Movies like Windy City

Although set on the opposite coast, Sleepless in Seattle shares Windy City's deep-dive into the complexities of love and loss. It’s a film filled with both sweet and sorrowful moments, making it a solid recommendation for those who appreciate the emotional depth of Windy City.

My Best Friend's Wedding, starring Julia Roberts, is a comedy about love and friendship. It delves into themes of unrequited love and commitment, all in the bustling setting of Chicago, much like Windy City.

Set in the heart of Chicago, While You Were Sleeping is a charming rom-com that wins viewers over with its quirky premise and down-to-earth characters. Fans of Windy City will enjoy another lighthearted look at love and fate in the big city.

High Fidelity's Chicago setting is as vibrant and integral as that of Windy City. With a blend of humor, romance, and self-reflection, this film explores the intricacies of relationships through the lens of a record store owner's past loves.

Set against the backdrop of Chicago, The Break-Up provides a candid look at the dissolve of a relationship and the ensuing struggle for apartment ownership. Like Windy City, it offers a mix of romantic and more serious moments, reflecting the realities of modern love.

Return to Me, filmed on location in Chicago, tells a heartwarming story of love and second chances, with a unique twist. As in Windy City, the Windy City itself plays a significant role, and the emphasis on serendipitous connections will resonate with romantics.