Dynamic Watchlist Hub: Apr 18, 2026

10 Best Movies Like Rendezvous in Chicago

If you loved Rendezvous in 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 Rendezvous in Chicago.

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#1
My Fake Boyfriend

My Fake Boyfriend

2022★ 5.9

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

A young man in a tricky situation follows the advice of his unconventional best friend and uses social media to create a fake boyfriend to keep his awful ex-lover out of his life. ...

#2
Bros

Bros

2022★ 6.7

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

Two gay men are possibly, probably, stumbling towards love. Maybe. They're both very busy....

#3
Puppy Love

Puppy Love

2023★ 7.0

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

After a disastrous first date, wild-child Nicole and socially-anxious Max vow to lose each other’s numbers until they learn that their dogs found a love match, and now puppies are ...

#4
Benjamin

Benjamin

2019★ 6.1

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

Benjamin, a rising star filmmaker, is on the brink of premiering his difficult second film No Self at the London Film Festival when Billie, his hard drinking publicist, introduces ...

#5
Dean

Dean

2016★ 5.8

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

A comedy about loss, grief, and the redemptive power of love. Dean is a NY illustrator who falls hard for an LA woman while trying to prevent his father from selling the family hom...

#6
The Last Summer

The Last Summer

2019★ 6.0

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

Standing on the precipice of adulthood, a group of friends navigate new relationships, while reexamining others, during their final summer before college....

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