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. The Second City’s tech sector has grown by 18 percent over the past decade, adding more than 106,000 direct jobs and nearly 150,000 indirect jobs, according to the Chicagoland Chamber of Commerce . The city’s universities produce more computer science graduates than anywhere else in the US.…