What to Do in Chicago If You’re Here for Business (2025)

Chicago always has something to prove. When it went up against New York for the 1893 World’s Fair, a New York Sun reporter called out its “windbag” campaigners. Illinois ended up hosting the fair, and Chicago embraced its new identity as the Windy City. That chip-on-the-shoulder energy still defines this metropolis, a city that builds, innovates, and competes like it has everything to lose.

Chicago’s tech scene is a diverse landscape that shouldn’t be slept on—but you probably know that. Over the…