NoBadPicks

Movies Like Chicago

If you loved Chicago's Comedy and Crime storytelling, these films deliver a similar experience — carefully selected for tone, themes, and emotional depth. Each pick includes where to watch it right now.

Top Picks

The Blues Brothers
7.7

The Blues Brothers

1980

Jake Blues, just released from prison, puts his old band back together to save the Catholic home where he and his brother Elwood were raised.

Risky Business
6.6

Risky Business

1983

Meet Joel Goodson, an industrious, college-bound 17-year-old and a responsible, trustworthy son. However, when his parents go away and leave him home alone in the wealthy Chicago suburbs with the Porsche at his disposal he quickly decides he has been good for too long and it is time to enjoy himself. After an unfortunate incident with the Porsche Joel must raise some cash, in a risky way.

The Outfit
7.1

The Outfit

2022

Leonard is an English tailor who used to craft suits on London’s world-famous Savile Row. After a personal tragedy, he’s ended up in Chicago, operating a small tailor shop in a rough part of town where he makes beautiful clothes for the only people around who can afford them: a family of vicious gangsters.

Cadillac Records
7.1

Cadillac Records

2008

The story of sex, violence, race and rock and roll in 1950s Chicago, and the exciting but turbulent lives of some of America's musical legends, including Muddy Waters, Leonard Chess, Little Walter, Howlin' Wolf, Etta James and Chuck Berry.

Capone
5.8

Capone

1975

Young Al Capone catches the eye of Johnny Torrio, a criminal visiting New York from Chicago. Torrio invites Capone to move to Illinois to help run his Prohibition-era alcohol sales operation. Capone rises through the ranks of Torrio's gang and eventually takes over. On top, he works to consolidate his power by eliminating his enemies, fixing elections to his advantage and getting rich. In his spare time, Capone courts the principled Iris Crawford.

The First Great Train Robbery
6.7

The First Great Train Robbery

1978

In Victorian England, a master criminal makes elaborate plans to steal a shipment of gold from a moving train.

Dillinger
6.6

Dillinger

1973

After a shoot-out kills five FBI agents in Kansas City the Bureau target John Dillinger as one of the men to hunt down. Waiting for him to break Federal law they sort out several other mobsters, while Dillinger's bank robbing exploits make him something of a folk hero. Escaping from jail he finds Pretty Boy Floyd and Baby Face Nelson have joined the gang and pretty soon he is Public Enemy Number One. Now the G-men really are after him.

Sweeney Todd: The Demon Barber of Fleet Street
7.2

Sweeney Todd: The Demon Barber of Fleet Street

2007

The infamous story of Benjamin Barker, a.k.a Sweeney Todd, who sets up a barber shop down in London which is the basis for a sinister partnership with his fellow tenant, Mrs. Lovett. Based on the hit Broadway musical.

More Movies Like Chicago

The Sting
8.0

The Sting

1973

A novice con man teams up with an acknowledged master to avenge the murder of a mutual friend by pulling off the ultimate big con and swindling a fortune from a big-time mobster.

Thief
7.2

Thief

1981

Frank is an expert professional safecracker, specialized in high-profile diamond heists. He plans to use his ill-gotten income to retire from crime and build a nice life for himself complete with a home, wife and kids. To accelerate the process, he signs on with a top gangster for a big score.

Bad Boys
7.0

Bad Boys

1983

Mick O'Brien is a young Chicago street thug torn between a life of petty crime and the love of his girlfriend. But when the heist of a local drug dealer goes tragically wrong Mick is sentenced to a brutal juvenile prison where violence is a rite of passage and respect is measured in vengeance.

The United States of Leland
6.5

The United States of Leland

2003

A withdrawn young man, Leland Fitzgerald is imprisoned for the murder of a mentally disabled boy, who also happened to be the brother of his girlfriend, Becky. As the community struggles to deal with the killing, Pearl Madison, a teacher at the prison, decides to write about Leland's case. Meanwhile, others affected by the murder, including Becky and her sister, Julie, must contend with their own problems.

Primal Fear
7.7

Primal Fear

1996

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 Chicago. Vail finds himself up against his ex-pupil and ex-lover, but as the case progresses and the Church's dark secrets are revealed, Vail finds that what appeared a simple case takes on a darker, more dangerous aspect.

The Valachi Papers
6.5

The Valachi Papers

1972

When Joe Valachi has a price put on his head by Don Vito Genovese, he must take desperate steps to protect himself while in prison. An unsuccessful attempt to slit his throat puts him over the edge to break the sacred code of silence.

Taking Off
6.9

Taking Off

1971

Unable to deal with her parents, Jeannie Tyne runs away from home. Larry and Lynn Tyne search for her, and in the process meet other people whose children ran away. With their children gone, the parents are now free to rediscover/enjoy life.

Extremely Wicked, Shockingly Evil and Vile
7.0

Extremely Wicked, Shockingly Evil and Vile

2019

A chronicle of the crimes of Ted Bundy, from the perspective of his longtime girlfriend, Elizabeth Kloepfer, who refused to believe the truth about him for years.

Till
7.3

Till

2022

The true story of Mamie Till Mobley’s relentless pursuit of justice for her 14 year old son, Emmett Till, who, in 1955, was lynched while visiting his cousins in Mississippi.

Butterfly on a Wheel
6.4

Butterfly on a Wheel

2007

A sociopathic kidnapper methodically pushes a desperate pair of parents to their absolute breaking point.

Arsenic and Old Lace
7.6

Arsenic and Old Lace

1944

Mortimer Brewster, a newspaper drama critic, playwright, and author known for his diatribes against marriage, suddenly falls in love and gets married; but when he makes a quick trip home to tell his two maiden aunts, he finds out his aunts' hobby - killing lonely old men and burying them in the cellar!

Robin and the 7 Hoods
6.2

Robin and the 7 Hoods

1964

Set in Prohibition era Chicago, bootlegger Robbo and his cronies refuse to pay the greedy Guy Gisborne a cut of their profits after Guy shoots mob boss Big Jim and takes over. When Big Jim's daughter, Marian, gives Robbo a large sum, believing he has avenged her father's death, the gangster donates to an orphanage, cementing his reputation as a softhearted hood.

Why These Movies Are Similar

These recommendations share core qualities with Chicago (2002): Comedy and Crime themes, similar narrative structure, and comparable emotional depth. NoBadPicks uses a combination of TMDB collaborative filtering, genre matching, and AI analysis to surface films most likely to resonate with fans of Chicago.

See full details for Chicago (2002)

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