film The Best Chicago Movies  

Ranker Film
932 votes 80 voters 3.0k views 43 items Embed

List Rules Movies about or set in Chicago, Illinois

McCormick Place, the Lincoln Park Zoo, Western Avenue, the Harold Washington Library, the Oceanarium, the Field Museum – these are the things that come to mind when we talk about Chicago, Illinois. Often referred to as “The Windy City” or “Second City," Chicago is the setting for many Hollywood films. But what are the best Chicago movies? 

Since Chicago is such a large city and is home to some of the most iconic structures in the United States it only makes sense that movies like Mickey One, Medium Cool, and The Color of Money all feature this famous city. Whether you're in the mood for action, romance, comedy, or drama there's a Windy City film for you.

This list has the best movies about Chicago, ranked by film lovers and including: High Fidelity, Hoop Dreams, Ferris Bueller’s Day Off, Risky Business, The Dark Night, Barbershop, The Blues Brothers, The Fugitive, Public Enemies, Stir of Echoes, Cooley High, and Road to Perdition.

Vote up your favorite Chi-Town classic or add one you love that isn't already on the list.

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The Blues Brothers Carrie Fisher, Aretha Franklin, Steven Spielberg

75+ Celebrities Who Live in Chicago The Best Paranormal Movies Streaming on Hulu

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Ferris Bueller’s Day Off

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The Fugitive Julianne Moore, Harrison Ford, Tommy Lee Jones

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clash1977 added The Breakfast Club Judd Nelson, Molly Ringwald, Anthony Michael Hall

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Home Alone is listed (or ranked) 5 on the list The Best Chicago Movies
Home Alone Macaulay Culkin, Joe Pesci, John Candy

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Planes, Trains and Automobiles is listed (or ranked) 6 on the list The Best Chicago Movies
clash1977 added Planes, Trains and Automobiles Steve Martin, Kevin Bacon, John Candy

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The Untouchables is listed (or ranked) 7 on the list The Best Chicago Movies
The Untouchables Robert De Niro, Sean Connery, Kevin Costner

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The Dark Knight is listed (or ranked) 8 on the list The Best Chicago Movies
The Dark Knight Christian Bale, Morgan Freeman, Gary Oldman

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Sixteen Candles is listed (or ranked) 9 on the list The Best Chicago Movies
Sixteen Candles John Cusack, Molly Ringwald, Joan Cusack

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Risky Business Tom Cruise, Megan Mullally, Rebecca De Mornay

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High Fidelity is listed (or ranked) 11 on the list The Best Chicago Movies
High Fidelity Catherine Zeta-Jones, Bruce Springsteen, Jack Black

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Backdraft is listed (or ranked) 12 on the list The Best Chicago Movies
Backdraft Robert De Niro, Kurt Russell, Jennifer Jason Leigh

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North by Northwest Cary Grant, Alfred Hitchcock, Eva Marie Saint

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Road to Perdition Tom Hanks, Daniel Craig, Paul Newman

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clash1977 added The Sting Paul Newman, Robert Redford, Robert Shaw

The Best Movies About Disease Outbreaks These Disney Princess Were Absolutely Terrible Role Models

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Primal Fear Edward Norton, Richard Gere, Laura Linney

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clash1977 added Eight Men Out Charlie Sheen, Christopher Lloyd, John Cusack

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Bootsdad added Child's Play Brad Dourif, Catherine Hicks, Chris Sarandon

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When Harry Met Sally... is listed (or ranked) 19 on the list The Best Chicago Movies
When Harry Met Sally... Meg Ryan, Billy Crystal, Carrie Fisher

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Ordinary People Mary Tyler Moore, Donald Sutherland, Adam Baldwin

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About Last Night Demi Moore, Rob Lowe, Megan Mullally

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Public Enemies Johnny Depp, Christian Bale, Channing Tatum

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The Color of Money is listed (or ranked) 24 on the list The Best Chicago Movies
The Color of Money Tom Cruise, Paul Newman, Martin Scorsese

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Barbershop Ice Cube, Eve, Janina Gavankar

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Stir of Echoes Jennifer Morrison, Kevin Bacon, Illeana Douglas

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Soul Food Vivica A. Fox, Nia Long, Vanessa L. Williams

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My Best Friend’s Wedding

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While You Were Sleeping Sandra Bullock, Monica Keena, Bill Pullman

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clash1977 added Above the Law Sharon Stone, Steven Seagal, Pam Grier

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Candyman Virginia Madsen, Tony Todd, Vanessa A. Williams

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Call Northside 777 James Stewart, Thelma Ritter, Lee J. Cobb

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Nothing in Common Tom Hanks, Sela Ward, Jackie Gleason

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clash1977 added Mad Dog and Glory Robert De Niro, Uma Thurman, Bill Murray

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Cooley High Garrett Morris, Glynn Turman, Steven Williams

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clash1977 added The Package Tommy Lee Jones, Gene Hackman, Pam Grier

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Medium Cool Peter Boyle, Robert Forster, Peter Bonerz

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Only the Lonely Macaulay Culkin, John Candy, Maureen O'Hara

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Thief Willie Nelson, James Caan, Tuesday Weld

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Continental Divide John Belushi, Blair Brown, Tim Kazurinsky

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Mickey One Warren Beatty, Hurd Hatfield, Alexandra Stewart

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Mercury Rising Bruce Willis, Alec Baldwin, Kim Dickens

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His New Job Charlie Chaplin, Gloria Swanson, Ben Turpin