Dynamic Watchlist Hub: Jan 19, 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.

🏆

Expert Review & Ratings

See our full critical analysis and audience score for Chicago.

View Review →
#1
The Bachelor

The Bachelor

1999★ 5.1

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

Jimmie is seeing his single friends get married one by one. He isn't too worried until his girlfriend Anne catches the bouquet at his friend Marco's wedding. Suddenly, his wild mus...

#2
Moulin Rouge!

Moulin Rouge!

2001★ 7.5

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

A celebration of love and creative inspiration takes place in the infamous, gaudy and glamorous Parisian nightclub, at the cusp of the 20th century. A young poet, who is plunged in...

#3
Chocolat

Chocolat

2000★ 7.0

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

In the winter of 1959, a single mother and her young daughter arrive in a rural French town, where they open an unusual chocolate shop that disrupts the moral fiber of the strictly...

#4
Hairspray

Hairspray

1988★ 6.8

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

'Pleasantly plump' teenager Tracy Turnblad achieves her dream of becoming a regular on the Corny Collins Dance Show. Now a teen hero, she starts using her fame to speak out for the...

#5
Nine

Nine

2009★ 5.5

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

Arrogant, self-centered movie director Guido Contini finds himself struggling to find meaning, purpose, and a script for his latest film endeavor. With only a week left before shoo...

#6
Cabaret

Cabaret

1972★ 7.4

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

Inside the Kit Kat Club of 1931 Berlin, starry-eyed singer Sally Bowles and an impish emcee sound the clarion call to decadent fun, while outside a certain political party grows in...