Entertainment

The Best Chicago Movies 

Ranker Film
Updated October 24, 2019 1.4k votes 141 voters 4.4k 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

Released: 1980

Directed by: John Landis

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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#82 of 624 The Greatest Guilty Pleasure Movies #99 of 1,699 The Most Rewatchable Movies #53 of 508 The Best Duos of All Time

2
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Charlie Sheen, Matthew Broderick, Jeffrey Jones

Released: 1986

Directed by: John Hughes

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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#29 of 1,009 The All-Time Greatest Comedy Films #10 of 125 Movies That Should Never Be Remade 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

Released: 1993

Directed by: Andrew Davis

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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#797 of 1,196 The Absolute Funniest Movies Of All Time #1 of 114 The Best Movies Based on TV Showslisted 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

Released: 1990

Directed by: Chris Columbus

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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#15 of 1,699 The Most Rewatchable Movies 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

Released: 1985

Directed by: John Hughes

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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#27 of 1,699 The Most Rewatchable Movies #78 of 1,009 The All-Time Greatest Comedy Films #12 of 125 Movies That Should Never Be Remade

6
The Dark Knight is listed (or ranked) 6 on the list The Best Chicago Movies
Christian Bale, Michael Caine, Heath Ledger

Released: 2008

Directed by: Christopher Nolan

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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#1 of 67 Every Movie Coming To Netflix In February 2020 Behind-The-Scenes Stories From The Set Of 'The Dark Knight'listed 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

Released: 1987

Directed by: John Hughes

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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#185 of 1,699 The Most Rewatchable Movies #20 of 1,196 The Absolute Funniest Movies Of All Time

8
The Untouchables is listed (or ranked) 8 on the list The Best Chicago Movies
Robert De Niro, Sean Connery, Kevin Costner

Released: 1987

Directed by: Brian De Palma

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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#101 of 351 The Best Movies Based On Books #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

Released: 1991

Directed by: Ron Howard

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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#122 of 624 The Greatest Guilty Pleasure Movies #47 of 568 The Greatest Disaster Movies of All Time

10
Ranker Video
Tom Cruise, Megan Mullally, Rebecca De Mornay

Released: 1983

Directed by: Paul Brickman

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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#278 of 1,009 The All-Time Greatest Comedy Films #177 of 460 The Most Quotable Movies of All Time

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

Released: 2000

Directed by: Stephen Frears

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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#1,021 of 1,699 The Most Rewatchable Movies #27 of 302 The Greatest Soundtracks of All Time

12
Sixteen Candles is listed (or ranked) 12 on the list The Best Chicago Movies
John Cusack, Molly Ringwald, Joan Cusack

Released: 1984

Directed by: John Hughes

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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#165 of 1,699 The Most Rewatchable Movies #169 of 1,009 The All-Time Greatest Comedy Films The Funniest Quotes From 'Sixteen Candles'

13
Ranker Video

Released: 1994

Directed by: Steve James

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 722 The Best Black Movies Ever Made, Ranked #31 of 398 The Greatest Documentaries of All Time #12 of 102 The 100+ Best Movies Streaming On The Criterion Channel

14
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Cary Grant, Alfred Hitchcock, Eva Marie Saint

Released: 1959

Directed by: Alfred Hitchcock

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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#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

Released: 2002

Directed by: Sam Mendes

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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#60 of 165 The Greatest Comic Book Movies of All Time #14 of 113 The Best Mafia Filmslisted on Every Oscar Winning Film Ever

16
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clash1977 added Charlie Sheen, Christopher Lloyd, John Cusack

Released: 1988

Directed by: John Sayles

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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#167 of 265 The Best Ensemble Movies #8 of 90 The All-Time Best Baseball Films #98 of 212 The Best Historical Drama Movies of All Time, Ranked

17
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clash1977 added Paul Newman, Robert Redford, Robert Shaw

Released: 1973

Directed by: George Roy Hill

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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#393 of 1,699 The Most Rewatchable Movies #288 of 1,196 The Absolute Funniest Movies Of All Timelisted on Every Oscar Winning Film Ever

18
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Bootsdad added Brad Dourif, Catherine Hicks, Chris Sarandon

Released: 1988

Directed by: Tom Holland

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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#164 of 624 The Greatest Guilty Pleasure Movies #20 of 799 The Best Horror Movies Of All Time #195 of 571 The Greatest Movies Of The 1980s, Ranked

19
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Edward Norton, Richard Gere, Laura Linney

Released: 1996

Directed by: Gregory Hoblit

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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#5 of 24 The Best Movies with Twist Endings #22 of 59 The Best Movies Where the Bad Guy Wins

20
When Harry Met Sally... ... is listed (or ranked) 20 on the list The Best Chicago Movies
Meg Ryan, Billy Crystal, Carrie Fisher

Released: 1989

Directed by: Rob Reiner

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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#196 of 1,699 The Most Rewatchable Movies #456 of 508 The Best Duos of All Time When Harry Met Sally is All About Mansplaining, And It's Really Obvious

21
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Ice Cube, Eve, Janina Gavankar

Released: 2002

Directed by: Tim Story

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 722 The Best Black Movies Ever Made, Ranked #12 of 32 The Best Comedies About the Workplace

22
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Demi Moore, Rob Lowe, Megan Mullally

Released: 1986

Directed by: Edward Zwick

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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#567 of 1,196 The Absolute Funniest Movies Of All Time #313 of 710 The Best Movies Roger Ebert Gave Four Stars

23
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Sandra Bullock, Monica Keena, Bill Pullman

Released: 1995

Directed by: Jon Turteltaub

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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#94 of 624 The Greatest Guilty Pleasure Movies #57 of 803 The Greatest Chick Flicks Ever Made #143 of 493 The Funniest '90s Movies

24
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Virginia Madsen, Tony Todd, Vanessa A. Williams

Released: 1992

Directed by: Bernard Rose

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 722 The Best Black Movies Ever Made, Ranked #25 of 60 The Most Rewatchable Horror Movies 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

Released: 1988

Directed by: Andrew Davis

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 571 The Greatest Movies Of The 1980s, Ranked #254 of 748 The Greatest Action Movies of All Time