Website Redesign Services in Chicago: 10 Mistakes to Avoid

Website Redesign Services in Chicago go far beyond cosmetic updates—they're about performance, conversions, and connecting with the city's diverse audiences. Whether you're a growing startup, a nonprofit, or a well-established B2B firm, your site needs to deliver results in a market known for its complexity and high expectations.

Still, many redesign projects fall short—not due to poor design, but because they skip critical steps, such as UX strategy, SEO integration, and understanding local user behavior.

Take Baltimore as a cautionary example. According to Technical.ly, the city's website redesign has been delayed for over two years and has cost taxpayers an additional $1 million. The last major update was in 2014, and with over 19,000 pages to migrate, the project has been marred by turnover, disorganization, and "unnecessary coding," highlighting what can go wrong without a clear strategy, planning, and execution.

In this blog, we'll walk through 10 of the most common (and costly) mistakes companies make when redesigning their websites—and how to avoid them. You'll also learn what to expect from a high-performing website redesign and why working with a trusted Chicago-based partner can make all the difference. 

Key Takeaways

• Website redesign services in Chicago must prioritize local relevance, mobile optimization, and SEO readiness.
• Avoiding common pitfalls—like ignoring performance data or underestimating content needs—saves time, money, and visibility.
• Your web partner matters. Local firms like Imaginary Landscape bring technical depth, business understanding, and regional insight to every project.
• A strategic redesign is not just an aesthetic upgrade—it's a business growth engine.

1. Neglecting Strategy in Website Redesign Services in Chicago

Many redesigns begin with one question: "How can we make the site look better?" That's not wrong—but it's only a small part of the conversation.

When form takes priority over function, businesses often end up with a visually appealing site that fails to convert, engage, or scale. A successful redesign starts with strategy, not surface.

Ask yourself:

• What's your main business goal?
• Are visitors converting into leads?
• Are they finding what they need?
• How is the current site performing on search engines?

The reality is, design and functionality are not trade-offs—they're co-dependent. As seen in a recent study of large-scale web ecosystems, sites that unify usability, backend efficiency, and consistent design outperform those that treat aesthetics as a siloed goal. An innovative redesign should marry both, because when function works, form becomes even more meaningful.

Website redesign services in Chicago that begin with strategy—not just style—help ensure your new website not only looks great but also performs at its full potential.

2. Overlooking Local User Behavior in Website Redesign Services in Chicago

Generic UX won't work—Chicago audiences require local relevance.

Chicago isn't just another U.S. metro. It's a dynamic intersection of corporate headquarters, cultural institutions, and fast-moving startups. The way users interact online here reflects that complexity. A templated website that might resonate in Dallas or Phoenix could fall flat in Chicago's fast-paced, mobile-heavy digital landscape.

Website localization—often associated with multilingual capabilities—goes beyond translation. In the context of website redesign services in Chicago, it means aligning your site with the local culture, behavior, and expectations. This includes everything from tone of voice and visual design to navigation structure and regional trust signals.

Many Chicago users access business websites on the go—during commutes, at events, or while working on-site. To meet them where they are, local redesign efforts should prioritize:

• Mobile-first user journeys
• Local SEO and Chicago-specific content
• Fast load times and accessibility across devices

Designing without considering these behaviors leaves a gap that more locally aware competitors will gladly fill.

3. Skipping Mobile-First Priorities in Website Redesign Services in Chicago

Mobile-first isn't optional—it's the standard.

 There are approximately 7.2 billion mobile users worldwide, and this number is expected to continue rising. In a city like Chicago, where decision-makers are constantly on the move, that global trend becomes a local expectation.

Mobile usage isn't just rising—it's reshaping how people interact online.

 As of late 2024, mobile devices (excluding tablets) accounted for over 62% of global website traffic. That's not a passing trend—it's the new default. Since 2020, smartphones have consistently driven the majority of web sessions worldwide.

In Chicago, this means users are engaging with websites on their terms—checking vendor info between meetings, browsing from coworking spaces, or reviewing proposals from a client site. If your site isn't optimized for mobile, you're not just behind—you're invisible to the users who matter most.

Yet many businesses still treat mobile optimization as a secondary concern during a redesign. That mistake can cost you leads, engagement, and local trust.

An innovative approach to website redesign services in Chicago starts by prioritizing:

• Mobile-first user journeys built for real-world usage
• Chicago-centric SEO and on-the-go content delivery
• Fast, responsive layouts that adapt to screen sizes and mobile networks
• Frictionless UX that encourages action—no matter where or how users find you

If you're redesigning for desktop first, you're designing for yesterday's web.

4. Focusing on Form Follows Function for Website Redesign Services in Chicago

The phrase "form ever follows function” wasn't coined for web design, but its relevance today couldn't be more clear.

Initially introduced by architect Louis Sullivan to guide the design of buildings, the idea is simple: purpose should drive design. In other words, how something works should shape how it looks—not the other way around.

That mindset applies perfectly to website redesign, especially for B2B companies. Flashy animations, cinematic visuals, and bold typography may win awards—but if they confuse your users, slow down your site, or hide your key message, they're not helping your business.

Websites that function well often convert better than those that simply look impressive. That includes:

• Clear, visible calls-to-action
• Fast load speeds and mobile responsiveness
• Logical navigation and user flow
• A visual hierarchy that guides decision-making
• Practical, intuitive search functionality

In a city like Chicago—where business moves fast and competition is fierce—your visitors don’t have time to guess what you offer. Form should support function at every step.

Design isn't just about aesthetics. It's about outcomes.
And the most effective website redesign services in Chicago start with function first—then build a form that works.

5. Ignoring SEO During Website Redesign 

When it comes to visibility, paid ads may grab quick attention—but SEO builds staying power.

Search engine optimization (SEO) remains one of the most effective ways to grow organic traffic and build long-term brand visibility. But here's the catch: unlike paid campaigns, SEO doesn't produce results overnight. It's a compounding strategy that pays off over time—typically between six months to a year. Still, when done right, it delivers sustainable growth and measurable ROI.

Nearly every modern business—from fast-growing eCommerce brands to local B2Bs—has integrated SEO into its marketing strategy. The numbers speak for themselves. The North American SEO services market alone was valued at $5 billion in 2023, with projected annual growth of 10% through 2030. As online competition intensifies, businesses of all sizes are investing in SEO to stay relevant and discoverable.

Yet during a website redesign, SEO is often the first thing sacrificed—and that's a costly mistake.

Failing to consider SEO during a redesign can wipe out years of earned rankings and organic visibility. In extreme cases, traffic plummets after launch because critical elements, such as redirects or metadata, weren't handled properly.

If you're exploring website redesign services in Chicago, ensure that SEO is integrated into the process from the outset. That means:

• Thoughtful redirect planning to preserve link equity
• Retention of on-page SEO elements like meta titles and descriptions
• Reviewing and improving URL structures for clarity and consistency
• Updating internal links to match the new navigation
• Refreshing content with search intent and keywords in mind

A well-executed redesign shouldn't reset your progress—it should accelerate it. The right Chicago-based partner will treat SEO not as an add-on, but as a foundational part of the redesign strategy. 

6. Failing to Audit Current Performance

You can't fix what you haven't measured. Many businesses jump into a redesign without evaluating their current site's analytics. That means they miss insights about:

• Which pages drive the most conversions
• Where users drop off
• How site speed affects bounce rate
• What content ranks well organically

Data should guide every significant decision in the redesign—from layout and CTA placement to page structure and content investment.

7. Underestimating Content Migration

Content often becomes an afterthought. However, once the new design is in place, the content must be updated, migrated, optimized, and formatted to fit the new layout.

If this isn't planned early, launch dates get pushed back, messaging becomes inconsistent, and SEO rankings suffer.

A smooth redesign includes:

• A content audit
• Keyword refinement
• Voice and tone alignment
• Smart formatting for UX and mobile

And yes—proofreading. Lots of proofreading.

8. Overcomplicating the Backend

Post-launch, your internal team needs to maintain and update the site. If the content management system (CMS) or admin dashboard is too complex, your shiny new site becomes a bottleneck.

Choose a partner who:

• Builds for user-friendliness
• Offers documentation and training
• Can customize CMS features based on your workflows

In other words: avoid tech debt in pursuit of unnecessary complexity.

9. Working With a Partner Who Doesn't Understand Your Market

Some agencies can build beautiful sites, but fall short when it comes to understanding your local market, industry dynamics, or internal operations.

That's where local advantage matters. Website redesign services in Chicago that are rooted in the city's business environment bring:

• Local SEO insight
• Familiarity with regional competitors
• An understanding of industry trends in healthcare, education, manufacturing, or finance—key verticals in Chicago

Your digital partner should feel like an extension of your team—not a vendor who parachutes in with a template.

10. Rushing the Launch Without Testing

You'd be surprised how many companies launch before checking basic functionality.

Pre-launch QA must include:

• Cross-browser compatibility
• Mobile responsiveness
• Form submissions and automations
• Page speed testing
• Accessibility review

Skipping this phase can lead to support tickets, damage brand perception, and hinder your launch momentum.

Why Work With Imaginary Landscape

When it comes to website redesign services in Chicago, few firms can match the experience and technical depth of Imaginary Landscape.

With over 25 years of experience in web development, Imaginary Landscape specializes in building high-performance websites using open-source technologies, especially Django and Python. Their team is based in Chicago, and they understand the unique blend of Midwestern pragmatism and enterprise-scale ambition that local businesses bring to the table.

Here's what sets Imaginary apart:

• Full-stack development tailored for performance, accessibility, and scale
• Deep SEO expertise is baked into every redesign.
• Security-first builds for healthcare, legal, and nonprofit sectors
• Custom backend functionality with intuitive CMS interfaces
• A collaborative process that respects your business goals and timelines

Whether you're scaling fast or modernizing after years of legacy architecture, Imaginary Landscape delivers websites that don’t just look better—they work smarter.

Frequently Asked Questions

Q: How often should a company redesign its website?
 A: Every 2–3 years, or whenever business goals, technology, or user behavior shift significantly.

Q: Can a redesign hurt our search rankings?
 A: Only if SEO isn't part of the process. A redesign done right—like Imaginary Landscape provides—can actually boost your visibility.

Q: What platform does Imaginary Landscape use?
 A: While they're experts in Django, Imaginary Landscape is platform agnostic—working seamlessly with systems like WordPress, dotCMS, and others to meet clients where they are and deliver scalable, high-performing solutions.

Q: Do we need to supply all the content ourselves?
 A: No. A good redesign includes content strategy, audits, optimization, and migration services to align with your goals.

Your Website: A Future-Proof Growth Engine

Your website isn't just a digital brochure—it's a growth engine. But growth doesn't happen by accident. Whether you're a startup or a legacy brand, redesigning your website without a clear strategy, local insight, and technical alignment often leads to missed opportunities.

From mobile-first priorities to search engine visibility and usability, each mistake can stall performance—or worse, undo years of progress. That's why working with a partner who understands both the technical and local dynamics of website redesign services in Chicago is more than a convenience—it's a competitive advantage.

If your current site isn't pulling its weight, an innovative redesign could be the reset your business needs. Done right, it's not just a new look. It's a more functional, findable, and future-proof online presence.

Ready to see what a smarter site could do for your business? Explore how Imaginary Landscape delivers website redesign services in Chicago that are built to perform—today, and in the long run.