Chicago is a city defined by deep-dish pizza, Al Capone-like mobsters, and one giant stainless steel bean. With its beautiful architecture and a history that dates back centuries, Chicago is one of the best places to watch your creative ideas come to life. In fact, the city has lent itself to many different aspects of pop culture, most notably that of television and film. Many films use this classic American city as a backdrop; Chicago’s landscape and rich diversity has helped many productions to elevate the plot at hand and provide a setting that has elements of both urban and suburban lifestyles.
Movies of all genres have picked Chicago as the perfect place to film, and for good reason. From A League of Their Own to When Harry Met Sally, we take a look at some of the best classic films that were shot in the Windy City.
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11 A League of Their Own (1992)
Columbia Pictures
Another film based on a true story, A League of Their Own follows an all-women’s baseball team as they overcome public scrutiny and prove themselves to be worthy, strong athletes regardless of gender. The movie is set in the 1940s, taking place in Chicago amidst the second World War, raising the stakes of this film even higher.
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It is largely shot in Chicago, showcasing some of the typical houses and neighborhoods of the area. However, one of the biggest feature locations of the film is that of Wrigley Field, home of the real-life Chicago Cubs. The girls are seen in one scene playing ball in the stadium, though it is called “Harvey Field” in the movie.
10 Never Been Kissed (1999)
20th Century Fox
This classic rom-com features a star-studded cast and certainly, some awe-inspiring locations. Never Been Kissed tells the story of a girl named Josie, played by Drew Barrymore, who is sent back to high school to report on a story undercover. Throughout the movie, Josie reveals that not only has she never been in a real relationship, but also, that she has never had someone kiss her.
Being that main character Josie works for the Chicago Sun-Times, it makes sense that many of the office shots were taken right in Chicago. Furthermore, Josie’s house was also filmed and located in Chicago, though the address today is that of a private residence.
9 Ocean’s Eleven (2001)
Warner Bros.
This crime comedy features prominent names like Brad Pitt and George Clooney, and certainly packs a punch. Ocean’s Eleven follows main character, Danny Ocean, as he plots an elaborate heist against a Las Vegas Casino. With the help of a group of eleven henchmen, the team planned to take millions of dollars from one of the well-known casino owners, Terry Benedict.
Though Chicago is not known for its gambling and casino-based nightlife, movie producers were able to use the city in a stealthier way. They opted to feature a scene inside a Chicago pub known as Emmit’s.
8 Risky Business (1983)
Geffen Pictures
Since its release in 1983, Risky Business has become a staple of the ’80s, thanks to its iconic performances and scenes. Starring Tom Cruise as teen-hustler Joel, Risky Business sees a high school kid turn his home into a brothel while his parents are away unsuspectingly on vacation. Silly, sensual, and certainly raunchy, this movie has easily cemented its place as a timeless classic.
The main love interest, Lana, saw her apartment aptly located in the hustle and bustle of Chicago. Other Chicago staples were put to use in this film including O’Hare International Airport, where Joel sees his family off as they embark on their vacation. Chicago certainly added the right amount of flair for this flick!
7 The Untouchables (1987)
Paramount Pictures
The Untouchables is a 1987 film that was not only shot in Chicago, but set there as well. The film tells the true story of notorious gangster Al Capone. Set in the prohibition era in the heart of our favorite city, The Untouchables follows lead character Elliot Ness and his team as they attempt to bust and take down the aforementioned criminal.
The filmmakers famously had some difficulty transforming modern Chicago into Chicago of the past to fit this period piece, as Chicago is constantly evolving and changing with the times. However, they were able to create an epic movie that perfectly encapsulated life in Chicago during the prohibition era, helping this film to earn the mark of modern classic.
6 Home Alone (1990)
20th Century Studios
Home Alone is one of the few holiday entries on this list. But whether its Christmas or not, Home Alone is a perfect and funny watch for the whole family at anytime of the year! Here, we follow Kevin McCallister as he aims to protect his home from robbers after his family accidentally leaves him behind on a holiday vacation to France. The little boy is shown to be quite the ruthless protector as he sternly defends his family’s mansion from the bandits who aim to vandalize it.
One of the most notable aspects of the film is the McCallister house, a giant manor that was shown to be big enough to easily hold two families; it seemed to be the perfect target for the “Wet Bandits.” The mansion was located just outside of Chicago in nearby suburbs, however, O’Hare International Airport also was used for some of the film’s key scenes.
5 When Harry Met Sally (1989)
When Harry Met Sally is another classic romantic comedy entry on this list. The movie tells the tale of two people as they continuously encounter one another through the years. In the end, the two, who start out as friends, ultimately come together and wed in the film’s conclusion after sharing a New Year’s kiss.
Though much of the movie is set in New York City, Chicago certainly lends itself to a few key scenes. In the film, the two graduate from the University of Chicago, which is aptly used as a setting in the film. In another scene, the pair are seen driving down Chicago’s famous Lake Shore Drive.
4 My Best Friend’s Wedding (1997)
TriStar Pictures
My Best Friend’s Wedding follows main character Julianne as she attempts to break up her friend, Michael’s wedding out of jealousy. The catch is, she made a pact with her friend to get married if neither of the two had found anyone else to be with. Alone and growing more desperate to be with the man she loves, Julianne’s actions set off general chaos, making for an entertaining watch.
Practically the entire film was shot in and around Chicago. Some notable locations include the Drake Hotel, the Fourth Presbyterian Church, as well as O’Hare International Airport, which has made a cameo in quite a few entries on this list.
3 Ferris Bueller’s Day Off (1986)
Ferris Bueller’s Day Off is another classic ’80s film that makes it onto this list. Here, audiences watch the titular lead, Ferris, as he plays hooky from school on what initially seems like a normal day. However, the three main teens are shown gallivanting through the city of Chicago, reeking havoc, and having some much-needed fun.
Here, Chicago is on full display. Not only are there countless scenes where the city is used as a backdrop for the main leads, but it also takes center stage during the parade scene. Here, Ferris is seen singing and dancing atop a float through the lively city streets, with passersby joining in on the fun. The movie also features locations like Wrigley field, the Art Institute and Willis Tower!
2 Sixteen Candles (1984)
Universal Pictures
Molly Ringwald is now one of the most recognizable faces of the ’80s thanks to her performance in the beloved film Sixteen Candles. The film follows a young girl, Sam, on her sixteenth birthday as she pines for the local teen heartthrob, Jake Ryan. Complete with slapstick ’80s humor and annoying-but-love able sidekick named Ted, Sixteen Candles is nothing short of sweet and enjoyable. In the end, Sam gets the guy, but not without some drama and laughs along the way.
Sixteen Candles was primarily filmed at the suburbs outside of Chicago; both Jake Ryan’s and the Baker family houses were located in the surrounding areas. Even the middle school and the high school that is included in the film is located in the Windy City!
1 The Dark Knight (2008)
Warner Bros. Pictures
The Dark Knight is the 2008 Batman movie, made all the more iconic by the hideously horrible villain, the Joker, played by the late Heath Ledger. The story is set almost a year after the events of the first film, Batman Begins, and follows the Joker as he creates chaos and torment throughout the city of Gotham.
Here, Chicago is transformed into Gotham City, complete with gothic skyscrapers and city streets, filled to the brim with innocent civilians. The opening scene takes place in the beautiful Chicago Post Office, which is transformed into a bank that the Joker and his goons ransack. Batman, or rather, Bruce Wayne’s place of work is also stationed in Chicago, with Wayne Enterprises being set at one of the most commanding and gigantic buildings in the city!
