US Cities on Screen: Chicago

Going to Chicago was like going out of the world.
— Muddy Waters

This month we’re shining a spotlight on The Windy City. The birthplace of the skyscraper and the Twinkie. The home of Kevin McCallister and Muddy Waters. At the movies, Chicago has been the backdrop to countless adventures, from teens playing hooky to criminals on the run. With its iconic Sears Tower always looming large in the background, and its river that famously flows backwards, Chicago has been immortalized on the silver screen many times. Here are the cinematic snapshots capturing the city at its very best. Did we miss any?


Ferris Bueller’s Day Off


Chicago native Ferris Bueller lives out every kid’s dream of ditching school to run wild in the big city. Which for him means driving his friend’s dad’s sports car downtown, singing “Twist and Shout” on a parade float, and pulling pensive poses in front of paintings in the Art Institute of Chicago. The city is his urban playground, and his adventure comes courtesy of Chicago’s most faithful chronicler, John Hughes. “Chicago is what I am,” Hughes once said. “A lot of Ferris is sort of my love letter to the city.”


High Fidelity


John Cusack plays a hapless vinyl-obsessive who knows a lot about music but not so much about women. High Fidelity ushers you through Chicago during the summer of 2000. It was filmed on location, although you can’t visit Championship Vinyl, the record store where Cusack works and where the genre “old sad bastard music” is coined. A storefront located in the trendy district of Wicker Park was converted for the movie. Interestingly, Nick Hornby’s source novel was set in London. The movie’s writers switched location because they were more familiar with Chicago and its “great alternative music scene”. Now you can’t imagine it set anywhere else, right?


Ordinary People


Robert Redford’s first stab at directing is a devastating drama – and a best picture winner no less – set in the suburbs of Chicago. There, an upper-middle-class family is coming apart at the seams as they deal with a death in the family. They live in what looks like a giant dollhouse in an affluent suburb. The son’s high school was in Lake Forest, while other parts of the movie were shot in Lake Bluff and Fort Sheridan, Illinois. Ultimately, this is a side of Chicago you might recognize from John Hughes movies, but you’ve never seen it used to foreground this kind of drama. Do. Not. Watch. Without. Kleenex.


He Got Game


Spike Lee’s name is synonymous with New York City. Yet in 1997, when he was filming locations for He Got Game – a father-son story about a basketball player's ex-con dad (Denzel Washington) who tries to convince his son to go to college – the filmmaker ventured to Chicago. He shot the early family scenes in the city’s Cabrini–Green housing projects on Near North Side. Other scenes were shot at United Center on Near West Side, with Montrose Beach providing the backdrop to the opening credits. 17 years later, Lee would return to Chicago to shoot something entirely different. More on that in a sec.


The Fugitive


Who’d have thought a Harrison Ford thriller would contain such a treasure trove of Chicago movie locations? First there’s Dr Richard Kimble’s flashy apartment in Lincoln Park (which was recently on the market for a cool $3.95 million). Then there’s the University of Chicago, Cook County Hospital, and the John Crerar Library. And that’s not forgetting Downtown, where the St. Patrick's Day Parade was filmed; and the Four Seasons, where Kimble locks horns with his backstabbing colleague. Someone start a movie locations tour now, please.  


Hoop Dreams


Steve James, aka one of the world’s leading doc-makers, spent five years filming his Chicago-set film often referred to as “one of the greatest documentaries ever made”. In it, he follows two African-American high school students who dream of becoming professional basketball players. It’s both inspiring and heartbreaking, not to mention something of a marvel when you realize James weaved the story from 250-plus hours of footage!


Adventures in Babysitting


On the surface, it’s a cheesy 80s teen comedy with big hair and station wagons. Dig a little deeper and this is a pretty well-rounded view of Chicago in the late 80s: from polite suburbia to a criminal underworld on the industrial fringes of the city. The titular babysitter, Chris Parker, drives a bunch of kids into the city when her friend gets stranded at a bus station. Then her car breaks down and adventures ensue: spontaneous singing in blues bars, kids climbing around the “Stone Container” building in downtown. Also: look out for legendary Chicago bluesman Albert Collins in an unforgettable cameo.


Medium Cool


Haskell Wexler’s countercultural caper takes place in Chicago during the summer of 1968, the heyday of student activism in America. It follows a TV news reporter who becomes entangled in the violence that erupts around the 1968 Democratic National Convention. It’s thrillingly unique to watch now. Why? Because Wexler filmed parts at real anti-war protests, the actors moving among real student activists. Meaning, as well as being a movie that questions the role and responsibilities of the media, it’s something of a historical document, a time capsule of America’s late-60s student movements.




Step inside Michael Mann’s vision of a crime underworld populated by jewel thieves and crooked car salesman. James Caan is the thief in question with plans of going straight; not after one last big score though. In this moody neo-noir, Chicago is a perpetually drizzly and dark metropolis, a seedy underbelly where shady criminals thrive in the shadows. In fact, Mann hired real-life thieves as technical advisors. How’s that for authenticity. Ultimately, it’s a gloriously gritty portrait of the Windy City in the early 80s. Keep your eyes peeled for Willie Nelson in a supporting role, and soak up that dreamy synth score courtesy of Tangerine Dream.




Spike Lee’s controversial Chicago-set musical, with the tagline ‘NO PEACE, NO PIECE’, is based on the Classical Greek play Lysistrata, in which women withhold sex from their husbands for fighting in the Peloponnesian War. In Lee’s fiercely political version, the action takes place on the crime-ridden south side of Chicago, where women blackmail their trigger-happy men by refusing to have sex with them. This is Chicago as you’ve never seen it before, all splashes of cartoonish purples and oranges, in an aesthetic that blends gritty urbanism with big studio Technicolor.


Want more "US Cities on Screen"? Check out Oliver's guide to New York.


Words: Oliver Lunn