Chicago Carves Out Spot as the City for Technology Services Deals

  • Thoughtworks, Ahead, West Monroe were targets for investors
  • City is now home to 26 unicorns, up from eight in 2016

A Michigan Avenue street sign in Chicago, Illinois, U.S., on Monday, May 24, 2021. 

Photographer: Taylor Glascock/Bloomberg
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U.S. technology investors have traditionally fixated on scouring the two coasts in search of the next startup ready for the big time. Now, instead of flying over Chicago en route to Silicon Valley, private jets are increasingly touching down in search of targets.

Chicago’s startup scene -- with a lift from some hometown boosterism -- has carved out an expanding niche in technology services that’s attracting outside investment.