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. FromA League of Their OwntoWhen Harry Met Sally, we take a look at some of the best classic films that were shot in the Windy City.
11A League of Their Own (1992)
Another film based on a true story,A League of Their Ownfollows 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.
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 ofWrigley Field, home of the real-lifeChicago Cubs. The girls are seen in one scene playing ball in the stadium, though it is called “Harvey Field” in the movie.
Related:Best Movies Set in Chicago, Ranked
10Never Been Kissed (1999)
This classic rom-com features a star-studded cast and certainly, some awe-inspiring locations.Never Been Kissedtells 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 theChicago 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.
9Ocean’s Eleven (2001)
This crime comedy features prominent names like Brad Pitt and George Clooney, and certainly packs a punch.Ocean’s Elevenfollows 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 asEmmit’s.
8Risky Business (1983)
Since its release in 1983,Risky Businesshas become astaple of the ’80s, thanks to its iconic performances and scenes. Starring Tom Cruise as teen-hustler Joel,Risky Businesssees 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 includingO’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!
7The Untouchables (1987)
The Untouchablesis 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 Untouchablesfollows lead character Elliot Ness and his team as they attempt to bust and take down the aforementioned criminal.
The filmmakers famously had somedifficulty transforming modern Chicagointo 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.
6Home Alone (1990)
Home Aloneis one of the few holiday entries on this list. But whether its Christmas or not,Home Aloneis 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 innearby suburbs,however, O’Hare International Airport also was used for some of the film’s key scenes.
5When Harry Met Sally (1989)
When Harry Met Sallyis 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 aNew 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 famousLake Shore Drive.
4My Best Friend’s Wedding (1997)
My Best Friend’s Weddingfollows 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 theDrake 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.
3Ferris Bueller’s Day Off (1986)
Ferris Bueller’s Day Offis 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 takescenter 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!
2Sixteen Candles (1984)
Molly Ringwald is now one of the most recognizable faces of the ’80s thanks to her performance in the beloved filmSixteen 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 Candlesis 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 thesuburbs 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!
