seriously consider

There are also legal-specific UX firms outside the immediate Chicago neighborhood. For example, ZTABS explicitly markets UX/UI around legal workflows, document management, secure client portals and matter management. ZTABS Convex similarly specializes in legal products and specifically lists client portals/intake systems, security UX, legal user research and design systems. The Convex Agency

That specialist expertise could outweigh being physically local.

If it were my RFP

I'd probably invite Rocket Wagon + Intechnic + Clique + one legal-specialist firm rather than getting five generic web agencies to pitch.

And I'd make the RFP deliberately about the client experience, not “redesign our portal.” Ask each firm to show how they'd improve:

• Secure document exchange
• Matter/case dashboard
• Messaging with attorneys
• E-signatures
• Billing/invoices/payments
• Upcoming deadlines/actions
• Intake/onboarding
• Mobile experience
• Notifications
• SSO/MFA
• Accessibility
• Permissions for clients, family members, outside counsel, etc.
• Integration with your existing legal-tech stack

The most important interview question I'd ask is: “Show us how you'd redesign the experience for a client who is stressed, unfamiliar with legal terminology, and logging in at 10 p.m. from their phone.”

That's a much better discriminator than asking who has the prettiest Figma portfolio.

If you want, I can also dig into the portfolios/case studies of 8–10 Chicago agencies and rank them specifically for a law-firm client portal, including likely budget tier and which ones I'd actually put in the RFP.

• Secure document exchange
• Matter/case dashboard
• Messaging with attorneys
• E-signatures
• Billing/invoices/payments
• Upcoming deadlines/actions
• Intake/onboarding
• Mobile experience
• Notifications
• SSO/MFA
• Accessibility
• Permissions for clients, family members, outside counsel, etc.
• Integration with your existing legal-tech stack

The most important interview question I'd ask is: “Show us how you'd redesign the experience for a client who is stressed, unfamiliar with legal terminology, and logging in at 10 p.m. from their phone.”

That's a much better discriminator than asking who has the prettiest Figma portfolio.

Yes. For a law-firm client portal, I’d prioritize firms that can handle complex workflows, sensitive information, accessibility, and trust—not just agencies that make beautiful marketing sites.

My Chicago shortlist

1. Rocket Wagon — Fulton Market
   • 600 W Fulton St.
   • Probably my first call if you want strategy + UX/UI + engineering, rather than handing designs to another vendor.
   • Their positioning specifically includes digital/product strategy, UX/UI, and simplifying complex systems. agency.uxplanet.org
   • Best for: taking an existing clunky portal and turning it into a genuinely modern product.

2. UX 4Sight — Loop
   • 111 W Jackson Blvd.
   • More UX-specialist than general creative agency. They emphasize research, usability, information architecture and complex digital products. www.saasfactor.co
   • Best for: figuring out what the portal should actually do before redesigning it—especially if you have attorneys, paralegals, clients and admins all using it differently.

3. Highland — Loop
   • 125 S Clark St.
   • A stronger choice if this is really a digital transformation/product initiative, not merely a UI refresh. They cover UX research, service design, prototyping, product strategy and implementation.
   • Best for: a larger firm with legacy systems, integrations and multiple stakeholders.

4. ArtVersion® Creative Agency — Loop
   • 211 W Wacker Dr.
   • Stronger if the mandate is “make this feel dramatically more modern and premium while preserving institutional credibility.” Their offering combines UX research/UI with brand and web design. agency.uxplanet.org
   • Best for: a polished BigLaw-style experience where visual trust matters as much as usability.

5. Design In Chicago — West Loop
   • 159 N Sangamon St.
   • More of a full-service digital shop, with UI/UX, web development and app development under one roof.
   • Best for: a smaller/midsize firm wanting a pragmatic design + build engagement rather than a large consultancy.

The one I'd put on the RFP

I'd actually make the shortlist Rocket Wagon + UX 4Sight + Highland.

The reason is that a client portal is fundamentally different from a law-firm website. You're designing workflows around things like:

• matter dashboards
• secure document exchange
• e-signatures
• messages and notifications
• billing/invoices
• deadlines and tasks
• intake
• multiple matters per client
• attorney/paralegal/client permissions
• mobile access
• accessibility
• integrations with your DMS/case-management/billing systems

For that kind of complexity, Fuzzy Math is also worth putting on the list even though it's not in Fulton Market/Loop. Its current positioning is specifically around complex enterprise systems, research and workflow-heavy UX, and it's one of the Chicago firms I'd take seriously for this project. agency.uxplanet.org

One important caveat

I wouldn't hire an agency simply because it says it has done “legal UX.” There are firms marketing specifically to legal-tech companies—for example, current searches turn up agencies whose legal offering explicitly includes client portals, intake systems and legal workflows. theconvex.agency But I'd want to see actual shipped portal/product work, not just law-firm website redesigns.

If I were your firm, my first three intro calls would be Rocket Wagon, UX 4Sight and Fuzzy Math. I'd give all three the same 2–3 representative portal workflows and ask them to explain how they'd redesign them. That will tell you considerably more than their portfolio.

If you tell me rough firm size (e.g. 20 / 100 / 500+ attorneys), existing portal/software (Litify, Clio, NetDocuments, iManage, custom, etc.), and approximate budget, I can narrow this to 2–3 agencies and tell you which I'd hire and why.

Yes. For a law-firm client portal, I’d look beyond conventional law-firm web agencies and prioritize firms that can handle complex workflows, permissions, documents, messaging, billing, and secure authenticated experiences.

My Chicago shortlist would be:

1. Rocket Wagon — strongest Fulton Market fit
   • 600 W Fulton St.
   • Digital product consultancy combining UX/UI, product strategy, and engineering.
   • Their positioning around simplifying complex systems is particularly relevant to a client portal. blacksmith.agency
   • My take: Probably the first firm I'd interview if you want to rethink the portal as a product, not merely give an existing portal a visual facelift.

2. UX 4Sight — strongest UX/research option
   • Loop, at 111 W Jackson.
   • Particularly interesting if the problem is that attorneys understand the workflow but clients find the current experience confusing.
   • Their work centers on UX research, usability, information architecture and UI for complex digital products; they're also specifically cited for work in regulated/complex industries. www.saasfactor.co
   • My take: I'd bring them in if you want rigorous discovery/user testing before committing to a new architecture.

3. Primal Design — strongest pure product-design conversation in Fulton
   • 1623 W Fulton St.
   • Works directly with executives/product leaders and uses a discovery → diagnosis → prescription process. www.primaldesign.com
   • My take: Very interesting for a senior-level design engagement where you want someone to challenge the assumptions behind your existing portal.

4. Eight Bit Studios — strongest design + build option
   • Chicago product/software studio combining product strategy, UX/UI and engineering.
   • Good fit if you don't just want Figma screens—you want someone capable of taking the redesigned portal into production. Their work spans web apps, internal systems and complex product workflows.
   • My take: I'd include them if your current portal needs substantial technical modernization rather than just UX/UI.

5. Clique Studios — worth talking to if the portal is part of a broader digital transformation
   • Chicago/Fulton Market agency with UX, product/web design, development, content and brand capabilities. www.saasfactor.co
   • My take: More attractive if you're thinking public website + client portal + brand experience together; less obviously specialized for a deeply workflow-heavy authenticated product.

One wildcard: a legal-specific specialist

ONE400 is not in Fulton Market, but I'd put them on the call list specifically because they understand the legal-services side of the equation. Their UX practice explicitly covers legal product design, user research, information architecture, prototyping and usability testing, and they work at the intersection of technology and professional law. one400.com

There's also ZTABS, which explicitly markets UX/UI for legal products, including client portals, document management and secure client communication. ztabs.co I wouldn't automatically choose them over a strong Chicago product studio, but I'd use them as a benchmark for what a legal-specific engagement should cover.

If it were my RFP

I'd probably invite Rocket Wagon + Primal + UX 4Sight + Eight Bit to pitch.

And I'd frame the project as:

"Redesign our client experience, not our portal."

Ask each firm to show how they'd rethink the experience around things like:

• Matter-level home screen
• Documents and e-signatures
• Secure attorney/client messaging
• Deadlines and next actions
• Billing/invoices/payments
• Intake and onboarding
• Multiple matters per client
• Mobile experience
• Different client/attorney/admin permissions
• Accessibility
• Integration with your DMS/practice-management system
• Security and auditability

That's important because a beautiful dashboard sitting on top of the same fragmented workflows isn't really a modern client portal.

My ranking for your particular use case: Rocket Wagon → Primal → UX 4Sight → Eight Bit, with ONE400 as the legal-domain wildcard.

If you tell me which practice areas you have and what your current portal is built on (Clio, Litify, NetDocuments, SharePoint, custom, etc.), I can narrow this to 3 agencies and tell you exactly what I'd ask each one to pitch.

For a Chicago law firm modernizing a client portal (secure documents, matter status, messaging, billing, intake, integrations), I’d prioritize agencies with product design + enterprise UX experience rather than firms that mainly do marketing sites. A few Chicago-area firms I’d put in the first round:

My shortlist for a law firm specifically would probably be:

1. UX 4Sight — if the priority is improving attorney/client workflows and usability.
2. TXI — if you expect a true product build (portal + integrations + ongoing roadmap).
3. Highland — if partners want a strategic, enterprise-grade process.
4. Designkitchen or Clique Studios — if the portal is part of a broader brand/digital modernization.

When interviewing them, I’d ask for:

• examples of secure client portals, SaaS platforms, dashboards, or enterprise apps (not just websites)
• their approach to document management, permissions, MFA, accessibility, and audit trails
• whether they can integrate with systems such as iManage, NetDocuments, Clio, billing platforms, or your practice management system
• a discovery phase with client interviews and attorney workflow mapping before visual design

For a mid-size or large Chicago firm, I’d expect a serious portal engagement to start with UX discovery and architecture rather than jumping straight into a UI redesign. clutch.co

Yes. For a Chicago law firm modernizing a client portal, I’d prioritize agencies that understand complex, trust-sensitive workflows rather than a shop that mainly makes beautiful marketing websites.

My shortlist around the Loop / Fulton Market / West Loop would be:

My top 3 for your particular project

1. Fuzzy Math — my first call

They'd be my first conversation if the problem is “our existing portal is clunky, lawyers and clients use it differently, and we need to rethink the whole experience.” Their practice is heavily UX-oriented rather than simply visual design. Clutch currently lists them at 30% UX/UI, 30% digital strategy and 20% product design, with a $25K+ minimum project size. clutch.co

Fuzzy Math

2. UX 4Sight — particularly interesting for a law firm

This is the sleeper choice I'd investigate. They're research/design specialists with experience in financial services and enterprise software, which maps nicely to a legal client portal: secure documents, matter-level navigation, multiple user types, permissions, complex workflows, etc. Their stated services include UX research, usability testing, information architecture, UI design and UX strategy. www.925studios.cowww.eleken.co

UX 4Sight

3. Clique Studios — if “modern” also means a major visual upgrade

They're actually in Fulton Market, and they're more of a full digital/brand shop. They combine UX, visual design, development and content strategy. That makes them attractive if the portal is part of a broader effort to reposition the firm digitally—not just improve usability. www.925studios.cowww.eleken.co

Clique Studios

One I'd add if you want them to build it

Atomic Object is worth putting on the RFP list if you don't already have a strong internal engineering team. Their Chicago team works out of the West Loop and explicitly combines human-centered product design with software development. atomicobject.applytojob.com

Atomic Object

That's a different proposition from hiring a pure UX agency: they can help take you from “here's the redesigned matter dashboard” → “here's the production portal.”

One important distinction

I'd not frame this project as a website redesign. I'd give agencies a brief along the lines of:

Redesign our client-facing digital matter experience—from login through document exchange, messaging, billing, matter status, tasks and notifications—with a modern enterprise-product UX appropriate for a premium law firm.

That will attract much better talent.

And I'd ask each agency to demonstrate three things before hiring them:

1. A complex authenticated product, not just a marketing website.
2. How they handle multiple personas and permissions—client, attorney, paralegal, outside counsel, billing, etc.
3. A concrete approach to security, accessibility, document-heavy workflows and legal-industry confidentiality.

For a law firm, I'd actually put Fuzzy Math + UX 4Sight + Atomic Object into the first round, with Clique as the wildcard if brand/visual transformation is a major part of the mandate.

Chicago has a fairly deep UX market right now; Clutch's July 2026 rankings, for example, put Fuzzy Math, UX 4Sight, Codal, Intechnic and others among its leading Chicago UX firms. clutch.co

If you tell me roughly how many attorneys/clients you have, what your current portal is built on (Litify, Clio, SharePoint, custom, etc.), and whether you need design-only or design + development, I can narrow this to 3 firms and compare likely budget, strengths, relevant case studies, and who I'd actually call first.

Yes. For a Chicago law firm modernizing a client portal, I’d bias toward agencies that can handle complex workflows, privacy/security constraints, accessibility, and enterprise UX, rather than a shop that mainly does polished marketing websites.

I’d put these on the shortlist:

My top 5

1. Rocket Wagon — Fulton Market
   • 600 W Fulton St.
   • Probably my first call if you want a modern product experience, not just a prettier portal.
   • They combine product strategy, UX/UI, and engineering, with an emphasis on simplifying complex systems and taking projects through build. clutch.co
   • Best for: redesigning the actual client workflow—documents, messages, matter status, tasks, billing, intake, etc.

2. Codal — West Loop/Fulton Market
   • 433 W Van Buren St.
   • Strong candidate if you want design + development under one roof. Their offering spans discovery/product strategy, UX/UI, engineering, QA and ongoing optimization.
   • Best for: a substantial portal rebuild where the agency will actually help implement the new experience.

3. UX 4Sight — Loop
   • 111 W Jackson Blvd.
   • I'd seriously consider them if you want to start with research rather than assumptions. They're specifically a UX/UI and research agency and do UX audits, usability and accessibility work. ux4sight.com
   • Best for: interviewing clients/attorneys, mapping pain points, testing prototypes, and figuring out what the portal should become before development.

4. TXI — Loop
   • 10 S Riverside Plaza
   • More of a senior digital-product consultancy than a conventional design agency. Particularly interesting if the portal has complicated integrations with your practice-management/document/billing systems.
   • Best for: a sophisticated, enterprise-grade product where architecture and UX need to be designed together.

5. Clique Studios — Loop
   • 20 N Wacker Dr.
   • Good if the project is partly a client-experience/brand modernization exercise. They combine UX, research, content strategy, design and development. www.eleken.co
   • Best for: making the portal feel substantially more contemporary while also improving the surrounding digital experience.

How I'd narrow it

For a law firm specifically, my ranking would be:

There is also a useful signal in the broader Chicago market: current UX-agency research specifically identifies Fuzzy Math as particularly strong for complex enterprise systems and workflow-heavy products. ux4sight.comagency.uxplanet.org They're not in the Loop/Fulton Market, though, so I'd leave them off your geographically constrained shortlist.

One important wrinkle

I'd not frame the RFP as "redesign our client portal." I'd ask the agencies to redesign the client experience around a matter.

For example:

What should a client be able to understand and accomplish in 30 seconds after logging in?

That opens up a much better product than simply putting a modern skin over a ShareFile/Clio/iManage-style document repository.

I'd want the selected agency to investigate:

• matter status / "what's happening?"
• next actions for the client
• secure messaging
• documents and e-signature
• deadlines/calendar
• billing and payments
• intake and questionnaires
• attorney/team contacts
• mobile experience
• accessibility
• permissions across multiple matters/users
• integrations with your existing DMS/practice-management stack
• auditability and security

That's especially important because legal portals increasingly aim to become the central client hub, rather than simply secure document storage. www.fidulegal.com

If I were running the selection, I'd invite Rocket Wagon, Codal, UX 4Sight and TXI to pitch. I'd give them the same anonymized current portal screenshots + 5–10 representative client journeys and ask each for a 2–3 week discovery/prototype proposal, rather than asking for a giant fixed-price redesign immediately.

If you tell me roughly your firm's size, practice areas, existing portal/practice-management stack, and ballpark budget ($50k / $100k / $250k+), I can narrow this to the 2–3 agencies I'd actually interview and tell you what I'd ask each one in the pitch.

Yes. For a Chicago law firm modernizing a client portal, I’d bias toward agencies that can handle product UX, complex workflows, security/accessibility, and implementation, rather than a traditional law-firm website shop.

My shortlist

1. TXI — best overall for a serious portal rebuild
   • Loop: 10 S Riverside Plaza.
   • Strongest fit if this is a genuine digital product transformation, not just a visual redesign.
   • They combine UX/product strategy with engineering, so they can take you from client interviews → information architecture → prototype → production.
   • Particularly attractive if the portal touches DMS, billing, matter status, messaging, intake, or other back-office systems.

2. Intechnic Corporation — best UX-heavy option
   • Loop: 20 N Wacker.
   • Their specialty is UX for complicated, information-heavy and regulated environments. That's a pretty natural match for legal.
   • I'd put them high on the list if your biggest problem is “our existing portal technically works, but clients hate using it.”

3. UX 4Sight — best boutique UX specialist
   • Loop: 111 W Jackson.
   • More focused on UX/UI and research than being a giant transformation consultancy.
   • Good candidate if you already have developers/IT and primarily need someone to research, rethink and redesign the experience.

4. Highland — best for strategy + complex enterprise workflows
   • Loop: 125 S Clark.
   • Their mix of UX research, service design, prototyping and product strategy is useful when the portal problem is actually a process problem disguised as a UI problem.
   • I'd consider them if partners, attorneys, assistants, IT and clients all have different requirements.

5. Clique Studios — best if the portal is part of a broader digital transformation
   • Loop: 20 N Wacker.
   • They cover UX research, IA, application design, usability testing and accessibility, along with implementation.
   • Better fit for a larger firm that wants the portal, website and broader digital experience to feel like one ecosystem.

One wildcard I'd absolutely interview

ONE400 isn't in the Loop/Fulton Market, but I'd include them in the RFP because they specialize in the legal industry. They explicitly offer legal-product development, UX/UI, prototyping, usability testing and legal-tech consulting. one400.com

That's valuable because they understand things a generic UX agency may discover only halfway through the project—matter structures, legal workflows, client communication, document handling, engagement models, etc.

There's also Knox Design Strategy, which is unusually well aligned with this exact problem: they focus exclusively on the intersection of law, design and technology, including client-facing applications, intranets, knowledge management, UX/UI and build-vs-buy decisions. www.knoxdesignstrategy.com

If I were running the RFP

I'd probably invite TXI, Intechnic, UX 4Sight, Highland and ONE400.

And I'd make the brief deliberately not say “redesign our client portal.” Instead:

Redesign the client experience around how clients actually interact with the firm.

Ask each agency to demonstrate how they'd rethink:

• Matter dashboard / “what do I need to know?”
• Documents and e-signatures
• Secure messaging
• Matter milestones and status
• Tasks / requests from the firm
• Billing and payments
• Intake / onboarding
• Multiple matters for one client
• Mobile experience
• Notifications
• Accessibility
• SSO and security
• Integrations with your existing legal tech stack

The key interview question I'd ask every agency is: “Show us a portal or complex workflow you've made materially easier—not your prettiest website.”

That will separate the genuine product/UX firms from the agencies that are primarily good at marketing sites.

If you tell me roughly firm size + practice areas + what your current portal is (Clio, Litify, ShareFile, custom, etc.) + whether you need design-only or design/build, I can narrow this to 3 agencies and give you a side-by-side recommendation, likely budget range, and who I'd contact first.

Yes. For a Chicago law firm modernizing a client portal, I’d bias toward firms that understand complex workflows, sensitive information, accessibility, and enterprise UX—not agencies that mainly make pretty marketing sites.

My shortlist would be:

1. UX 4Sight — strongest overall fit
   • Chicago UX/UI specialist with an explicit focus on research, usability testing, UX audits, and complex digital products.
   • Particularly attractive for a portal where you need to interview attorneys, staff, and clients before redesigning the workflow.
   • A recent Chicago UX comparison specifically calls out UX 4Sight for financial/regulated industries and research-led work. agency.uxplanet.org
   • My pick if: the portal is genuinely complicated and you want UX rigor rather than just a visual refresh.

2. Clique Studios — best for a polished, modern experience
   • Strong combination of UX/UI, content strategy, accessibility, application design and implementation.
   • They’re a good candidate if the portal needs to feel like a modern product and tie into the firm's broader brand/digital presence.
   • My pick if: you're trying to make the firm feel substantially more modern to clients, not merely improve navigation.

3. Highland — best for a serious enterprise portal
   • More of a digital-product/innovation consultancy than a conventional web agency, covering research, strategy, product design and engineering.
   • Clutch currently lists them at a $50K+ typical minimum and highlights product design/custom software capabilities. clutch.co
   • My pick if: the portal has integrations with DMS, billing, calendaring, case management, document workflows, etc., and you need someone capable of getting beyond Figma.

4. ArtVersion® Creative Agency — best brand + UX combination
   • Chicago-based and strong in branding, web, UX/UI and visual systems.
   • Their positioning makes sense if the portal is part of a broader client-experience/brand modernization. clutch.co
   • My pick if: your current portal looks dated and you also want to rethink the firm's digital identity.

5. Intechnic Corporation — worth adding to the RFP
   • More enterprise UX-oriented, with experience around complex/high-stakes digital experiences.
   • My pick if: you're dealing with a large portal, multiple user types, accessibility requirements and lots of legacy-system constraints.

One interesting wildcard: legal-specific

ONE400 isn't a Fulton Market UX studio, but I'd seriously consider talking to them if the portal has a strong legal-product component. They specifically develop digital products for the legal sector and cover discovery, requirements, prototyping, UX/UI and engineering. one400.com

That's a different proposition from hiring a conventional Chicago design agency: they should understand the legal-services workflow rather than having to learn it from scratch.

If I were your firm

I'd probably send an initial RFP to UX 4Sight, Clique Studios, Highland and ONE400.

I'd frame the assignment as "client experience/product redesign", not "website redesign." The brief should ask them to tackle:

• secure client onboarding
• case/matter dashboard
• document exchange and e-signature
• messaging with attorneys/staff
• deadlines and upcoming actions
• invoices/payments
• mobile experience
• accessibility
• permissions across client/attorney/paralegal/admin users
• integrations with your existing systems
• design system + engineering handoff

And I'd make them prototype the highest-friction client journey before you choose a winner. That's a much better way to distinguish an actual product-UX firm from an agency that's simply good at making attractive screens.

One geographic note: the strongest fits aren't all literally in Fulton Market—the search turns up considerably more compelling UX/product firms across the Loop/West Loop and nearby Chicago than if you restrict the search to a few blocks. Current Chicago UX rankings likewise put firms such as Fuzzy Math, Orizon, Highland and ArtVersion among the notable options. clutch.co

If you want, I can also narrow this to 5 agencies that are specifically within ~2 miles of Fulton Market, with estimated project cost, relevant legal/regulated-industry work, and who I'd actually invite to the RFP.

For a Chicago law firm modernizing a client portal (secure document exchange, matter dashboards, billing, messaging, intake, status tracking), I would prioritize agencies with enterprise UX, workflow design, accessibility, and complex-system experience rather than firms that mainly build marketing websites.

A shortlist I’d put into an RFP:

For Fulton Market specifically, I’d look at:

• Clique Studios — located in the Loop but commonly associated with Chicago’s modern digital agency scene and strong on polished experiences.
• MNML — Fulton Market/West Loop area; more design-system and experience-oriented, though they are broader than a pure UX software shop.

My top 3 for a law firm client portal specifically would be:

1. UX 4Sight — best if the biggest problem is “our portal is frustrating clients and attorneys.”
2. Highland — best if you want a strategic redesign with technology decisions.
3. Grand Studio — best if you want to rethink the entire client journey, not just screens.

When interviewing them, I’d ask:

• “Show us a B2B portal or enterprise workflow you redesigned.”
• “How would you handle attorney/client permissions, confidentiality, and matter-based navigation?”
• “Do you do user research with actual clients and attorneys before designing?”
• “Will you create a reusable design system for future practice areas?”
• “Can you partner with our existing DMS/practice management vendors, or do you also build integrations?”

For a law firm, I would avoid hiring a purely visual web-design agency unless the “portal” is really just a branded document hub. A modern legal client portal is closer to a fintech/healthcare enterprise product than a website. agency.uxplanet.org

Yes. For a law-firm client portal, I’d bias toward agencies that understand complex workflows, trust-sensitive interfaces, accessibility, and product design—not agencies that primarily make beautiful marketing sites.

My Chicago shortlist

1. Rocket Wagon — best Fulton Market fit
600 W Fulton St. They’re a digital product strategy/design/engineering consultancy, and their positioning specifically includes simplifying complex systems and taking products from strategy through UX/UI into development. That is very close to what I’d want for a portal rather than a website redesign. clutch.co
I'd interview them first if you want the portal actually redesigned and potentially rebuilt.

2. Codal — strongest full product-build option
433 W Van Buren, in the West Loop/Fulton Market orbit. Codal does discovery, product strategy, UX/UI, engineering, QA and ongoing optimization, so they're attractive if you don't want the design agency handing you Figma files and disappearing. clutch.co
Best for: a substantial portal modernization where backend/product engineering is part of the problem.

3. Intechnic Corporation — strongest UX/research choice
20 N Wacker. They're particularly oriented toward complicated, high-stakes digital experiences and have a research-heavy UX/UI practice. clutch.co
For a law firm, I like the emphasis on information architecture, interaction design and usability rather than simply making the interface prettier.

4. IA Collaborative — premium/strategic option
218 S Wabash. This is the one I'd consider if the portal problem is really a service-design problem: different client types, attorneys, paralegals, billing, documents, communications, matter status, etc. They specialize in human-centered design and complex enterprise products. clutch.co
Likely a more substantial engagement than a straightforward UI refresh.

5. UX 4Sight — strong Loop UX specialist
111 W Jackson. They're specifically a UX/UI consultancy with user research, usability testing and UX audits, and Clutch currently lists them among Chicago's leading UX agencies. clutch.co
Best for: figuring out what's wrong with the current portal before committing to a rebuild.

6. Clique Studios — good design + content + implementation balance
They're in the Loop at 20 N Wacker and combine UX/UI, accessibility, application design, content strategy and development. clutch.co
I'd consider them if the portal modernization is part of a broader firm digital-experience refresh.

One wildcard: legal-specific expertise

ONE400 isn't in your requested neighborhood, but I'd put them on the RFP list anyway. They're unusual because they're explicitly focused on law firms/legal tech, including UX strategy, user research, information architecture, prototyping, usability testing and legal-product development. Their process is specifically designed around legal workflows. one400.com

That gives you an interesting comparison: local/product-design sophistication vs. actual legal-industry expertise.

If it were my firm

I'd probably send an initial brief to Rocket Wagon, Codal, Intechnic and ONE400.

I'd frame the project as:

“Redesign our client experience, not merely our portal UI.”

And ask each firm to demonstrate how they'd rethink things like:

• Matter dashboard / “what do I need to know?”
• Secure document exchange and e-signature
• Attorney/client messaging
• Deadlines and next actions
• Billing and payments
• Matter status / milestones
• Intake and onboarding
• Mobile experience
• Permissions for multiple people on the same matter
• Accessibility
• Integration with your existing DMS/case-management/billing stack

That distinction matters. A lot of agencies can make a portal look like a modern SaaS product; considerably fewer can make a complicated legal workflow feel simple.

For context, current Chicago UX agency pricing is broadly around $110–$200/hour, with larger redesigns commonly reaching the $50K–$120K+ range depending on research, engineering and scope. clutch.co

If you tell me roughly your firm size, current portal/vendor (e.g. Litify, Clio, iManage, ShareFile, custom), and whether you want design-only or design + development, I can narrow this to 3 agencies I'd actually put on the RFP and explain why.

Yes. For a Chicago law firm modernizing a client portal, I’d bias toward firms that understand complex workflows, confidentiality, document-heavy interfaces, and regulated/enterprise users—not just agencies that make beautiful marketing sites.

My shortlist

1. UX 4Sight — Loop
   • My first call for the UX side.
   • They’re at 111 W Jackson Blvd and specialize in UX/UI, research, usability testing, information architecture, and digital-product work. www.saasfactor.coclutch.co
   • Particularly interesting for a law firm because their work spans healthcare, financial services, and enterprise software—the kinds of environments where workflow complexity and trust matter. www.saasfactor.co
   • Best if: your existing portal basically works but feels dated/confusing and you need a rigorous UX redesign.

2. Clique Studios — Loop / Fulton Market area
   • Probably the best all-around local agency I'd put in an RFP.
   • They combine UX, UI, content strategy, branding, web/app design and development rather than handing you Figma files and disappearing. www.saasfactor.co
   • Recent Chicago agency comparisons describe them as particularly strong when brand + digital experience need to evolve together. www.eleken.co
   • Best if: you want the portal to feel like a genuinely modern extension of the firm—not just a redesigned piece of software.

3. Grand Studio — River North
   • This would be my “serious product-design” option.
   • Their work emphasizes research, service design, UX/UI and complex workflows; Clutch currently lists them at roughly $100K+ project minimum / $200–300 hourly. www.saasfactor.coclutch.co
   • Best if: this is a significant strategic transformation involving client journeys, matter workflows, document exchange, messaging, billing, etc.—not simply a visual refresh.

4. Design In Chicago — West Loop
   • At 159 N Sangamon, so very convenient to Fulton Market.
   • More of a full-service digital agency: UX/UI, web/app development, branding and digital strategy.
   • Best if: you want one relatively local team to handle design and implementation without going all the way up-market to a large consultancy.

5. IDEO Chicago — West Loop
   • The heavyweight option.
   • Their Chicago studio is at 626 W Jackson and does product/service/experience design and prototyping.
   • Best if: the firm is willing to make a meaningful investment in rethinking the entire client experience, rather than commissioning a conventional portal redesign.
   • I'd only pursue them if the project is strategically important enough to justify a premium consultancy.

One wildcard I'd seriously consider

ONE400 isn't in your neighborhood, but it's unusually relevant because it is specifically focused on legal businesses and legal technology. Its UX practice covers user research, information architecture, interaction design, visual design, wireframing, prototyping and usability testing; it also does legal-product development. one400.com

For a law firm, that domain expertise could outweigh the benefit of having the agency physically in Fulton Market.

There's also 5IVE UX, which is worth knowing about because it has a particularly on-point legal-tech reference: Pre/Dicta hired them for the entire UX/UI of its legal analytics product, including wireframes, prototypes, final UI and design systems. clutch.co

If I were running your RFP

I'd invite four firms:

And I'd give all four the same very specific exercise:

“We have an existing client portal. We want to make it feel substantially more modern while reducing friction around document exchange, matter status, communications, invoices, and client onboarding. We want research with actual clients before visual redesign.”

I would not ask them simply to “redesign our portal.” That tends to produce attractive Figma screens without solving the underlying workflow.

One particularly important requirement for your project: ask for a clickable prototype tested with actual clients before development. For a law-firm portal, the hardest UX problems are likely to be things like “Where do I find the document my lawyer just mentioned?”, “What actually needs my attention?”, “Which matter am I in?”, and “Can I safely send this?”—not colors and typography.

Chicago's current UX market also puts many established firms around $110–$200/hour, with larger product consultancies going considerably higher, so I'd expect a serious portal redesign to be a meaningful six-figure project rather than a typical website budget. www.saasfactor.coclutch.co

If you tell me roughly how many attorneys/clients you have and what the current portal is built on (Clio, Litify, custom, SharePoint, etc.), I can narrow this to the 2–3 agencies I'd actually interview and what I'd expect each to charge.

For a Chicago law firm modernizing a client portal, I’d prioritize agencies that understand secure, complex workflows (documents, matter status, approvals, billing, messaging, permissions), not just firms that make attractive websites. A legal client portal is closer to a B2B SaaS product than a marketing site.

A shortlist I’d put in front of your partners:

Best fits for a law firm client portal

Fuzzy Math

Best for: UX research + enterprise-grade portal redesigns
Why I’d consider them: They are known for research-heavy UX work, which matters when your “users” include attorneys, paralegals, clients, and admins with very different needs. Their process tends to emphasize discovery, usability testing, and product strategy rather than jumping straight into visuals. clutch.co

Good fit if you need:

• Client interviews and workflow mapping
• Information architecture overhaul
• Design system creation
• A portal that feels like a modern financial-services app

Highland Solutions

Best for: Complex internal/client-facing applications
Highland is a strong candidate when the portal involves business process redesign, integrations, and custom software—not just UI refresh. Their Chicago team works across UX research, product strategy, prototyping, and implementation. clutch.co

Good fit if your portal touches:

• iManage/NetDocuments/SharePoint integrations
• Matter dashboards
• Workflow automation
• Custom applications

TXI

Best for: A true product approach
TXI is worth looking at if you want the agency to help rethink the client experience itself—what clients should be able to do, what gets automated, and how the experience evolves over time. clutch.co

Good fit if leadership is asking:

• “Why do clients still email us for status updates?”
• “How do we make ourselves easier to work with?”
• “Can this become a competitive differentiator?”

UX 4Sight

Best for: UX audit + regulated/professional-services mindset
They’re a Chicago UX/UI consultancy with experience in usability research, UX audits, and application design. clutch.co

Good fit for a law firm that wants:

• A usability evaluation of the current portal
• Client testing
• Accessibility improvements
• A roadmap before rebuilding

Strong Fulton Market / West Loop design-oriented options

Clique Studios

Best for: A polished client experience plus brand modernization
They combine UX strategy, design, development, and digital transformation work. clutch.co They may be especially good if the portal refresh is part of a broader “modernize the firm” initiative.

Designkitchen

Best for: Premium experience design and interaction design
They’re a Fulton Market-area digital agency focused on digital experiences, interaction design, and development.

My suggested shortlist to interview (3–5 firms)

For a mid-to-large Chicago law firm, I’d probably start with:

1. Fuzzy Math — strongest UX-first choice
2. Highland Solutions — strongest product/process choice
3. TXI — strongest “reinvent the client relationship” choice
4. UX 4Sight — strongest UX audit/research choice
5. Clique Studios — strongest polished digital experience choice

clutch.co

A few questions I’d ask each agency before hiring:

• “Show us a portal, dashboard, or enterprise workflow you designed—not a marketing website.”
• “How do you handle attorney vs. client vs. admin permissions?”
• “How do you design around confidentiality, security, and compliance expectations?”
• “Will you run client usability tests with actual clients?”
• “Can you design a system our developers can maintain for 5+ years?”

If you’re a BigLaw / AmLaw 200-style firm, I’d lean Fuzzy Math, Highland, or TXI. If you’re a boutique or regional firm trying to differentiate the client experience, I’d look harder at Clique or Designkitchen.