7 Titans of Chicago Web Application Development

As a Chicago native and web developer, I often think about how the city’s tech scene has evolved. Some standout names in web development have played a big role in shaping it. This post reflects on a few of those Chicago-based innovations, highlighting their impact and what makes them pillars of Chicago’s tech history.

Visual Properties, L.L.C., a Chicagoland apartment locator company, launched their “Apartments Plus” website in 1997 to support its service offerings. Later that year, they decided to include listings spanning beyond the Chicagoland area. This attracted the likes of Classified Ventures, a joint venture between the companies behind The Chicago Tribune, The Washington Post, and other media giants, who acquired Apartments Plus and deployed it as their online apartment advertising solution for newspapers nationwide. Apartments Plus was then re-launched as Apartments.com in 1998, focusing solely on the Internet landscape.

This web platform revolutionized how renters searched for housing, replacing print classifieds with searchable, filterable online listings. At a time when the majority of Americans relied on newspaper ads, print booklets at grocery stores and gas stations, word-of-mouth, or simply driving around town, Apartments.com helped usher in the concept of web-based apartment hunting. As Internet usage grew in the late ’90s and early 2000s, the platform grew rapidly, becoming a trusted name for apartment listings. Its clean interface, national reach, and intuitive search tools brought millions of users, and eventually tens of millions of users, every single month.

In 2014, CoStar Group acquired Apartments.com for $585 million, marking a major milestone for Chicago tech and real estate innovation. This success paved the way for other real estate tech companies and showed how web-first thinking could scale traditional industries.

While Apartments.com was reshaping how people searched for rentals, another Chicago-born innovation was taking aim at the car-buying experience. In 1998, Classified Ventures, the same media-backed joint venture behind Apartments.com, launched Cars.com as a purpose-built online marketplace for new and used vehicles.

Also similar, while people were mostly relying on newspaper classifieds or weekend dealership visits, Cars.com introduced a radical shift that gave buyers the ability to browse listings from multiple dealerships, compare prices, read expert reviews, and contact sellers from their computer. It quickly attracted car shoppers nationwide.

Cars.com was more than just listings. It emphasized transparency and trust: integrating editorial reviews, pricing tools, and side-by-side comparisons long before these became industry norms. As dealerships saw the web’s growing importance, they leaned into the platform, which helped fuel its rapid expansion.

By the late 2000s, Cars.com had become a cornerstone of automotive retail. It ran Super Bowl ads, partnered with Yahoo! Autos, and grew into one of the most visited car shopping sites in the U.S. In 2014, Gannett acquired full ownership of Cars.com, valuing the company at $2.5 billion, and by 2017, it was spun off as a public company traded on the NYSE.

Cars.com’s success proved that web-native platforms could upend entrenched industries — even ones as big and legacy-driven as auto sales. From a Chicago launchpad, it helped rewrite the rules of car shopping for the modern age.

37signals was founded in Chicago by Jason Fried, Carlos Segura, and Ernest Kim in 1999. However, it was when David Heinemeier Hansson (DHH) joined in 2001, later becoming a co-owner of the company, when they built and released Basecamp. Basecamp is a web-based project management app whose success helped popularize the concept of “software as a service” prior to it becoming a mainstream model. Focused on simplicity and remote collaboration (years before “WFH” became normal), Basecamp gained over 100,000 users within its first few years, had paying customers in over 180 countries, and gained huge traction among agencies, startups, and teams.

More than just a product, Basecamp helped bring the now-legendary web development framework Ruby on Rails to the tech world. With virtually no outside funding, the company grew profitably, remained independent, and proved that a Chicago-based company could influence not only global team collaboration but also the open source community powering much of the Web.

Grubhub launched in Chicago in 2004 with a simple idea: let people order local food online. It was one of the first to aggregate restaurants into a web platform, helping pave the way for the food delivery boom. As smartphones emerged, Grubhub’s timing positioned it perfectly for mobile growth.

The company scaled rapidly, expanding to 4,000+ cities, even going international. It merged with Seamless, went public, and later sold to Just Eat Takeaway for $7.3 billion. Grubhub helped establish Chicago as a hub for consumer-facing web apps. It was one of the city’s biggest tech success stories of the 2000s and helped inspire a wave of local startups focused on logistics, convenience, and app-driven experiences.

In 2007, Braintree, founded by Bryan Johnson, entered the fintech space with a developer-first payment platform. Headquartered in Chicago, it quickly became the payments engine for some of the fastest-growing web startups, including Airbnb and Uber. Its robust APIs and mobile-first design made it a favorite for modern web apps. To me, its “developer-first” model felt like Stripe… before Stripe.

By 2013, Braintree was processing $12 billion annually, with $4 billion via mobile. It also acquired Venmo, expanding its reach in peer-to-peer payments. That same year, PayPal acquired Braintree for $800 million, integrating it into a global payments ecosystem.

Braintree’s success showed that Chicago could produce developer-centric, scalable platforms just like Silicon Valley. It became a symbol of how fintech, APIs, and mobile web development could thrive in the Midwest.

Groupon exploded onto the scene in 2008 with its daily deal model. What started as a local Chicago idea quickly became a global E-Commerce giant, with 50 million users in 500 cities by 2010. Groupon’s ability to scale web operations so rapidly was unprecedented at the time, and helped it serve as a serious inspiration for the entire Chicago startup scene.

Groupon priced its IPO at $20 per share, which gave the company an initial market value around $12.7 billion. In fact, by the end of the first trading day (Nov. 4, 2011), Groupon’s market capitalization rose to about $16.5 billion. These numbers highlight its huge influence on how people discovered and bought local services online. Groupon also helped popularize email marketing and viral sharing mechanics as key parts of web-based user growth.

The company became a cornerstone of Chicago’s web tech reputation, proving that bold, viral consumer platforms could be built and scaled right here in the Windy City.

Cameo, launched in 2017, brought a new kind of web product to the spotlight: personalized video messages from celebrities. Based in Chicago, Cameo became a cultural phenomenon, especially during COVID, when digital connections with talent became more widespread and meaningful.

By 2020, the platform had onboarded 30,000+ celebrities, and in 2021 it hit a $1 billion valuation. Its simple interface and user-friendly mobile experience made it one of the most popular Chicago startups in recent years.

Cameo represents the evolution of Chicago’s web scene: from classifieds and marketplaces to social-driven, creator-focused platforms. It shows how far the local ecosystem has come, embracing both traditional web infrastructure and modern entertainment tech.