Although not set in the city's limits, the John Hughes directed films Sixteen Candles, The Breakfast Club, Pretty in Pink (1986) (#1 film in U.S.), and Weird Science take place in the fictional town of Shermer, Illinois, which is based on Northbrook, Illinois.
A scene of Weird Science was filmed at Northbrook Court mall.
In The Matrix (1999, directed by the Wachowskis from Chicago), the subway sets were based on the CTA.
This is a list of video games in which a major part of the action takes place in the city.
This list does not count sports games or flight simulators, save for Pilotwings 64 and Tom Clancy's H.A.W.X.