Chicago, Illinois is a large and sprawling city with a rich culture and deep history. The city has iconic landmarks and locations that make for great cinema. Legendary filmmaker John Hughes set virtually all of his movies in Chicago, which expressed his deep love for the city. Ferris Buellers’s Day Off, Home Alone, The Breakfast Club, and more all took place in the Windy City. There have been films of all genres that take place in Chicago including comedies, crime, romance, and coming-of age. Much of Christopher Nolan’s The Dark Knight was filmed on-location in Chicago, even though it obviously took place in Gotham City.

When you are picking a location for a film, you want a dynamic city with a lot to offer. The sprawling skyscrapers of Chicago make a fantastic backdrop for action and/or crime films. There are also beautiful rivers and landmarks that are the perfect fit for a romance. It is a beautiful city that has a lot to offer including amazing food, great tourist attractions, and more. If you are looking for a great city to take your next vacation, then look no further than Chicago. Before then, let’s dive into the best films that were set in the windy city.

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7 Ferris Bueller’s Day Off

     Paramount Pictures

The classic film Ferris Bueller’s Day Off, written and directed by John Hughes, follows Ferris Bueller (Matthew Broderick) and his epic day skipping school with his friends. It is a legendary teen comedy that is still quoted and referenced to this day. Ferris and his friends cruise around the streets of Chicago, and the film features several iconic landmarks including Wrigley Field and the famous scene at the Art Institute of Chicago. There is also the classic scene where Ferris puts on an epic lip-syncing performance at the parade.

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6 The Fugitive

     Kopelson Entertainment

Andrew Davis’ The Fugitive is a classic action film that features a thought-provoking story and memorable characters. The movie follows Dr. Richard Kimble (played by Harrison Ford) who is on the run from law enforcement after he is wrongly convicted of murdering his wife. Tommy Lee Jones plays Deputy U.S. Marshal Sam Gerard, who is leading the man-hunt. It is a solid crime film completely set in the Chicago area, and Jones gives one of the greatest performances of his career.

5 The Blues Brothers

     Universal Pictures

The Blues Brothers is a legendary comedy film starring John Belushi and Dan Aykroyd, based on the Saturday Night Live sketch. Of all the films based on SNL sketches, The Blues Brothers is certainly at the top. The movie follows the duo on a series of adventures throughout Chicago as they try to put their old band together to put on a charity show to save an orphanage. The movie is hilarious from beginning to end, and it also offers action and great music.

4 High Fidelity

     Buena Vista Pictures

The classic film High Fidelity was based on the 1995 novel of the same name. The film follows the relationship turmoil of a record store owner named Rob Gordon (John Cusack). We watch as he tries to break down every failed relationship while also managing his business. The movie gives you a good look at the music scene in Chicago, and it is entertaining from beginning to end. Cusack is at his very best, and his character breaks the fourth wall throughout the film, giving it a unique edge. At the same time, there are several great supporting performances from Jack Black, Lisa Bonet, Joan Cusack, and more.

3 The Breakfast Club

The Breakfast Club is a classic story following five very different teens sentenced to a Saturday detention at a Chicago high school. Each cast member represents a different high school clique, and it features fine performances from all of them. During their detention, each of the students learn truths about each other, form new friendships, and discover new love. It is a brilliantly written film with a great blend of drama and comedy.

2 Chicago

     Miramax Films

It should be no surprise that the adaptation of the famous Broadway musical earned a top spot on this list. Rob Marshall’s Chicago was a cinematic triumph that featured stellar performances, amazing set designs, and brilliant music. Adapting Chicago was no easy feat, but Marshall delivered the goods. The movie takes place during the Jazz Age in Chicago and gives us a good look into the show business and crime world of that time. The film took home six Academy Awards, including Best Picture. Catherine Zeta-Jones also, deservingly, won the Academy Award for Best Supporting Actress.

1 The Sting

     Universal Pictures 

The Sting is a legendary heist film, regarded as one of the greatest films of all time. The movie brings together the iconic duo of Paul Newman and Robert Redford, who play two con men who put together an epic con to rob a mob boss, played by Robert Shaw. The film is brilliant from beginning to end and Newman and Redford were at the top of their game. At the same time, it features a legendary score and several memorable supporting characters.