Crying at the Shed: Chicago’s Most Beautifully Heartbroken Valentine’s Film Festival Returns

In a world of candy hearts and predictable romance, Chicago offers something deeper, stranger, and far more human.

From February 12 through 14, The Salt Shed welcomes back Crying at the Shed, its annual film festival devoted not to fairy-tale love, but to the complicated, messy, breathtaking reality of it. This is cinema that aches. Cinema that remembers. Cinema that stays with you long after the theater lights rise.

This year’s edition leans fully into yearning, romantic, existential, and sometimes absurd, tapping directly into the cultural moment where love can be found in unexpected places, including the growing emotional landscape of human connection in the age of AI. It’s Valentine’s Day reimagined, less roses and chocolates, more truth and feeling.

For the holiday weekend, Elston Electric transforms into Fat Bernie’s Arcade from Licorice Pizza, an immersive cinematic portal that pulls guests inside the emotional universe of the festival. Opening night sets the tone with a live performance from Lael Neale, whose hypnotic, minimalist drone-pop creates a dreamlike soundtrack for a weekend about vulnerability, memory, and connection.

The film lineup reads like a love letter to modern cinema, featuring works from Sofia Coppola, Paul Thomas Anderson, Alice Rohrwacher, Mike Mills, Spike Jonze, Alfonso Cuarón, and Gus Van Sant. From the restless tenderness of Licorice Pizza to the aching loneliness of Lost in Translation, from the intimate grief of Beginners to the surreal longing of La Chimera, each film explores love in its many fragile, luminous forms. Even the timeless warmth of Lady and the Tramp finds its place, reminding audiences that love stories, no matter how simple, endure.

More than a screening series, Crying at the Shed is a fully curated cultural experience blending film, music, space, and emotion into what has quietly become one of Chicago’s most resonant Valentine’s traditions. For those seeking something real, raw, and unforgettable, this is where the heart goes to feel.

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