Entertainment The Best Chicago Movies  

Ranker Film
1.3k votes 129 voters 4k views 46 items

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.
list ordered by
1
69 8
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Carrie Fisher, Aretha Franklin, Steven Spielberg
The Blues Brothers is a 1980 American musical comedy film directed by John Landis and starring John Belushi and Dan Aykroyd as "Joliet" Jake and Elwood Blues, characters developed from ...more
2
70 10
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Charlie Sheen, Matthew Broderick, Jeffrey Jones
Ferris Bueller's Day Off is a 1986 American comedy film written, produced and directed by John Hughes. The film follows high school senior Ferris Bueller, who skips school and spends the day in ...more
3
47 6
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Julianne Moore, Harrison Ford, Tommy Lee Jones
This film is a 1993 American action film based on the 1960s television series of the same name created by Roy Huggins. The film was directed by Andrew Davis and stars Harrison Ford and Tommy Lee ...more
4
53 13
Home Alone is listed (or ranked) 4 on the list The Best Chicago Movies
Macaulay Culkin, Joe Pesci, John Candy
Home Alone is a 1990 American Christmas family comedy film written and produced by John Hughes and directed by Chris Columbus. The film stars Macaulay Culkin as Kevin McCallister, a boy who is ...more
5
47 12
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clash1977 added Judd Nelson, Molly Ringwald, Anthony Michael Hall
The Breakfast Club is a 1985 American coming-of-age comedy-drama film written, produced, and directed by John Hughes and starring Emilio Estevez, Paul Gleason, Anthony Michael Hall, John ...more
6
42 16
The Dark Knight is listed (or ranked) 6 on the list The Best Chicago Movies
Christian Bale, Michael Caine, Heath Ledger
The Dark Knight is a 2008 superhero film directed by Christopher Nolan, based on the DC Comics character, Batman. Bruce Wayne (Christian Bale), Police Lieutenant James Gordon (Gary Oldman) and ...more
7
33 11
The Untouchables is listed (or ranked) 7 on the list The Best Chicago Movies
Robert De Niro, Sean Connery, Kevin Costner
The Untouchables is a 1987 American drama film directed by Brian De Palma and written by David Mamet. Based on the book The Untouchables, the film stars Kevin Costner as government agent Eliot ...more
8
35 13
Planes, Trains and Automobiles is listed (or ranked) 8 on the list The Best Chicago Movies
clash1977 added Steve Martin, Kevin Bacon, John Candy
Planes, Trains and Automobiles is a 1987 American comedy film written, produced and directed by John Hughes. The film stars Steve Martin as Neal Page, a high-strung marketing executive, who ...more
9
27 10
Sixteen Candles is listed (or ranked) 9 on the list The Best Chicago Movies
John Cusack, Molly Ringwald, Joan Cusack
Sixteen Candles is a 1984 American coming-of-age comedy film starring Molly Ringwald, Michael Schoeffling and Anthony Michael Hall. It was written and directed by John Hughes.
10
31 15
Backdraft is listed (or ranked) 10 on the list The Best Chicago Movies
Robert De Niro, Kurt Russell, Jennifer Jason Leigh
Backdraft is a 1991 action thriller film directed by Ron Howard and written by Gregory Widen. The film stars Kurt Russell, William Baldwin, Scott Glenn, Jennifer Jason Leigh, Rebecca De Mornay, ...more
11
28 13
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Tom Cruise, Megan Mullally, Rebecca De Mornay
Risky Business is a 1983 American romantic comedy film written by Paul Brickman in his directorial debut. It stars Tom Cruise and Rebecca De Mornay. The film launched Cruise to stardom. It ...more
12
29 14
High Fidelity is listed (or ranked) 12 on the list The Best Chicago Movies
Catherine Zeta-Jones, Bruce Springsteen, Jack Black
High Fidelity is a 2000 American comedy-drama film directed by Stephen Frears and starring John Cusack and Iben Hjejle. The film is based on the 1995 British novel of the same name by Nick ...more
13
23 10
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Hoop Dreams is a 1994 American documentary film directed by Steve James and written by James and Frederick Marx, with Kartemquin Films. It follows the story of two African-American high school ...more
14
21 10
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Cary Grant, Alfred Hitchcock, Eva Marie Saint
North by Northwest is a 1959 American spy thriller film directed by Alfred Hitchcock and starring Cary Grant, Eva Marie Saint and James Mason. The screenplay was written by Ernest Lehman, who ...more
15
22 11
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Tom Hanks, Daniel Craig, Paul Newman
Road to Perdition is a 2002 American thriller film directed by Sam Mendes. The screenplay was adapted by David Self, from the graphic novel of the same name by Max Allan Collins. The film stars ...more
16
16 7
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clash1977 added Charlie Sheen, Christopher Lloyd, John Cusack
Eight Men Out is a drama film based on Eliot Asinof's 1963 book 8 Men Out. It was written and directed by John Sayles. The film is a dramatization of Major League Baseball's Black Sox scandal, ...more
17
18 9
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clash1977 added Paul Newman, Robert Redford, Robert Shaw
The Sting is a 1973 American caper film set in September 1936, involving a complicated plot by two professional grifters to con a mob boss. The film was directed by George Roy Hill, who had ...more
18
19 11
When Harry Met Sally... is listed (or ranked) 18 on the list The Best Chicago Movies
Meg Ryan, Billy Crystal, Carrie Fisher
When Harry Met Sally… is a 1989 American romantic comedy film written by Nora Ephron and directed by Rob Reiner. It stars Billy Crystal as Harry and Meg Ryan as Sally. The story follows the ...more
19
19 11
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Ice Cube, Eve, Janina Gavankar
Barbershop is a 2002 American comedy film directed by Tim Story, produced by State Street Pictures and released by Metro-Goldwyn-Mayer on September 13, 2002. Starring Ice Cube, Cedric the ...more
20
14 7
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Edward Norton, Richard Gere, Laura Linney
Primal Fear is a 1996 American neo-noir thriller film, based on William Diehl's 1993 novel of the same name and directed by Gregory Hoblit. The film tells the story of Chicago defense attorney ...more
21
15 8
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Demi Moore, Rob Lowe, Megan Mullally
About Last Night is a 1986 American romantic dramedy film. The film was directed by Edward Zwick, and stars Rob Lowe and Demi Moore as Chicago yuppies who enter a committed relationship for the ...more
22
16 9
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Sandra Bullock, Monica Keena, Bill Pullman
While You Were Sleeping is a 1995 romantic comedy film directed by Jon Turteltaub and written by Daniel G. Sullivan and Frederic Lebow. It stars Sandra Bullock as Lucy, a Chicago Transit ...more
23
17 11
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Bootsdad added Brad Dourif, Catherine Hicks, Chris Sarandon
Child's Play is a 1988 American horror film directed by Tom Holland, written by Tom Holland, Don Mancini, and John Lafia, and starring Catherine Hicks, Chris Sarandon, Alex Vincent, and Brad ...more
24
12 7
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clash1977 added Sharon Stone, Steven Seagal, Pam Grier
Above the Law is a 1988 American action film written, produced and directed by Andrew Davis, and also produced by and starring Steven Seagal in his film debut. The film co-stars Pam Grier, ...more
25
19 14
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Johnny Depp, Christian Bale, Channing Tatum
Public Enemies is a 2009 American film directed by Michael Mann and written by Mann, Ronan Bennett and Ann Biderman. It is an adaptation of Bryan Burrough's non-fiction book. Set during the ...more