Here we've displayed a list of the best Chicago films : The Sting(1973), Hoop Dreams(1994), Some Like It Hot(1959), I Am a Fugitive From a Chain Gang(1932), A Raisin in the Sun(1961), Indestructible(2007), Anita O'Day: The Life of a Jazz Singer(2007), The Untouchables(1987), The Fugitive(1993), Days of Heaven(1978), Scarface(1932), Nightmare Alley(1947) ... ...
8.3/10
Comedy, Drama
USA
1973
129 Minutes
Paul Newman Robert Redford Robert Shaw Charles Durning Ray Walston Eileen Brennan Harold Gould John Heffernan Dana Elcar Jack Kehoe Dimitra Arliss
con artist mentor gangster amusing witty engaging chicago deception shady dealings revenge scams gambling revenge quest underdog 1930s
Two grifters team up to pull off the ultimate con.
8.3/10
Documentary, Drama
USA
1994
174 Minutes
William Gates Arthur Agee Sheila Agee Isiah Thomas Bill Gleason
basketball player teenager mother father coach teacher uplifting powerful gutsy emotional chicago westchester, ill. basketball court family home basketball ambition high school racism class distinctions growing up
A film following the lives of two inner-city Chicago boys who struggle to become college basketball players on the road to going professional.
8.2/10
Comedy
USA
1959
120 Minutes
Tony Curtis Jack Lemmon Marilyn Monroe George Raft Pat O'Brien Joe E. Brown Nehemiah Persoff Joan Shawlee Billy Gray George E. Stone Dave Barry
musician friend sexy woman millionaire mobster playful hilarious wild chicago train florida beach hotel nightclub deception sex friendship wealth escape love
After two male musicians witness a mob hit, they flee the state in an all-female band disguised as women, but further complications set in.
8.2/10
Drama
USA
1932
93 Minutes
Paul Muni Glenda Farrell Helen Vinson Preston Foster Edward Ellis Allen Jenkins Noel Francis Berton Churchill
veteran prisoner guard landlady lawyer bleak brutal intense georgia diner prison chicago construction site prison injustice torture escape aspirations jealousy escape
Wrongly convicted James Allen serves in the intolerable conditions of a southern chain gang, which later comes back to haunt him.
8.0/10
Drama
USA
1961
128 Minutes
Sidney Poitier Claudia McNeil Ruby Dee Diana Sands Ivan Dixon John Fiedler Louis Gossett Jr. Stephen Perry Joel Fluellen Roy E. Glenn Sr. Ray Stubbs
son mother wife widow sister suitor emotional moving chicago apartment american dream aspirations family racism social change money love discovery underdog 1950s
A substantial insurance payment could mean either financial salvation or personal ruin for a poor black family.
7.9/10
Documentary
USA
2007
118 Minutes
Josh Byer Oliver Sacks Ben Byer John Byer Rebeccah Rush
ben byer sick person doctor inspiring emotional sad moving china jamaica greece israel doctor's office chicago illness survival journey quest 2000s
Diagnosed with ALS, a fatal neurodegenerative disease, film-maker Ben Byer starts documenting his life. One of the most intimate and powerful films you will encounter on a degenerative illness.
7.9/10
Documentary, Music
USA
2007
93 Minutes
Anita O'Day Buddy Bregman Leonard Feather Will Friedwald Russell Garcia Johnny Mandel
jazz singer friend critic musician inspiring engaging chicago stage anita o'day drug addiction poverty performance struggle imprisonment rise underdog 1960s
A tribute to jazz diva Anita O'Day, completed just weeks before her death in November 2006.
7.9/10
Crime, Drama
USA
1987
119 Minutes
Kevin Costner Sean Connery Robert De Niro Andy Garcia Charles Martin Smith Billy Drago Richard Bradford Jack Kehoe
al capone eliot ness cop gangster accountant bootlegger engaging gutsy spirited suspenseful gritty chicago office train station courtroom police station border crooked cops corruption organized crime
During the era of Prohibition in the United States, Federal Agent Eliot Ness sets out to stop ruthless Chicago gangster Al Capone and, because of rampant corruption, assembles a small, hand-picked team to help him.
7.8/10
Mystery & Thriller, Crime, Drama, Action
USA
1993
127 Minutes
Harrison Ford Tommy Lee Jones Sela Ward Julianne Moore Joe Pantoliano Jeroen Krabbé Andreas Katsulas Daniel Roebuck L. Scott Caldwell
surgeon marshal widower wife gripping thrilling suspenseful chicago train mystery conspiracy murder escape pursuit quest 1990s
Dr. Richard Kimble, unjustly accused of murdering his wife, must find the real killer while being the target of a nationwide manhunt led by a seasoned U.S. Marshal.
7.8/10
Drama
USA
1978
95 Minutes
Richard Gere Brooke Adams Sam Shepard Linda Manz Robert Wilke Jackie Shultis Stuart Margolin Timothy Scott Richard Libertini Doug Kershaw
worker sister girlfriend farmer wealthy man sad emotional dark texas chicago farm factory river fugitives jealousy farming illness love triangle deception escape
A hot-tempered farm laborer convinces the woman he loves to marry their rich but dying boss so that they can have a claim to his fortune.
7.8/10
Crime, Drama
USA
1932
93 Minutes
gangster sister criminal fiery frenetic gripping thrilling chicago jealousy crime murder underdog wretched excess rivalry 1930s
An ambitious and nearly insane violent gangster climbs the ladder of success in the mob, but his weaknesses prove to be his downfall.
7.8/10
Crime, Drama
USA
1947
111 Minutes
geek mind reader psychiatrist strong man con artist dark incredible carnival hotel chicago con game ambition rise fall 1940s
The rise and fall of Stanton Carlisle, a mentalist whose lies and deceit prove to be his downfall.
7.8/10
Comedy
USA
1986
103 Minutes
Matthew Broderick Alan Ruck Mia Sara Jennifer Grey Jeffrey Jones Edie McClurg Lyman Ward Cindy Pickett Charlie Sheen Ben Stein Del Close
teenager best friend girlfriend principal sister amusing charming chicago family home restaurant school rebellion siblings scams school escape rivalry 1980s
A high school wise guy is determined to have a day off from school, despite what the Principal thinks of that.
7.7/10
Crime, Drama
USA
1931
84 Minutes
James Cagney Jean Harlow Mae Clarke Edward Woods Beryl Mercer Donald Cook Joan Blondell
gangster bootlegger police officer veteran friend melodramatic brash gripping suspenseful prison chicago slum nightclub bar organized crime gangs prohibition great depression family dysfunction growing up
An Irish-American street punk tries to make it big in the world of organized crime.
7.7/10
Crime, Drama
USA
1952
71 Minutes
Charles McGraw Marie Windsor Jacqueline White Gordon Gebert Queenie Leonard David Clarke Peter Virgo Don Beddoe Paul Maxey Harry Harvey
widow gangster partner police officer detective suspenseful train los angeles chicago courtroom protection trial testimonies secret mafia murder rescue revenge 1950s
A woman planning to testify against the mob must be protected against their assassins on the train trip from Chicago to Los Angeles.
7.7/10
Crime, Drama
USA
2002
116 Minutes
Tom Hanks Paul Newman Jude Law Jennifer Jason Leigh Stanley Tucci Daniel Craig Tyler Hoechlin Liam Aiken Dylan Baker Ciarán Hinds
hit man mobster son psychopath father dark suspenseful chicago cemetery elevator murder violence robbery betrayal jealousy mafia escape sacrifice 1930s
A mob enforcer's son witnesses a murder, forcing him and his father to take to the road, and his father down a path of redemption and revenge.
7.6/10
Comedy, Other
USA
1987
92 Minutes
Steve Martin John Candy Laila Robins Michael McKean Kevin Bacon Dylan Baker William Windom Edie McClurg
salesman husband wife thief police officer madcap endearing chicago wichita, kan. motel airport truck airplane travel thanksgiving friendship family luck weather transformation
A man must struggle to travel home for Thanksgiving with a lovable oaf of a shower curtain ring salesman as his only companion.
7.6/10
Western
USA
1951
118 Minutes
Robert Taylor Denise Darcel Jacqueline Wells Beverly Dennis John McIntire Hope Emerson Lenore Lonergan Marilyn Erskine
prostitute trail guide mail-order bride pregnant woman native american cook amusing bleak sad gritty thrilling california chicago wild west camp wilderness wagon train marriage journey death
A trail guide escorts a group of women from Chicago to California to marry men that have recently began settling there.
7.6/10
Comedy
USA
1933
69 Minutes
Stan Laurel Oliver Hardy Charley Chase Mae Busch Dorothy Christy Lucien Littlefield John Elliott Charley Young John Merton William Gillespie Charles McAvoy
husband wife friend veterinarian ruler best friend cheery hilarious madcap lighthearted amusing intense chicago hawaii family home ballroom redemption ship friendship male bonding
When Stan and Ollie trick their wives into thinking that they are taking a medicinal cruise while they're actually going to a convention, the wives find out the truth the hard way.
7.6/10
Comedy, Kids & Family, Other
USA
1990
102 Minutes
Macaulay Culkin Joe Pesci Daniel Stern Catherine O'Hara John Heard Roberts Blossom John Candy Angela Goethals Devin Ratray Gerry Bamman
boy mother old man con artist brother polka band hilarious heartwarming frenetic chicago paris airport family home church abandonment family christmas robbery children vs. adults growing up
An eight-year-old troublemaker must protect his house from a pair of burglars when he is accidentally left home alone by his family during Christmas vacation.
7.5/10
Drama
USA
1933
68 Minutes
Frankie Darro Dorothy Coonan Edwin Phillips Rochelle Hudson Sterling Holloway Arthur Hohl Ann Hovey Minna Gombell
teen boy high-school student police officer teen girl aunt panhandler gritty dark profound train cleveland chicago camp dump new york state great depression unemployment child labor friendship quest
In the depths of the Depression, two teenage boys strike out on their own in order to help their struggling parents and find life on the road tougher than expected.
7.5/10
Romance, Gay & Lesbian
USA
1997
108 Minutes
Larenz Tate Nia Long Isaiah Washington Lisa Nicole Carson Khalil Kain Leonard Roberts Bernadette L. Clarke Bill Bellamy
writer photographer ex-boyfriend cool passionate chicago bar record store party new york city love at first sight poetry romance love pursuit 1990s
Darius Lovehall is a young black poet in Chicago who starts dating Nina Mosley, a beautiful and talented photographer. While trying to figure out if they've got a "love thing" or are just "... See full summary »
7.5/10
Comedy, Drama, Music
USA|UK|France
2013
104 Minutes
Oscar Isaac Ethan Coen Carey Mulligan John Goodman Garrett Hedlund F. Murray Abraham Justin Timberlake Ethan Phillips Robin Bartlett Max Casella Jerry Grayson
musician singer-songwriter music producer mogul confident engaging passionate greenwich village new york city club stage chicago folk music struggle success social event rise 1960s
A week in the life of a young singer as he navigates the Greenwich Village folk scene of 1961.
7.5/10
Adventure, Fantasy, Drama, Kids & Family, Musical
USA|South Korea
2007
113 Minutes
Freddie Highmore Keri Russell Jonathan Rhys-Meyers Terrence Howard Robin Williams William Sadler Leon Thomas III Jamia Simone Nash
orphan homeless person boy cellist mother father touching emotional new york city orphanage abandoned theater street chicago central park search music schemes paternity reunion unlikely friendship
An orphaned musical prodigy uses his gift to try to find his birth parents.
7.5/10
Romance
USA
2017
120 Minutes
Kumail Nanjiani Zoe Kazan Holly Hunter Ray Romano Anupam Kher Zenobia Shroff Adeel Akhtar Bo Burnham Aidy Bryant Kurt Braunohler Vella Lovell
comedian graduate student young woman parent muslim charming emotional heartwarming chicago house hospital apartment romance interracial romance family gathering arranged marriage forbidden love transformation discovery 2010s
Pakistan-born comedian Kumail Nanjiani and grad student Emily Gardner fall in love but struggle as their cultures clash. When Emily contracts a mysterious illness, Kumail finds himself forced to face her feisty parents, his family's expectations, and his true feelings.
7.5/10
Documentary
USA
2002
93 Minutes
singer guitarist drummer musician manager uplifting fascinating uneasy chicago recording studio country music music industry recordings adventure rise quest 2000s
First-time filmmaker and award-winning photographer Sam Jones documents the recording of Wilco's album, "Yankee Hotel Foxtrot."
7.5/10
Romance
UK|USA
2000
113 Minutes
John Cusack Iben Hjejle Todd Louiso Jack Black Lisa Bonet Catherine Zeta-Jones Joan Cusack Tim Robbins Chris Rehmann Ben Carr Lili Taylor
owner girlfriend customer ex-girlfriend amusing witty record store chicago funeral music business love loss midlife crisis love growing up 2000s
Rob, a record store owner and compulsive list maker, recounts his top five breakups, including the one in progress.
7.4/10
Action, Crime, Drama
USA
1981
122 Minutes
James Caan Tuesday Weld Willie Nelson James Belushi Robert Prosky Tom Signorelli Dennis Farina Nick Nickeas
thief girlfriend gangster criminal gripping tense chicago los angeles bar car dealership heist crime one last job dangerous assignment aspirations wretched excess quest escape 1980s
A former ace safe-cracker is trying to go straight--if he can score one last big heist for the mob.
7.4/10
Drama
USA
1974
115 Minutes
Art Carney Ellen Burstyn Chief Dan George Geraldine Fitzgerald Larry Hagman Arthur Hunnicutt Josh Mostel Melanie Mayron Herbert Berghof Barbara Rhoades Philip Bruns
widower cat son daughter hitchhiker former lover touching endearing amusing quirky new york city apartment chicago los angeles suburbia aging family america road trip discovery
When his apartment building is torn down, a retired lifelong New Yorker goes on a cross-country odyssey with his beloved cat Tonto.
7.4/10
Musical
USA
1936
113 Minutes
Irene Dunne Allan Jones Charles Winninger Helen Westley Paul Robeson Helen Morgan Donald Cook Sammy White Queenie Smith J. Farrell MacDonald Arthur Hohl
singer gambler actress actor father daughter spectacular emotional melodramatic river boat chicago nightclub theater mississippi show business interracial romance racism love marriage
Despite her mother's objections, the naive young daughter of a show boat captain is thrust into the limelight as the company's new leading lady.
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