top 10 coolest companies to work for in chicago

By o.c. tanner


Famous for great pizza, multiple professional sports teams, Oprah, and the Magnificent Mile, Chicago always seems to have a great buzz about it. America’s third most populated city has attracted an abundance of awesome companies that take employee appreciation to the next level. Let’s take a peek at the 10 coolest companies to work for in Chicago.

Tasty Catering


Tasty Catering has helped Chicago gain its reputation for excellent food. Besides providing quality cuisine, this catering company is also a cool place to work. Employees receive regular bonuses and awards for reaching their company’s goals. Tasty Catering also gives its workers free lunch every day. Excellent wages, great benefits, bonuses, and free lunch all make Tasty Catering an obvious choice for this top ten list.



The ever-growing ad agency, Tris3ct, is another clear-cut choice for our cool company list. Its nearly 100 employees enjoy working in an open, loft-styled office and having a voice in the company. During meetings, the company’s executives expect to hear from even the lowest ranked employee. Tris3ct gives its workers a paid comprehensive health care plan and a “perk du jour”—an employee indoor soccer team, Iron Ch3f competitions, and an employee art gallery. As if that’s not enough, Tris3ct is also known to have spontaneous team-building exercises like Jenga.

SWC Technology Partners


SWC is a team oriented company. They have a reputation for being loyal to their employees, giving their workers a lot of exposure to different environments and technology, and organizing a lot of fun, expensive after hour activities. In the company’s quest to help their employees live balanced lives, SWC organizes happy hours,  lunch activities, employee talent shows, trivia contests, and even dodgeball games. It’s safe to say that SWC is one of the coolest companies in Chicago.

Red Frog Events


Any company that has a $100,000 tree house is bound to be a crazy fun place to work. Red Frog employees are allowed to work in this tree house or anywhere else around the office. On their breaks, workers can enjoy the in-house zip line, foosball tables, or even grab a free beer. Seriously. Red Frog employees also enjoy unlimited vacation time, a 401k, and a health plan with no deductible. When looking to hold a meeting, employees are encouraged to use a table surrounded by swings or one made of LEGOS.  What’s not to love in that kind of environment? Well done, Red Frog. Well done.



Nitel, a company that provides telecom services to rural areas, holds at least one major activity for its employees every month. Some past activities include an office massage day, Cubs games, and even a beach volleyball tournament. Nitel also hosts an employee 5k run/walk  and donates all the proceeds to charity.

Model Metrics


Model Metrics trusts its employees to get the job done, no matter where they are. Many of its workers use  subsidized iPads and smart phones to work from wherever they are. The company also allows employees to take as much time off as they want, as long as they fulfill their job requirements. The new office building doesn’t have any offices, either. Employees can sit wherever and with whomever.

Milhouse Engineering and Construction Inc.


Milhouse Engineering and Construction is all about Fridays. Every Friday is called “Orange Friday”, and employees are encouraged to wear their best and brightest orange clothing. Whoever wears the most orange (one of Milhouse’s primary colors) gets a reward that day. It could be cash or paid time off.The company’s CEO also has a lunch delivered to the office every other Friday. Plus, with a monthly happy hour event at various local restaurants and bars, Milhouse works hard to make sure  its employees feel appreciated.



If vacation is a priority for you, kCura is the place to work. Its employees get 18 paid days off, plus another 11 paid holidays. That’s essentially a whole month of PTO! Throw in a lunchroom with darts, a game room, and a ping-pong table, and kCura is looking like a pretty cool place to work. In addition to the fun workplace environment, kCura throws parties and has activities outside of work. Monthly happy hours, cook offs, and family picnics help employees enjoy time away from work, as well.

Assurance Agency


At Assurance, a property and casualty insurance company, having a life/work balance is key.  The company has multiple staff appreciation days, where the CEO and other executives go out of their way to make sure  employees know how much their work is valued. They have had fresh fruit delivered, dance classes, and even an massage day. Employee wellness programs are also important at Assurance. The company provides its employees with exercise classes, a 5k run, and nutrition seminars to help improve wellness at work.

Centro LLC


As an employee at Centro, you can expect yoga classes, fresh fruit, concerts, basketball games and more. Check out this video where employees brag about what a cool place it is to work. Besides these perks, Centro also provides employees with a ton of benefits and lots of time off, too—15 paid days off, 10 personal days, paid holidays, paid maternal and paternal leave, tuition reimbursement, and a three week paid sabbatical after your first year. Workers even get a free gym membership.

Whether it’s unlimited time off, free drinks, or employee appreciation days, it’s easy to see why these companies made our top ten list of coolest places to work in Chicago. Interested in other cool companies in the U.S.? Check out which organizations made our lists in Dallas, Philadelphia, Seattle, and Boston.

Categories: Culture, Work We Love

Moore Onich

This list is nice but, how do you pick the companies for this list? If I recall Kcura has a lot of unhappy former employees. Some of the reviews on are ugly. If your big selling point is the PTO (The time you spend away from work) and the “parties” then what does that say? It says you don’t have much to say about how the company is actually run. And by the way….How a company is run is what makes and breaks a company. In this case, the company is actually not run very well, has poor management, and has a reputation for dishonesty. Also, while they have this really great mission statement that they put all over the walls and preach about; They prefer the do as I say not as I do method. Also, they have a high turnover rate that they manage to hide from people by sweeping it under the rug. Next time you might want to do a little more digging.

Tuesday, October 29th, 2013 07:17 pm GMT -6   |   Reply   |  
O.C. Tanner

Hi Moore. Thank you for your comment. We do check reviews on as well as contacting the companies directly. The list is then further vetted by a third-party firm which looks at other publicly available information as well as the social profile and activity of each company (to further vet what employees themselves are saying.) The company’s employee benefits and celebrations, recognition rewards, and programs are all taken into consideration.

Wednesday, October 30th, 2013 11:04 am GMT -6   |   Reply   |  

How can a company submit an application to be considered as one of the cool places to work?

Thank you!

Wednesday, May 20th, 2015 08:00 am GMT -6   |   Reply   |  
O.C. Tanner

Hi Rebecca. Click here to tell us why your company is one of the coolest to work for!

Wednesday, May 20th, 2015 09:12 am GMT -6   |   Reply   |  
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