Best Chicago Movies
The windy city. The second city. The city of big shoulders and big dreams.
It’s Chicago!
And we’re ranking the city’s top 10 best movies.
10 Best Chicago Movies (Filmed and Set in the City)
Alright, let’s get down into the nitty-gritty of how this cinematic experiment is going to work.
First off, we have some stipulations. Our discussions cover movies with two critical ingredients:
The movie has to be set in Chicago or reflect the spirit of the city in the story.
The movie has to have scenes shot on location in the city of Chicago.
For instance, Sleepless in Seattle features scenes shot on location in Chicago at the start of the movie, but it isn’t primarily set there. So, it wouldn’t make the list. Either would be the Breakfast Club and Home Alone, because while they’re famously shot in the Chicago suburbs, it’s not set in the city, and the city isn’t really a character in the movie.
Our criteria also rule out movies like My Big Fat Greek Wedding, Christmas Vacation, and Chicago the musical, all Chicago-based stories that weren’t shot here, instead in Toronto or on a set in Hollywood.
So, when I first picked this topic, I thought I was familiar with Chicago movies, but wow…there are so many to choose from, especially in the 80s and 90s, which were a boom era for Chicago.
Here’s a spreadsheet I created of more than 70-plus movies that fit our criteria in the show notes.
With help from listeners of Least Important Things and a panel of Chicago cinephiles, we narrowed down the list to a top 10 that capture the spirit of the city and are the most well-known Chicago movies.
But your top ten list might look totally different, and I encourage you to check out the full list and build your own top ten using the scoring system we used.
So, it’s time to take a shot of Melort and a big bite of a Chicago dog to find out the top 10 best Chicago movies.
10 - My Best Friend's Wedding
1997’s My Best Friend's Wedding, directed by P. J. Hogan, starring Julia Roberts, Dermot Mulroney, and Cameron Diaz.
This film tells the story of a successful food critic who attempts to sabotage the wedding of her college boyfriend/supposed best friend over a magical wedding weekend in Chicago.
Notable Chicago moments:
Kimberly Wallace is a 20-year-old University of Chicago architecture student whose father owns the Chicago White Sox and an imaginary sports broadcast company
River boat architecture tour
Karaoke at a dive bar
The Drake Hotel
Picking up and dropping off a friend at O’Hare
Eating a hot dog on the stairs to the El
A romantic chase sequence at Union Station
Multiple scenes at Cominsky Park, including a catfight confrontation in the public bathroom
9 - The Sting
1973’s The Sting, directed by George Roy Hill, starring Paul Newman, the late-great Robert Redford, and Robert Shaw. This caper classic is the oldest on our list and most decorated, winning seven of its 10 Oscar nominations, including Best Picture, Best Director, Best Film Editing, and Best Original Screenplay.
It follows the story of a young con, played by Robert Redford, who teams up with the old guard con Newman to settle the score of a murdered friend by the villainous crime lord played by Robert Shaw.
This film almost didn’t make the list because much of it was shot on sets in Burbank; however, a few scenes qualify, and this movie truly captures Depression-era Chicago.
Notable Chicago moments:
Prohibition era crime culture
Union Station
Robert Redford’s EL chase
The adapted score from Scott Joplin's ragtime music
8 - The Dark Knight
2008’s The Dark Knight, directed by Christopher Nolan, starring Christian Bale, Heath Ledger, and Gary Oldman.
The Dark Knight returns in the second installment of Nolan’s Batman trilogy, where Bruce Wayne/Batman faces off against the agent of chaos–the incorruptible Joker, who’s set on bringing Gotham City to its knees and turning the city against the caped crusader.
Our panel debated whether this film qualifies for the list, and while Chicago plays Gotham, the imagery is distinctive of the Gothic architecture and raw underbelly of the city.
Notable Chicago moments:
The IMAX film shots of the Loop
Bridge and lower street action
Night shots of Batman on the roofs with the Chicago skyline
At Jim Gordon’s place, Batman shows up in the distinctive Chicago stairwell
S. Lasalle St. at night, facing the Chicago Board of Trade Building
7 - Barbershop
2002’s Barbershop, directed by Tim Story, written by Mark Brown, Don D. Scott, and Marshall Todd, starring Ice Cube, Cedric the Entertainer, Eve, Anthony Anderson, Keith Anderson, and a huge cast of names that would go on to do a lot.
Ice Cube plays Calvin Palmer, a third-generation barber shop owner on the Southside of Chicago, who’s attempting to keep the shop afloat amid a cast of characters and storylines flowing through his place of business. The story unfolds over one dramatic day at the Barbershop and its surrounding neighborhood, where the characters and storylines intertwine to shape the shop's future.
Now, I’m sure people want to hear the thoughts of a white thirty-something male podcast host from Michigan on the black experience on the South Side of Chicago…but this movie was a sensation for the comedy genre and Chicago. It was a huge hit with a $12 million budget and made more than $77 million.
Notable Chicago moments:
Starting a side hustle in a Chicago basement
Oprah’s guesthouse references
Hauling an ATM up and down a Chicago stairwell
Walter Payton and Michael Jordan jokes
Beautiful slow-motion chase scene under the EL
6 - Candyman (1992)
1992’s Candyman, directed by Bernard Rose, starring Tony Todd and Virginia Madsen.
The proto-prestige horror thriller tells the lore of Candyman, a murdered slave who comes back to haunt a grad student investigating an urban myth on the south side of Chicago.
Notable Chicago moments:
A gorgeous pre-drone helicopter shot over Interstate 290, going Westbound Out Of Chicago
Haunting, bleak, wintry imagery of Chicago, including a Randolph Street Bridge featuring Virginia Madsen.
Details the racial and class divide in the city, specifically the redlining on the South Side of Chicago
5 - The Fugitive
1993’s The Fugitive, directed by Andrew Davis, starring Harrison Ford and Tommy Lee Jones, who won an Oscar for Best Supporting Actor.
This action thriller depicts Dr. Richard Kimball, played by Ford, who is framed for murdering his wife in a gorgeous Gold Coast home, and escapes custody to prove his innocence, only to be persuaded by the dashing Samuel Gerard and his endearing crew of US Marshals.
Notable Chicago moments:
The finale sequence is at a medical conference in the Plaza Hotel.
One of the key clues that places Kimball in Chicago is the sound of the EL over a pay phone.
The chase sequence during the Chicago St. Patrick’s Day Parade.
Brown Line fight sequence between Kimball and the one-armed man.
4 - The Untouchables
1987’s The Untouchables, directed by Brian De Palma, written by David Mamet, with a score by
David Mamet, starring Kevin Costner, Sean Connery, Andy Garcia, and Robert DeNiro as Al Capone. This is a dramatic interpretation of the Prohibition era in Chicago and Elliot Ness’ takedown of Capone for not paying his income tax.
Notable Chicago moments:
Captures the Art Deco architecture of the era
Ness Meeting Malone On The Bridge / N. Michigan Avenue Bridge
Walking the beat bridge scene
Union Station scene
Rooftop chase and white suit guy killed on the ivy
“What is bootlegging? On a boat, it’s bootlegging. On Lake Shore Drive, it’s hospitality. I’m a businessman.”
“That’s the Chicago Way.”
“Mr. Ness, I do not approve of your methods.” “Yeah, well, you’re not from Chicago.”
3 - Ferris Bueller’s Day Off
1986’s Ferris Bueller's Day Off, directed by John Hughes, starring Matthew Broderick, Alan Ruck, Mia Sara, and Jennifer Grey.
Ferris Bueller is a suburban high school senior and beloved slacker who decides to take advantage of a rare warm and sunny Spring day in Chicago by skipping school with his best friend and girlfriend to explore the city of Chicago for the best day off ever–all while avoiding getting caught by his little sister, parents, and deplorable principal.
The Ferris Bueller’s Day Off Challenge:
Rent a sports car in the suburbs
Visit Glenbrook North High School
Drive into the loop
Visit the Sears tower
Eat at a fancy restaurant for lunch in the Gold Coast
Visit the Chicago Board of Trade Building
The Chicago Art Institute
Cubs game
Daley Plaza (parade optional)
Walk by the lake
Drive home by dinner
2 - High Fidelity
2000’s High Fidelity, directed by Stephen Frears and adapted from a Nick Hornby book.
It stars John Cusack as a Chicago record store owner, who talks third-person to the audience and trapes through his list of heartbreaks and associated music. This also stars John’s sister, Joan, Lisa Bonet, Catherine Zeta-Jones, and a breakout performance by Jack Black.
Notable Chicago moments:
The record store Milwaukee and Honor - Now a second store
Truly captures the Chicago rough and tumble music nerds.
Lakeshore walk in the lake spray.
Tons of nightlife venue shots and references: Biograph Theater, The Double Door,
Venue posters in his apartment, The Metro, Shubas,
Kinzie Street Bridge scene “top 5 things about Laura”
The Reader interview
The Green Mill
Really good CTA shots: Purple Line, Armitage station
1 - The Blues Brothers
1980’s The Blues Brothers, directed by John Landis, starring Dan Aykroyd, John Belushi,
John Candy, and a legendary list of music icons like Cab Calloway, Aretha Franklin, and James Brown.
This was the first SNL sketch turned into a movie, and tells the tale of Joliet Jake and Elwood Blues on a mission from God to reunite their band and save the Catholic orphanage they grew up in. All while eluding the Chicago PD.
The Blues Brothers is about driving and music, and they shot everywhere in the Chicagoland area, except for the final concert, which was shot at the Hollywood Palladium. I don’t have time to list them all.
Notable Chicago moments:
Chez Paul is the same restaurant as in Ferris Bueller
Selling the orphanage to the Board of Education
County Assessor’s Office
“How often does the train go by? So often you won’t even notice.”
“No, sir, Mayor Daily no longer dines here. He’s dead, sir.”
“Sweet Home Chicago”
Daley Plaza scene
Wrigley Field
Rank Your Best Chicago Movies
Listen to part one and part two of our podcast to understand our reasoning for the rankings, then build your top 10 list to make your own best Chicago movie list.
Now, I’m not so good at math, but here’s how it’s going to work. We’re going to go through our top 10 list alphabetically, and we’ll go around the horn, revealing our ranking of the movie out of 15 points from three categories:
Cinematic Quality (1-5)
Chicago Scenery (1-5)
Chicago Aura (1-5)
Each panel member shared they’re ranking out of 15, and we will add the total scores up. The movie with the most total points will earn the title of best Chicago movie.
Start ranking today!