Bootleggers Ball

Step back into the smoky, electric world of the Roaring Twenties at the legendary Carol's Pub in Chicago. The Bootleggers Ball is a wildly entertaining live performance experience that blends theatrical storytelling with high-energy music, bringing the underground spirit of the Prohibition era roaring back to life. Carol's Pub, a beloved Chicago institution known for its raw honky-tonk charm and unpretentious authenticity, sets the perfect stage for a night that feels like you've stumbled into a secret speakeasy. On Sunday, May 31, 2026, the Bootleggers Ball takes center stage with a full performance by Bootleggers Ball, a group renowned for their infectious energy, period-soaked showmanship, and toe-tapping musical chops. Expect a raucous evening filled with swinging rhythms, theatrical flair, and an audience atmosphere that blurs the line between spectator and co-conspirator in the night's illicit festivities. Whether you're a die-hard fan of the era, a lover of immersive live theatre, or simply someone looking for a night out unlike any other in Chicago, the Bootleggers Ball delivers an unforgettable collision of history, performance art, and pure entertainment. Grab your fedora, channel your inner gangster, and prepare for a night that would make even Al Capone crack a smile.