Movies Like Windy City

If you liked Windy City (1984), a drama and romance movie directed by Armyan Bernstein, 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
Winter Spring Summer or Fall (2024)
★ 7.3/10Also romance and drama
Remi and Barnes, two very different teenagers, meet by chance in the winter of their senior year, then spend four days together over the course of a year that will change their lives forever.
2
Newness (2017)
★ 6.1/10Also romance and drama
In contemporary Los Angeles, two millennials navigating a social media–driven hookup culture begin a relationship that pushes both emotional and physical boundaries.
3
Ashes in the Snow (2018)
★ 6.4/10Also drama and romance
The coming-of-age tale of 16-year-old Lina Vilkas who is deported to Siberia amid Stalin's reign of terror in the Baltic region during WWII. An aspiring artist, she secretly documents her harrowing journey with her…
4
All of You (2025)
★ 6.3/10Also romance and drama
Laura and Simon have been best friends since college. Over the years, they've realized their bond is more than platonic. Can they—and should they—risk everything to explore a love that has existed all along?
5
Circle of Friends (1995)
★ 6.3/10Also drama and romance
Three girlhood friends now at college share first loves, first kisses and first betrayals. At the center of it all is the best-looking boy on campus. Can a self-conscious dreamer hook the biggest fish in the pond?
6
Time Is Up (2021)
★ 6.5/10Also romance and drama
Vivien, an accomplished student with a passion for physics, and Roy, a troubled young man, are involved in an accident that forces them to reclaim their lives one minute at the time.
7
On the Edge (2001)
★ 6.7/10Also drama and romance
A suicidal young man is committed to a Dublin psychiatric hospital where he meets new friends who greatly influence his life.
8
A Journal for Jordan (2021)
★ 6.9/10Also drama and romance
Based on the true story of First Sergeant Charles Monroe King, a soldier deployed to Iraq begins to keep a journal of love and advice for his infant son. Back at home, senior New York Times editor Dana Canedy revisits…
9
London (2005)
★ 6/10Also drama and romance
London is a drug laden adventure that centers on a party in a New York loft where a young man is trying to win back his ex-girlfriend.
10
Fire with Fire (1986)
★ 6.2/10Also drama and romance
A tough, street-smart kid serving a sentence in a state youth reformatory meets a beautiful, innocent girl studying at a nearby convent. When forbidden love blossoms between them, they must fight the prison…
11
Heartstopper Forever (2026)
★ 7.2/10Also romance and drama
It's a new school year for the Truham-Higgs gang. As Nick and Charlie's relationship deepens, their thoughts turn to life after the last bell rings.
12
The Vanishing of Sidney Hall (2018)
★ 6.7/10Also drama and romance
Over the course of 12 years, and three stages of life, Sidney Hall falls in love, writes the book of a generation and then disappears without a trace.
13
Attraction (2001)
★ 6.9/10Also romance
A writer/radio advice show host fails to heed his own advice as he stalks his ex-girlfriend and then becomes involved with an actress friend of hers.
14
See You Soon (2019)
★ 5.9/10Also romance and drama
A U.S. soccer star suffers a career-threatening injury in the run-up to the World Cup, and during his recovery, embarks on an epic romance with a Russian single mom.
15
Game of Love (2022)
★ 6.1/10Also romance and drama
Follows Vivien and Roy as their love story continues and leads them to Roy’s childhood home in Sicily to prepare for the sale of the family estate. During the visit, a mysterious woman arrives and befriends Vivien…
16
The Edge of Love (2008)
★ 6.2/10Also drama and romance
When the Welsh poet Dylan Thomas and his flirtatious wife Caitlin sweep into war-torn London, the last thing they expect is to bump into Dylan's childhood sweetheart Vera. Despite her joy at seeing Dylan after so many…
17
Maria's Lovers (1984)
★ 6/10Also drama and romance
A World War II prisoner returns home to his childhood sweetheart. However, back home, he discovers that he has to compete to win her love.
18
The Map That Leads to You (2025)
★ 6.7/10Also romance and drama
Heather is a young woman traveling Europe with friends before starting her perfectly planned life. A chance meeting with Jack sparks an unexpected romance that leads to deep emotional discovery. As secrets and life…
19
Crazy/Beautiful (2001)
★ 6.6/10Also drama and romance
At Pacific Palisades High, a poor Latino falls hard for a troubled girl from the affluent neighborhood.
20
Marked Men: Rule + Shaw (2025)
★ 6.7/10Also romance and drama
Shaw Landon has loved Rule Archer from the moment she laid eyes on him. Rule, a fiery-tempered rebel tattoo artist, doesn’t have time for a good girl pre-med student like Shaw — even if she’s the only one who can see…