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Remember when you moved to Chicago and everything was charming (even the snow)?

News flash: You can recreate the feeling anytime you want, and it's as easy as streaming a classic flick.

We rounded up nine iconic comedies for reigniting your love affair with Chicago.


“My Best Friend's Wedding”

For the love of the Windy City, you can't top that scene where Julia Roberts and Dermot Mulroney slow dance on the boat as they cruise along the river.


“The Blues Brothers”

"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."


“About Last Night”

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


“While You Were Sleeping”

There are two token scenes involving the CTA in recent movie history that we must discuss. The first is Sandra Bullock's heroic rescue of Peter Gallagher from the tracks, which kicks off this rom-com...


“Risky Business”

And the second is the steamy "L" train scene from this '80s classic featuring Tom Cruise and that song by Phil Collins.


“Sixteen Candles”

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


“Never Been Kissed”

Drew Barrymore's Josie went to Northwestern, copyedits for the Chicago Sun Times, lives in Lincoln Park and wins over Michael Vartan.


“High Fidelity”

Doubtful there is anyone better suited to play the owner of a Wicker Park record store than local golden boy John Cusack.



This John Hughes masterpiece needs no explanation. #SaveFerris

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