Last night we crowned the Coolest Companies winners at our annual Chicago Fest summer bash. There were food trucks, cornhole, life size Operation, a killer band, and 11 cool companies walked away with crowns and awards. It was a blast.

If you missed out on all the fun, here’s a breakdown of last night’s winners, along with excerpts from their nominations on what makes them a cool company. (You can learn more about how we picked the winners here.)

Datascope Analytics

  • Has a structured betting system to facilitate employees’ competitive instincts. People bet on things like which CTA train line is slower, whether a team member can complete 1,000 jumping jacks in an hour, or if a team member can taste the difference between different brands of bottled water.
  • Has an “Internal Talks” series, where the company gets together over lunch while a team member gives a talk. Topics range from a new tech skill that a team member just learned, to a summary of a completed project, to a practice session for a talk that the team member will give at an upcoming conference.
  • Other perks like unlimited vacation, a coffee bar, and Divvy memberships.

Maestro Health 

  • Plans bring your kids and bring your parents to work day, chili cookoffs, Cinco de Mayo pinata competitions, Whirlyball tournaments, and more.
  • Has a Frogger machine and a beach volleyball team.
  • Has an office scooter.


  • Is introducing an employee program in 2017 for a paid month-long sabbatical.
  • Is based out of Frank Lloyd Wright’s old office.
  • Is actively involved in the Chicago-community through Epsilon’s Community Outreach program, fully managed and run by a group of volunteer associates to sponsor and plan local events.


  • Has local beers on tap, a rooftop deck, free opera tours and events each month.
  • Has unlimited vacation, and the co-founders encourage everyone to unplug for a week.
  • Its most regular activity as a team is tasting all of the donuts Chicago has to offer.


  • Praises employee accomplishments with a 5’3’’ trophy that’s passed around.
  • Celebrate anniversaries with extended vacations and gifts.
  • In January the company takes a plane to an all-expense paid trip to a five-star resort in Mexico.


  • Has a streaming audio and video system where every team member is the DJ via Spotify.
  • Free Friday lunch and end-of-day beers.
  • Monthly anniversary/birthday bash.


  • Has an open space that houses the office, engineering workshop, test kitchen, a “tree house,” and an upcoming indoor herb garden.
  • Every day is bring your pet to work day, and there’s a mandatory three-week vacation policy.
  • Has a fully stocked test kitchen and a world class chef.


  • Has daily catered lunches.
  • Does company events like a battle at Whirlyball, a company BBQ 36-stories up on the Skybridge roof deck, and a team dragon boat race on the Chicago River.
  • Does an on-site biweekly Happy Hour.

Impact Networking (Reader’s Choice)

  • Has an Employee Innovation Program that encourages and formally recognizes ideas submitted by Impact employees that positively affect the company in one or more of the following areas: Growth, Culture, Efficiency, Savings, etc.

Allstate (Reader’s Choice)

  • Has free breakfast, drinks, healthy snacks, a ping pong table, and life-sized Jenga
  • Has an open mic night.
  • Gives employees discounts for activities around Chicago, personal vacations, apparel, cell phones and more.

Curiosity (Alumni Champ)

  • Has weekly team lunches, happy hours, and an indoor s’mores bar.
  • Holds gaming nights at Dave & Buster’s.

Image by Karis Hustad