Entertainment

The Best Chicago Movies  

Ranker Film
1.4k votes 141 voters 4.3k views 47 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
Ranker Video
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

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#83 of 630 The Greatest Guilty Pleasure Movies #63 of 336 'Old' Movies Every Young Person Needs To Watch In Their Lifetime #30 of 440 The Funniest '80s Movies

2
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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

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#9 of 59 Every Movie Coming To Netflix In January 2020 #10 of 336 'Old' Movies Every Young Person Needs To Watch In Their Lifetimefeaturing Behind The Scenes Of The Famous Parade Scene In 'Ferris Bueller's Day Off'

3
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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

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#123 of 257 The Best Psychological Thrillers of All Time #941 of 1,699 The Most Rewatchable Movieslisted on Every Oscar Winning Film Ever

4
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

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#23 of 630 The Greatest Guilty Pleasure Moviesfeaturing The Story Behind ‘Angels With Filthy Souls,’ The Fake Black-And-White Movie Inside ‘Home Alone’listed on The Highest Grossing 90s Movies

5
Ranker Video
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

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#14 of 336 'Old' Movies Every Young Person Needs To Watch In Their Lifetime #5 of 304 The Greatest Soundtracks of All Time #14 of 440 The Funniest '80s Movies

6
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

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#181 of 571 Things That Are Not As Cool As People Think They Arefeaturing Gaping Plot Holes You Won't Be Able To Unsee In The Dark Knightlisted on Every Oscar Winning Film Ever

7
Planes, Trains and Autom... is listed (or ranked) 7 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

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#89 of 336 'Old' Movies Every Young Person Needs To Watch In Their Lifetime #8 of 440 The Funniest '80s Movies #185 of 1,699 The Most Rewatchable Movies

8
The Untouchables is listed (or ranked) 8 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

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#120 of 336 'Old' Movies Every Young Person Needs To Watch In Their Lifetime #299 of 1,699 The Most Rewatchable Movieslisted on Every Oscar Winning Film Ever

9
Backdraft is listed (or ranked) 9 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

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#119 of 630 The Greatest Guilty Pleasure Movies #467 of 1,699 The Most Rewatchable Movieslisted on All Movies About Fire

10
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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

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#129 of 336 'Old' Movies Every Young Person Needs To Watch In Their Lifetime #196 of 304 The Greatest Soundtracks of All Time #90 of 440 The Funniest '80s Movies

11
High Fidelity is listed (or ranked) 11 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

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#28 of 304 The Greatest Soundtracks of All Time #1,021 of 1,699 The Most Rewatchable Movies #355 of 710 The Best Movies Roger Ebert Gave Four Stars

12
Sixteen Candles is listed (or ranked) 12 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.

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#65 of 336 'Old' Movies Every Young Person Needs To Watch In Their Lifetime #57 of 304 The Greatest Soundtracks of All Time #34 of 440 The Funniest '80s Movies

13
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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

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#258 of 719 The Best Black Movies Ever Made, Ranked #336 of 710 The Best Movies Roger Ebert Gave Four Stars #34 of 396 The Greatest Documentaries of All Time

14
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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

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#76 of 257 The Best Psychological Thrillers of All Time #560 of 1,699 The Most Rewatchable Movies #279 of 460 The Most Quotable Movies of All Time

15
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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

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#223 of 410 The Best Rainy Day Movies #104 of 291 The Top Tearjerker Movies That Make Men Crylisted on Every Oscar Winning Film Ever

16
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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

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#176 of 265 The Best Ensemble Movies #33 of 180 The Best Sports Movies Ever Made #8 of 90 The All-Time Best Baseball Films

17
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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

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#24 of 93 The Very Best Oscar-Winning Movies #392 of 1,699 The Most Rewatchable Movieslisted on Every Oscar Winning Film Ever

18
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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

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#166 of 630 The Greatest Guilty Pleasure Movies #125 of 336 'Old' Movies Every Young Person Needs To Watch In Their Lifetime #18 of 769 The Best Horror Movies of All Time

19
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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

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#19 of 257 The Best Psychological Thrillers of All Time #257 of 347 The Best Movies Based On Books #5 of 24 The Best Movies with Twist Endings

20
When Harry Met Sally... ... is listed (or ranked) 20 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

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#122 of 336 'Old' Movies Every Young Person Needs To Watch In Their Lifetime #61 of 440 The Funniest '80s Moviesfeaturing When Harry Met Sally is All About Mansplaining, And It's Really Obvious

21
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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

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#34 of 719 The Best Black Movies Ever Made, Ranked #17 of 84 The Funniest Black Movies Ever Made #12 of 32 The Best Comedies About the Workplace

22
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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

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#313 of 710 The Best Movies Roger Ebert Gave Four Stars #567 of 1,204 The Absolute Funniest Movies Of All Time #207 of 440 The Funniest '80s Movies

23
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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

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#93 of 630 The Greatest Guilty Pleasure Movies #184 of 336 'Old' Movies Every Young Person Needs To Watch In Their Lifetime #145 of 493 The Funniest '90s Movies

24
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Virginia Madsen, Tony Todd, Vanessa A. Williams
Candyman is a 1992 American horror film written and directed by Bernard Rose, based on the short story "The Forbidden" by Clive Barker, though the film's scenario is switched from ...more

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#418 of 719 The Best Black Movies Ever Made, Ranked #45 of 769 The Best Horror Movies of All Timefeaturing The Increasingly Odd And Convoluted ‘Candyman’ Sequels Never Held A Candle To Their Predecessor

25
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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

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#331 of 575 The Greatest Movies Of The 1980s, Ranked #53 of 95 The Best Action Movies of the 1980s #32 of 42 The Best Kung Fu Movies of the 1980s