Dynamic Watchlist Hub: Jan 21, 2026

10 Best Movies Like In Old Chicago

If you loved In Old 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 In Old Chicago.

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#1
You Can't Take It with You

You Can't Take It with You

1938★ 7.5

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

Alice, the only relatively normal member of the eccentric Sycamore family, falls in love with Tony Kirby, but his wealthy banker father and snobbish mother strongly disapprove of t...

#2
San Francisco

San Francisco

1936★ 6.5

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

A beautiful singer and a battling priest try to reform a Barbary Coast saloon owner in the days before the great earthquake and subsequent fires in 1906....

#3
The Adventures of Sherlock Holmes

The Adventures of Sherlock Holmes

1939★ 6.9

Why watch this? A perfect follow-up to In Old Chicago for fans of Crime. It captures a similar compelling atmosphere.

Having once again avoided criminal conviction, Professor Moriarity develops a murderous plan to “finish off” his last major nemesis, Sherlock Holmes, by making him fail to prevent ...

#4
Topper

Topper

1937★ 6.7

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

Madcap couple George and Marion Kerby are killed in an automobile accident. They return as ghosts to try and liven up the regimented lifestyle of their friend and bank president, C...

#5
Broadway Melody of 1940

Broadway Melody of 1940

1940★ 6.7

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

Johnny Brett and King Shaw are an unsuccessful dance team in New York. A producer discovers Brett as the new partner for Clare Bennett, but Brett, who thinks he is one of the peopl...

#6
Avengers: Infinity War

Avengers: Infinity War

2018★ 8.2

Why watch this? A perfect follow-up to In Old Chicago for fans of Adventure. It captures a similar adrenaline-pumping atmosphere.

As the Avengers and their allies have continued to protect the world from threats too large for any one hero to handle, a new danger has emerged from the cosmic shadows: Thanos. A ...