Make the Case: 5 Best Movies Set in Chicago

There are likely more movies about Chicago than you might realize.

There will ever be a time in my life where a movie set in a city I’ve never visited can be at least one of the potential selling points. As a U.S. Green Card holder, I’m going to be waiting a while until I can leave the continent and maybe check some of those places out. Movies continue to help fill in the gap inherently left by my longing to get out of the country for a while.

At the same time, I also love movies set in places with a lot of personal memories attached to going there and hanging around for a while. Chicago is a great example. With a long history of movies set in Chicago, the city quickly became one I wanted to experience for myself from a very young age.

I’ve been to Chicago twice. Chicago for me represents a litany of good movies, food that absolutely wrecks human cholesterol in the best way possible, stark steel architecture, and some of my favorite bars. It has been entirely too long since the last time I went.

Hopefully, that will change sometime soon. In the meantime, I remain content to watch some movies.

For this month’s Make the Case, I’m going to list off some of my favorite movies about Chicago. Anything (mostly) shot/set in the town that gave us such unforgettable names as Harrison Ford, Andre Braugher, and Shorty Hamilton qualifies.

For simplicity’s sake, movies that were only shot in Chicago, standing in for a fictional city, do not count.

And John Hughes only gets one.

Maybe.

 

5. The Blues Brothers (1980)

Director: John Landis

While technically more of a road trip movie, The Blues Brothers puts Chicago on memorable display throughout its manic pace, legendary musical numbers with artists like Ray Charles and Aretha Franklin, and insane comedic twists. The car chase through Downtown Chicago in particular is a highlight.

You also can’t forget that Blues Brothers star John Belushi, who would never be funnier in a movie than he is here (yes, that includes Animal House), was a proud native of Chicago. The same can be said for brother Jim, who has appeared in several films and TV shows set in Chicago over the years, including nine seasons of a sitcom.

There are so many things to like about The Blues Brothers, including how it spotlights famous black musicians, creates likable characters, and never loses momentum. A good portion of the film’s enduring appeal can be traced to how it showcases places like the Palace Hotel Ballroom and the Maxwell Street Flea Market circa 1970s.

The additional time capsule appeal of this film can’t be denied either.

 

4. High Fidelity (2000)

Director: Stephen Frears

John Cusack at his peak powers of almost tangible charm and likability gets me over the fact that Rob is kind of a dick. Occasionally, you may feel compelled to throw something at his mopey head and tell him to stop hanging out with hilarious, deeply maladjusted music nerds at a record store in the Wicker Park district.

Granted, he’s working on it, and we get to watch him doing that while also seeing Chicago in its storied glory, but when Joan Cusack’s character (I guess they’re related) walks into the store, screams five words, and leaves, it’s hard to argue with her frustration.

However, Rob is not a complete jerkass. Between Cusack’s performance and an exceptional script based on a book by Nick Hornby, most will find Rob worth getting behind. He’s funny, engaging, and has enough situational awareness to keep him from being hopeless. Chicago is a beautiful, memorable part of his story.

 

3. Cooley High (1975)

Director: Michael Schultz

Cooley High is another entry on this list where at least some of the film’s appeal can be derived from its use of the geography. Cooley High gives you another brilliant time capsule tour of the city. Some of Cooley High’s most notable Chicago shooting locations include the Lincoln Park Zoo, Navy Pier, and parts of the Gold Coast area.

Along with being a vital depiction of these places during this era, Cooley High is also a timeless comedy-drama that’s one of the best movies of the 1970s. If you won’t accept that, it’s definitely one of the most underrated.

The electrifying performances by the cast, particularly Glynn Turman and Lawrence Hilton-Jacobs, are naturally the heart of this film. You can also look to a complex, affecting, and very personal script by Eric Monte, drawn from his own childhood in Chicago’s Near-North Side projects. The impassioned direction by the legendary Michael Schultz must be mentioned, as well.

 

2. Ferris Bueller’s Day Off (1986)

Director: John Hughes

To be honest, even as a kid, I sided with Cameron from start to finish. Ferris is fun. His decision to take a day off from high school so close to graduation powers one of the most iconic comedies of the 1980s.

Still, I felt bad for Cameron more often than not, and I thought his sister (Jennifer Grey, whose performance and scowl don’t get nearly enough time in this movie for me) had a right to be a little sick of his nonsense. I felt this way as a child, and the annoyance with the character has only grown over the years.

None of this changes the fact that Ferris Bueller’s Day Off is a blast as a comedy in every possible way. John Hughes loved Chicago on a level I can’t help but admire. The city is a significant portion of his entire filmography. No other filmmaker did more to create an impression, at least in my childhood, of a city you might want to experience for yourself.

This was one of my earliest film introductions to Chicago. Wrigley Field (I’ve been there for my to-date one Major League Baseball game), the Chicago Art Institute, Downtown Chicago (where the parade was filmed), and other locations are spotlighted in a way that is now distinctly Hughes.

The film also features Sears Tower. It is now called Willis Tower, but I would suggest visitors just call it Sears Tower. The locals are still cranky about the change — they might yell at you.

 

1. Hoop Dreams (1994)

Director: Steve James

Fictional films have done so much for my wanderlust, particularly when I was growing up. The list above is far from a complete range of what the movies have done to depict Chicago. The Fugitive, Candyman, and Hellcab are further examples of movies giving me a complex, multifaceted impression of a place that can seem absolutely fascinating to an outsider.

Film can’t do, show, or say everything about a place or culture, but I think it can still be really helpful in its own way. These films don’t just show the landmarks, the architecture, or a skyline with the potential to take your breath away. They also give you at least an idea of the atmosphere and energy generated by the seemingly endless array of peoples who live there.

Hoop Dreams, one of the best documentaries of the past 30 years, is also one of the best films ever made about this particular city. You won’t learn everything about Chicago by watching a 27-year-old documentary, but I would venture to say you’ll see why the city is different from places like New York City, Los Angeles, or anywhere else. It isn’t just cultural differences between regions.

The film itself, if you have never seen it, is an unforgettable story of two African-American teenagers who aspire to NBA stardom. Hoop Dreams follows their story at considerable length, building an impression of not only their lives, but the nature of the reality which exists around those lives.

Hoop Dreams is also the most organic, grounded presentation of Chicago to be found anywhere on this list. There isn’t much stylization here, which I like. What you see is what you get.

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