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Top 20 Movies Filmed in Chicago

‘A League of Their Own’ (1992)
‘A League of Their Own’ (1992) | © Columbia / Kobal / REX / Shutterstock
While Chicago may not be the first place that springs to mind when you think movies, the Windy City has in fact helped to set the stage for some of the greatest films of all time.

From romantic comedies to science fiction, Culture Trip has compiled a list of some of the best movies filmed in Chicago, so you can run around the city as a Chicago Transit Authority token collector, a Chicago Sun-Times reporter or even Spider-Man, without ever having to get up off your couch.

‘My Best Friend’s Wedding’ (1997)

When Michael (Dermot Mulroney) tells his lifelong best friend Julianne, played by Julia Roberts, that he is getting married in four days, she immediately flies to Chicago and makes every attempt to stop the wedding. You can visit various film locations in the city, including the wedding church (the Fourth Presbyterian Church) and Julianne’s hotel (The Drake).

Editorial use only. No book cover usage. Mandatory Credit: Photo by Tri-Star/Kobal/REX/Shutterstock (5881590e) Cameron Diaz, Julia Roberts, Dermot Mulroney My Best Friend's Wedding - 1997 Director: P.J. Hogan Tri-Star USA Scene Still Comedy Le Mariage de mon meilleur ami © Tri-Star / Kobal / REX / Shutterstock

‘Sixteen Candles’ (1984)

In this 1980s coming-of-age teen comedy, writer and director John Hughes explores the struggles of the American teenager by taking the viewer through the events of Sam Baker’s (Molly Ringwald) 16th birthday. The movie was filmed mainly in Chicago’s North Shore neighborhoods.

Editorial use only. No book cover usage. Mandatory Credit: Photo by Universal/Kobal/REX/Shutterstock (5881806n) Molly Ringwald, Michael Schoeffling Sixteen Candles - 1984 Director: John Hughes Universal USA Scene Still Comedy 16 Candles Happy Birthday © Universal / Kobal / REX / Shutterstock

‘When Harry Met Sally…’ (1989)

This romantic comedy follows the chance encounters of Harry (Billy Crystal) and Sally (Meg Ryan), who have been friends ever since they graduated from the University of Chicago. Despite various other relationships, the two always come back to each other and ultimately ask the question, “Can a man and a woman be just friends?”

Editorial use only. No book cover usage. Mandatory Credit: Photo by Snap Stills/REX/Shutterstock (1933418a) Meg Ryan, Billy Crystal When Harry Met Sally - 1989 © Snap Stills / REX / Shutterstock

‘While You Were Sleeping’ (1995)

Sandra Bullock plays Lucy, a Chicago Transit Authority token collector, who is secretly in love with Peter (Peter Gallagher) and saves his life from an oncoming train. Peter falls into a coma, and Lucy follows him to the hospital, where a nurse misinterprets her when she mumbles that she “was going to marry him.” The movie includes various Windy City landmarks and proves that love really can be found on the L train.

Editorial use only. No book cover usage. Mandatory Credit: Photo by Mike Weinstein/Hollywood/Kobal/REX/Shutterstock (5879803b) Sandra Bullock, Jack Warden While You Were Sleeping - 1995 Director: Jon Turteltaub Hollywood Pictures USA Scene Still Comedy L'Amour à tout prix © Mike Weinstein / Hollywood / Kobal / REX / Shutterstock

‘The Boss’ (2016)

In this comedy, Melissa McCarthy is The Boss, who is sent to prison after being caught doing insider trading. When she gets out, she tries to rebrand herself as America’s biggest sweetheart. Most of the film was shot in Atlanta, but it is set in Chicago, and various iconic Chicago exteriors were shot for the film.

Editorial use only. No book cover usage. Mandatory Credit: Photo by Hopper Stone/Universal/Gary Sanchez Prods/Kobal/REX/Shutterstock (5881721f) Melissa McCarthy, Ella Anderson The Boss - 2016 Director: Ben Falcone Universal Pictures/Gary Sanchez Productions USA Scene Still Comedy © Hopper Stone / Universal / Gary Sanchez Prods / Kobal / REX / Shutterstock

‘Home Alone’ (1990)

Home Alone is an American classic. The Christmas comedy follows the story of a little boy (Macaulay Culkin) who is accidentally left home alone when his family goes to Paris for Christmas vacation. You can visit Kevin McCallister’s home just north of Chicago on Lincoln Avenue.

Editorial use only. No book cover usage. Mandatory Credit: Photo by Moviestore/REX/Shutterstock (1592500a) Home Alone, Daniel Stern, Macaulay Culkin Film and Television © Moviestore / REX / Shutterstock

‘The Dark Knight’ (2008)

In this sequel to Batman Begins, The Joker (Heath Ledger) wreaks havoc on the people of Gotham. In order to save his city, Batman (Christian Bale) fights him, but he also must face the problems thrown up by his own personal values and beliefs. The Joker robs Gotham National Bank, which is actually the Old Chicago Main Post Office. The funeral of the police commissioner is on South LaSalle Street, and the evacuation of Gotham happens at the Navy Pier.

Editorial use only. No book cover usage. Mandatory Credit: Photo by Warner Bros/Dc Comics/Kobal/REX/Shutterstock (5885982bk) Heath Ledger The Dark Knight - 2008 Director: Christopher Nolan Warner Bros/DC Comics USA Scene Still Action/Adventure The Batman - Dark Knight The Dark Knight, Le Chevalier Noir © Warner Bros / Dc Comics / Kobal / REX / Shutterstock

‘Risky Business’ (1983)

Risky Business is often considered the film that made Tom Cruise famous. When a Chicago teenager’s parents go out of town, he takes advantage of the time by having a little too much fun. But things take a turn for the worse when his mother’s glass egg is stolen and when he crashes his dad’s Porsche into Lake Michigan.

Editorial use only. No book cover usage. Mandatory Credit: Photo by Warner Bros/Kobal/REX/Shutterstock (5883482t) Tom Cruise Risky Business - 1983 Director: Paul Brickman Warner Bros USA Scene Still © Warner Bros/Kobal/REX/Shutterstock

‘High Fidelity’ (2000)

Rob Gordon (John Cusack), a former DJ, now owns a used record store in Chicago. Rob loves making top-five lists, and the movie recounts his top five break-ups, spurred by his most recent one with Laura who, to his satisfaction, does not make it on the list.

Editorial use only. No book cover usage. Mandatory Credit: Photo by Moviestore/REX/Shutterstock (1591364a) High Fidelity, John Cusack Film and Television © Moviestore / REX / Shutterstock

‘Divergent’ (2014)

Set in a futuristic Chicago, Divergent‘s society is divided into five different factions representing five different virtues. Teenagers have to decide which faction they want to stay in. When Tris Prior (Shailene Woodley) discovers she is divergent, meaning that she doesn’t fit into any category, she is faced with some tough decisions and an intense journey to save herself and hundreds of others.

Editorial use only. No book cover usage. Mandatory Credit: Photo by Red Wagon Entertainment/Kobal/REX/Shutterstock (5886189bu) Shailene Woodley, Theo James Divergent - 2014 Director: Neil Burger Red Wagon Entertainment USA Scene Still © Red Wagon Entertainment / Kobal / REX / Shutterstock

‘Ferris Bueller’s Day Off’ (1986)

Ferris Bueller (Matthew Broderick) believes that life’s too short to not skip a day of high school, so he creates an elaborate plan in order to avoid his parents and his principal. He convinces both his best friend and girlfriend to take the day off with him and they spend their new-found free time exploring the city of Chicago, including the Sears Tower (now the Willis Tower) and the Art Institute of Chicago.

Editorial use only. No book cover usage. Mandatory Credit: Photo by Paramount/Kobal/REX/Shutterstock (5885124m) Alan Ruck, Mia Sara, Matthew Broderick Ferris Bueller's Day Off - 1986 Director: John Hughes Paramount USA Scene Still Comedy La folle Journée de Ferris Bueller © Paramount / Kobal / REX / Shutterstock

‘The Vow’ (2012)

In The Vow, a terrible car accident turns a newly married couple’s life completely upside down. Paige (Rachel McAdams) ends up with severe memory loss and has no recollection of her husband, Leo (Channing Tatum). He tries his best to help her regain her memory and win her love back. Paige and Leo were married inside the Art Institute of Chicago.

Editorial use only. No book cover usage. Mandatory Credit: Photo by Moviestore/REX/Shutterstock (1587666e) The Vow - Channing Tatum and Rachel McAdams The Vow - 2012 © Moviestore / REX / Shutterstock

‘Transformers: Dark of the Moon’ (2011)

When the Autobots learn about the spacecraft hidden on the moon, they fight against the Decepticons in order to reach it first. The third installment of the Transformers movies, Transformers: Dark of the Moon was filmed in various locations, including Chicago, Florida and Moscow. The film includes a lot of stunt work and pyrotechnics that took place on Michigan Avenue.

Editorial use only. No book cover usage. Mandatory Credit: Photo by Paramount/Kobal/REX/Shutterstock (5883581k) Shia Labeouf Transformers - Dark Of The Moon - 2011 Director: Michael Bay Paramount Pictures USA Scene Still Action/Adventure Transformers 3 - La Face cachée de la Lune © Paramount / Kobal / REX / Shutterstock

‘Ocean’s Eleven’ (2001)

When Danny Ocean (George Clooney) gets out of prison, he creates a group with 11 of his friends and plans to rob three Las Vegas casinos at the same time. Even though the majority of the film is based in Las Vegas, Matt Damon’s character was recruited at Emmit’s Irish Pub in Chicago.

Editorial use only. No book cover usage. Mandatory Credit: Photo by Bob Marshak/Warner Bros/Kobal/REX/Shutterstock (5882784c) Don Cheadle, George Clooney, Shaobo Qin, Casey Affleck Ocean's Eleven - 2001 Director: Steven Soderbergh Warner Bros USA Scene Still Ocean's 11 / Oceans 11 © Bob Marshak / Warner Bros / Kobal / REX / Shutterstock

‘Spider-Man 2’ (2004)

In the sequel to Spider-Man (2002), Peter Parker (Tobey Maguire) finds himself in an intense battle with Doctor Otto Octavius.(Alfred Molina). Peter struggles to balance his roles as superhero and crime-fighter with being a friend, boyfriend and son. The runaway train scene was filmed on the Chicago L train.

Editorial use only. No book cover usage. Mandatory Credit: Photo by Moviestore/REX/Shutterstock (1618161a) Spider-man 2 (Spiderman 2), Tobey Maguire Film and Television © Moviestore / REX / Shutterstock

‘The Fugitive’ (1993)

Dr Richard Kimble, played by Harrison Ford, is wrongfully accused of murdering his wife. After he is tried, convicted and sentenced to death, he miraculously escapes on the way to prison. He runs all over Chicago, including through the St Patrick’s Day Parade and the Cook County Hospital, in order to find the real killer before the Chicago police can catch him.

Editorial use only. No book cover usage. Mandatory Credit: Photo by Stephen Vaughan/Warner Bros/Kobal/REX/Shutterstock (5882309k) Harrison Ford The Fugitive - 1993 Director: Andrew Davis Warner Bros USA Scene Still Action/Adventure Le Fugitif © Stephen Vaughan / Warner Bros / Kobal / REX / Shutterstock

‘Never Been Kissed’ (1999)

In Never Been Kissed, Josie Geller (Drew Barrymore) is an insecure journalist for the Chicago Sun-Times. She has never been in a relationship and never been kissed, but when her boss assigns her to go undercover at a her old high school for a report, all of that begins to change.

Never Been Kissed, 1999 © Suzanne Hanover / 20th Century Fox / Kobal / REX / Shutterstock

‘The Blues Brothers’ (1980)

When Jake Blues (John Belushi) gets out of prison, he tries to get his old band back together in order to save the Catholic boarding school where he and his brother grew up. The race to raise the money leads to high-speed car chases and run-ins with Nazis, Aretha Franklin, Ray Charles and James Brown. However, in their do-good efforts, they end up making more enemies than friends. The Palace Hotel Ballroom and the place where the Bluesmobile finally comes to an end can both be found in downtown Chicago.

Editorial use only. No book cover usage. Mandatory Credit: Photo by Universal/Kobal/REX/Shutterstock (5885886c) Dan Aykroyd, John Belushi The Blues Brothers - 1980 Director: John Landis Universal Pictures USA Scene Still Comedy © Universal / Kobal / REX / Shutterstock

‘Space Jam’ (1996)

This comic fantasy combines animation with live action. Michael Jordan agrees to help the Looney Tunes characters create a team and play a basketball game against the alien slavers in a competition that will determine their freedom. In the film (and in reality at the time) Michael Jordan plays for the Chicago Bulls.

Editorial use only. No book cover usage. Mandatory Credit: Photo by Moviestore/REX/Shutterstock (1613572a) Space Jam, Bugs Bunny, Michael Jordan Film and Television © Moviestore / REX / Shutterstock

‘A League of Their Own’ (1992)

The film is set during World War II. While the men were off at war, the owners of baseball teams decided to create women’s teams. Two sisters, played by Lori Petty and Geena Davis, join the first-ever professional all-female baseball league and have to sort out their own rivalry in order to see the team succeed. Team tryouts are held at Harvey Field, which is actually Chicago’s Wrigley Field.

Editorial use only. No book cover usage. Mandatory Credit: Photo by Louis Goldman/Columbia/Kobal/REX/Shutterstock (5882562b) Madonna A League Of Their Own - 1992 Director: Penny Marshall Columbia USA Scene Still Comedy Une équipe hors du commun © Louis Goldman / Columbia / Kobal / REX / Shutterstock