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The 27 best Chicago movies

From the gangster flicks to coming-of-age stories, here are the most memorable movies ever made about Chicago

Written by
Time Out Chicago editors
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Chicago is referred to as the Second City, but it’s often come a distant third to New York and Los Angeles as a movie town. But while the sheer output of film productions might pale in comparison to those other American metropolises, the city has a high cinematic batting average. From the silent movie days of Essanay Studios to numerous gangster flicks to John Hughes's many love letters to his hometown, Chicago has served as a muse for many cinematic classics. So grab a hot dog and a Cubbies jersey – here are 27 of the best Chicago movies ever made.

Recommended:

🗽 The 101 best New York movies of all-time
🌴 The best Los Angeles movies of all-time
💂 The 32 best London movies

The best Chicago movies

The Blues Brothers (1980)
Photograph: Courtesy Universal Pictures

1. The Blues Brothers (1980)

From its depiction of the bustling, late ’70s Maxwell Street flea market to a climactic chase sequence that winds through Lower Wacker Drive to Daley Plaza, The Blues Brothers is a loving homage to John Belushi’s hometown. The film’s soundtrack reaches beyond the city’s limits, including tracks by Ray Charles, Aretha Franklin and James Brown, who also appear in cameo roles. Jake and Elwood’s journey takes them many places throughout the rollicking musical comedy, but the vivid portrait of the pair’s “Sweet Home Chicago” is what makes it memorable.

High Fidelity (2000)
Photograph: Moviestore/Shutterstock

2. High Fidelity (2000)

John Cusack transferred the action of Nick Hornby's novel, about a man-child record store owner whose rock-snob music knowledge is no help in saving his failing relationship, from London to Chicago. With screenwriting partners D.V. DeVincentis and Steve Pink (like Cusack, Chicago-area natives), Cusack set up protagonist Rob Gordon's shop in a storefront at Milwaukee Avenue and Honore Street, next door to Nick's Beer Garden and down the block from Reckless Records at the height of Wicker Park's boho moment. There are references to local record labels Wax Trax!, Touch and Go and Drag City, authentic gig posters from Chicago venues like Schubas, and scenes shot at Double Door, Green Mill and Lounge Ax. High Fidelity makes it easy to believe that Rob and his friends were an authentic part of Chicago's ’90s music scene, without hitting you over the head with landmarks recognizable to non-locals. That's why this pic about an obsessive maker of top-five lists tops ours.

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Cooley High (1975)
Photograph: Aip/Kobal/Shutterstock

3. Cooley High (1975)

Often described as a "black American Graffiti," Cooley High looked back with nostalgia on the early ’60s at the real-life Old Town high school that was largely fed by the Cabrini-Green housing project. A seminal African-American coming-of-age movie and a touchstone for a generation (or more) of Chicago kids, it was also the loose basis for the late-’70s TV sitcom What's Happening!!

Ferris Bueller’s Day Off (1986)
Photograph: Courtesy Paramount Pictures

4. Ferris Bueller’s Day Off (1986)

Ferris Bueller is up to no good in this ’80s John Hughes classic, in which the high school senior plays hooky and gets into all kinds of trouble with friends as they run around downtown Chicago, including stopping for a little tour of the Art Institute of Chicago, catching a Cubs game and riding center stage in a downtown parade. The next time you watch Ferris (Matthew Broderick) wreak havoc on almost everyone around him, also keep your eyes peeled for great shots of the Chicago Board of Trade, Lake Shore Drive and Willis Tower, among other sites.

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  • Film
  • Documentaries

Few films capture the life and, yes, dreams of inner city Chicago youth quite like Steve James’s acclaimed documentary about high-school kids who see basketball as a means to rising above the poverty and crime surrounding them. Insightful, inspiring and deeply affecting, it’s not just one of the best Chicago documentaries, but one of the best ever.

The Untouchables (1987)
Photograph: Courtesy Paramount Pictures

6. The Untouchables (1987)

Brian De Palma's 1987 take on the dueling forces of Al Capone (Robert DeNiro) and Eliot Ness (Kevin Costner) has a screenplay by Chicago scribe David Mamet; the creative team's vision is full of violence and style—witness the famous scene in which the pair turn a Union Station shootout into an homage to Eisenstein's Battleship Potemkin; for nearly two and a half minutes all you hear in the soundtrack are gunshots, Ennio Morricone's urgent score, and the sound of a baby carriage's wheels speeding down a staircase.

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  • Film
  • Thrillers

Michael Mann’s breakthrough feature is, like a lot of his films, mostly nocturnal, but even lit only by streetlights and neon signs, the city is instantly recognisable to any Chicagoan. The most Chicago thing about the movie, though, is James Caan’s loose-cannon performance as an expert safecracker trying – and ultimately failing – to tamp down his criminal tendencies and go straight. Caan plays him like Joe Pesci channelling Ric Flair, with a heavy South Side accent.  

Medium Cool (1969)
Photograph: Courtesy Paramount Pictures Corp

8. Medium Cool (1969)

John Cassellis (Robert Forster) is a hardened TV news cameraman who manages to keep his distance while he captures daring footage of a nation in the throes of violent change. He maintains this professional detachment when he covers the social unrest in Chicago surrounding the 1968 Democratic National Convention. But when he discovers that the TV network has been quietly cooperating with the FBI, the enraged Cassellis realizes that he too must join the fight against the establishment.

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Ordinary People (1980)
Photograph: Courtesy Paramount Pictures Corp.

9. Ordinary People (1980)

Robert Redford's directorial debut, filmed largely on the North Shore, follows a family reeling from the accidental death of their son. Timothy Hutton won an Oscar as tormented teen Conrad, blaming himself for his brother's death; Mary Tyler Moore got a nomination as his ice-cold mother, who blames him too. The subject material may be difficult to identify with, but the scenery of suburban Lake Forest is easily recognizable.

The Fugitive (1993)
Photograph: Courtesy Warner Bros.

10. The Fugitive (1993)

An incredibly frantic Harrison Ford portrays a Chicago doctor accused of killing his wife, with a crew of U.S. marshals, led by Tommy Lee Jones, hot on his trail. Although much of this chase thriller was shot in North Carolina, some of its most rollicking action sequences feature a rolodex of Chicago landmarks, from city hall to the St. Patrick's Day Parade (in which then-Mayor Richard M. Daley and state attorney general Roland Burris make brief cameos). 

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Mean Girls (2004)
Photograph: Courtesy Paramount Pictures

11. Mean Girls (2004)

Tina Fey's first feature film was this inventive and instantly iconic teen comedy, set at the fictional North Shore High School (sources alternatively cite its inspiration as Evanston Township High School or Winnetka's New Trier High School) and partially informed by Fey's time working a day job in Evanston while studying at Second City.

  • Film
  • Comedy

John Hughes is perhaps the most ‘Chicagoan’ of directors, but the guy is actually from the ’burbs – which makes Home Alone the most truthful to his actual childhood. No, he didn’t get left behind on a family vacation, forcing him to hyper-violently protect his massive tree-lined home from two bungling burglars, but he did grow up in Northbrook, the next city over from Winnetka, where the movie was shot.   

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  • Film
  • Horror

Set in the now-demolished Cabrini-Green public housing projects on Chicago’s Near North Side, Candyman follows a young graduate student investigating an urban legend that describes a killer armed with a hook. The thriller is filled with shocking plot twists and grisly murders, but the most interesting aspect of the movie might be its footage of Cabrini-Green—Candyman features scenes shot within the housing projects. Plus, the latest sequel (written in part by Jordan Peele) is coming out later this year, so now's the perfect time to rewatch.

The Breakfast Club (1985)
Photograph: Courtesy Universal Studios

14. The Breakfast Club (1985)

The famous movie with six kids stuck in their school’s library for detention takes place in the city’s suburbs—the library is modeled after the one belonging to Maine North High School, which closed prior to the filming. Fun fact: The school makes an appearance in another famous film, Ferris Bueller’s Day Off. As for that final fist pump, well, that was filmed on the school’s football field too.

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  • Film
  • Thrillers

Sam Mendes followed up the Oscar-winning American Beauty with this melancholic period piece about a mob hitman (Tom Hanks) whose work-life balance collapses after his son discovers what he does for a living. Mendes shot on location in Chicago, believably transforming several locales – including the century-old University Club – back into how they looked circa the Al Capone years and truly turning the city into a character itself.

The Man With The Golden Arm (1955)
Photograph: Courtesy United Artists/Kobal/Shutterstock

16. The Man With The Golden Arm (1955)

Based on the Nelson Algren novel of the same name, this 1955 drama casts Frank Sinatra as a heroin-addicted drummer—scandalous subject matter for the time. Newly released from prison, Sinatra’s character reunites with his wife at the couple’s home on the North Side of Chicago and attempts to get an audition with a band. Though it was shot in a studio instead of on location in Chicago, Sinatra’s powerful portrayal of a man grappling with addiction places this film among his most essential on-screen appearances.

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  • Film
  • Comedy

Chicago is a baseball town, but the city’s best baseball movie isn’t about the Sox or the Cubbies but the 1943 Rockford Peaches of the All-American Girls Professional League. Yes, Penny Marshall’s classic is mostly fictional, but the team of all-female sluggers actually existed – and while it was called Harvey Field in the movie, the memorable tryout scene was shot at storied Wrigley Field.  

  • Film
  • Comedy

Sure, Wayne and Garth technically shoot their public access chat show from a basement in Aurora, Illinois, which is about 40 minutes west of Chicago proper. But the unquestioned GOAT Saturday Night Live spinoff is also unquestionably a Chicago movie – even if a lot of it was shot in Los Angeles. The crew’s hang spot, Stan Mikita’s Donuts, isn’t real, but the shoutout to the Blackhawks legend is enough to earn placement on this list.

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Widows (2018)
Photograph: Courtesy Twentieth Century Fox

19. Widows (2018)

An embattled Chicago Teachers Union delegate (Viola Davis) rallies a group of widows—their husbands recently killed in a robbery gone awry—to steal $5 million from the home of a wealthy South Side political family in order to pay back a local crime boss. Co-writers Gillian Flynn (of Gone Girl fame) and Steve McQueen cook up a stylish tale of grim determination and dirty aldermanic politics, complete with sweeping shots of the lake and skyline.

The Sting (1973)
  • Film

If you’re going to shoot an old-timey crime caper, Chicago is the place to do it. The team of Paul Newman, Robert Redford and director George Roy Hill struck box-office gold with this story of Depression-era grifters out to con a mob boss. With cameos from Union Station and the now-defunct LaSalle Street Station, The Sting was one of the biggest hits of the ’70s and cleaned up at the Oscars, and its soundtrack revived interest in Scott Joplin, whose performance at the Chicago World’s Fair in 1893 is credited with sparking the ragtime craze.

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  • Film
  • Thrillers

Daniel Kaluuya took home an Oscar for Best Supporting Actor for his portrayal of Fred Hampton, leader of the Illinois chapter of the Black Panthers, in this striking biographical drama. LaKeith Stanfield was nominated in the same category for his depiction of William O’Neal, an FBI informant who infiltrated the organisation in the ‘60s. It’s a searing piece of cinema, dramatising a crucial moment of Chicago history.

Henry: Portrait of a Serial Killer (1986)
  • Film

It certainly won’t get pushed by the tourism board, but this up-close look at the everyday life of a violent lunatic takes you to the dark corners of Chicago few films of the era dare tread. While the film itself is hard to stomach, the documentary-style cinematography acts as a vivid time capsule of the city’s working class neighbourhoods of the 1980s. 

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Southside With You (2016)
Courtesy Miramax/Matt Dinerstein

23. Southside With You (2016)

A South Side filming location and a bevy of Chicago actors in the supporting cast entice, and the story—the first date between young Barack Obama (Patrick Sawyers) and Michelle Robinson (Tika Sumpter)—has to count, at this point, as a modern Chicago legend.

Drinking Buddies (2013)
Photograph: Courtesy Magnolia Pictures

24. Drinking Buddies (2013)

Olivia Wilde and Jake Johnson mumble their way through the story of two coworkers who fall for each other (existing significant others be damned). The pair works at Revolution Brewing, with scenes taking place in the large taproom at the brewery. There are ample nods to Chicago's drinking culture in Joe Swanberg's film—for instance, Wilde is seen wearing a Half Acre shirt, Johnson dons an Old Style Hat, the coworkers spend time at the Empty Bottle, and locally brewed suds flow liberally.

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  • Film

This buddy-cop flick is somewhat forgotten, but it’s one of the few in the genre to take place outside of the major crime comedy hubs of New York and Los Angeles. But it doesn’t make this list just because Billy Crystal wears a Cubs shirt through most of it and the many establishing shots of the L train – the interplay between Crystal and Gregory Hines, as partners roped into taking one last job in the city before retiring to Key West, is sharp and witty, and the movie feels at home in its North Chicago setting.

Adventures in Babysitting (1989)
Photograph: Courtesy Touchstone/Warners/Kobal/Shutter

26. Adventures in Babysitting (1989)

Chris Columbus's kid-caper film about a babysitter (Elisabeth Shue) who is forced to drag her suburban charges into the city to rescue a friend in trouble was largely filmed in Toronto, with some location shoots involving the CTA. But the movie hilariously and accurately captures the suburban fear of "downtown," and it made the Smurfit-Stone (now Crain's) building famous.

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My Best Friend’s Wedding (1997)
Photography: Courtesy Sony/TriStar Pictures

27. My Best Friend’s Wedding (1997)

Ah, Julia Roberts. Watch as she dashes to and from O'Hare, the home of the White Sox, the El and, of course, Fourth Presbyterian Church on East Chestnut Street. The classic 1997 tearjerker never lets you down when you need a good cry, as Roberts’ character realizes, perhaps too late, that she's in love with her longtime pal (Dermot Mulroney) who is about to tie the knot.

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