Stuck halfway between the cinematic hubs of New York and Los Angeles, Chicago, Illinois has come to represent the unique atmosphere of the urban midwest. Though, ironically, most of the Oscar-winning musical Chicago was shot in Toronto, Canada, the Windy City has played host to no small number of cinematic hits. Brian De Palma’s The Untouchables depicts an Al Capone-era Chicago within the city’s actual streets, capturing such famous landmarks as The Grand Army of the Republic Rotunda and the Chicago Theater movie house. Likewise, John Hughes’ Ferris Bueller’s Day Off is as much an ode to the Second City as it is to youthful spontaneity. While Ferris and his friends play hooky, they visit Wrigley Field, the Art Institute of Chicago and Sears Tower.Several upcoming films have also included Chicago in their roster of locations, including Marc Forster’s Stranger Than Fiction, Gabriel Range’s Death of a President and Clint Eastwood’s Flags of Our Fathers.

Other famous flicks with Chicago as their backdrop include:

Planes, Trains, and Automobiles
The Blues Brothers
A League of Their Own
Road to Perdition
North by Northwest