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The Best Movies Set In Chicago And How To Watch Them

Steve Martin and John Candy in Planes, Trains And Automobiles
(Image credit: Paramount Pictures)

New York has a lot of great movies, and awesome Los Angeles movies have been at the center of some of cinema's best moments, but Chicago, a.k.a. “The Windy City,” a.k.a. “The Second City,” is home to some of the best movies of all time. Just look at films like The Blues Brothers, most of John Hughes’ timeless classics, and a whole slew of other movies set in the Midwestern metropolis. Hell, movies not even set in Chicago have used the city’s landmarks and architecture to help better tell their stories. 

Below is a list of some of the best Chicago movies that have ever been released in theaters, whether they be iconic comedies like Ferris Bueller’s Day Off, action thrillers like The Fugitive, and romantic comedies like High Fidelity. Let’s dig into this deep dish of great movies. 

Dan Aykroyd and John Belushi in The Blues Brothers

(Image credit: Universal)

The Blues Brothers (1980)

John Landis’ landmark 1980 comedy, The Blues Brothers, follows Elwood Blues (Dan Aykroyd) and “Joliet” Jake Blues (John Belushi) as they attempt to get their band back together in hopes of raising enough cash to save their former orphanage from being shut down. This beloved musical comedy checks all the boxes to be one the of best Chicago movies in that it shows the city’s unique charm, touches on its musical legacy, and also gives you a look at the most Chicago Police cruisers ever captured on film in the logic-defying chase sequence.

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Matthew Broderick in Ferris Bueller's Day Off

(Image credit: Paramount Pictures)

Ferris Bueller's Day Off (1985)

It is hard to find a movie that shows off the city of Chicago more than John Hughes’ Ferris Bueller’s Day Off. Once Ferris (Matthew Broderick), his girlfriend Sloane (Mia Sara), and best friend Cameron (Alan Ruck) escape the dullness of suburbia with one hell of a “senior skip day” in the big city, the movie plays like a tourism video for Chicago, and that’s not a dig. I’ve been to Chicago countless times over the years, but I still can’t help but point out all those famous locations with “Hey, that was in Ferris Bueller’s Day Off.”

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Macaulay Culkin as Kevin McCallister in Home Alone

(Image credit: 20th Century Fox)

Home Alone (1990)

Even though only one scene takes place in Chicago (The McAllisters running through O’Hare), it’s hard to deny Home Alone as being one of the best movies set in the Windy City. Just like he did throughout the 1980s, John Hughes does a masterful job of adding the Chicago flare to a movie that is primarily set in the suburbs. If you’ve ever ventured out to the small villages, towns, and cities in northern Chicagoland, you’ll see that Home Alone is about as Chicago as it gets.

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The Adventures in Babysitting cast

(Image credit: Buena Vista Pictures Distribution)

Adventures In Babysitting (1987)

With Adventures in Babysitting, Chris Columbus takes Chris Parker (Elisabeth Shue) and a group of kids under her care out of their comfort zone (suburbia) and into the heart of Chicago. But, unlike with Ferris Bueller’s Day Off, which featured one iconic landmark after another, this classic comedy shows the darker and seedier side of the city at night, which makes the movie all the better with its increased sense of danger and heightened stakes.

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Daniel Kaluuya in Judas and the Black Messiah

(Image credit: Warner Bros. Pictures)

Judas And The Black Messiah (2021)

Shaka King’s Academy Award-winning historical drama, Judas and the Black Messiah, with its standout performances by Daniel Kaluuya as Fred Hampton and LaKeith Stanfield as Bill O’Neal, is as beautiful as it is heartbreaking in its recounting of the final days of the Black Panther leader. Instead of shying away from one of Chicago’s darkest days, the movie approaches it head on with an unflinching narrative.

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Robert Redford and Paul Newman in The Sting

(Image credit: Universal Pictures)

The Sting (1973)

George Roy Hill’s The Sting, which is more than deserving of a remake, is one of the all-time great crime capers and follows schemers Johnny Hooker (Robert Redford) and Henry Gondorff (Paul Newman) as they get revenge on a Chicago crime boss. Set in Great Depression-era Chicago, this Best Picture winner gives you one of the best glimpses of life in the big city during that long-ago crime-ridden era, in addition to setting the tone for other crime capers later on.

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James Caan in Thief

(Image credit: United Artists)

Thief (1981)

In 1981, Michael Mann made his feature directorial debut with Thief, a dark, moody, and influential neo-noir crime thriller starring an on-top-of-his-game James Caan as a master jewel thief. If you haven’t seen this movie stop what you’re doing right and give it a try. Everything about it is damn near perfect, including its lead, the engrossing story, and the long list of supporting actors, specifically the menacing Leo (Robert Prosky). 

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Renee Zellweger in Chicago

(Image credit: Miramax Films)

Chicago (2002)

Rob Marshall’s 2002 sensational crime musical, Chicago, follows Roxie Hart (Renée Zellweger in one of her best performances) as she goes from aspiring singer to a media sensation after murdering a man who claimed he could help her career. This star-studded affair won a ton of awards upon its release and continues to fan-favorite with viewers of the movie and the Broadway hit on which it was based.

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Vince Vaughn and Jennifer Aniston in The Break-Up

(Image credit: Universal Pictures)

The Break-Up (2006)

A lot of the great romantic comedies over the years follow a similar path, but every now and then a movie like The Break-Up comes around and flips the script. Directed by Peyton Reed, this 2006 comedy follows Brooke Meyers (Jennifer Aniston) and Gary Grobowski (Vince Vaughn) as they split up and refuse to move out of their shared apartment. The two find themselves bickering and getting revenge in their cramped space as well on the streets (and waterways) of Chicago.

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Sean Connery and Kevin Costner in The Untouchables

(Image credit: Paramount Pictures)

The Untouchables (1987)

Brian De Palma’s 1987 historical crime drama, The Untouchables, follows Bureau of Prohibition agent Eliot Ness (Kevin Costner) as he teams up with Jim Malone (Sean Connery) in an attempt to nab Chicago crime boss Al Capone (Robert De Niro) once and for all. With a figure like Capone comes the territory of Chicago, which almost becomes another character with all its charm and personality.

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John Candy in Uncle Buck

(Image credit: Universal Pictures)

Uncle Buck (1989)

John Hughes’ seminal 1989 comedy, Uncle Buck, shows what happens when the city goes to the suburbs opposed to the other way around. When Buck Russell (John Candy) is asked to take care of his nieces and nephew while their parents are away for a family emergency, the cigar-smoking bowler is forced to leave his Wrigleyville apartment and help out at the family’s upper middle-class home, causing a clash of cultures and some of the best scenes in any ‘80s comedy.

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John Cusack in High Fidelity

(Image credit: Buena Vista)

High Fidelity (2000)

If you ever go to the Wicker Park neighborhood of Chicago, you’ll quickly think to yourself “doesn’t this look a lot like High Fidelity?” And that’s because its where a lot of Stephen Frears’ 2000 romantic comedy takes place (especially those Championship Vinyl scenes). One of the best John Cusack movies, the movie centers on record store owner and hopeless romantic Rob Gordon (John Cusack), as he tries to save his business and love life. Not your typical Chicago movie (no Sears Tower or Lake Shore Drive), but it does give you a glimpse at life outside “The Loop.”

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Tom Hanks in Road to Perdition

(Image credit: DreamWorks Pictures)

Road To Perdition (2002)

Although it takes place in various locations around the Great Lakes region, Sam Mendes’ 2002 crime drama, Road to Perdition, gets its start in Chicago. After his son finds himself in the wrong place at the wrong time, mob enforcer Michael Sullivan, Sr. (Tom Hanks) attempts to protect him from the dangers that await. This marvelous accomplishment in film does a tremendous job of incorporating multiple elements of Depression-era Chicago, and the crime that came with it, better than just about anything that came before it.

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The Eight Men Out cast

(Image credit: Orion Pictures Corporation)

Eight Men Out (1988)

One of the most infamous scandals in all of professional sports is told in great detail in John Sayles 1988 historical drama Eight Men Out. The star-studded movie, which features everyone from John Cusack to Charlie Sheen, follows the 1919 Chicago White Sox as they throw the World Series after being paid off by the city’s criminal elements. Though one of the best baseball movies of all time, this moving drama goes beyond the realm of sports and dives headfirst into how greed and corruption can push people to the brink. 

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Harrison Ford in The Fugitive

(Image credit: Warner Bros.)

The Fugitive (1993)

After being falsely accused of murdering his wife and being sent to a prison downstate, Richard Kimble (Harrison Ford) returns to Chicago in an attempt to find the real killer and clear his name. But, even though he knows the city better than just about anyone, Kimble is being chased by the unflinching and determined Samuel Gerard (Tommy Lee Jones) and his team of U.S. Marshals, in The Fugitive.

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Steve Martin and John Candy in Planes, Trains & Automobiles

(Image credit: Paramount)

Planes, Trains And Automobiles (1987)

John Hughes’ Planes, Trains and Automobiles could be on a list of the best road trip movies or the most iconic buddy comedies, but like this piece, all roads lead to Chicago in the beloved 1987 classic. The movie centers on Neal Page (Steve Martin), a high-strung advertising executive trying to get home for Thanksgiving, who meets and starts various misadventures with the irritating but well-meaning Del Griffith (John Candy). When the pair finally makes it the Windy City, the movie’s real magic starts.

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Hopefully, this list of the best Chicago movies will help you remember why the city has such a prestigious cinematic history. And, who knows, maybe that tradition will continue and Chicago will be featured in some of the upcoming 2022 movies.

Philip Sledge
Philip Sledge

Philip grew up in Louisiana (not New Orleans) before moving to St. Louis after graduating from Louisiana State University-Shreveport. When he's not writing about movies or television, Philip can be found being chased by his three kids, telling his dogs to stop yelling at the mailman, or yelling about professional wrestling to his wife. If the stars properly align, he will talk about For Love Of The Game being the best baseball movie of all time.