Movies Like Windy City

Sleepless in Seattle is a 1993 American romantic comedy-drama film directed by Nora Ephron, featuring Tom Hanks and Meg Ryan. The story revolves...

The Break-Up is a 2006 romantic comedy-drama film directed by Peyton Reed. Starring Vince Vaughn and Jennifer Aniston, it follows the story of Brooke...

High Fidelity is a 2000 American romantic comedy-drama film based on the 1995 British novel of the same name by Nick Hornby. Directed by Stephen...

My Best Friend's Wedding is a 1997 American romantic comedy film starring Julia Roberts, Dermot Mulroney, Cameron Diaz, and Rupert Everett.

While You Were Sleeping is a 1995 American romantic comedy film featuring Sandra Bullock as a transit worker who saves a man's life and gets mistaken...

Return to Me is a 2000 American romantic comedy-drama film about a widowed architect who falls for a witty waitress at a unique Irish-Italian eatery....