One of our favorite cities has been a beautiful backdrop and leading character in many great films (and a lot of guilty pleasures too). If there's one decade where the Windy City dominated the screen, it's of course the 1980s, when John Hughes channelled our high school angst into films that became cultural beacons of a decade. Beyond the 80s of course, there are powerful documentaries and dramas in the mix. And if you're in need of some authentic Chicago popcorn to pair with this list, might we recommend some Garrett Popcorn

[Editor's note: we omitted The Breakfast Club because although it was filmed mostly at Shermer High School, the term breakfast club and inspiration for the movie actually came from morning detention at New Trier High School. We couldn't decide which location would be a more accurate listing, and so left it off in a bout of decision paralysis.]

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The Movie

Ferris Bueller's Day Off (1986)

High Fidelity (2000)

Chi-Raq (2015)

Risky Business (1983)

Ordinary People (1980)

The Blues Brothers (1980)

Medium Cool (1968)

Thief (1981)

Planes, Trains & Automobiles (1987)

Adventures in Babysitting (1987)

Hoop Dreams (1994)

Home Alone (1990)

Finding Vivian Maier (2013)

My Bodyguard (1980)

 About Last Night (1986)


The Spot

Philip Johnson's Ben Rose House

Reckless Records

Chicago Cultural Center

The Drake Hotel

Lake Forest Beach

Daley Plaza 

Grant Park

Green Mill Cocktail Lounge

The LaSalle/Van Buren El Stop

Crain Communications Building

Cabrini-Green (former location)

O'Hare Airport 

Marshall Field & Company Store Building (now Macy's)

Ambassador East Hotel (Now Public Chicago)

Mother's Bar