From a daring leap from the East 95th Street Bridge to crashing through the doors at Richard J. Daley Center Plaza, “The Blues Brothers” were “on a mission from God.” Iconic movie moments like these stick in the minds of Chicago cinephiles.
With awards season in full swing, we thought there was no better way to mark the occasion than tackling this question from a Curious City listener: What is the best movie shot in Chicago?
From “The Blues Brothers” (1980) to “Candyman” (1992 and 2021), Chicago holds its own as an award-winning movie location. But with hundreds of potential candidates, it may be impossible to name a definitive best.
We took a stab anyway. We asked Curious City listeners, coming up with a few categories that seemed popular, and then tapped a few professional film critics for their opinion. Of course, if the top title were based on the highest grossing movie at the box office, the answer could disappoint Chicagoans: It’s “Transformers: Dark of the Moon” (2011). Partially filmed in the city during the summer of 2010, the Michael Bay action bonanza earned more than $1.1 billion worldwide. Love it or hate it, according to the Illinois Film Office, the blockbuster’s economic impact was $25.5 million in qualified spending for the state.
But the best is not determined by box office dollars. It comes down to storytelling and how well a film showcases the city. As for our categories, we took a look at Chicago movies that were recognized by the Academy of Motion Picture Arts and Sciences, ones that told us about love in the city and ones that took us on a wild ride.
Best ‘And the Oscar goes to…’
When it comes to lists of best movies of all time, Chicago films don’t usually make a strong showing. Obviously, this is a mistake. Only one Chicago movie cracked the top 100 of Metacritic’s best movies of all time, the documentary “Hoop Dreams” (1994) at No. 33. We don’t see a Chicago movie on Rotten Tomatoes’ 300 Best Movies list until No. 130 with “The Big Sick” (2017).
In terms of most Academy Awards won, “The Sting” (1973) took home seven statues. But this Chicago story may be disqualified because it was mostly filmed in Hollywood. “Ordinary People” (1980) is a favorite of Pope Leo XIV and took home four Oscars, but it too may be disqualified because it was filmed in the suburbs and not the city. So that leaves “The Dark Knight” (2008); with eight nominations, it took home two statues, for sound editing and best supporting actor posthumously awarded to Heath Ledger.
“Even though it’s Gotham, Gotham is partly inspired by Chicago, and so there is some kind of Chicago history, some kind of Chicago culture, and [Gotham] relies heavily on the architecture,” said Robert Daniels, associate editor of RogerEbert.com.
Crime classic “The Untouchables” (1987) received one Oscar for best supporting actor, awarded to Sean Connery. The movie features some iconic scenes in timeless locations like Preston Bradley Hall at the Chicago Cultural Center, where nearly 40 years later, you can still admire the glass Tiffany Dome.
“Road to Perdition” (2002) won an Oscar for best cinematography, and plenty more films received nominations but no wins.
For many Curious City listeners, the best movie shot in the city is “The Fugitive” (1993). Of its seven Academy Award nominations, it won best supporting actor, awarded to Tommy Lee Jones (seems Chicago does well for supporting actors).
Listener Max Kroll said director Andrew Davis uses city locations to further the story.
“When Harrison Ford’s character, Dr. Kimble, is on the run and comes back to Chicago, he approaches his friend Dr. Nichols in Lower Wacker Drive,” Kroll said. “Lower Wacker is a place that everyone has gotten lost in at some point, and you can get how it’s a place where a person could disappear easily if they were on the run.”
Best depiction of Chicago for lovers
Chicago has hosted dozens of rom-coms over the decades, from “About Last Night” (1986) to “The Break-Up” (2006). Hat tip to “Never Been Kissed” (1999) for featuring the Chicago Sun-Times.
For freelance film critic and author Marya E. Gates, the best is “While You Were Sleeping” (1995). Sandra Bullock plays a CTA employee who falls in love with a comatose rich guy. Gates said that through its love triangle antics, the movie feels reflective of the city.
“It shows Northwestern Hospital. It shows the giant fancy buildings that Peter Gallagher’s [comatose rich guy] character lives in. They’re by the WBEZ offices,” she said. “It shows a CTA station that doesn’t exist anymore, Randolph and Wabash. So it has a sense of history. It’s almost an archival piece because so much of it is shot in there.”
Another archival piece is “Love Jones” (1997) starring Larenz Tate and Nia Long. An aspiring writer and an aspiring photographer bond over the arts after a chance meeting at a club.
“It’s a love letter to the city,” said Curious City listener Danielle A. Scruggs. “The movie starts out with scenes from the South Side of Chicago, and then we see [record store] Dr. Wax, which is no longer around. But I used to go there when I was younger, so I have fond memories of that.”
The movie aptly depicts the Black art scene of the 1990s in Chicago, which is rarely seen on the big screen, according to Daniels.
“I think in terms of Black artists, New York [is always] the Black artist city,” he said. “But [in “Love Jones,”] you get to go through their social circles and see this thriving Black intellectual community in Chicago.”
Daniels noted that a delay pushed some filming into the fall, which ended up working to the production’s advantage. Natural fog off Lake Michigan gave the movie’s Buckingham Fountain scene an extra dose of romantic ambience.
Best teenage romp
Chicago perfectly lends itself to coming-of-age movies, and the best among them feature teenage antics and a little bit of trouble.
“Ferris Bueller’s Day Off” (1986) takes viewers from the northern suburbs to all over Downtown. Is it possible to go to the Willis Tower, the Chicago Board of Trade, a fancy restaurant, a game at Wrigley Field, the Art Institute and a random weekday parade and make it back up to the suburbs before your parents get home at 6 p.m.? People have tried and failed, but North Shore teens can dream.
“I remember having to tell my out-of-town college friends that’s not how parades are here,” Daniels said. “But you get a great sense, at least in that scene, of the city Downtown … Like the construction workers, but then the German dancers in there, which gives the German heritage of the city. And then there’s the Irish component in there too. So it’s actually a really interesting showing of the melting pot of the city.”
If there was a “Ferris Bueller” parallel, Daniels said it would be “Cooley High” (1975). The Chicago classic follows two Black students as they ditch class to hang out at Lincoln Park Zoo before meeting up with some girls at a soul food hangout. But it’s not long before things go wrong with the police and a couple of rivals.
“It’s a blaxploitation film, and the city actually has a very rich history of blaxploitation movies, because many of them actually world premiered in Chicago,” Daniels said. “Having a Black director who was able to make a film specifically about Chicago but also make it specifically about Black coming of age, it’s incredibly rare, and it still stands.”
Daniels said that, like “Ferris Bueller,” “Cooley High” starts off as a fun romp. Where the movies diverge speaks to the difference in race, class and privilege in the city.
Honorable mention
‘Medium Cool’ (1969)
“This is one of the most important films of the 20th century. A mix of documentary and narrative filmmaking. It demonstrates what life was like in working-class Chicago during one of the nation’s most tumultuous years, 1968. The film showcases still-relevant politics about race relations, social class and the truth portrayed to audiences in media.” - Salvador Salazar, West Lawn
‘Thief’ (1981)
“Michael Mann (himself a Chicagoan) films the city with a sense of mood it’s rarely had elsewhere; it becomes a perfect backdrop for the first of his lonely-man-criminal movies, and arguably the purest. James Caan is a cat burglar out for one last score so that he can buy himself the perfect domestic fantasy life the carceral system denied him, and ‘80s Chicago offers the movie just the right blend of bitter cold and loneliness.” - Curious City listener
‘Adventures in Babysitting’ (1987)
“It’s a campy, hilarious fish-out-of-water tale. It’s about kids coming from suburban Oak Park to rescue their babysitter’s friend in the big, chaotic city, so you know some wild stuff’s about to go down. You pair that with a colorful cast of characters, including a young Anthony Rapp, and you’re in for a good time. Second of all, this movie has some pretty iconic Chicago footage, most notably the scene when the little girl Sarah is climbing up the side of the Crain Communications Building. I think of that part literally every time I walk past that building.” - Natalie Terchek, Lake View East
‘High Fidelity’ (2000)
“This movie is a love letter to analog media, relationships and early 2000s Wicker Park. The film features many iconic Chicago landmarks, like Double Door, Rainbow Club, the Green Mill and others. If you’ve seen it, you know there’s a scene where Rob and one of his dates visit the Music Box Theatre. My favorite ‘High Fidelity’ memory is attending a special screening at the Music Box a couple of years ago and clapping and cheering with the sold-out crowd when that scene came on.” - Melissa Postlethwait, Bridgeport
‘Widows’ (2018)
“Wonderful script, phenomenal performances, understands how power and corruption work in Chicago. There is also a sequence where the camera follows a car as an aldermanic candidate talks that I think about a lot.” - Monica R., Austin
Susie An is the editor of Curious City.
