15 Must-Watch Movies Set in the Windy City

1. Wayne’s World 1992，IMDB Rating: 7.0, IMDB Votes: 172653, ID: 0105793
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Wayne’s World is a hilarious and iconic comedy that captures the spirit of 1990s Chicago. Mike Myers and Dana Carvey are unforgettable as Wayne and Garth, two rock-loving slackers who host a public-access TV show. The film’s quirky humor, memorable catchphrases, and energetic performances make it a timeless classic.
2. Chi-Raq 2015，IMDB Rating: 5.9, IMDB Votes: 10792, ID: 4594834
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Chi-Raq is a bold and provocative film that tackles the serious issue of gun violence in Chicago’s South Side. Spike Lee’s modern adaptation of Aristophanes’ Lysistrata is both powerful and poignant, with standout performances from Teyonah Parris and Nick Cannon. The film’s unique blend of satire, drama, and musical elements creates a compelling narrative that is both entertaining and thought-provoking.
3. Judas and the Black Messiah 2021，IMDB Rating: 7.4, IMDB Votes: 92307, ID: 9784798
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Judas and the Black Messiah is a gripping and intense portrayal of the betrayal of Fred Hampton, the charismatic leader of the Illinois Black Panther Party. Set against the backdrop of 1960s Chicago, the film features stellar performances from Daniel Kaluuya and LaKeith Stanfield. The movie’s powerful storytelling and historical significance make it a must-watch for those interested in civil rights and social justice.
4. Road to Perdition 2002，IMDB Rating: 7.7, IMDB Votes: 286431, ID: 0257044
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Road to Perdition is a visually stunning and emotionally charged crime drama set in Depression-era Chicago. Tom Hanks delivers a compelling performance as a mob enforcer on a quest for vengeance. The film’s dark and moody cinematography, combined with its poignant exploration of father-son relationships, makes it a standout in the genre.
5. Adventures in Babysitting 1987，IMDB Rating: 6.9, IMDB Votes: 49860, ID: 0092513
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Adventures in Babysitting is a delightful romp through the chaotic streets of Chicago, where a simple babysitting gig turns into a night of wild escapades. Elisabeth Shue shines as the resourceful babysitter, navigating a series of hilarious and heart-pounding situations. The film captures the essence of 1980s Chicago, blending comedy and adventure seamlessly. It’s a nostalgic and entertaining ride that showcases the city’s vibrant energy.
6. The Sting 1973，IMDB Rating: 8.3, IMDB Votes: 281936, ID: 0070735
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Set in the 1930s Chicago, The Sting is a masterful caper film that captures the essence of the city’s gritty underworld. With Paul Newman and Robert Redford delivering stellar performances, the film’s intricate plot and charming style make it a timeless classic. The movie’s depiction of Chicago’s bustling streets and iconic landmarks adds to its authenticity and allure. A must-watch for those who appreciate clever storytelling and historical settings.
7. Home Alone 1990，IMDB Rating: 7.7, IMDB Votes: 658636, ID: 0099785
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Home Alone is a delightful holiday classic set in the suburbs of Chicago. Macaulay Culkin’s portrayal of Kevin McCallister, a young boy left to defend his home against bumbling burglars, is both heartwarming and hilarious. The film’s charming depiction of a snowy Chicago neighborhood adds to its festive appeal. A perfect blend of comedy and adventure, Home Alone remains a beloved family favorite.
8. The Untouchables 1987，IMDB Rating: 7.8, IMDB Votes: 333609, ID: 0094226
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The Untouchables is a gripping crime drama set in Prohibition-era Chicago. Kevin Costner, Sean Connery, and Robert De Niro deliver powerful performances in this tale of law enforcement’s battle against Al Capone. The film’s authentic portrayal of Chicago’s historic landmarks and its intense action sequences make it a standout in the genre. A must-see for fans of crime dramas and historical films.
9. My Best Friend’s Wedding 1997，IMDB Rating: 6.3, IMDB Votes: 156945, ID: 0119738
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My Best Friend’s Wedding is a charming romantic comedy set in the heart of Chicago. Julia Roberts shines as a woman trying to sabotage her best friend’s wedding, leading to hilarious and heartfelt moments. The film’s use of iconic Chicago locations, such as the Fourth Presbyterian Church and Union Station, adds to its romantic allure. A delightful watch for fans of love stories and cityscapes.
10. Chicago 2002，IMDB Rating: 7.2, IMDB Votes: 244821, ID: 0299658
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Chicago is a dazzling musical that brings the Jazz Age to life with its vibrant performances and stunning visuals. Renée Zellweger and Catherine Zeta-Jones captivate as two murderesses vying for fame in 1920s Chicago. The film’s energetic dance numbers and sharp satire of celebrity culture make it a standout. A must-watch for musical lovers and those fascinated by the glitz and glamour of old Chicago.
11. Hoop Dreams 1994，IMDB Rating: 8.3, IMDB Votes: 28203, ID: 0110057
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Hoop Dreams is a powerful documentary that captures the essence of Chicago’s inner city through the lives of two aspiring basketball players. The film’s raw portrayal of ambition, race, and class struggles makes it a compelling watch. The six-year journey of William Gates and Arthur Agee is both heartbreaking and inspiring, showcasing the harsh realities and fleeting hopes of chasing a dream. This film is a testament to the resilience of the human spirit and the socio-economic challenges faced by many in urban America.
12. Ferris Bueller’s Day Off 1986，IMDB Rating: 7.8, IMDB Votes: 391093, ID: 0091042
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Ferris Bueller’s Day Off is a delightful romp through Chicago, capturing the city’s vibrant spirit and iconic landmarks. John Hughes’ love letter to Chicago is evident in every frame, from the Art Institute to Wrigley Field. The film’s whimsical and rebellious tone, combined with Ferris’ infectious charm, makes it a timeless classic. It’s a joyous celebration of youth, freedom, and the beauty of playing hooky in one of America’s greatest cities.
13. High Fidelity 2000，IMDB Rating: 7.4, IMDB Votes: 191126, ID: 0146882
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High Fidelity is a quirky and heartfelt exploration of love, music, and self-discovery set against the backdrop of Chicago’s eclectic neighborhoods. John Cusack’s portrayal of Rob, a record store owner navigating the complexities of relationships, is both relatable and endearing. The film’s soundtrack and witty dialogue add to its charm, making it a must-watch for music lovers and romantics alike. It’s a film that beautifully captures the essence of Chicago’s indie spirit.
14. The Fugitive 1993，IMDB Rating: 7.8, IMDB Votes: 322178, ID: 0106977
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The Fugitive is a gripping thriller that masterfully uses Chicago’s urban landscape to heighten its suspense. Harrison Ford’s portrayal of Dr. Richard Kimble, a man wrongfully accused of his wife’s murder, is both intense and compelling. The film’s cat-and-mouse chase through the city’s streets and landmarks adds a layer of authenticity and excitement. It’s a classic that showcases Chicago’s gritty charm and architectural beauty.
15. The Blues Brothers 1980，IMDB Rating: 7.9, IMDB Votes: 216373, ID: 0080455
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The Blues Brothers is an electrifying musical comedy that takes viewers on a wild ride through Chicago. John Belushi and Dan Aykroyd’s dynamic performances, combined with the film’s iconic soundtrack, make it an unforgettable experience. The movie’s depiction of Chicago, from its bustling streets to its soulful music scene, is both nostalgic and exhilarating. It’s a film that celebrates the city’s rich cultural heritage and its love for rhythm and blues.