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, 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.
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.
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.
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.
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.