Dynamic Watchlist Hub: May 09, 2026

10 Best Movies Like Chicago

If you loved Chicago, we've curated the perfect watchlist for you based on shared genres, themes, and directorial style.

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Expert Review & Ratings

See our full critical analysis and audience score for Chicago.

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#1
The Blues Brothers

The Blues Brothers

1980★ 7.7

Why watch this? A perfect follow-up to Chicago for fans of Comedy & Crime. It captures a similar light-hearted atmosphere.

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....

#2
Connie and Carla

Connie and Carla

2004★ 5.9

Why watch this? A perfect follow-up to Chicago for fans of Comedy & Crime. It captures a similar light-hearted atmosphere.

After accidentally witnessing a mafia hit in the Windy City, gal pals Connie and Carla skip town for L.A., where they go way undercover as singers working the city's dinner theater...

#3
Bernie

Bernie

2012★ 6.6

Why watch this? A perfect follow-up to Chicago for fans of Comedy & Crime & Drama. It captures a similar light-hearted atmosphere.

In small-town Texas, affable and popular mortician Bernie Tiede strikes up a friendship with Marjorie Nugent, a wealthy widow well known for her sour attitude. When she becomes con...

#4
The Cat's Meow

The Cat's Meow

2001★ 5.8

Why watch this? A perfect follow-up to Chicago for fans of Crime & Drama. It captures a similar emotionally gripping atmosphere.

Semi-true story of the Hollywood murder that occurred at a star-studded gathering aboard William Randolph Hearst's yacht in 1924....

#5
Down by Law

Down by Law

1986★ 7.3

Why watch this? A perfect follow-up to Chicago for fans of Comedy & Crime & Drama. It captures a similar light-hearted atmosphere.

A disc jockey, a pimp and an Italian tourist escape from jail in New Orleans....

#6
Unconditional Love

Unconditional Love

2002★ 6.0

Why watch this? A perfect follow-up to Chicago for fans of Comedy & Drama. It captures a similar light-hearted atmosphere.

After her husband leaves her, a woman travels to London for the funeral of the pop star, Victor Fox, she's adored all her life. There, she meets the lover of the dead pop star, and...

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