Film The Best Chicago Movies  

Ranker Film
1.2k votes 113 voters 3.7k 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.

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The Blues Brothers 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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Ferris Bueller’s Day Off 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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The Fugitive Julianne Moore, Harrison Ford, Tommy Lee Jones The Fugitive 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 ...more

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Home Alone is listed (or ranked) 4 on the list The Best Chicago Movies
Home Alone 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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clash1977 added The Breakfast Club 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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The Untouchables is listed (or ranked) 6 on the list The Best Chicago Movies
The Untouchables Robert De Niro, Sean Connery, Kevin Costner The Untouchables is a 1987 American crime 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 ...more

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Planes, Trains and Automobiles is listed (or ranked) 7 on the list The Best Chicago Movies
clash1977 added Planes, Trains and Automobiles 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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The Dark Knight is listed (or ranked) 8 on the list The Best Chicago Movies
The Dark Knight Christian Bale, Michael Caine, Heath Ledger The Dark Knight is a 2008 superhero film directed by Christopher Nolan, based on the DC Comics character. Bruce Wayne (Christian Bale), Police Lieutenant James Gordon (Gary Oldman) and District ...more

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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 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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Hoop Dreams 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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High Fidelity is listed (or ranked) 11 on the list The Best Chicago Movies
High Fidelity 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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Backdraft is listed (or ranked) 12 on the list The Best Chicago Movies
Backdraft 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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Risky Business 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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Road to Perdition Tom Hanks, Daniel Craig, Paul Newman Road to Perdition is a 2002 American crime 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 ...more

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clash1977 added Eight Men Out 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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clash1977 added The Sting 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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North by Northwest 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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Primal Fear Edward Norton, Richard Gere, Laura Linney Primal Fear is a 1996 American neo-noir crime-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 ...more

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While You Were Sleeping 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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About Last Night 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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When Harry Met Sally... is listed (or ranked) 21 on the list The Best Chicago Movies
When Harry Met Sally... 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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Barbershop 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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Public Enemies Johnny Depp, Christian Bale, Channing Tatum Public Enemies is a 2009 American biographical crime drama film directed by Michael Mann and written by Mann, Ronan Bennett and Ann Biderman. It is an adaptation of Bryan Burrough's non-fiction ...more

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clash1977 added Above the Law 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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Bootsdad added Child's Play 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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Ordinary People Mary Tyler Moore, Donald Sutherland, Adam Baldwin Ordinary People is a 1980 American drama film that marked the directorial debut of actor Robert Redford. It stars Donald Sutherland, Mary Tyler Moore, Judd Hirsch and Timothy Hutton. The story ...more

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My Best Friend’s Wedding

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Soul Food Vivica A. Fox, Nia Long, Vanessa L. Williams Soul Food is a 1997 American comedy-drama film, produced by Kenneth "Babyface" Edmonds, Tracey Edmonds, and Robert Teitel, and released by Fox 2000 Pictures. Featuring an ensemble ...more

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The Color of Money is listed (or ranked) 29 on the list The Best Chicago Movies
The Color of Money Tom Cruise, Paul Newman, Martin Scorsese The Color of Money is a 1986 drama film directed by Martin Scorsese from a screenplay by Richard Price, based on the 1984 novel of the same name by Walter Tevis. The film stars Paul Newman and ...more

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Candyman 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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The Hunter is listed (or ranked) 31 on the list The Best Chicago Movies
Samurai Mike added The Hunter Steve McQueen

Filmed in 1980, the El and Marina Towers co-star with Steve McQueen doing his own stunts in an epic action scene that still looks good today.

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Samurai Mike added Code of Silence Chuck Norris, John Mahoney, Dennis Farina Code of Silence is a 1985 American action film directed by Andrew Davis, and starring Chuck Norris and Henry Silva. The film was released in the United States on May 3, 1985. It was typical for ...more

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Samurai Mike added My Bodyguard Matt Dillon, Jennifer Beals, Joan Cusack My Bodyguard is a 1980 comedy-drama film released by 20th Century Fox, directed by Tony Bill, and written by Alan Ormsby. The film stars Chris Makepeace, Adam Baldwin, Matt Dillon, Martin Mull, ...more

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Cooley High Garrett Morris, Glynn Turman, Steven Williams Cooley High is a 1975 American film based upon the real high school located on the near north side of Chicago, produced and released by American International Pictures and written by Eric Monte. ...more

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Nothing in Common Tom Hanks, Sela Ward, Jackie Gleason Nothing in Common is a 1986 comedy-drama film, directed by Garry Marshall. It stars Tom Hanks and Jackie Gleason in what would prove to be Gleason's final film role - he was suffering from colon ...more

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clash1977 added The Package Tommy Lee Jones, Gene Hackman, Pam Grier The Package is 1989 Action, Crime, Drama film written by John Bishop and directed by Andrew Davis.

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Stir of Echoes Jennifer Morrison, Kevin Bacon, Illeana Douglas Stir of Echoes is a supernatural horror-thriller released in the US in 1999, starring Kevin Bacon and directed by David Koepp. The film is loosely based on the novel A Stir of Echoes by Richard ...more

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Call Northside 777 James Stewart, Thelma Ritter, Lee J. Cobb Call Northside 777 is a 1948 documentary-style film noir directed by Henry Hathaway. It is based on the true story of a Chicago reporter who proved that a man in prison for murder was wrongly ...more

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Thief Willie Nelson, James Caan, Tuesday Weld Thief is a 1981 neo-noir film written and directed by Michael Mann and based on the 1975 novel The Home Invaders: Confessions of a Cat Burglar by "Frank Hohimer". The film stars James ...more

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clash1977 added Mad Dog and Glory Robert De Niro, Uma Thurman, Bill Murray Mad Dog and Glory is a 1993 American comedy-drama film directed by John McNaughton and starring Robert De Niro, Uma Thurman, and Bill Murray.

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Only the Lonely Macaulay Culkin, John Candy, Maureen O'Hara Only the Lonely is a 1991 American romantic comedy-drama film written and directed by Chris Columbus and starring John Candy, Maureen O'Hara, Ally Sheedy and Anthony Quinn. The plot is similar ...more

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Medium Cool Peter Boyle, Robert Forster, Peter Bonerz Medium Cool is a 1969 American drama film written and directed by Haskell Wexler and starring Robert Forster, Verna Bloom, Peter Bonerz, Marianna Hill and Harold Blankenship. It takes place in ...more

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Mickey One Warren Beatty, Hurd Hatfield, Alexandra Stewart Mickey One is a 1965 surrealistic dramatic film starring Warren Beatty and directed by Arthur Penn from a script by Alan Surgal. Its kaleidoscopic camerawork, film noir atmosphere, lighting and ...more

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Mercury Rising Bruce Willis, Alec Baldwin, Kim Dickens Mercury Rising is a 1998 American action thriller film starring Bruce Willis and Alec Baldwin. Directed by Harold Becker, the movie is based on Ryne Douglas Pearson's 1996 novel originally ...more

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Continental Divide John Belushi, Blair Brown, Tim Kazurinsky Continental Divide is a 1981 American romantic comedy, starring John Belushi and Blair Brown. It was directed by Michael Apted from an original screenplay by Lawrence Kasdan, and executive ...more

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His New Job Charlie Chaplin, Gloria Swanson, Ben Turpin His New Job is a 1915 American short silent comedy film written by, directed by, and starring Charlie Chaplin. Gloria Swanson appears as an uncredited extra. The title is an inside reference to ...more