The city of Chicago is a beautiful and lively urban sprawl that has been the backdrop for a number of films. While some films, like Candyman or The Dark Knight, were shot in the city, their plots don't quite showcase the city as a real place.
These 10 films all capture the city with realism, historical accuracy, or just slightly fantasized admiration. They come from a genuine place of wanting to do more than show the big bean and tall building in an establishing drone shot. These are the films that best capture the city.
10 Home Alone
The classic tale about Kevin McCallister, a boy left behind by his family, who then terrorizes bumbling criminals with SAW-like traps. Written by John Hughes, this Christmas staple is applauded for its portrayal of Wintertime in the Northern suburbs of Chicago and was shot in Winnetka, a neighboring suburb of Northbrook.
There is also a short section where Kevin visits an actual church in Oak Park.
9 The Weather Man
One of Nicolas Cage's many fantastic dramatic performances is as a Chicago weatherman. The film showcases one of the worst parts of Chicago, its cold weather.
The freezing cold is used to make Cage's isolation and family struggles even worse. The chilling weather is always present as these characters are just trying to go about their day and deal with their own issues. It adds a bleakness to the whole thing, but at least the shots of the frozen river and ice skating in Millenium Park sure look nice.
8 About Last Night... (1986)
Chicagoan writer David Mamet originally wrote the script as a play that was performed in Chicago for some time before being adapted to film. The movie captures what it is like being a promiscuous young adult living in the city and in doing so it consistently features a number of real Chicago locations. Wrigley Field, Grant Park, and a number of actual bars all make appearances during the film.
This all makes it even stranger that the 2014 remake is set in Los Angeles instead of trying to showcase a more modern Chicago.
7 The Fugitive
While the first half of the film takes place in rural areas, the finale of the film comes to Chicago and uses the city to its fullest potential. The L train and the Pullman and Lincoln Park neighborhoods are all featured but the real spectacle is the city's annual St. Patrick's Day parade.
The film uses the parade for an action set-piece, but it also accurately captures the celebration, even down to the dyeing of the river green.
6 The Untouchables
Chicago has a rich history and this film does an excellent job of recreating a violent piece of it. The story of detectives trying to bring down Al Capone recreates the city accurately and showcases many historic parts of the city that still look the same today.
Places like The Chicago Theater and Union Station make prominent appearances along with the best depiction of old Chicago caught on film.
5 Drinking Buddies
One of the pivotal figures of the mumblecore movement, Joe Swanberg is a Chicago resident and has used the setting for a number of films and for his Netflix show Easy. Many of which, including this one, include Chicago-native actor Jake Johnson.
Drinking Buddies gets the nod on this list because the characters spend their time in some of Chicago's more low key places instead of the major landmarks. Nearly every bar and restaurant featured in the film is a real place that they shot inside. Also notable is that Olvia Wilde's character takes a shot of Malört, which is sure to make Chicagoans cringe.
4 Chi-Raq
Spike Lee's 2015 exploration of race and violence deserves a spot on the list for shining light on a part of the city that most films ignore, the Southside. When a stray bullet hits a child, a group of women organizes a movement in an effort to challenge the violent ways of the area they live in.
Lee's film is a modern retelling of the Greek play Lysistrata and setting it in the Southside of Chicago is a bold vision that works hard to bring the area's culture and needs to the minds of people who might not know much about that part of Chicago.
3 High Fidelity
Like Drinking Buddies, High Fidelity is an unabashedly Chicago film without all the glitz and glamour. Lead actor John Cusack actually grew up outside the city in Evanston, IL, and his portrayal of a young adult unsure of himself in the city is an accurate one.
Cusack lives life in the film with a regularity that Chicago locals could almost definitely relate to. He has posters and shirts for actual local bands, he sees a movie at the historic Music Box Theater, and he even DJs at an actual bar in Wicker Park.
2 The Blues Brothers
Making a run for the ultimate Chicago movie, The Blues Brothers gives more love to the city than almost every other film on the list, mostly by causing property damage all over it. What makes this one especially Chicagoan is that the titular brothers go to some of the smaller nooks and crannies of the city.
The two venture to iconic parts of the Southside, Northside, and then have their finale downtown. The whole journey exudes a familiarity with the city that many films shot there don't. Plus, they even sing a song titled Home Sweet Chicago, which is pretty tough to beat.
1 Ferris Bueller's Day Off
The most iconic Chicago film of all time is John Hughes's love letter to his own adolescence. Hughes grew up in Lake Forest next to Lake Michigan, and he made it a point to shoot his films in Chicago suburbs whenever possible (which explains why he has two on this list).
While all the movies on this list showcase the city, this is the one that makes it a character. The story moves so fast that location after location is being featured. Hughes went out of his way to feature as many staples of Chicago as he could in a tight film, and he succeeded.
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