The Essential Chicago Movies
by Elegantone1 | created - 03 Aug 2021 | updated - 1 month ago | Public- Instant Watch Options
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1. A Raisin in the Sun (1961)
Approved | 128 min | Drama
A substantial insurance payment could mean either financial salvation or personal ruin for a poor black family.
Director: Daniel Petrie | Stars: Sidney Poitier, Claudia McNeil, Ruby Dee, Diana Sands
Votes: 9,573
2. Silver Streak (1976)
PG | 114 min | Action, Comedy, Crime
On a long-distance train trip, a man finds romance but also finds himself in danger of being killed, or at least pushed off the train.
Director: Arthur Hiller | Stars: Gene Wilder, Richard Pryor, Jill Clayburgh, Patrick McGoohan
Votes: 21,725
3. Somewhere in Time (1980)
PG | 103 min | Drama, Fantasy, Romance
A Chicago playwright uses self-hypnosis to travel back in time and meet the actress whose vintage portrait hangs in a grand hotel.
Director: Jeannot Szwarc | Stars: Christopher Reeve, Jane Seymour, Christopher Plummer, Teresa Wright
Votes: 32,549 | Gross: $9.71M
4. Ordinary People (1980)
R | 124 min | Drama
The accidental death of the older son of an affluent family deeply strains the relationships among the bitter mother, the good-natured father and the guilt-ridden younger son.
Director: Robert Redford | Stars: Donald Sutherland, Mary Tyler Moore, Judd Hirsch, Timothy Hutton
Votes: 56,698 | Gross: $54.80M
5. The Blues Brothers (1980)
R | 133 min | Action, Adventure, Comedy
Jake Blues rejoins with his brother Elwood after being released from prison, but the duo has just days to reunite their old R&B band and save the Catholic home where the two were raised, outrunning the police as they tear through Chicago.
Director: John Landis | Stars: John Belushi, Dan Aykroyd, Cab Calloway, John Candy
Votes: 214,553 | Gross: $57.23M
6. The Breakfast Club (1985)
R | 97 min | Comedy, Drama
Five high school students meet in Saturday detention and discover how they have a great deal more in common than they thought.
Director: John Hughes | Stars: Emilio Estevez, Judd Nelson, Molly Ringwald, Ally Sheedy
Votes: 436,717 | Gross: $45.88M
7. Girls Just Want to Have Fun (1985)
PG | 90 min | Comedy, Music, Romance
Janey is new in town and soon meets Lynne, who shares her passion for dancing in general and "Dance TV" in particular.
Director: Alan Metter | Stars: Biff Yeager, Kristi Somers, Richard Blade, Ian Michael Giatti
Votes: 12,945 | Gross: $6.33M
8. Ferris Bueller's Day Off (1986)
PG-13 | 103 min | Comedy
A popular high school student, admired by his peers, decides to take a day off from school and goes to extreme lengths to pull it off, to the chagrin of his Dean, who'll do anything to stop him.
Director: John Hughes | Stars: Matthew Broderick, Alan Ruck, Mia Sara, Jeffrey Jones
Votes: 386,626 | Gross: $70.14M
9. Adventures in Babysitting (1987)
PG-13 | 102 min | Adventure, Comedy, Crime
A babysitter must battle her way through the big city after being stranded there with the kids she's looking after.
Director: Chris Columbus | Stars: Elisabeth Shue, Maia Brewton, Keith Coogan, Anthony Rapp
Votes: 49,143 | Gross: $34.37M
10. Uncle Buck (1989)
PG | 100 min | Comedy
Laid back commitment-phobe Buck babysits his brother's rebellious teenage daughter and her cute younger brother and sister.
Director: John Hughes | Stars: John Candy, Macaulay Culkin, Jean Louisa Kelly, Gaby Hoffmann
Votes: 107,770 | Gross: $66.76M
11. Home Alone (1990)
PG | 103 min | Comedy, Family
An eight-year-old troublemaker, mistakenly left home alone, must defend his home against a pair of burglars on Christmas Eve.
Director: Chris Columbus | Stars: Macaulay Culkin, Joe Pesci, Daniel Stern, John Heard
Votes: 653,027 | Gross: $285.76M
12. Curly Sue (1991)
PG | 101 min | Comedy, Drama, Family
A homeless man and his young companion, who survive by conning people, meet a woman who may need them even more than they need her.
Director: John Hughes | Stars: Jim Belushi, Kelly Lynch, Alisan Porter, John Getz
Votes: 23,243 | Gross: $33.69M
13. Straight Talk (1992)
PG | 91 min | Comedy, Drama, Romance
A woman ditches her small-town life for big-city Chicago, where she becomes a sensation as a radio-show host.
Director: Barnet Kellman | Stars: Dolly Parton, James Woods, Griffin Dunne, Michael Madsen
Votes: 3,993 | Gross: $21.20M
14. The Fugitive (1993)
PG-13 | 130 min | Action, Crime, Drama
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.
Director: Andrew Davis | Stars: Harrison Ford, Tommy Lee Jones, Sela Ward, Julianne Moore
Votes: 318,809 | Gross: $183.88M
15. Baby's Day Out (1994)
PG | 99 min | Adventure, Comedy, Crime
After three kidnappers lose the baby they have kidnapped, both the cops and kidnappers go looking for the baby.
Director: Patrick Read Johnson | Stars: Lara Flynn Boyle, Joe Mantegna, Joe Pantoliano, Brian Haley
Votes: 55,684 | Gross: $16.67M
16. While You Were Sleeping (1995)
PG | 103 min | Comedy, Drama, Romance
A hopelessly romantic Chicago Transit Authority ticket booth operator is mistaken for the fiancée of a comatose patient.
Director: Jon Turteltaub | Stars: Sandra Bullock, Bill Pullman, Peter Gallagher, Peter Boyle
Votes: 114,047 | Gross: $81.06M
17. Space Jam (1996)
PG | 88 min | Animation, Adventure, Comedy
In a desperate attempt to win a basketball match and earn their freedom, the Looney Tunes seek the aid of retired basketball champion, Michael Jordan.
Director: Joe Pytka | Stars: Michael Jordan, Wayne Knight, Theresa Randle, Manner Washington
Votes: 213,569 | Gross: $90.46M
18. Soul Food (1997)
R | 115 min | Comedy, Drama
One person can keep a family together and, when that one person is gone, a family can be torn apart.
Director: George Tillman Jr. | Stars: Vanessa Williams, Vivica A. Fox, Nia Long, Michael Beach
Votes: 9,014 | Gross: $43.49M
19. My Best Friend's Wedding (1997)
PG-13 | 105 min | Comedy, Drama, Romance
When a woman's long-time friend reveals he's engaged, she realizes she loves him herself and sets out to get him, with only days before the wedding.
Director: P.J. Hogan | Stars: Julia Roberts, Dermot Mulroney, Cameron Diaz, Rupert Everett
Votes: 155,470 | Gross: $127.12M
20. Never Been Kissed (1999)
PG-13 | 107 min | Comedy, Drama, Romance
A newspaper reporter enrolls in high school as part of research for a story.
Director: Raja Gosnell | Stars: Drew Barrymore, David Arquette, Michael Vartan, Molly Shannon
Votes: 97,591 | Gross: $55.47M
21. Return to Me (2000)
PG | 115 min | Comedy, Drama, Romance
A man who falls in love with the woman who received his wife's heart must decide which woman it is who holds his heart.
Director: Bonnie Hunt | Stars: David Duchovny, Minnie Driver, Carroll O'Connor, Robert Loggia
Votes: 22,798 | Gross: $32.66M
22. High Fidelity (2000)
R | 113 min | Comedy, Drama, Music
Rob, a record store owner and compulsive list maker, recounts his top five breakups, including the one in progress.
Director: Stephen Frears | Stars: John Cusack, Iben Hjejle, Todd Louiso, Jack Black
Votes: 189,818 | Gross: $27.29M
23. Barbershop (2002)
PG-13 | 102 min | Comedy, Drama
A day in the life of a South Side Chicago barbershop.
Director: Tim Story | Stars: Ice Cube, Cedric The Entertainer, Eve, Anthony Anderson
Votes: 33,549 | Gross: $75.78M
24. My Big Fat Greek Wedding (2002)
PG | 95 min | Comedy, Drama, Romance
A young Greek woman falls in love with a non-Greek and struggles to get her family to accept him while she comes to terms with her heritage and cultural identity.
Director: Joel Zwick | Stars: Nia Vardalos, John Corbett, Michael Constantine, Christina Eleusiniotis
Votes: 144,660 | Gross: $241.44M
25. Road to Perdition (2002)
R | 117 min | Crime, Drama, Thriller
A mob enforcer's son in 1930s Illinois witnesses a murder, forcing him and his father to take to the road, and his father down a path of redemption and revenge.
Director: Sam Mendes | Stars: Tom Hanks, Tyler Hoechlin, Paul Newman
Votes: 284,603 | Gross: $104.45M
26. The In-Laws (I) (2003)
PG-13 | 98 min | Action, Comedy, Thriller
Right before his daughter's wedding, a mild-mannered foot doctor discovers that his future son-in-law's father is a free-wheeling international spy.
Director: Andrew Fleming | Stars: Albert Brooks, Michael Douglas, Ryan Reynolds, Lindsay Sloane
Votes: 17,882 | Gross: $20.44M
27. Nothing Like the Holidays (2008)
PG-13 | 98 min | Comedy, Drama, Romance
A Puerto Rican family living in the area of Humboldt Park in west Chicago face what may be their last Christmas together.
Director: Alfredo Rodriguez de Villa | Stars: John Leguizamo, Freddy Rodríguez, Debra Messing, Alfred Molina
Votes: 4,700 | Gross: $7.50M
28. Little Fockers (2010)
PG-13 | 98 min | Comedy, Romance
Family-patriarch Jack Byrnes wants to appoint a successor. Does his son-in-law, the male nurse Greg Focker, have what it takes?
Director: Paul Weitz | Stars: Ben Stiller, Teri Polo, Robert De Niro, Owen Wilson
Votes: 119,074 | Gross: $148.38M
29. Office Christmas Party (2016)
R | 105 min | Comedy
When his uptight CEO sister threatens to shut down his branch, the branch manager throws an epic Christmas party in order to land a big client and save the day, but the party gets way out of hand...
Directors: Josh Gordon, Will Speck | Stars: Jason Bateman, Olivia Munn, T.J. Miller, Jennifer Aniston
Votes: 88,218 | Gross: $54.77M
30. Proof (2005)
PG-13 | 100 min | Drama, Mystery
The daughter of a brilliant but mentally disturbed mathematician, recently deceased, tries to come to grips with her possible inheritance: his insanity. Complicating matters are one of her father's ex-students, who wants to search through his papers, and her estranged sister, who shows up to help settle his affairs.
Director: John Madden | Stars: Gwyneth Paltrow, Anthony Hopkins, Hope Davis, Jake Gyllenhaal
Votes: 46,319 | Gross: $7.52M
31. The Weather Man (2005)
R | 102 min | Comedy, Drama
A Chicago weather man, separated from his wife and children, debates whether professional and personal success are mutually exclusive.
Director: Gore Verbinski | Stars: Nicolas Cage, Hope Davis, Nicholas Hoult, Michael Caine
Votes: 83,321 | Gross: $12.48M
32. The Big Sick (2017)
R | 120 min | Comedy, Drama, Romance
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.
Director: Michael Showalter | Stars: Kumail Nanjiani, Zoe Kazan, Holly Hunter, Ray Romano
Votes: 143,621 | Gross: $42.87M
33. The Color of Money (1986)
R | 119 min | Drama, Sport
Fast Eddie Felson teaches a cocky but immensely talented protégé the ropes of pool hustling, which in turn inspires him to make an unlikely comeback.
Director: Martin Scorsese | Stars: Paul Newman, Tom Cruise, Mary Elizabeth Mastrantonio, Helen Shaver
Votes: 93,307 | Gross: $52.29M
34. Three to Tango (1999)
PG-13 | 98 min | Comedy, Romance
A rich businessman's assumption that his new colleague is gay leads him to ask the man to keep an eye on his mistress. However, the man is not gay--and he begins to fall for the woman himself.
Director: Damon Santostefano | Stars: Neve Campbell, Matthew Perry, Dylan McDermott, Oliver Platt
Votes: 20,088 | Gross: $10.54M
35. Running Scared (1986)
R | 107 min | Action, Comedy, Crime
Two street-wise Chicago cops have to shake off some rust after returning from a Key West vacation to pursue a drug dealer who nearly killed them in the past.
Director: Peter Hyams | Stars: Gregory Hines, Billy Crystal, Steven Bauer, Darlanne Fluegel
Votes: 15,014 | Gross: $38.50M
36. On the Line (2001)
PG | 85 min | Comedy, Family, Romance
A shy advertising employee meets his dream girl on the El train, but doesn't remember to get her phone number, resulting in an all-out search for the mystery girl
Director: Eric Bross | Stars: Lance Bass, Joey Fatone, Emmanuelle Chriqui, GQ
Votes: 4,409 | Gross: $4.36M
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