13 Chicago Movies and TV Shows on Netflix

Whether you’re enjoying the Evanston suburbs via Mean Girls, the surprising romantic CTA stop via While You Were Sleeping, or The Art Institute via Ferris Bueller’s Day off, there are plenty of Chicago-based movies and shows on Netflix for you to watch right now.

The New Year is right around the corner and we know you’ll probably be recovering from NYE celebrations. Check out these shows and movies when you’re binge watching Netflix this weekend.


Drinking Buddies

Those who’ve been on the brewery tour at the Revolution Brewing Taproom will recognize the workplace of the two main characters Kate (Olivia Wilde) and Luke (Jake Johnson). Realistically, the plot is everyone’s worst nightmare: falling in love with your co-worker and best friend when you’re both already dating someone. Throw in a trip to a cabin in the woods and things get positively complicated.*

Ferris Bueller’s Day Off

Do we really need to explain one of the city’s best fictional Chicagoans? Well, it stars a young, strapping Matthew Broderick as one Ferris Bueller, a rowdy teenager who plays hooky with his friends to romp around Chicago. This is definitely one must-see film for all in the city.*

Happy Christmas

Anna Kendrick stars in this dramatic comedy as a young woman named Jenny, fresh off a breakup, who moves in with Kelly, a writer, her pianist husband and their 2-year-old son. Jenny and her friend Carson (Lena Dunham), shake up the family’s domestic life and force Kelly to redefine what it means to be happy in her life and profession.*

Mean Girls

There’s some debate over whether Tina Fey based the cliquish North Shore High School, where new girl Cady meets the Plastics and learns to wear pink on Wednesdays, on Evanston Township High School or Winnetka’s New Trier High. Getting a definitive answer, much like “fetch,” isn’t going to happen. Watch to remember there was a time when Lindsay Lohan could play a naïve innocent.*

Only the Lonely

It seems almost every extremely famous comedian has done a romantic comedy at some time in their career, and John Candy is no different. This one has him playing a 38-year-old Chicago cop who still lives with his very strict, very Irish mother and falls in love with an introverted funeral home worker.*

While You Were Sleeping

Sandra Bullock, another queen of romantic comedies, plays Lucy, a CTA fare collector (in the era before Ventra) who’s secretly fallen hard for Peter, a daily commuter she’s barely spoken to. One day, she rescues him from an oncoming train after muggers push him on the tracks. Despite this, Peter falls into a coma. When she visits him in the hospital, a nurse introduces her to Peter’s family as his fiancée, and she doesn’t deny it.*

Sixteen Candles

Considered the role that made Molly Ringwald a star, there’s never a bad time to re-watch this 1984 classic. Could you imagine if your family forgot your sixteenth birthday?!

Adventures in Babysitting

We’re talking about the original Adventures in Babysitting movie here, not the 2016 Disney Channel remake. A normal night of babysitting turns into a night young Chris Parker (Elisabeth Shue) will never forget.

30 for 30: The ’85 Bears

The Bears have been absolutely brutal this year and at times it has been too hard to watch. Go back to a simpler, sweeter time with this documentary on the ’85 Bears who won it all.



Kelsey Grammer (yes, Frasier himself), plays Chicago mayor Tom Kane who is diagnosed with a degenerative neurological disorder. Kane hides his dementia from his wife, his co-workers—everyone but the doctor who diagnosed him—but slowly clues slip through the cracks to his friends and enemies.*

The Crazy Ones

It’s a shame this comedy series was filmed in Los Angeles because The Crazy Ones was the last time Robin Williams would “return” to Chicago onscreen. In the show, Williams plays Simon Roberts, who runs an ad agency with his daughter Sydney (Sarah Michelle Gellar). The story is loosely based on the life and career of John R. Montgomery, an ad executive who spent more than 30 years at Leo Burnett.*

The League

Chicago is the logical setting for a show all about a fantasy football league. While FX’s winning sitcom isn’t actually shot in Chicago, much of the action takes place at our own Gibsons with appearances by Matt Forte and Jay Cutler. This show is as much for comedy nerds as football fans with an ensemble including Nick Kroll (Kroll Show), Paul Scheer (Human Giant) and multi-talented Mark Duplass.*

The Chicago Code

This is the Chicago-based crime drama that just didn’t make it. A few years before the start of the NBC Chicago trilogy (Fire, P.D., Med) this show aired on Fox. You’re probably enjoying the trilogy but if you’re looking for a bit of nostalgia you should check this out.

*Denotes movie write-up by Time Out Chicago

Written by @properties
@properties Christie’s International Real Estate is Chicagoland’s #1 brokerage. Through our affiliation with Christie’s International Real Estate, our network spans nearly 50 countries. No matter your real estate needs, we’ve got you covered.