Chicago’s Commercial Real Estate Market for Startup Entrepreneurs

Due partially to the efforts of several private and public projects, Chicago commercial real estate is now receiving media coverage throughout the country. Although it’s not the top nationwide contender for city with the most startups, Chicago, IL is currently establishing its own respectable reputation for nurturing entrepreneurial concepts and bringing them to life… and that’s why now is a very good time to invest in Chicago office spaces in this flourishing startup city.

Listed below are four startup businesses representing every stage of the Chicago commercial real estate life cycle, with a brief caption on how they are succeeding.

chicago startup companies chicago commercial real estate startup june 22 2024

Rent Like a Champion

First stepping into the public eye after getting backed for $200,000 on TV’s Shark Tank, Rent Like A Champion has been assisting homeowners to lease their space for office usage ever since. The company has chosen to operate from Catapult Chicago, a not-for-profit business incubator in the entrepreneur-rich River North community. They reportedly love being integrated into a similar-minded neighborhood of entrepreneurs, where they can easily network and build professional relationships with other startups.

According to company CEO Mike Doyle, the fact that the space is shared doesn’t mean there aren’t ample opportunities for business owners to express their own customs and cultures. Because the company’s ventures revolve a lot around college football, they’ve adorned their space with the trademarks and mascots of their most profitable college towns. Although they have dodged paying the typically high River North rental fees for their office space, it still provides all the comforts the area is famous for, which includes convenient lunch locales, cafes, delis, high-end restaurants, and innumerable bars for unwinding after work.

BlueLine Labs

Full-scale iOS and Android design business BlueLine Labs continues to establish a reputation for its services in addition to its programs. Despite the company’s relative youth in the industry, it allots between 5% and 10% of its budget to cheap and free apps for law and not-for-profit businesses. Located near the Chicago Blue Line building in the River West area, its slightly obscure location equates to affordable rental fees, but without foregoing easy access to the downtown area.

According to CEO Reed Rawhouser, the business office layout allows workers to manage their work tasks, yet doesn’t make them feel in any way boxed-in. Instead, their office space is spacious, homey, and low-key, with a number of extra amenities including a full-sized kitchen, super-high ceilings, and high-end restrooms.


Rocketmiles is a newly renovated hotel booking agency that allows users to accumulate points for future discounts every time they stay in an approved hotel room. To engender a more communicative setting for employees, Rocketmiles tore down several walls and exchanged their single desks for long, multi-person tables. Walls that were not deconstructed are now used to split up some of the meeting rooms, which are all named after significant team-ups like “Winter 1904 Has Been Adjudicated,” an homage to their current Diplomacy matches.

For those who seek a short reprieve away from the desk, Rocketmiles has also built a book collection and audio lounge. New employees can request their preferred book and CD for every room, helping them to discover more about one another and find new content.

Director of sponsorships Daniel Fohrman believes location provided the motivating force behind their selection, as they are only a short distance from the popular Fulton Market and have quick access to CTA and Metra stations.


Finishing off the list is ContextMedia, which stands amongst Chicago’s fastest-growing tech businesses. Pioneering treatment products used in medical offices, they provide electronic room waiting monitors, cell phone apps, and checkup room notepads, all connected by pertinent, high-quality medical care content.

Commonly seen in different “Best Employer” lists, their office is loaded with ergonomic seats, yoga lessons, walking machines, table tennis courts, and video game rooms. Like any good business related to the medical industry would do, the company focuses a lot of its attention on the security and comfort of its staff members.

Featuring designs influenced by Charlie Green Studio’s Jason Hall, the office layout is open, well-lit, and modernized, with ceiling-to-floor windows that provide eye-popping, wide-range views of Chicago’s city lines. Even though a full-time cafe is on hand in the building, ContextMedia’s millennial-rich staff at its River North location will appreciate the easy access to the area’s varied selection of clubs, lounges, and cafes.

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