Movies like Rendezvous in Chicago (2018)
The best movies like Rendezvous in Chicago (2018) are Zack and Miri Make a Porno (2008), Bros (2022) and My Fake Boyfriend (2022). If Rendezvous in Chicago hooked you with its comedy and romance, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedCity Lights (1931)8.2/10 from 2,591 votes
- NewestOne Night Only (2026)Released 2026
Zack and Miri Make a Porno (2008)
Lifelong 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 other than they previously thought.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisBros (2022)
Two gay men are possibly, probably, stumbling towards love. Maybe. They're both very busy.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisMy Fake Boyfriend (2022)
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. But everything backfires when he meets the real love of his life, and breaking up with his fake boyfriend proves hard to do.
Why it matches: Recommended by TMDB viewers · both comedy & romance
SnoozefestMovies like thisPuppy Love (2023)
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 on the way! The hilariously mismatched Nicole and Max are forced to become responsible co-parents, but may end up finding love themselves.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Worth the HypeMovies like thisDean (2016)
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 home in the wake of his mother's death.
Why it matches: Recommended by TMDB viewers · both romance & comedy
SnoozefestMovies like thisStraight Talk (1992)
Honest 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 station insists she call herself Doctor, and as her popularity grows a local reporter starts digging for the truth. Problem is, the more he is around her the more he fancies her.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisLittle Italy (2018)
Former 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?
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisAll Over the Guy (2001)
A contemporary romantic comedy exploring the unlikely pairing of two 20-somethings thrown together by their respective best friends in hopes of igniting their own romance.
Why it matches: Recommended by TMDB viewers · both comedy & romance
SnoozefestMovies like thisA Hollywood Christmas (2022)
Jessica, 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 movie, Jessica’s assistant, Reena, points out the irony: Jessica isn’t just trying to save her Christmas movie, she’s actually living in one. Jessica must now juggle all the classic tropes—her actors falling in and out of love, a wayward elf dog, and her own stirring romantic feelings for her perceived nemesis—in order to get her movie and her life to their happy endings.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisThe Last Summer (2019)
Standing on the precipice of adulthood, a group of friends navigate new relationships, while reexamining others, during their final summer before college.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisThe Wrong Paris (2025)
Dawn 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.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisThe Long Weekend (2005)
Cooper 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 brother hooked up with a girl, thus a long weekend of stress and beautiful women, culminating in Ed meeting, and making love to, the woman of his dreams.
Why it matches: Recommended by TMDB viewers · both comedy & romance
SnoozefestMovies like thisYoh! Bestie (2026)
Thando 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.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisOne Night Only (2026)
Two love-starved strangers crash into each other on the one night of the year when single people are allowed to have sex.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisSomeone Like You... (2001)
Jane 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 begins an extensive study of the male animal, including her womanizing roommate Eddie. Jane puts her studies and romantic misadventure to use as a pseudonymous sex columnist -- and becomes a sensation.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisGirl on a Bicycle (2013)
Paolo, 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 turns Paolo's life upside down.
Why it matches: Recommended by TMDB viewers · both comedy & romance
SnoozefestMovies like thisLet's Make Love (1960)
When 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.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisSplendor (1999)
Veronica is a white-bread beauty searching for a good man in Los Angeles. While slam dancing at a Halloween rave, she meets Abel, a sensitive poet. Then she meets Zed, a supersexy tattooed drummer with incredible biceps. Who will she choose? Does she go for true love or cheap sex? She can't decide so she chooses both. But after managing to nurture a picture-perfect threesome, along comes Ernest, a rich movie director with deep baby blues that sweep Veronica off her feet. What's a girl to do now?
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisChasing Papi (2003)
Playboy 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 socialite Patricia -- spiral out of control, he suffers a mental breakdown. His doctor recommends that he choose just one girlfriend -- but can he choose in time before they discover his deception?
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisSex Appeal (2022)
Avery, a teenager with a tendency towards perfectionism, enlists her friend Larson to help her prepare for her first time with her long-distance boyfriend.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisKedi Özledi (2013)
Kıymet and Kadir are a couple in their mid-thirties, having problems with relationship. They decide to fix those by getting a cat.
Why it matches: Similar story and style · both comedy & romance
Something Blue (2025)
Lifelong friends Óscar and Eli find themselves in a messy situation after a drunken night leads to unexpected consequences. Forced to replace a ruined wedding dress, they embark on a chaotic journey filled with setbacks and awkward run-ins with their exes.
Why it matches: Similar story and style · both romance & comedy
Somewhat Agree (2004)
Jérémie has a job recruiting subjects for testing. He'd rather recruit Rodrigue for something else entirely.
Why it matches: Similar story and style · both romance & comedy
City Lights (1931)
A tramp falls in love with a beautiful blind flower girl. His on-and-off friendship with a wealthy man allows him to be the girl's benefactor and suitor.
Why it matches: Similar story and style · both comedy & romance
Absolute CinemaMovies like thisStranger Than Fiction (2006)
Harold Crick is a lonely IRS agent whose mundane existence is transformed when he hears a mysterious voice narrating his life.
Why it matches: Similar story and style · both comedy & romance
Worth the HypeMovies like thisShortbus (2006)
In post-9/11 New York City, an eclectic group of citizens find their lives entangled, personally, romantically, and sexually, at Shortbus, an underground Brooklyn salon infamous for its blend of art, music, politics, and carnality.
Why it matches: Similar story and style · both romance & comedy
Popcorn FlickMovies like thisImagine Me & You (2006)
During her wedding ceremony, Rachel notices Luce in the audience and feels instantly drawn to her. The two women become close friends, and when Rachel learns that Luce is a lesbian, she realizes that despite her happy marriage to Heck, she is falling for Luce. As she questions her sexual orientation, Rachel must decide between her stable relationship with Heck and her exhilarating new romance with Luce.
Why it matches: Similar story and style · both comedy & romance
Worth the HypeMovies like thisLove Conquers Paul (2009)
Paul has a chance encounter with a free-spirited artist named Esoterica that provides the spark that ignites his first passionate relationship. She changes he way he looks at love and life and introduces him to the person he could be, inspiring a new confidence. But just as soon as their fairy-tale romance begins to sizzle, Paul discovers that Esoterica has a secret of her own.
Why it matches: Similar story and style · both comedy & romance
Don Juan DeMarco (1994)
John Arnold DeMarco is a man who believes he is Don Juan, the greatest lover in the world. Clad in a cape and mask, DeMarco undergoes psychiatric treatment with Dr. Jack Mickler to cure him of his apparent delusion. But the psychiatric sessions have an unexpected effect on the psychiatric staff and, most profoundly, Dr Mickler, who rekindles the romance in his complacent marriage.
Why it matches: Similar story and style · both romance & comedy
Popcorn FlickMovies like thisShabbat Dinner (2012)
Shabbat Dinner is boring as usual for William Shore. His mother has invited two crazy hippies and their son and is doing her best to show off, his father is drunk and berating their oddball guests, and he doesn't have much in common with their son Virgo. That is, until Virgo tells him that he has just come out as gay.
Why it matches: Similar story and style · both romance
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Frequently asked questions
What are the best movies like Rendezvous in Chicago?
The closest matches to Rendezvous in Chicago are Zack and Miri Make a Porno (2008), Bros (2022) and My Fake Boyfriend (2022). Below are 27 more, each with the reason it matches.
What should I watch after Rendezvous in Chicago?
Start with Zack and Miri Make a Porno (2008), the closest match to Rendezvous in Chicago.
What is the highest-rated movie like Rendezvous in Chicago?
City Lights (1931), rated 8.2/10 by 2,591 TMDB users.
What is the newest movie like Rendezvous in Chicago?
One Night Only (2026) is the most recent release on this list.
Are there English movies like Rendezvous in Chicago?
Yes: Zack and Miri Make a Porno (2008), Bros (2022) and My Fake Boyfriend (2022).
How are movies similar to Rendezvous in Chicago chosen?
First come films that Trakt’s viewers watch alongside Rendezvous in Chicago, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.