Movies Like Chicago

If you liked Chicago (1927), a comedy and drama movie directed by Frank Urson, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

1
Breaking News in Yuba County (2021)
★ 5.9/10Also comedy and drama
An overlooked pencil-pusher catches her husband in bed with another woman, the shock of which causes him to die of a heart attack. So she buries his body and takes advantage of the growing celebrity status that comes…
2
Thick as Thieves (1999)
★ 6/10Also drama and comedy
Two master thieves go at odds with one another as one sets the other up for a crime. The first, a suave pro who does his job and then hides in his own privacy, listening to old jazz records and caring for his ailing…
3
Small Apartments (2012)
★ 5.9/10Also comedy and crime
When a clumsy deadbeat accidentally kills his landlord, he must do everything in his power to hide the body, only to find that the distractions of lust, the death of his beloved brother, and a crew of misfit characters…
4
Where the Money Is (2000)
★ 5.9/10Also comedy and crime
Henry Manning has come up with a new way to break out of prison: fake a stroke and get transferred to a nursing home. It's a perfect plan, except for one thing: the woman assigned to take care of him at the nursing…
5
Intermission (2003)
★ 6.2/10Also comedy and crime
A raucous story of the interweaving lives and loves of small-town delinquents, shady cops, pretty good girls and very bad boys. With Irish guts and grit, lives collide, preconceptions shatter and romance is tested to…
6
Breathless (2012)
★ 5.9/10Also comedy and crime
Lorna is a strong-willed Texas woman who’s had enough of her untrustworthy husband Dale’s criminal acts and lack of husbandry. Fed up, she enlists the help of her old friend, Tiny, to help her figure out what to do…
7
Blindspotting (2018)
★ 7.3/10Also comedy and crime
Collin must make it through his final three days of probation for a chance at a new beginning. He and his troublemaking childhood best friend, Miles, work as movers, and when Collin witnesses a police shooting, the two…
8
Thin Ice (2012)
★ 6.5/10Also comedy and crime
A dishonest insurance salesman's life quickly disintegrates during a Wisconsin winter when he teams up with a psychopath to steal a rare violin at the home of a reclusive farmer.
9
Fun with Dick and Jane (1977)
★ 6.6/10Also comedy and crime
When an upwardly mobile couple find themselves unemployed and in debt, they turn to armed robbery in desperation.
10
Psycho Therapy: The Shallow Tale of a Writer Who Decided to Write About a Serial Killer (2025)
★ 6.8/10Also crime and comedy
A struggling writer in the midst of a divorce befriends a retired serial killer who incidentally becomes his marriage counselor by day, and killing counselor for his next book by night.
11
Panic (2000)
★ 6.2/10Also crime and drama
Alex is going through a midlife crisis and it has become a very difficult time for him. His marriage is struggling, he's worried about his son, and his job of killing people for his family has become the most stressful…
12
True Believer (1989)
★ 6.2/10Also crime and drama
Eddie Dodd is a burnt out former civil rights lawyer who now specializes in defending drug dealers. Roger Baron, newly graduated from law school, has followed Eddie's great cases and now wants to learn at his feet…
13
Things Change (1988)
★ 6.2/10Also comedy and crime
Jerry, a misfit Mafia henchman, is assigned the low-level job of keeping an eye on Gino, a shoe repairman fingered by the Mob to confess to a murder he didn't commit. But Gino's mistaken for a Mafia boss, and the two…
14
The Enforcer (2022)
★ 7/10Also crime and drama
A noir thriller set in Miami, the film follows an enforcer who discovers his femme fatale boss has branched out into cyber sex trafficking, putting a young runaway he’s befriended at risk. He sacrifices everything to…
15
Defendor (2009)
★ 6.4/10Also drama and comedy
A crooked cop, a mob boss and the young girl they abuse are the denizens of a city's criminal underworld. It's a world that ordinary Arthur Poppington doesn't understand and doesn't belong in, but is committed to…
16
One Last Thing... (2005)
★ 6/10Also comedy and crime
Sixteen-year-old Dylan is dying of cancer. When a charitable organization offers to grant Dylan his final wish, the teen has a surprising request: to meet supermodel Nikki Sinclair. Much to his mother's dismay, Dylan…
17
Lady Windermere's Fan (1925)
★ 6.9/10Also comedy and drama
A society woman believes her husband is having an affair, a misconception which may have dire personal consequences for all involved.
18
CQ (2001)
★ 5.9/10Also comedy and drama
A young filmmaker in 1960s Paris juggles directing a cheesy sci-fi debacle, directing his own personal art film, coping with his crumbling relationship with his girlfriend, and a new-found infatuation with the sci-fi…
19
One Night at McCool's (2001)
★ 5.9/10Also comedy and crime
On an ordinary night, in an ordinary part of town, a beautiful young woman walks into a bar. Her name is Jewel, and before long she is chatting to bartender Randy. The pair leave together, but he ends up getting into a…
20
The Dream Team (1989)
★ 6.1/10Also comedy and crime
Four mental patients on a field trip in New York City must save their caring chaperone, who ends up being taken to a hospital in a coma after accidentally witnessing a murder, before the killers can find him and finish…