Movies Like Rendezvous in Chicago
If you liked Rendezvous in Chicago (2018), a comedy and romance movie directed by Michael Glover Smith, 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
Zack and Miri Make a Porno (2008)
★ 6.3/10Also comedy and romanceLifelong platonic friends Zack and Miri look to solve their respective cash-flow problems by making an adult film together. As the cameras roll, however, the duo begin to sense that they may have more feelings for each…
- 2
Bros (2022)
★ 6.6/10Also comedy and romanceTwo gay men are possibly, probably, stumbling towards love. Maybe. They're both very busy.
- 3
Puppy Love (2023)
★ 7/10Also comedy and romanceAfter 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 on the way! The hilariously mismatched…
- 4
A Hollywood Christmas (2022)
★ 6.1/10Also comedy and romanceJessica, a young, up-and-coming filmmaker in Hollywood has made a name for herself directing Christmas movies. But when handsome network executive Christopher shows up threatening to halt production on her latest…
- 5
Little Italy (2018)
★ 6.6/10Also comedy and romanceFormer childhood pals Leo and Nikki are attracted to each other as adults—but will their feuding parents' rival pizzerias put a chill on their sizzling romance?
- 6
The Wrong Paris (2025)
★ 6.7/10Also romance and comedyDawn thinks she's joining a dating show in Paris, France, only to land in Paris, Texas. She has an exit plan — until sparks fly with the cowboy bachelor.
- 7
Yoh! Bestie (2026)
★ 6.2/10Also romance and comedyThando is perpetually unlucky in love, but when her bestie returns from his travels with a fiancée in tow, she's forced to face a new emotion — jealousy.
- 8
The Last Summer (2019)
★ 6/10Also romance and comedyStanding on the precipice of adulthood, a group of friends navigate new relationships, while reexamining others, during their final summer before college.
- 9
One Night Only (2026)
★ 6.4/10Also romance and comedyTwo love-starved strangers crash into each other on the one night of the year when single people are allowed to have sex.
- 10
Let's Make Love (1960)
★ 6.4/10Also comedy and romanceWhen billionaire Jean-Marc Clement learns that he is to be satirized in an off-Broadway revue, he passes himself off as an actor playing him in order to get closer to the beautiful star of the show, Amanda Dell.
- 11
Someone Like You... (2001)
★ 6/10Also comedy and romanceJane Goodale has everything going for her. She's a producer on a popular daytime talk show, and is in a hot romance with the show's dashing executive producer Ray. But when the relationship goes terribly awry, Jane…
- 12
Straight Talk (1992)
★ 6.1/10Also comedy and romanceHonest and straightforward small-town Shirlee Kenyon chucks her boyfriend and heads for Chicago. Accidentally having to host a radio problem phone-in show, it is clear she is a natural and is hired on the spot. But the…
- 13
The Long Weekend (2005)
★ 5.8/10Also comedy and romanceCooper is an actor who sees life as one big party, while Ed is in advertising and takes life too seriously. When Ed gets stressed over a deadline he has to meet, his brother Cooper works hard in trying to get his…
- 14
Sex Appeal (2022)
★ 6.6/10Also comedy and romanceAvery, a teenager with a tendency towards perfectionism, enlists her friend Larson to help her prepare for her first time with her long-distance boyfriend.
- 15
My Fake Boyfriend (2022)
★ 5.9/10Also comedy and romanceA 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. But everything backfires when he meets…
- 16
Girl on a Bicycle (2013)
★ 5.9/10Also comedy and romancePaolo, an Italian tour bus driver living in Paris, has just summoned up the courage to propose marriage to his German girlfriend Greta. However, a chance encounter with a French woman on a bicycle the very next day…
- 17
Players (2024)
★ 6.1/10Also romance and comedyNew York sportswriter Mack has spent years devising successful hook-up "plays" with her friends, but when she unexpectedly falls for one of her targets, she must learn what it takes to go from simply scoring to playing…
- 18
Desperados (2020)
★ 6/10Also comedy and romanceA panicked young woman and her two best friends fly to Mexico to delete a ranting email she sent to her new boyfriend. On arrival, they run into her former beau, who soon gets caught up in their frantic scheme.
- 19
Single All the Way (2021)
★ 6.4/10Also romance and comedyDesperate to avoid his family’s judgment about his perpetual single status, Peter convinces his best friend Nick to join him for the holidays and pretend that they’re now in a relationship. But when Peter’s mother sets…
- 20
Chasing Papi (2003)
★ 6.7/10Also comedy and romancePlayboy Thomas Fuentes has so far been able to skate by in life on good looks and charm alone. But when his duplicitous relationships with three women -- impassioned waitress Cici, meticulous lawyer Lorena and bored…