When you think of Chicago, perhaps it’s obvious that the first thought that comes to mind is that it’s a global financial powerhouse. If you know its olden-day crime heritage, you might even think of the Chicago Outfit and bootlegging, especially during the Prohibition Era. Al Capone is sure to cross your mind.
But Chicago was and still is so much more than just the financial allure and the quaint glamor of the bygone age. It’s an ageless station of culture and arts. It’s renowned for its iconic skyline. Its skyscrapers, its “El train,” its groundbreaking architecture, the shiny bean, the parks, its status as an MLB heavyweight, its colorful and vibrant neighborhoods, deep-dish pizza, and last but not least, its rich Jazz and Blues scene. I mean, the city is “loaded” in every possible way.
So it would be a surprise if Hollywood didn’t turn to it to add value to its stories. And it really does. Chicago is a cinematic powerhouse that breathes life into every frame it touches. Be it the noir, gangster era of the Roaring ‘20s, the suburban angst of the ‘80s, or the sleek swagger of today, Chicago wears many masks. Over the years, many filmmakers have chosen this stormy, husky, brawling “City of Big Shoulders” as a backdrop for their films, so much so that she feels like one of the characters.
This is not a list of movies where Chicago is just “there,” for the sake of it. This is a list of movies that are quietly fueled by Chicago’s unique energy and heartbeat.
14 Movies That Captured the Spirit of Chicago
1. Some Like It Hot (1959)
Written by: Billy Wilder, I. A. L. Diamond | Directed by: Billy Wilder
In the Prohibition-Era Chicago, Joe (Tony Curtis), a jazz saxophonist, and Jerry (Jack Lemmon), a jazz double bass player, witness a mob hit. To evade the gangsters, they dress up as women and join an all-female band. Now, technically, it’s a road movie and takes place en route from Chicago to Florida, but its Chicago opening sets a frantic, noir-inspired pace. The city’s dark alleys come in handy while establishing high stakes, and Chicago’s “urban danger” vibe blends nicely with the film’s slapstick humor.
2. The Sting (1973)
Written by: David S. Ward | Directed by: George Roy Hill
Set in 1936, two professional grifters, Johnny Hooker (Robert Redford) and Henry Gondorf (Paul Newman), pull a massive con on a crime boss. In this movie, aside from the characters and events, you meet Depression-era Chicago. The meticulous production design uses the city’s historic architecture to create a lived-in, authentic experience.
3. Risky Business (1983)
Written by: Paul Brickman | Directed by: Paul Brickman
Joel Goodsen (Tom Cruise) turns his house into a temporary brothel while his parents are away. The film interestingly amalgamates the city’s sterile suburban life with its neon-lit late-night lure. The director smartly uses the film’s famous chase scene on the “El” train (or “L” train) to symbolize Joel’s active departure from his parents’ expectations; in short, his loss of innocence.
4. Sixteen Candles (1984)
Written by: John Hughes | Directed by: John Hughes
As her family forgets her birthday amidst her sister’s wedding chaos, Samantha Baker (Molly Ringwald) tries balancing her unrequited crush on a high school senior and being pursued by a freshman geek. The film will show you the quintessential suburban aesthetic of the ‘80s. The use of local schools and residential streets creates a sense of relatability.
5. Ferris Bueller’s Day Off (1986)
Written by: John Hughes | Directed by: John Hughes
A full-of-personality high school slacker, Ferris Bueller (Matthew Broderick) skips school by faking a serious illness and instead spends the day frolicking and engaging in shenanigans with his best friend and girlfriend. Consider this movie a vibrant city tour through Chicago. It shows several prominent landmarks, from the Art Institute to Sears Tower. Wide shots and upbeat soundtrack celebrate Ferris’ and the city’s spirit of freedom. The film is a legit “Chicago Day” captured on film.
6. The Untouchables (1987)
Written by: David Mamet | Directed by: Brian De Palma
This one goes back to the Prohibition Era. An incorruptible (The Untouchable) team of federal agents, led by idealistic Eliot Ness (Kevin Costner), attempts to take down Al Capone’s (Robert De Niro) bootlegging empire. Take away the narrative drama, and this film is practically a love letter to Chicago’s majestic architecture. Through sweeping camera angles and slow-motion sequences, De Palma elevates the city to a mystic status.
7. Child’s Play (1988)
Written by: Don Mancini | Directed by: Tom Holland
A dying serial killer, Charles Lee Ray (Brad Dourif), transfers his soul into a “Good Guy” doll using voodoo magic. The doll, now going by the name “Chucky,” then ends up with the film’s protagonist, little Andy Barclay (Alex Vincent), who goes through a nightmare trying to prevent Chucky from possessing him. Keeping up with the film’s horror theme, here we see a cold, urban Chicago, complete with its gritty apartments and snowy streets. This chilly atmosphere adds a layer of bleakness and supernatural horror and creates a sense of isolation. And since the director uses Chucky’s low-angle POV shots, we see the regular domestic spaces turning into hunting grounds.
8. Home Alone (1990)
Written by: John Hughes | Directed by: Chris Columbus
The McCallister family flies to Paris for vacation, but accidentally leaves behind their eight-year-old, bratty but quick-witted son, Kevin (Macaulay Culkin). Two bumbling bandits take an ill-conceived decision to rob his house, which Kevin thwarts with his imaginative resourcefulness. It’s a Christmas movie, so the Chicago you see is cozy, snowy, and beautifully lit. The wide-angle shots make the large McCallister house feel like a fortress. Warm lighting and festive production design give us the perennial picture of the Chicago winter.
9. While You Were Sleeping (1995)
Written by: Daniel G. Sullivan, Fredric Lebow | Directed by: Jon Turteltaub
In this romantic comedy, Lucy (Sandra Bullock), a lonely “L” train token collector, saves Peter (Peter Gallagher), whom she has a crush on, from an oncoming train. While Peter remains in a coma, his family assumes Lucy is his fiancée. But she is now falling in love with Peter’s younger brother, Jack (Bill Pullman). The film leans heavily into the romantic aspects of the “L” train and, all in all, the city of Chicago. Soft-focus lenses and warm color palettes are smartly used to emphasize the theme of belonging. Overall, the film captures the gentle, neighborly version of Chicago that feels intimate and expansive.
10. My Best Friend’s Wedding (1997)
Written by: Ronald Bass | Directed by: P. J. Hogan
High-strung and neurotic New York food critic Julianne Potter (Julia Roberts) hears her best friend, Michael (Dermot Mulroney), a Chicago sports writer, is marrying Kimmy (Cameron Diaz), and suddenly has an epiphany that she is in love with him. So naturally, she sets out to prevent this fairy tale marriage from happening. In this film, Chicago comes across as a sophisticated backdrop, complete with its high-end architecture and riverfront vista, to highlight the brash tug-of-war. The Chicago River plays an important part here, visually as well as symbolically, in the characters’ ever-shifting emotions. The film is fun and also comes in handy if you want to explore Chicago’s modern, upscale charm.
11. Road to Perdition (2002)
Written by: David Self | Directed by: Sam Mendes
Set in 1931, a mobster, John Rooney (Paul Newman), kills his enforcer, Michael Sullivan’s (Tom Hanks), wife and younger son. As he goes on the run with his elder son, Michael Jr. (Tyler Hoechlin), Michael seeks vengeance against Rooney. The story progresses through the rain-sodden and hauntingly beautiful Chicago. The use of desaturated color palettes and deep shadows brings out the city’s somber side. Against the city’s massive, cold structures, you can feel the character’s isolation growing.
12. Chicago (2002)
Written by: Bill Condon | Directed by: Rob Marshall
In 1920’s Chicago, a housewife, Roxie Hart (Renée Zellweger), and a vaudeville star, Velma Kelly (Catherine Zeta-Jones), compete for fame, celebrity, and the attention of a smooth-talking, duplicitous lawyer, Billy Flynn (Richard Gere), while being on death row. Technically, the movie is shot on a soundstage, so you don’t see the actual city. However, the production design perfectly captures the vaudevillian soul of Chicago’s Jazz Age. Also, theatrical lighting, fast-paced editing, and the overall musical glitz stimulate the city’s reputation for razzle-dazzle.
13. Divergent (2014)
Written by: Evan Daugherty, Vanessa Taylor | Directed by: Neil Burger
Set in a futuristic, dystopian Chicago, society is divided into five virtue-based factions. The protagonist, Tris Prior (Shailene Woodley), discovers that she doesn’t fit in any single faction since she possesses the traits of multiple factions. Since this anomaly is considered dangerous, she must hide it as she goes through the grueling initiation process. In this movie, we see Chicago, but not as we know it. Instead, it offers a uniquely dilapidated, Orwellian version of the city’s skyline. CGI is used to show iconic landmarks, such as the Navy Pier Ferris Wheel, in ruins. The director has a keen focus on the verticality of the city, and he does it by using the skyscrapers for intense training sequences. It redefines the urban geography.
14. The Trial of the Chicago 7 (2020)
Written by: Aaron Sorkin | Directed by: Aaron Sorkin
In this historical legal drama, seven activists are accused of inciting violence at the 1968 Democratic National Convention and are charged with conspiracy by the Nixon administration. The movie turns the courtroom into a tense, political battleground against systemic injustice. Since most of the film is confined to the courtroom, the city of Chicago mainly comes across through archival footage. It still shows you the city on the brink of a revolution. Especially Grant Park and the legal halls represent the intense political conflict. The film’s tight pacing is also indicative of the city’s chaotic energy during the era’s civil unrest.