Dorothy

Dorothy is a capacity-unpublished, lower-level lounge in Chicago’s West Town, entered through a red door and shaped around a 1970s-inspired queer-bar identity. Its concrete distinction comes in the format: this is a cocktail room whose calendar makes space for indie and rock-adjacent shows alongside social gatherings, burlesque, speed dating, and trans and nonbinary programming. Expect a close-range setting where the room itself carries as much weight as the bill.

A Valentine’s opening, then a long pause

Chef Zoë Schor and Split-Rail beverage director Michelle Szot spent three years developing Dorothy beneath their restaurant, opening it on Valentine’s Day, February 14, 2020. The launch arrived 29 days before Illinois ordered bars and restaurants closed on March 15; Dorothy then went dark for nearly two years. Schor and Szot reopened the room in January 2022, restoring a project designed as a queer-friendly gathering place with flexible terminology and a come-as-you-are approach.

The ground-floor operation later changed again: Split-Rail and adjacent gallery The Martin closed in November 2023, becoming the events venue Villanelle; Villanelle closed in October 2025. Dorothy continued downstairs, now owned by Schor and Whitney LaMora as part of their queer-focused hospitality group.

The room now

Dorothy works best for listeners who enjoy a show folded into a social night. The dominant musical lane is indie and rock, while the wider booking mix favors queer-centered events and artist-led gatherings. Inside, wood paneling, disco balls, plush brown couches, a piano, vinyl music, and stools around a low square bar give the open basement a lounge-first layout. Full buyouts include staff, a photobooth, outside food, and guest-selected music; the elevated bed lounge seats 20.