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OK, so Chicago doesn’t get as much screen time as New York or L.A., but the films and TV shows that do take place here have a special, gritty quality that’s all their own. From the buzziest Netflix series of the season to classic ’80s flicks, the Windy City makes the perfect backdrop for all sorts of drama (and LOLs).


while you were sleeping

“While You Were Sleeping”

Before Peter Gallagher and his on fleek brow game (are we using that slang correctly?) captured our hearts in The O.C., he swept us away in While You Were Sleeping. Lucy (Sandra Bullock in her rom-com heyday) rescues pre-Sandy Cohen from muggers who pushed him onto the “L” tracks. Isn’t that how all great Chicago love stories start?



Not only will you swoon over the star-studded cast (Emily Ratajkowski plays a provocative art student), you’ll perk up every time you recognize spots we locals actually frequent, like Dark Matter Coffee and Revolution Brewing.

happy endings

“Happy Endings”

Canceled too soon, this was Friends for the millennial age, following six young Chicagoans trying to make it in the Windy City. The perfect mix of smart yet silly, this ensemble cast will remind you of all the people who helped you get through your 20s.


“Ferris Bueller's Day Off”

A young Matthew Broderick does a top-notch job of showing audiences what a playground Chicago can be when you’re young (and playing hooky). Also, Sloane’s killer style is something to be cherished and studied every time you watch.

drinking buddies

“Drinking Buddies”

This full-length feature showcases the Chicago that we all know exists but rarely see on the big screen. You’ll see Olivia Wilde hanging out on that grimy couch at Empty Bottle like it’s no big deal and Jake Johnson of New Girl perfectly playing the part of every slow-to-grow-up guy you’ve met since living here.

my bffs wedding
Tristar pictures

“My Best Friend's Wedding”

Yeah, we’ll take an order of Dermot Mulroney with a side of the Chicago River. This ‘90s favorite has so many iconic scenes that we couldn’t begin to cover them in this round-up. Wrigley Field, the Drake Hotel and architecture boat tours? This movie’s got you covered.

risky buiness


That steamy scene on the "L" train makes us think about our daily commute completely differently.

never been kissed
Fox 2000 Pictures


Drew Barrymore's Josie went to Northwestern, copyedits for the Chicago Sun-Times, lives in Lincoln Park and wins over Michael Vartan. If only all Chicagoans could have it that way...

about last night 2
TriStar Pictures


Chicago runs deep in this flick. Not only was it shot around the city (Wrigley Field, Bootleggers) but it was adapted from a play written by David Mamet, it was directed by Edward Zwick and it costars John Belushi—all Chicagoans.

family matters

“Family Matters”

Even the opening credits of this long-running TGIF standout give us the warm fuzzies for our oh-so-cold city. If you really want to get your fill of nostalgia, you can take selfies of the Family Matters house anytime you want, as it’s still standing in all its ‘90s glory on the Near North Side.

sixteen candles
Universal Pictures


OK, this one takes place out in the suburbs. But we are Molly Ringwald, and Molly Ringwald is us.

blues brothers1
Universal Pictures


"It's 106 miles to Chicago, we got a full tank of gas, half a pack of cigarettes, it's dark... and we're wearing sunglasses."

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