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The Best Movies Set in Chicago

Posted on April 30, 2024   |   Updated on September 30, 2025
City Cast Chicago staff

City Cast Chicago staff

Tony Todd holds onto Virginia Madsen in a scene from the 1992 film “Candyman.”

Tony Todd holds onto Virginia Madsen in a scene from the 1992 film “Candyman.” (TriStar / Getty)

There are plenty of beloved films set in Chicago — including Minhal Baig’s recently released “We Grown Now,” a coming-of-age story set in Cabrini-Green in the ‘90s. We’re revisiting other Chicago films that make cinephiles laugh, cry, and think.

If you are looking for another movie set in Cabrini-Green, the 1992 horror cult classic follows an urban legend of a man with a hook arm haunting the public housing complex.

City Cast

'Candyman' Has Been Scaring Chicago for 30 Years

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The weather is warming up, and you might want to play hooky like Ferris Bueller in the iconic 1986 John Hughes movie. One local reporter actually followed Ferris’ itinerary in a day — squeezing in a Cubs game, Art Institute visit, and even the Von Steuben parade.

City Cast

It’s Time to Take a Day Off Like Ferris Bueller

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There’s no denying that the 1997 film starring Larenz Tate and Nia Long belongs in rom-com canon. Between all the poetry and on-screen chemistry, you’re guaranteed to be in your feels.

City Cast

Why ‘Love Jones’ Belongs in Rom-Com Canon

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More than 30 years after it first came out, the thriller starring Harrison Ford as a wrongly accused surgeon looking to clear his name and find his wife’s murderer still has us on the edge of our seats.

City Cast

Is ‘The Fugitive’ Chicago’s Greatest Movie?

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Steve Martin and John Candy in a scene from the 1987 film “Planes, Trains & Automobiles.”

Steve Martin and John Candy in a scene from the 1987 film “Planes, Trains and Automobiles.” (Paramount / Getty)

The Thanksgiving comedy starring Steve Martin and John Candy follows two accidental travel companions trying to make it back to Chicago for the holiday. Trust us: It’s funny year-round.

City Cast

‘Planes, Trains, and Automobiles’ Is the Best Thanksgiving Movie

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A CTA worker’s longtime crush ends up in a coma, and she gets mistaken for his fiancee by his family. If you dig transit and romance, this film starring Sandra Bullock is for you.

City Cast

Why Chicago is Perfect for a Holiday Rom-Com

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