16 Must-Watch Movies Set in the Windy City

1. The Blues Brothers 1980，IMDB Rating: 7.9, IMDB Votes: 216360, ID: 0080455
Photo by blogspot.com, is licensed under CC BY-SA 4.0

The Blues Brothers is a classic Chicago film that showcases the city’s vibrant music scene and iconic locations. The film’s plot, centered around two brothers trying to save their childhood orphanage, is filled with high-energy musical numbers and car chases through the city streets. The film’s unique blend of comedy, music, and action, along with its affectionate portrayal of Chicago, makes it a must-watch.
2. High Fidelity 2000，IMDB Rating: 7.4, IMDB Votes: 191120, ID: 0146882
Photo by Wikipedia, is licensed under CC BY-SA 4.0

High Fidelity is a film that brilliantly captures the essence of Chicago’s music scene. The film’s protagonist, Rob, a record store owner, navigates his failing relationships while immersing himself in the city’s rich musical culture. The film’s authentic depiction of Chicago, combined with its exploration of love, music, and self-discovery, makes it a standout among movies set in the Windy City.
3. Cooley High 1975，IMDB Rating: 7.1, IMDB Votes: 5625, ID: 0072820
Photo by Wikipedia, is licensed under CC BY-SA 4.0

Cooley High provides a nostalgic look at the lives of African American teenagers in 1960s Chicago. The film’s portrayal of the city’s Cabrini-Green housing project and the challenges faced by its residents offers a unique perspective on Chicago’s history. Despite its serious themes, the film maintains a light-hearted tone, making it a memorable and enjoyable watch.
4. The Fugitive 1993，IMDB Rating: 7.8, IMDB Votes: 322158, ID: 0106977
Photo by Wikipedia, is licensed under CC BY-SA 4.0

The Fugitive is a thrilling chase movie set against the backdrop of Chicago. The film’s protagonist, Dr. Richard Kimble, navigates the city’s landmarks while being pursued by a relentless U.S. Marshal. The film’s intense action sequences, coupled with its exploration of themes of justice and innocence, make it a compelling watch.
5. Ferris Bueller’s Day Off 1986，IMDB Rating: 7.8, IMDB Votes: 391076, ID: 0091042
Photo by satyanash.net, is licensed under CC BY-SA 4.0

Ferris Bueller’s Day Off is a delightful comedy that showcases the city of Chicago in a fun and whimsical way. The film follows the titular character as he skips school and embarks on an adventurous day around the city. The film’s humorous tone, combined with its affectionate portrayal of Chicago, makes it a classic.
6. The Untouchables 1987，IMDB Rating: 7.8, IMDB Votes: 333600, ID: 0094226
Photo by flickr.com, is licensed under CC BY-SA 4.0

Set in the heart of Chicago, ‘The Untouchables’ is a gripping tale of justice against notorious mobster Al Capone. The film’s depiction of the city and its criminal underworld is both authentic and captivating. The performances, particularly by Robert De Niro as Capone, are compelling. However, the film’s true strength lies in its exploration of morality within the law enforcement system.
7. Candyman 1992，IMDB Rating: 6.7, IMDB Votes: 101055, ID: 0103919
Photo by cinematicrandomness.com, is licensed under CC BY-SA 4.0

‘Candyman’ is a chilling horror film set in Chicago’s Cabrini-Green housing projects. The film uses its setting to explore urban legends and societal fears, creating a haunting atmosphere that stays with you long after the credits roll. Despite its horror elements, the film also offers a poignant commentary on the living conditions and societal neglect faced by the residents of such projects.
8. Wayne’s World 1992，IMDB Rating: 7.0, IMDB Votes: 172643, ID: 0105793
Photo by blogspot.com, is licensed under CC BY-SA 4.0

‘Wayne’s World’ is a delightful comedy that, while filmed mostly in Los Angeles, is set in Aurora, a suburb of Chicago. The film’s humor is both intelligent and absurd, offering a unique take on the local access cable TV scene. Its portrayal of the life of its host, Wayne Campbell, is both amusing and relatable, making it a must-watch for comedy lovers.
9. Transformers: Dark of the Moon 2011，IMDB Rating: 6.2, IMDB Votes: 434793, ID: 1399103
Photo by blogspot.com, is licensed under CC BY-SA 4.0

Set in the aftermath of a battle that left Chicago in ruins, ‘Transformers: Dark of the Moon’ is a visual spectacle. The film’s depiction of the city, particularly during the climactic battle, is breathtaking. Despite some plot holes and an overlong runtime, the film delivers unparalleled big-screen spectacle, making it a thrilling watch.
10. Transformers: Age of Extinction 2014，IMDB Rating: 5.6, IMDB Votes: 333596, ID: 2109248
Photo by Wikidot, is licensed under CC BY-SA 4.0

‘Transformers: Age of Extinction’, while primarily filmed in Detroit and Hong Kong, is set in a post-invasion Chicago. The film offers a visually stunning portrayal of the city, albeit in ruins. Despite its lengthy runtime and some plot inconsistencies, the film’s action sequences and visual effects make it an entertaining watch.
11. Chi-Raq 2015，IMDB Rating: 5.9, IMDB Votes: 10791, ID: 4594834
Photo by oldaintdead.com, is licensed under CC BY-SA 4.0

Chi-Raq, directed by Spike Lee, is a modern-day musical satire about violence and guns in Chicago’s South Side. It’s a movie that only Lee could have directed with such imagination, high and low wit, and sorrow. The film is angry, horrified, mournful but also warm, sensual, life affirming, and so blisteringly funny. It’s a vivid portrait of the pair’s “Sweet Home Chicago”.
12. The Dark Knight 2008，IMDB Rating: 9.0, IMDB Votes: 2902431, ID: 0468569
Photo by kartjeeva.deviantart.com, is licensed under CC BY-SA 4.0

The Dark Knight, directed by Christopher Nolan, is a haunted film that leaps beyond its origins and becomes an engrossing tragedy. It creates characters we come to care about. The movie does not allow its spectacular special effects to upstage the humans. The whole moral foundation of the Batman legend is threatened. It’s a movie that takes advantage of Chi-Town’s unique mix of urban sophistication and midwestern charm.
13. My Best Friend’s Wedding 1997，IMDB Rating: 6.3, IMDB Votes: 156942, ID: 0119738
Photo by Wikipedia, is licensed under CC BY-SA 4.0

My Best Friend’s Wedding is a generally adorable story potion. It’s a scrumptious drama that should touch moviegoers’ hearts. The film is about a women’s baseball league that started up during World War II. It’s a movie that takes advantage of Chi-Town’s unique mix of urban sophistication and midwestern charm.
14. Risky Business 1983，IMDB Rating: 6.8, IMDB Votes: 100992, ID: 0086200
Photo by randomlyedible.com, is licensed under CC BY-SA 4.0

Risky Business is a movie about a nice boy losing his virginity. It’s a comedy because it deals with subjects that are so touchy, so fraught with emotional pain. It’s a movie that takes advantage of Chi-Town’s unique mix of urban sophistication and midwestern charm.
15. Adventures in Babysitting 1987，IMDB Rating: 6.9, IMDB Votes: 49852, ID: 0092513
Photo by Wikipedia, is licensed under CC BY-SA 4.0

Adventures in Babysitting is a movie about a babysitter who is entrusted with a small girl and ends up also babysitting for a couple of teenage boys. The movie takes place over a few days in summer in Chicago. It’s a movie that takes advantage of Chi-Town’s unique mix of urban sophistication and midwestern charm.
16. The Break-Up 2006，IMDB Rating: 5.8, IMDB Votes: 139674, ID: 0452594
Photo by Typepad, is licensed under CC BY-SA 4.0

The Break-Up, set in the heart of Chicago, is a romantic comedy that explores the complexities of relationships. The film showcases the city’s charm through the eyes of Gary and Brooke, played by Vince Vaughn and Jennifer Aniston. Their tumultuous relationship, filled with humorous and heartfelt moments, paints a vivid picture of love and loss in the Windy City.