The Third Coast. The Windy City. Sure, when people think of big cities in the movies, Los Angeles or New York leap to mind, if not European locales like Paris and Rome. But before LA, Chicago was America’s other major metropolis, a point that filmmakers have not forgotten. Some of the greatest movie makers of all time have set their films in Chicago, from Oscar Micheaux and Haskell Wexler to Michael Mann and Steve McQueen.
Here are twenty-five of the best movies set in Chicago, films that take advantage of Chi-Town’s unique mix of urban sophistication and midwestern charm.
The Exile (1931)
In a better world, Oscar Micheaux would be as well known as his contemporaries Michael Curtiz, Frank Capra, and other filmmakers of his era. Micheaux’s sensitive, well-observed movies captured African American experience ignored by most other filmmakers. Micheaux’s musical The Exile contrasts the cynical but bustling community in Chicago with the dangerous and wide-open spaces of South Dakota, as Jean Baptiste (Stanley Morrell) fights to find a place where he belongs.
Little Caesar (1931)
In the early 20th century, Chicago was synonymous with organized crime, making it the perfect home for film noir. Thus, there could be only one choice for the setting for Little Caesar, the breakout film of legend Edward G. Robinson. Robinson stars as Rico Bandello, a small-time crook who eventually comes to control the Chicago underworld. Director Mervyn LeRoy takes full advantage of the city’s shady corners, making the town as scary as the protagonist.
The Public Enemy (1931)
Released just a few months after Little Caesar, The Public Enemy further explores the dark side of Chicago with a crime story based on the real-world actions of Al Capone. Written by newspapermen John Bright and Kubec Glasmon, The Public Enemy stars a magnetic James Cagney as another petty criminal who becomes a boss during Prohibition. The movie shows the brutal downfall of Cagney’s Tom Powers, but it also shows the collateral damage he causes along the way. Not only is Little Caesar one of the best movies set in Chicago, it's also one of the great gangster films.
Call Northside 777 (1948)
While plenty of Chicago movies portray the gangsters and police who warred throughout the prohibition era, Call Northside 777 turns its attention to the people caught in the middle. Jimmy Stewart stars as P.J. McNeal, a reporter who fights for an innocent man (Richard Conte) convicted of killing a police officer. Based on a true story from earlier in the decade, Call Northside 777 earned praise for its documentary-style approach to fictionalizing real events in one of the best movies set in Chicago.
The Man With The Golden Arm (1955)
As the past entries show, Chicago certainly has its rough parts. The Frank Sinatra vehicle The Man With the Golden Arm walks those same streets, but from the perspective of a victim. Directed by Otto Preminger, The Man With the Golden Arm tells a strikingly gritty story of an addict (Sinatra) who struggles to stay clean after leaving prison. The film not only netted an Academy Award nomination for Sinatra but also one for the score by Elmer Bernstein.
A Raisin in The Sun (1961)
Based on playwright Lorraine Hansberry’s experiences when her family tried to move into a segregated suburb, A Raisin in the Sun powerfully challenges our assumptions about the American dream. Directed by Daniel Petrie from a script by Hansberry, A Raisin in the Sun shows the struggle of a family, which includes Sidney Poitier and Ruby Dee, who wants to move out of the city into a single-family home. Although A Raisin in the Sun is less enamored with Chicago than other films on this list, there’s no denying the electric performances from Poitier and Dee.
Medium Cool (1969)
Drawing its name from theorist Marshall McLuhan’s description of television as the “cool” medium, Haskell Wexler’s Medium Cool not only explores the power of tv but also the tensions at the heart of Chicago. When cynical photographer John Cassellis (Robert Forester) discovers that his footage is being used by the FBI, he becomes entwined in the riots at the Democratic National Convention. Although Medium Cool includes images of the city, its real power comes from the complex portrayal of the people who live in it.
The Sting (1973)
The Sting may be yet another movie about Chicago’s criminal underworld, but it’s far more playful than the others on this list, thanks to the endless charisma of stars Robert Redford and Paul Newman. As two con men looking to rob a brutal gangster (Robert Shaw), Redford and Newman bring easy charm to the heist movie, making it one of the best American movies ever…and one of the best movies set in Chicago, of course.
The Blues Brothers (1980)
To be fair, The Blues Brothers Jake and Elwood spend a lot of the movie outside of Chicago, following their mission from God to get the band back together. But throughout the entire film, they’ve got Chicago on their mind, determined to get back to the city and host a concert that will save the orphanage where they grew up. With an all-star supporting cast that features some of the greatest musicians of all time — including Aretha Franklin, Ray Charles, and Cab Calloway — The Blues Brothers captures the artistic spirit of Chicago, even when beyond city limits.
Thief (1981)
Michael Mann’s movie about a criminal looking for one last big score certainly isn’t the first film about the Chicago underworld, but it may be the most stylish. Nearly every shot in Thief features neon lights reflecting on rainy streets, set to a mesmerizing score from Tangerine Dream. But the real draw to Thief is the textured, vulnerable performances from James Caan and Tuesday Weld, ill-fated lovers who know they’ll never be able to make their way to the good life. Of all the best movies set in Chicago, this might be the saddest.
Ferris Bueller's Day Off (1986)
Suburban kid Ferris Bueller has it much better than the low-lives and criminals who populate many of the films on this list, but that doesn’t make him any less of a troublemaker. Desperate to play hooky from school, the inventive Ferris (Matthew Broderick) keeps his cool no matter how convoluted his plot becomes, much to the chagrin of best friend Cameron (Alan Ruck) and girlfriend Sloane (Mia Sara). But along the way, Ferris and company reveal everything great about the city, climaxing with a delirious downtown parade.
The Untouchables (1987)
Where previous gangster movies only had characters inspired by Al Capone, The Untouchables had the real thing. Sort of. Heavily fictionalized by writer David Mamet and director Brian DePalma, The Untouchables dramatized the battle between Eliot Ness (Kevin Costner) and Capone (Robert DiNero). It may not be the most realistic movie on this list, but The Untouchables captures Old Chicago at its most mythic.
Child’s Play (1988)
The murderous doll Chucky has become a true horror icon, but few remember the relatively gritty treatment of Chicago in the franchise starter Child’s Play. Chucky comes to life when killer Charles Lee Ray (Brad Dourif) puts his soul into a toy after being shot by Detective Mike Norris (Chris Sarandon). When not seeking revenge on the bad side of town, Chucky hides away in a fancy apartment, waiting to pounce on young Andy (Alex Vincent) and his mom (Catherine Hicks).
Home Alone (1990)
Given the prevalence of Chicago crime movies, few things seem scarier than leaving a kid alone in the city. But when that kid is Kevin McCallister (Macaulay Culkin), there’s nothing to worry about. Home Alone turns a stately suburban home into a house of horrors for the Wet Bandits (Joe Pesci and Daniel Stern), and makes child abandonment seem like a dream come true.
Candyman (1992)
Sure, plenty of horror movies are set in Chicago, but none are tied to the city like Candyman. The spirit of a murdered innocent man, Candyman (Tony Todd) haunts the Cabrini-Green housing project, calling for anyone who says his name five times in a mirror. Against all warnings, graduate student Helen (Virginia Madsen) searches for Candyman in Cabrini-Green, coming face-to-face with the terrifying inequality at the heart of the city.
Wayne’s World (1992)
True, lovable losers Wayne and Garth (Mike Myers and Dana Carvey) live in Aurora, not Chicago proper. But that distinction between the city and the suburbs captures the appeal of Wayne and Garth, a couple of guys who want to be rock and roll tv stars but are really just gentle knuckleheads. From the quiet streets where the boys play hockey to the rock clubs they visit, Wayne’s World takes full advantage of its location.
The Fugitive (1993)
The Fugitive begins within the city’s upper class, where Dr. Richard Kimball (Harrison Ford) is a celebrated physician. But after being framed for the murder of his wife, Kimball goes on the run, pursued by a relentless U.S. Marshall Sam Gerard (Tommy Lee Jones). Gerard chases Kimball through the streets of Chicago, making wisecracks about the Chicago River and other key locations in the process.
Go Fish (1994)
Instead of celebrating the city as a whole, the indie dramedy Go Fish focuses on Chicago’s lesbian community, specifically would-be couple Max (Guinevere Turner) and Ely (V.S. Brodie). Some may be put off by the movie’s artsier elements, such as its grainy black-and-white photography and whispered voiceover, but director Rose Troche (who co-wrote the film with Turner) keeps everything grounded in the lived experience of its characters.
My Best Friend’s Wedding (1997)
My Best Friend’s Wedding starts in New York; Julia Roberts’s Jules works as a food critic. But she soon heads to the midwest upon learning that her best friend, sportswriter Michael (Dermot Mulroney), is getting married. What follows is a delightful romp as Jules tries to end Michael’s engagement to the sweet Kimberly (Cameron Diaz), visiting several Chicago landmarks along the way.
High Fidelity (2000)
For his adaptation of the Nick Hornby novel High Fidelity, director Stephen Frears moved the central record store from London to Chicago, fundamentally changing protagonist Rob Gordon’s (John Cusack) relationship with the city. Rob both loves and loathes his Chicago home, thrilled by the musical acts that he watches and frustrated by the doofuses he works with, Barry (Jack Black) and Dick (Todd Louiso). The approach makes High Fidelity an authentic look at the good and bad of its setting.
Chicago (2002)
Of course, Chicago needs to be on this list. The Academy Award-winning musical combines the glamor and sleaze of the city’s heyday, following the murder trial of Roxy Hart (Renée Zellweger) and her rival/partner Velma Kelly (Catherine Zeta-Jones). Director Rob Marshall presents a more spectacular version of the city, even when not showing fantasy sequences that take the form of vaudeville performances, but Chicago presents a fantastic look at the legendary town.
The Dark Knight (2008)
What’s that you say? The Dark Knight takes place in Batman’s stopping grounds in Gotham City, just like every other Batman movie? Sure Bruce Wayne (Christian Bale) and others say they’re in Gotham City, but I defy you not to recognize South LaSalle Street when the Joker (Heath Ledger) and Batman face-off over Harvey Dent (Aaron Eckhardt) or Navy Pier during the evacuation sequence. In his pursuit of a grounded superhero story, Christopher Nolan barely disguises the Windy City, making it a good fit as one of the best Chicago movies of all time.
Widows (2018)
As with High Fidelity, Widows takes an English story and moves it to Chicago. But by following the various threads surrounding a group of women trying to make ends meet after the deaths of their criminal partners, director Steve McQueen presents a nuanced portrait of the city. Nowhere is that more notable than in a striking single shot, which follows alderman candidate Jack Mulligan (Colin Farrell) as he drives from the low-income neighborhood he wants to represent to his home in an upscale, gentrified area.
Ma Rainey’s Black Bottom (2020)
For his last film appearance, the late, great Chadwick Boseman puts in an absolutely electric performance as brash trumpeter Levee Green in the film adaptation of August Wilson’s play Ma Rainey’s Black Bottom. Green’s arrogance runs afoul of the proud and powerful singer Ma Rainey (Viola Davis, summoning all of her considerable presence) as she and the band try to record an album in 1927 Chicago.
Judas and The Black Messiah (2021)
A powerful portrait about the betrayal of Chicago Black Panthers leader Fred Hampton, Judas and the Black Messiah earned six Oscar nominations, including Best Actor nods for both LaKeith Stanfield and Daniel Kaluuya, with the award going to the latter. While FBI informant Bill O’Neill (Stanfeld) spies on Hampton (Kaluuya) and his community, director Shaka King and co-writers Will Berson, Kenny Lucas, and Kieth Lucas highlight oft-ignored parts of the city.
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