Movies Like Two Señoritas from Chicago

If you liked Two Señoritas from Chicago (1943), a comedy movie directed by Frank Woodruff, 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
The Big Store (1941)
★ 6.3/10Also comedy
A detective is hired to protect the life of a singer, who has recently inherited a department store, from the store's crooked manager.
2
Much Ado About Nothing (2013)
★ 6.8/10Also comedy
A modern retelling of Shakespeare's classic comedy about two pairs of lovers with different takes on romance and a way with words.
3
Love Happy (1949)
★ 5.8/10Also comedy
The Marx Brothers help young Broadway hopefuls when they get mixed up with gangsters due to a tin of sardines containing Romanoff diamonds.
4
Rookie of the Year (1993)
★ 6.2/10Also comedy
When the cast comes off his once broken arm, a 12-year-old boy can throw a 100-mile-an-hour fastball, and the Chicago Cubs want him as their new pitcher.
5
Fun with Dick and Jane (1977)
★ 6.6/10Also comedy
When an upwardly mobile couple find themselves unemployed and in debt, they turn to armed robbery in desperation.
6
Sneakerella (2022)
★ 5.9/10Also comedy
When El, an aspiring sneaker designer from Queens, meets Kira King, the fiercely independent daughter of legendary basketball star and sneaker tycoon Darius King, sparks fly as the two bond over their mutual affinity…
7
Little Big League (1994)
★ 6/10Also comedy
When the owner of the Minnesota Twins passes away, he bequeaths the team to his preteen grandson. The newly minted head honcho quickly appoints himself manager, causing unrest in an organization that struggles to take…
8
Godspell (1973)
★ 6.7/10Also comedy
In modern-day New York City, John the Baptist calls out to a group of young men and women to learn from the teachings of Jesus. Through song and dance, they relive Christ's crucifixion.
9
The Trouble with Angels (1966)
★ 6.7/10Also comedy
Mary and her friend, Rachel, are new students at St. Francis Academy, a boarding school run by the iron fist of Mother Superior. The immature teens grow bored and begin playing pranks on both the unsuspecting nuns and…
10
Beverly Hills Chihuahua 2 (2011)
★ 5.9/10Also comedy
Puppy mayhem turns the lives of newlywed Chihuahua parents Papi and Chloe upside down when their rambunctious, mischievous puppies present one challenge after another. But when their human owners end up in trouble, the…
11
Good Neighbor Sam (1964)
★ 6.6/10Also comedy
To help his divorced neighbor claim a substantial inheritance, a family man poses as her husband. The ruse spills over into his career in advertising, and his recent promotion relies on his wholesome and moral…
12
Malibu Rescue: The Next Wave (2020)
★ 6.2/10Also comedy
It’s summer again, and everyone’s favorite Junior Rescuers, The Flounders, are back at Tower 2. With the International Junior Rescue Championships headed to Southern California, the eyes of the entire planet are on…
13
The Air Up There (1994)
★ 6.1/10Also comedy
Jimmy Dolan is a college basketball coach who wants a big promotion. To get it, he needs to make a dramatic find. He ends up deep in Africa, hoping to recruit Saleh, a huge basketball prodigy Jimmy glimpsed in a home…
14
Animal Crackers (1930)
★ 6.9/10Also comedy
The well-known explorer and hunter Captain Spaulding has just returned from Africa, and is being welcomed home with a lavish party at the estate of influential society matron Mrs. Rittenhouse when a valuable painting…
15
The Loud House Movie (2021)
★ 7.2/10Also comedy
The Loud family travel to Scotland and discover they are descendants of Scottish royalty as they move into their giant ancestral castle.
16
Amy Schumer: Mostly Sex Stuff (2012)
★ 5.9/10Also comedy
A ratings hit! Amy Schumer debuts her one-hour special in front of a live audience at the Historic Fillmore Theatre in San Francisco. Nothing is off limits as Schumer airs every hilarious, messed up detail of her…
17
Taking Care of Business (1990)
★ 6.3/10Also comedy
An uptight advertising exec has his entire life in a filofax organizer which mistakenly ends up in the hands of a friendly convict who poses as him.
18
Gabriel Iglesias: Aloha Fluffy (2013)
★ 7.1/10Also comedy
ALOHAAAAA! Internationally acclaimed comedian, Gabriel Iglesias, returns to Comedy Central with his latest stand-up special taped at Honolulu’s Hawaii Theatre Center. Watch as Fluffy brings the house down yet again in…
19
The Pink Panther Strikes Again (1976)
★ 6.9/10Also comedy
Charles Dreyfus, who has finally cracked over inspector Clouseau's antics, escapes from a mental institution and launches an elaborate plan to get rid of Clouseau once and for all.
20
Gabriel Iglesias: Hot and Fluffy (2007)
★ 7.6/10Also comedy
Gabriel Iglesias is one of the fastest-rising comics today! With his unique brand of humor, lovable stage presence and wide range of voices and impressions, it's no wonder that he already has a huge fan following. Now…