20 Visually Stunning Movies Set in Chicago to Stream Now

With various films coming recently, we wonder about the history of films that have used Chicago as a backdrop. Many filmmakers like Steve James and John Hughes have made Windy City a famous place and name internationally. These are not the only filmmakers who are behind making this city a famous spot. The criteria that have been used while making this list is films have really utilized the beauty of the city. Plenty of movies are set in Chicago, like Blues Brothers and Windows.

Not all films could have been included, as this is a short list. These 20 films are essential in understanding how the city has been captured by many filmmakers time and time again.

20. The Blues Brothers (1980)

Director: John Landis
Writer: John Landis, Dan Aykroyd
Cast: Dan Aykroyd, John Belushi, and others
IMDb Ratings: 4.9/10
Rotten Tomatoes Score: 73%
Where to watch: Netflix

Are The Blues Brothers among the best Chicago movies? It certainly will get placed among the top three. This comedy movie was filmed in various places, like a South Side Church. Moreover, the climactic scenes of this movie were filmed downtown. Also, there are various guides present for the filming location online. Who can forget “Sweet Home Chicago”? Blue Brothers 2000 was also liked by many, and it guaranteed a fan base of its own. Moreover, the sequel of this film was shot in Toronto.

This film is surely the quintessential Chicago film. Elwood and Jake Blues are the Chicago boys. The car chases that fill the movie, and the streets of this town are filled with them. It is also filled with great musicians and covers all the famous spots of Chicago. When Jakes Blues (played by John Belushi) comes out of prison, he attempts to get back to his old band so that he can save the boarding school where he and his brother grew up.

19. My Best Friend’s Wedding (1997)

Director: P. J. Hogan
Writer: Rupert Everett, P. J. Hogan, and others
Cast: Julia Roberts, Dermot Mulroney, and others
IMDb Ratings: 6.3/10
Rotten Tomatoes Score: 73%
Where to watch: Hulu, ESPN+, Disney+

Whether Julianne Potter (played by Julia Robert) is seen eating at Trotter’s or on Lake Shore Drive, she is all over the city. This movie is among the various famous romantic comedies. Hogan has covered this Windy City. Whether it be places like Union Station or Comiskey Park, all the famous spots have been covered. You can get a tourist trip out of all the places that have been covered in the movie.

18. Thief (1981)

Director: Michael Mann
Writer: Michael Mann
Cast: James Caan, Jim Belushi, and others
IMDb Ratings: 7.5/10
Rotten Tomatoes Score: 94%
Where to watch: Prime Video, HBO, Tubi

This Chicago film is unique on its own. Michael Mann has captured Chicago as no one has ever done before. In his previous film (which is among his best works), we can see Dennis Farina and James Caan playing the main roles. They both are police consultants and Chicago cops, respectively. Then they both were also cast for Thief. It is a Chicago film through and through. Moreover, it has covered all the big spots of Chicago. Mann very well knew how to use Ashland and Diversey in this film which only Chicagoans knew well about.

17. Widows (2018)

Director: Steve McQueen
Writer: Steve McQueen, Gillian Flynn
Cast: Viola Davis, Michelle Rodriguez, and others
IMDb Ratings: 6.9/10
Rotten Tomatoes Score: 91%
Where to watch: Vudu, Amazon Instant Video, iTunes, Google Play

Windows is considered a film that not only has covered great parts of Chicago, but it was also able to get under the skin of this fantastic city. Windows is a Steve McQueen heist thriller in which we can see Liam Neeson, Viola Davis, and Colin Farrell. Gillian Flynn wrote the script, and McQueen also is very well-informed and descriptive about Chicago politics of the late ’10s. The director has used the beauty of this city very well, like the opening scene was shot in Lake Michigan.

16. While You Were Sleeping (1995)

Director: Jon Turteltaub
Writer: Fredric Lebow, Daniel G. Sullivan
Cast: Sandra Bullock, Bill Pullman, and others
IMDb Ratings: 6.7/10
Rotten Tomatoes Score: 81%
Where to watch: Disney+

Chicago’s elevated train system has been used as a backdrop by numerous films set in Chicago. So this helps by adding flavor to the film and reminding the viewers about the beauty of this city. The character Sandra Bullock plays rescues the character of Peter Gallagher after someone tries to kill him at Wabash station. As the film moves forward, we get to know a lot of downtown Chicago, including Northwestern Memorial Hospital and a well-known building on Lake Shore Drive. Near La Grange, a lot of family scenes were also shot for the film.

15. Cooley High (1975)

Director: Michael Schultz
Writer: Eric Monte
Cast: Lawrence Hilton-Jacobs, Glynn Turman, and others
IMDb Ratings: 7.1/10
Rotten Tomatoes Score: 85%
Where to watch: Tubi, Pluto

Even before Michael Schultz, John Hughes captured Chicago city; this film captured what it felt like to be a teenager in Chicago. His drama comedy film shot the entire city. Eric Monte, the writer, wanted to display what it felt like to be a kid in that city, including the time spent at Cooley Vocational High School. Also, the films set in Chicago are often seen capturing its beautiful spots. Moreover, in this film, places like Lincoln Park Zoo and Navy Pier have been covered. What Chicago looked like in the ’70s can be seen through this movie set in Chicago.

14. Ferris Bueller’s Day Off (1986)

Director: John Hughes
Writer: John Hughes
Cast: Matthew Broderick, Alan Ruck, and others
IMDb Ratings: 7.8/10
Rotten Tomatoes Score: 81%
Where to watch: Netflix

Many John Hughes films can be included in this list. Whether you like it or not, when one hears Chicago Movie, one thinks of the day when Ferris Bueller skipped school. Moreover, Hughes shot this film in a manner that appears like his love letter to the city. Spots like the Art Institute of Chicago and Wrigley Field have been covered in Ferris Bueller’s Day Off.

13. Home Alone (1990)

Director: Chris Columbus
Writer: John Hughes
Cast: Macaulay Culkin, Daniel Stern, and others
IMDb Ratings: 7.7/10
Rotten Tomatoes Score: 67%
Where to watch: Prime Video

Competition for films set in Chicago is not less, but only a few movies connect to the city’s suburbs. This film turned Macaulay Culkin into a household name. The movie was mostly shot in Winnetka, the place where John Hughes grew up. Northern suburbs are captured, while a quick sneak peek has also been provided to a church located in Oak Park. It will be hard to imagine the kids of North Chicago getting ready and not thinking of Kevin McCallister.

12. The Fugitive (1993)

Director: Andrew Davis
Writer: David Twohy, Jeb Stuart
Cast: Tommy Lee Jones, Harrison Ford, and others
IMDb Ratings: 7.8/10
Rotten Tomatoes Score: 96%
Where to watch: Vudu, HBO Max, Prime Video, Apple TV

Andrew Davis adapted the hit TV show into a beautiful film. They showed the Chicago city beautifully, especially the Chicago River Green and St. Patrick’s Day parade. Most of the film was shot in North Carolina. When the film sets were taken to Chicago, the whole advantage of the city was taken.

The plot follows Dr. Richard Kimble on his search for a one-handed man who killed his wife. Harrison Ford plays the role of Richard. Initially, everyone wrongfully accuses him of killing his own wife. After his conviction, he miraculously gets out of jail. Tommy Lee Jones earned an Oscar for Best Supporting Actor with the work he did in the movie.

11. The Dark Knight (2008)

Director: Christopher Nolan
Writer: Christopher Nolan, Jonathan Nolan, David S. Goyer
Cast: Christian Bale, Gary Oldman, and others
IMDb Ratings: 8.4/10
Rotten Tomatoes Score: 94%
Where to watch: HBO Max, Spectrum TV, Watch TNT, Vudu Movie, Redbox, Prime Video, Apple TV

Batman by Christopher Nolan might not have been set in Chicago. Few films that have been coming recently are seen using the city in more effective ways. Lower Wacker Drive has been taken full advantage of. One of the best sequences of the movie is set in Lasalle Street. All the filmmakers working on superhero films should learn from this movie how to use a natural setting instead of a created cityscape.

This movie serves as a sequel to Batman Begins. The Joker wreaks havoc on people living in Gotham. Batman needs to fight him to save the city, but he also has to struggle between his beliefs and values. Gotham National Bank is robbed by Joker, which is, in reality, the Old Chicago Main Post Office. In Navy Pier, the evacuation of people takes place, and in South LaSalle Street, the funeral of the police commissioner takes place.

10. Backdraft (1991)

Director: Ron Howard
Writer: Gregory Widen
Cast: William Baldwin, Donald Sutherland, and others
IMDb Ratings: 8.2/10
Rotten Tomatoes Score: 76%
Where to watch: Prime Video, Vudu, Redbox, Apple TV

Backdraft is a good Chicago movie in which we realize that Ron Howard desired to make a film about firefighting, for which he chose this wonderful city. Another reason for choosing Chicago was because Chicago Fire Department has one of the best reputations in the country. Howard has used this city well by choosing a great bungalow for Kart Russell’s home.

This firefighter thriller stars William Baldwin and Kurt Russell. This film has become a part of the city, and its influence can be felt by knowing the fact that Brighton Park Firehouse has been made into a great restaurant by the name Chicago Firehouse. A few shots of the “l” have also been taken, just like every great Chicago movie does.

9. Road to Perdition (2002)

Director: Sam Mendes
Writer: David Self
Cast: Tom Hanks, Paul Newman, and others
IMDb Ratings: NA
Rotten Tomatoes Score: 81%
Where to watch: Netflix

Sam Mendes’s film following the Best Picture-winning American Beauty is no less. Those who have enough contact with the regular bar visitors, they’ll tell you more about this one. Mendes and master cinematographer Conrad L. Hall transformed the locations of the city according to their requirements. Also, their hard work earned them a posthumous Oscar. Moreover, even the interiors were shot on the sets that were created in this city. The movie is truly a Chicago Production.

8. Running Scared (1986)

Director: Billy Crystal, Gregory Hines, Peter Hyams, and others
Writer: Jimmy Huston, Gary DeVore
Cast: Billy Crystal, Gregory Hines, and others
IMDb Ratings: 6.5/10
Rotten Tomatoes Score: 59%
Where to watch: Spectrum TV, Prime Video, VUDU, Apple TV

Most films about cops are shot in Los Angeles or New York. Also, this is a great Chicago cop film. Gregory Hines and Crystal are seen playing the role of cops who are ready to leave the city and go to Key West. Before they could leave, they got roped in on a case. It feels as if every shot in Running Sacred covers the “L.” Majority of this film’s shooting took place in Thompson Center.

7. Sixteen Candles (1984)

Director: John Hughes
Writer: John Hughes
Cast: Molly Ringwald, Anthony Michael Hall, and others
IMDb Ratings: 7/10
Rotten Tomatoes Score: 81%
Where to watch: Netflix

Writer and director John Hughes made this film in the 1980s, and it is a coming-of-age teen comedy that explores the struggles an American teenager faces. This movie includes the events of the 16th birthday of Sam Baker (Molly Ringwald plays Sam Baker). Also, mainly the location used in the film is the North Shore neighborhood in Chicago.

The director here has tried to show that even rich teenagers are not immune to the harsh impulses one has to face in their lives. He also has tried to convey that nothing can reverse the distress and isolation one feels in high school. The movie is a cinematic representation of the 1980s, and it can be said that it is even more accurate when compared to The Breakfast Club or Ferris Bueller.

6. High Fidelity (2000)

Director: Stephen Frears
Writer: John Cusack, Steve Pink, D.V. DeVincentis, Scott Rosenberg
Cast: John Cusack, Jack Black, and others
IMDb Ratings: 7.7/10
Rotten Tomatoes Score: 91%
Where to watch: Hulu

Nicky Hornby’s hit book was going to be adapted by Hollywood. Little changes were made, like the action was decided to relocate to Chicago from London. The result of this attempt is that the neighborhoods that are often not captured in movies have been beautifully shot in this one. Chicagoan John Cusack adds authenticity to the scenes shot in Wicker Park. Moreover, it was among one of the most vibrant neighborhoods at the time of the shooting. Rob Gordon (played by John Cusack) is a former DJ. He now has his own store in Chicago.

5. Henry: Portrait of a Serial Killer (1986)

Director: John McNaughton
Writer: John McNaughton, Richard Fire
Cast: Michael Rooker, John McNaughton, and others
IMDb Ratings: 4.9/10
Rotten Tomatoes Score: 89%
Where to watch: Prime Video

The majority of the movies that have been included in our list use the city of Chicago in a glamorous manner by showing places like Wrigley Field and Sears Tower. The movie can even be seen as a documentation of the lives of the working-class people in the neighborhood of Chicago during the mid-80s. One can feel how easy it is to get lost in a city such as Chicago by watching Otis and Henry. The city is an ideal hunting ground for lunatics.

4. A League of Their Own (1992)

Director: Penny Marshall
Writer: Tom Hanks, Penny Marshall, and others
Cast: Tom Hanks, Madonna, and others
IMDb Ratings: 7.3/10
Rotten Tomatoes Score: 80%
Where to watch: Amazon Prime Video

Chicago has two MLB Clubs, so it makes sense to make numerous baseball films in this city. However, no man plays this game in the film. The movie is about the women’s baseball league that began during World War II. A League of Their Own is not emotional, but there are many comedy scenes in the film.

While the men were off at war, the owners of the baseball teams came up with an idea. Also, they created a women’s team. Two sisters joined this team which was also the first professional all-women’s team in baseball. For the team to succeed, these sisters first need to sort out their rivalry. The tryouts of the film are at Harvey Field, which in reality is Wrigley Field of Chicago.

3. Adventures in Babysitting (1987)

Director: Chris Columbus
Writer: David Simkins
Cast: Elisabeth Shue, Sofia Carson, and others
IMDb Ratings: 5.9/10
Rotten Tomatoes Score: 69%
Where to watch: Disney+, Prime Video, Apple TV, VUDU

This film is quite silly and can be watched just for the amazing shots of Chicago that have been captured. A kid escapes the babysitter. So, this reunites the whole city of Chicago to look for the kid. Moreover, the search part of the movie is the best as it shows various parts of the city. The majority of this film was, however, shot in Toronto. Michigan Avenue is also a part of this film.

2. Ordinary People (1980)

Director: Robert Redford
Writer: Judith Guest, Nancy Dowd, Alvin Sargent
Cast: Mary Tyler Moore, Dinah Manoff, and others
IMDb Ratings: 7.7/10
Rotten Tomatoes Score: 90%
Where to watch: Prime Video, Spectrum TV, Apple TV, Vudu

This forms another Best Picture Winner on our list. This family drama movie won the award in 1980, and to win this award, it beat Raging Bull. Timothy Hutton also won an Oscar with this film that served as his film debut. However, after the death of his older brother, Conrad attempts suicide. After coming back from the psychiatric hospital, he connects again with his mother.

1. National Lampoon’s Christmas Vacation (1989)

Director: Jeremiah S. Chechik
Writer: John Hughes
Cast: Chevy Chase, Beverly D’Angelo, Randy Quaid, Johnny Galecki, and others
IMDb Ratings: 7.5/10
Rotten Tomatoes Score: 67%
Where to watch: Netflix

The Griswolds represent a Chicago family, but they go on vacation often. Either they go to Wally World or Vegas or Europe; they’re mostly traveling. Also, this film is about celebrating Christmas. Christmas vacation often means staying at home, but this film takes on a different approach.