Cult rom coms like When Harry Marry Met Sally and Drinking Buddies, coming-of-age movies ranging from Ferris Bueller’s Day Off to Sixteen Candles, mob movies like The Untouchables to adventure blockbusters like The Dark Knight and Divergent were all filmed in this lake front city. Check out some emblematic spots here (most of which are reachable by public transportation)! For the more avid watchers there are guided tours.
Chicago Union Station
Chicago Union Station, other than home to millions of passing travelers, is also home to the momentous shootout in The Untouchables, in addition to Michael Mann’s Public Enemies where the 110 foot atrium and gigantic marble floor time travel to the notorious mob history. Other famous Chicago gangster films have taken place on the same marble floor including Road to Perdition. So catch Oscar-winner Sean Connery in a movie about the infamous Al Capone amidst an already historic Chicago landmark. Also check out its appearance in My Best Friend’s Wedding.
University of Chicago
The Rom-Com about whether men and women can really be friends, When Harry Met Sally, aptly begins its journey on this English gothic-style college campus in the neighborhood Hyde Park. A shot of the beautiful Chicago campus opens preceedings where we meet Harry and Sally for the first time, as fresh-faced college grads about to embark on the stereotypical move to The Big Apple to find themselves. The warbled tones of Louis Armstrong’s Our Love Is Here To Stay crescendos as Harry and Sally drive out the UChicago Gate to start their new lives as New Yorkers.
“The L” Train
Emblematic of the Chicago experience, The L not only gets some serious face time in The Dark Knight, but it also (quite appropriately) plays a huge role in John Hughes film Planes, Trains, and Automobiles. Steve Martin and John Candy say their goodbyes before Martin has an epiphany that leads to a key scene in the movie – which we won’t spoil but look here for details. It’s also the site of A true to name Risky Business sex scene on the train. The train is also featured in the brimming romance of the protagonists, one of which is played by Miley Cyrus in the Chicagoan take of the French Film LOL.
The Art Institute of Chicago
A key scene in the classic movie Ferris Bueller’s Day Off takes place in the Art Institute featuring Cameron doing a bang up Magic Eye impression as he stares off into space at George Seurat’s “A Sunday on La Grande Jatte.” The most impressive part” They manage to condense over one million square feet of museum into a miraculous two-minute trip.
As you can imagine, prime scenes of many a baseball movie have taken place at Wrigley Field including A League of Their Own, Rookie of the Year, About Last Night, 8 Men Out, and Hardball just to name a few. A League of Their Own makes the on-screen jump back to 1943 before women, as the title suggests, had a league of their own, and illustrates the story of Geena Davis’ effort to make it happen. It also is also prominently featured in the hit – pun intended – film Rookie of the Year. The story details the somewhat goofy story of a unexpected accident turning a less than talented 12-year-old little league player into an all-star pitcher for the Cubs with an almost mechanically precise arm.
The more recent film Drinking Buddies staring the one and only Olivia Wilde, features multiple spots in the “hipster” neighborhood of Wicker Park. A good portion of the movie actually takes place in the protagonists’ place of work Revolution Brewing, an actually brewery with two nearby locations in Avondale and in the Logan Square neighborhood. The protagonists also shoot pool at cool music venue: The Empty Bottle.
This popular food spot gets its 15 minutes of fame in John Hugh’s 80’s film The Body Guard, where Cliff (the new kid on the block) dines nightly at the Ambassador East Hotel’s restaurant. Go for an omelet for brunch or check out the spot for its air time significance.
Music Box Theatre
John Cusack, already a component of Chicago history, filmed part of High Fidelity at the Music Box Theatre about a music snob living in Chicago. Rob, the protagonist snob, visits the Music Box and Biograph’s theatres as well as a variety of other Chicago spots.
O’Hare International Airport
The glam airport that a young Macaulay Culkin finds himself lost in is the setting of the second in the series of the family classics Home Alone 2. After the McCallisters depart from their Winnetka home, they race through O’Hare to make it to Terminal 3 but lose their troublemaking son in the process.