Top 10 Chicago Movies
By Cinema Sugar
Chicago is a world-class movie city that also happens to be Cinema Sugar’s hometown. The City of Big Shoulders is second to none for welcoming the most colorful characters, including the fugitive doctors, future presidents, truant teenagers, and nocturnal superheroes that pack our Top 10 Chicago Movies like game day at Wrigley.
10. Candyman
Whether you ‘ship the 1992 original or the 2021 reimagining, you know the rules: say his name five times in a mirror, then myth and reality and good and evil become terrifyingly intertwined in the Cabrini-Green projects of Chicago.
9. Southside With You
Sparks fly in this gentle and romantic portrayal of Barack and Michelle Obama’s first date at the churches, movie theaters, ice cream shops, and lakeside views of Chicago.
8. Return to Me
Written and directed by Chicagoan Bonnie Hunt, this lovely rom-com revels in both the touristy side of Chicago—Lincoln Park Zoo, Grant Park’s Buckingham Fountain—and the locals’ view of the beautiful, tree-lined streets of Lincoln Park and Oak Park.
7. Judas and the Black Messiah
Just as the stars aligned for Fred Hampton to be a leader of monumental impact, so too did they for the great Daniel Kaluuya in portraying him in this electrifying, Oscar-winning true story of corruption and betrayal.
6. While You Were Sleeping
Not only is this one of the best rom-coms in the game, but as a love letter to Chicago in wintertime it helps illustrate one of the unspoken tenets that matches the energy of the people who live there: city dwellers work hard to stay warm, palpably and lovingly—there’s no value assigned to coldness, within the movie or the city.
5. Uncle Buck
This 1989 comedy manages to be just a tinge darker than most John Hughes fare while still maintaining the traditional Hughes bookmark of suburban Chicago filming locations, all thanks to John Candy’s performance as a half-scumbag, half-sweetheart Mary Poppins to a residential family on the outskirts of the Windy City.
4. Ferris Bueller’s Day Off
Nearly 40 years later and there’s still nothing better than a cool-as-ice teenager and his friends outwitting grown-ups, waxing the poetry of youth, and taking over the great city of Chicago in a Ferrari.
3. High Fidelity
Have a day and a half in Chicago? Doing the Rob Gordon experience of hitting up a Championship Vinyl-esque record store in Wicker Park followed by a matinee at Music Box Theatre and drinks at Green Mill Cocktail Lounge would be hard to top.
2. The Fugitive
At its heart, The Fugitive is really just an indie movie made by two dudes from Chicago improvising the best way to tell this story in Chicago, an approach that—a one-armed man and dam jump later—gave us some of the most iconic moments in cinema history.
1. The Dark Knight
If you’ve never pretended to battle the Joker while driving through Lower Wacker, or imagined a semi truck upending on South La Salle Street, or reenacted Harvey Dent’s appearance at Twin Anchors bar in Old Town, are you even a real Chicagolander?
Contributors: Natalie Bauer, Chad Comello, Natalie Pohorski, and Kevin Prchal.