While most movies set in Chicago show the iconic shots of the Willis Tower and Wrigley Field, these movies go above and beyond to really bring the Windy City to the forefront. Beyond the tourist attractions, museums, and hotspots, learn about what real life in Chicago is about.
John Cusack’s character is just a regular guy doing regular Chicago things. A ton of real businesses are featured in this movie, like Schubas, the Double Door, and Music Box Theater. What lends this movie even more street cred is that Cusack grew up in the Chicago suburbs and spent a lot of time in Wicker Park.
This movie not only takes place in Chicago, it was largely filmed there. While many mob flicks are rooted here, this film takes the cake and really captures the essence of the city. There’s a lot of fiction to this film, but it embodies a wide variety of Chicago history and culture.
This flick goes where most tourists don’t—Chicago’s South Side. It depicts a cruel Chicago winter and one of Chicagoans favorite holidays, St. Patrick’s Day. You’ll see some of the beautiful downtown, but also the gritty side of this city that makes it real and rounded.