Entertainment
The Best Chicago Movies
List Rules
Movies about or set in Chicago, Illinois
McCormick Place, the Lincoln Park Zoo, Western Avenue, the Harold Washington Library, the Oceanarium, the Field Museum – these are the things that come to mind when we talk about Chicago, Illinois. Often referred to as “The Windy City” or “Second City," Chicago is the setting for many Hollywood films. But what are the best Chicago movies?
Since Chicago is such a large city and is home to some of the most iconic structures in the United States it only makes sense that movies like Mickey One, Medium Cool, and The Color of Money all feature this famous city. Whether you're in the mood for action, romance, comedy, or drama there's a Windy City film for you.
This list has the best movies about Chicago, ranked by film lovers and including: High Fidelity, Hoop Dreams, Ferris Bueller’s Day Off, Risky Business, The Dark Night, Barbershop, The Blues Brothers, The Fugitive, Public Enemies, Stir of Echoes, Cooley High, and Road to Perdition.
Vote up your favorite Chi-Town classic or add one you love that isn't already on the list.list ordered by
- After his release from prison, Jake (John Belushi) reunites with his brother, Elwood (Dan Aykroyd) -- collectively known as the "Blues Brothers." Jake's first task is to save the orphanage the ...more
- Wrongfully accused of murdering his wife, Richard Kimble (Harrison Ford) escapes from the law in an attempt to find her killer and clear his name. Pursuing him is a team of U.S. marshals led by ...more
- Ferris Bueller (Matthew Broderick) has an uncanny skill at cutting classes and getting away with it. Intending to make one last duck-out before graduation, Ferris calls in sick, "borrows" a Ferrari, ...more
- When bratty 8-year-old Kevin McCallister (Macaulay Culkin) acts out the night before a family trip to Paris, his mother (Catherine O'Hara) makes him sleep in the attic. After the McCallisters ...more
- Easily excitable Neal Page (Steve Martin) is somewhat of a control freak. Trying to get home to Chicago to spend Thanksgiving with his wife (Laila Robins) and kids, his flight is rerouted to a ...more
- After building an empire with bootleg alcohol, legendary crime boss Al Capone (Robert De Niro) rules Chicago with an iron fist. Though Prohibition agent Eliot Ness (Kevin Costner) attempts to take ...more
- Five high school students from different walks of life endure a Saturday detention under a power-hungry principal (Paul Gleason). The disparate group includes rebel John (Judd Nelson), princess ...more
- Ecstatic when his parents leave on vacation for a few days, high school senior Joel Goodsen (Tom Cruise) cuts loose with his best friend Miles. After an attempt at securing the services of a ...more
- With the help of allies Lt. Jim Gordon (Gary Oldman) and DA Harvey Dent (Aaron Eckhart), Batman (Christian Bale) has been able to keep a tight lid on crime in Gotham City. But when a vile young ...more
- Backdraft is a 1991 action thriller film directed by Ron Howard and written by Gregory Widen. The film stars Kurt Russell, William Baldwin, Scott Glenn, Jennifer Jason Leigh, Rebecca De Mornay, ...more
- The Chicago White Sox, who are set to play the Cincinnati Reds in the World Series of 1919, are at odds with their team's owner, Charles Comiskey (Clifton James), who pays his players unsatisfactory ...more
- Following the murder of a mutual friend, aspiring con man Johnny Hooker (Robert Redford) teams up with old pro Henry Gondorff (Paul Newman) to take revenge on the ruthless crime boss responsible, ...more
- With the occasion all but overshadowed by her sister's upcoming wedding, angst-ridden Samantha (Molly Ringwald) faces her 16th birthday with typical adolescent dread. Samantha pines for studly older ...more
- Every school day, African-American teenagers William Gates and Arthur Agee travel 90 minutes each way from inner-city Chicago to St. Joseph High School in Westchester, Illinois, a predominately white ...more
- Rob Gordon (John Cusack) is the owner of a failing record store in Chicago, where he sells music the old-fashioned way -- on vinyl. Although they have an encyclopedic knowledge of pop music and are ...more
- Defense attorney Martin Vail takes on jobs for money and prestige rather than any sense of the greater good. His latest case involves an altar boy, accused of brutally murdering the archbishop of ...more
- Depression-era bank robber John Dillinger's (Johnny Depp) charm and audacity endear him to much of America's downtrodden public, but he's also a thorn in the side of J. Edgar Hoover (Billy Crudup) ...more
18The Hunter
Filmed in 1980, the El and Marina Towers co-star with Steve McQueen doing his own stunts in an epic action scene that still looks good today.
- This classic suspense film finds New York City ad executive Roger O. Thornhill (Cary Grant) pursued by ruthless spy Phillip Vandamm (James Mason) after Thornhill is mistaken for a government agent. ...more
- Lonely transit worker Lucy Eleanor Moderatz (Sandra Bullock) pulls her longtime crush, Peter (Peter Gallagher), from the path of an oncoming train. At the hospital, doctors report that he's in a ...more
- A martial-arts expert and former CIA agent, Nico Toscani (Steven Seagal) is working as a Chicago cop when a relatively routine drug-trafficking investigation leads to an international conspiracy. ...more
- When Ahmad Simmons' (Brandon Hammond) diabetic grandmother, Josephine "Big Mama" Joseph (Irma P. Hall), falls into a coma during an operation to amputate her leg, it throws the Joseph family into ...more
![My Best Friend’s Wedding]()
23My Best Friend’s Wedding
- In this adaptation of David Mamet's hit 1974 off-Broadway play "Sexual Perversity in Chicago," Danny (Rob Lowe) and Bernie (James Belushi) are a couple of single guys who live in the Windy City and ...more
- Mike Sullivan (Tom Hanks) is an enforcer for powerful Depression-era Midwestern mobster John Rooney (Paul Newman). Rooney's son, Connor (Daniel Craig), is jealous of the close bond they share, and ...more
