10 Movies About Chicago That Capture the Spirit of the Windy City

The 1997 romantic comedy, My Best Friend’s Wedding, starring Julia Roberts, Dermot Mulroney, and Cameron Diaz, follows Julia Roberts’ character when her life-long best friend gets engaged and she realizes that she is in love with him. 

This classic tear-jerker of a romantic comedy is one of the classic movies about Chicago. The film captures the essence of the city as Julia Roberts is dashing around the city trying to figure out her romantic problems. From O’Hare International Airport, Union Station, to the Drake Hotel, My Best Friend’s Wedding is a fantastic representation of the Spirit of the Windy City. 

IMDb Rating: 6.3/10

Related: 25 Movies Like My Best Friend’s Wedding and Where to Stream Them

A League of Their Own is a 1992 film about the first all female professional baseball team during World War II. 

Chicago is known to be a baseball city with the Cubs and the White Sox. However, this film puts a spin on the city’s traditional love for the sport; it features the first all women’s baseball team, the 1943 Rockford Peaches. Though a mostly fictional story, this classic film captures the essence of the city’s love for the sport and just how much community baseball brings to Chicago. 

IMDb Rating: 7.3/10

High Fidelity is a 2000 comedy starring John Cusack. The film follows a record store owner who is recounting the tales of his five top breakups. 

Originally based on Nick Hornby’s novel of the same name, this film is a classic. Not only does High Fidelity represent the everyday, mundane aspects of life in the Windy City, but it is also a strong representation of the Chicago music scene in the ’90s. Referencing local record labels and stores, High Fidelity feels like one of the most authentic movies about Chicago. 

IMDb Rating: 7.4/10 

Ordinary People is a 1980 film about the accidental death of the oldest son in an affluent family. 

Set on the North Shore of Chicago, Ordinary People is one of those classic movies about Chicago. Though the content is hard to digest, the setting of suburban Lake Forest is a strong representation of Chicago suburban life. 

IMDb Rating: 7.7/10

Home Alone, often thought of as a Christmas movie, is another one of those classic movies about Chicago. The film follows a young boy named Kevin, who is accidentally left home alone while his family goes on vacation and he has to fend off burglars from his house. 

Home Alone is another film that provides a strong representation of suburban life in the Windy City. Directed by John Hughes, who is known for making movies set in Chicago, he grew up in the suburbs, so Home Alone holds true to his own childhood experience of the city. 

IMDb Rating: 7.7/10

The Untouchables is a 1987 crime drama set during the prohibition period in Chicago. The film follows a treasury agent who sets out to stop a Chicago gangster. 

Starring Kevin Costner, Sean Connery, and Robert De Niro, the film is not only a classic but one of the best movies about Chicago. Though a lot of The Untouchables is not necessarily historically accurate, it completely captures the essence of Chicago in the 1920s. 

IMDb Rating: 7.8/10 

The Breakfast Club is a 1985 film about five very different high school students who meet and bond during Saturday detention. 

The majority of The Breakfast Club takes place within the school, but it is actually set in the suburbs of Chicago. Though the film does not necessarily seep with the spirit of downtown Chicago, it is a good reminder that there is a lot of life happening in Chicago that does not necessarily take place in the big buildings or classic landmarks we first think about when thinking about the Windy City. 

IMDb Rating: 7.8/10 

Read More: 6 Breakfast Club Movie Quotes That Capture the Spirit of the Film

A personal favorite, Ferris Bueller’s Day Off is one of the most beloved movies about Chicago. Starring Matthew Broderick, the film follows a high school student who decides to skip school for the day, but has to go to great lengths in order to pull it off. 

In the film, Ferris gets into all kinds of trouble while running around downtown Chicago with his friends during his day off. From taking a tour at the Art Institute of Chicago, going to a Chicago Cubs game, to performing in a downtown parade, viewers of the film really get to feel the lively, boisterous spirit of Chicago. 

IMDb Rating: 7.8/10

The Blues Brothers is a 1980 film about two brothers who reunite in Chicago after one of them is released from prison. 

The Blues Brothers is an accurate and loving homage to the city of Chicago. From depictions of the Maxwell Street flea market in the 1970s and a chase scene through Lower Wacker Drive to Daley Plaza, The Blues Brothers is easily one of the most appreciated and loved movies about Chicago. 

IMDb Rating: 7.9/10 

Hoop Dreams is a 1994 sports documentary about two inner-city Chicago boys and their struggles to become college basketball players, with the hope of then going professional. 

Hoop Dreams is, without a doubt, one of the best movies about Chicago. Few films capture the life, sentiments, and dreams of kids from inner-Chicago, which comprises a major portion of both the city and the population. Hoop Dreams is hopeful, inspirational, and very touching, capturing the true spirit of the Windy City. 

IMDb Rating: 8.3/10