20 Chicago tech companies that have been around for over 20 years

by Andreas Rekdal
June 2, 2016

Part of the secret sauce behind current-day Chicago's success as a tech ecosystem is its long history of fostering innovative tech companies backed by solid business fundamentals. In fact, many of Chicago's biggest tech companies are over 20 years old. 

If you're wondering how you can build a company with lasting impact, look no further than these Chicago-based tech companies who've lived to see the big 2-0.


Founded: 1981

Having crunched numbers on athletic events for the past 35 years, STATS was way ahead of the curve when we entered the golden age of sports analytics. Today, the company provides data and insights to professional teams, leagues, reporters, broadcasters, fantasy leagues and fans of practically any sport worth watching.

Founded: 1984

Market analytics firm Morningstar got into the Big Data game before Big Data was cool. Founded as the publisher of a print investor guide, Morningstar launched its first digital product in 1997 and never looked back. Today, it is one of the best known brands in international finance.


Founded: 1989

Though best known for its runaway success with the CD-ROM game “You Don’t Know Jack,” Jellyvision actually got its start as a creator of children’s educational films. Today, the company uses its creativity and quirky sense of humor to create interactive applications that help employees make difficult decisions about confusing things like finance and healthcare options.


Founded: 1989

Founded as a shopping and delivery service in 1989, Peapod became one of the world’s first internet startups with the launch of Peapod.com in 1996. Today, the company delivers groceries in Illinois, Wisconsin and Indiana, as well as a number of metropolitan areas throughout the East Coast.


Founded: 1991

A provider of cloud-based enterprise communications solutions, Vail Systems has been around since before many of Chicago’s junior level developers were even born. But the company has stayed young and thriving by investing a substantial portion of its annual budget into research and development — and is currently hiring at a massive rate.


Founded: 1993

Founded by two developers back when the internet accounted for only one percent of telecommunications traffic, HS2 Solutions now delivers a suite of digital services including web and mobile development, UX design, marketing and analytics. The company’s portfolio of clients include brands like Spring Rewards, Zipcar and Dominos.


Founded: 1993

Another storied Chicago-based software company, ThoughtWorks employs 3,600 people distributed across every continent save for Antarctica. In addition to consulting companies on their software projects, the company licenses its proprietary tools for agile developers, helping them manage, test and deliver their projects.

Founded: 1994

As the name suggests, Trading Technologies builds trading software for professional traders, brokers, money managers and funds. Though founded more than two decades ago, Trading Technologies finds itself in the enviable position of its products having only become more relevant over time, as professional traders increasingly rely on software to do the heavy lifting.


Founded: 1995

With more than 3 million enterprise clients in 96 countries, Trustwave is a force to be reckoned with in the cybersecurity space. Notable moments in the company’s history include the 2005 launch of its SpiderLabs security research team, the release of its first annual Global Security Report in 2008 and SVP Phillip J. Smith’s expert testimony on cybersecurity before the U.S. Congress in 2014.


Founded: 1996

Though no doubt boosted by recent years’ shift toward online insurance enrollment, bswift has been leveraging technology to simplify health care enrollment for the past 20 years. Today, the company’s platform covers millions of consumers and has branched out to cover a broader range of companies’ HR needs.


Founded: 1978

Many tech companies boast decades in business followed by successful tech pivots in the 90s. But having launched its first piece of commercial software, Zoom Graphix, in 1979, Americaneagle.com has been a force to be reckoned with in digital tech for nearly 40 years. After a foray into building video games for the Apple II in 1982, Americaneagle.com found its calling as a full-service website developer and host. Some of its milestones include hosting a number of NFL teams’ websites through their Super Bowl appearances, as well as the registration system for President Obama’s first ever online town hall.


Founded: 1985

Known to many Chicago tech veterans as NAVTEQ, this navigation software company was an early pioneer in creating digital maps based on firsthand observation, as well as in allowing users to report map errors. Recently acquired by a consortium of German auto manufacturers, the company’s Chicago team is currently working on the foundations for autonomous cars.

Founded: 1987

A digital marketing agency centered specifically around the needs of the pharmaceutical industry, closerlook is only one year away from the big 3-0. Drawing on decades of experience in the field, the company helps pharmaceutical companies with traditional marketing as well as database management, user experience design and relationship management — all from a sweet loft space in River North.


Founded: 1989

An early entrant into the digital B2B marketing space, The Mx Group has been around for over 25 years. With a 100-person staff of marketing strategists, developers and creatives alike, the Burr Ridge-based company remains one of the biggest digital companies in Chicago.


Founded: 1992

A global finance firm with offices in London, New York, Montreal, San Francisco and Singapore, DRW’s headquarters remain in its native Chicago. Though its revenues come from trading, DRW is a technology company through and through, with custom software powering everything from its trades to its back office operations.


Founded: 1994

With services ranging from digital and mobile to in-store marketing, Upshot’s current clients include Google, Kraft, New Balance and Starbucks. In its 22nd year, the agency employs 150 people in its River North headquarters, and is regularly rated as one of the city’s best workplaces.

Founded: 1994

Clarity Consulting is a developer shop that specializes in platforms within the Microsoft ecosystem, including Windows, Lync, Xbox and Microsoft Kinect. The company’s services include design, prototyping and development, with clients like Intel, Kraft and Microsoft on the brag sheet.

Founded: 1994

Gorilla Group specializes in delivering the technology, hosting, design and strategy required to run a successful e-commerce business. The company offers services both in the B2B and the direct-to-consumer space, and has worked with brands like BucketFeet, PayPal, Inc. and Garrett Popcorn Shops.


Founded: 1995

Though the rise of e-commerce may have shed more light on the importance of retail analytics, online retailers like Amazon.com were hardly the first companies to use insights about consumer behavior to beef up bottom lines. Chicago’s ShopperTrak has been in the game since 1995 and currently track 20 billion visits to brick-and-mortar stores annually.


Founded: 1996

Major industrial players — whether they’re biotechnologists, contractors or utilities — rely on carefully planned routines to keep their employees safe and their environmental footprints in check. VelocityEHS — formerly known as MSDSonline — creates software that helps companies ensure compliance with those routines. And as emphasis on environmental impact has grown in board rooms across the country, so too has demand for this company’s services.

Images via listed companies.

Does your company have a story to tell? Shoot us an email, or follow us on Twitter @BuiltInChicago.

Chicago startup guides

Best Companies to Work for in Chicago
Coolest Offices in Chicago Tech
Best Perks at Chicago Tech Companies
Women in Chicago Tech