The Chicago vibe is strong in these 6 movies

By Lauren Chval, The RedEye in Chicago

“The Boss” hits theaters Friday, and it’s no surprise that Plainfield native Melissa McCarthy, who also co-wrote the script, set her latest comedy in her sweet home Chicago. Between taking rides on the CTA, talking to her reflection on the surface of the Bean and a funny reimaging of Trump Tower, our city is really on display in “The Boss.”

Plenty of movies have been filmed in Chicago over the years, but there are some that do the city justice better than others.


“My Best Friend’s Wedding”

This 1997 classic romantic comedy stars Julia Roberts as Julianne, a 27-year-old restaurant critic intent on breaking up the wedding between her best friend, Michael (Dermot Mulroney), and his 20-year-old fiancée, Kimmy (Cameron Diaz). Aside from the fact that Kimmy is a University of Chicago student, her dad also owns the White Sox, meaning two scenes take place at Comiskey Park (in the days before The Cell). The emotional climax takes place in Union Station, where Michael and Julianne have a heart-to-heart about their friendship and his desire to marry Kimmy. And in case you aren’t anxious enough for summer, there’s a great scene where the two of them take a boat ride down the Chicago River.

“Ferris Bueller’s Day Off”

This is such an obvious choice, but how could it not be on the list? John Hughes’ 1986 film is a love letter to Chicago, and Ferris’ ditch day has been inspiring delinquent teens for 30 years. They catch a ball game at Wrigley Field, observe the city from the top of the Sears Tower, fool around in the Art Institute and observe the traders in the Chicago Mercantile Exchange. If all of that wasn’t classically Chicago enough, the day ends with Ferris (Matthew Broderick) singing tunes from atop a parade float. Hughes, who went to high school in Northbrook, set the majority of his films in Chicago (or the ‘burbs), but this one stands out as the movie that captured the heart of the city.

“The Blues Brothers”


Another classic. Jake and Elwood Blues set out on a mission to put on a performance that earns $5,000 in order to save from foreclosure the orphanage in which they grew up. Their concert takes place in the “Palace Hotel ballroom,” which is now the South Shore Cultural Center. But perhaps the best display of Chicago is when the brothers race through the city, chased by dozens of police vehicles. Their car falls apart in front of the Daley Center, but they bolt into City Hall to pay the taxes on the orphanage before they’re arrested. Both director John Landis and star John Belushi were Chicago natives and clearly had an idea of how to show off the Windy City.

“The Break-Up”

Like any good Chicago couple, Gary (Vince Vaughn) and Brooke (Jennifer Aniston) met at a Cubs game at Wrigley Field. Once their relationship hits a rough patch, they break up but both refuse to move out of their condo. You can imagine how that goes. Vaughn went to high school in Lake Forest and is pretty much the celebrity you’re most likely to randomly spot in Chicago. The 2006 movie also features a concert filmed in the Riviera Theatre, a classic Chicago spot.

“Drinking Buddies”

Kate (Olivia Wilde) and Luke (Jake Johnson) are co-workers at Revolution Brewing, a craft brewery in Chicago. The two navigate a complicated friendship despite both having significant others. Released in 2013, the film feels like an ode to Chicago’s growing craft beer scene (Revolution Brewing is real!), and the actors actually drank the brewery’s beer while filming, which seems pretty Chicago to us. Johnson grew up in Evanston, and director Joe Swanberg is also a Chicago native.

“While You Were Sleeping”

Sandra Bullock stars as Lucy, a lonely CTA worker. How Chicago is that? A guy she has a crush on falls onto the “L” tracks, and she saves him from being crushed by a train. While he’s in a coma, she accidentally convinces his family that they’re engaged, and they all fall in love with her. The most convincingly Chicago aspect of this 1995 movie is the fact that Bullock is always bundled up in a giant coat with an ugly scarf and hat. Chicago winters aren’t a joke.


(c) 2016 RedEye (Chicago)

Visit RedEye (Chicago) at

Distributed by Tribune Content Agency, LLC.