Dorothy Debuts ft. DJs Cobra B & Queen Méabh

Sunroom, a Chicago-based vocal trio, brings an evening of folk and soul harmony to Dorothy's intimate underground space. Expect original compositions and thoughtfully arranged covers that showcase the kind of vocal interplay that makes you lean in and listen. Perfect for a Wednesday night when you want something genuine and unhurried.

Queer karaoke hits Dorothy's underground every third Friday—a monthly tradition where sapphic voices take over the mic and the room gets loud with everything from power ballads to guilty pleasures. Hosted by E., it's the kind of night that starts with nerves and ends with someone belting out their anthem while the whole bar sings along.

Forty years of pop perfection in one night. Dorothy POP brings the biggest Top 40 hits from 1986 to 2026 to the dance floor—expect the songs that defined decades, performances that hit different, and a room full of people who know every word. This is the kind of night that reminds you why you love dancing to pop music.

No cover, no pressure, just a Sunday night to actually meet people. Dorothy's basement is packed with queer singles who showed up for the same reason you did — to see who's worth talking to. Low-key vibe, good drinks, and a room full of people ready to make a real connection.

An intimate evening of tender, fierce, and unapologetically queer poetry celebrating dezireé a. brown's debut collection. This is the kind of night that reminds you why poetry matters — raw, honest voices in a room full of people who get it. Held in Dorothy's underground speakeasy, a space designed for every friend of Dorothy.

Venus brings tarot readings infused with mediumship and spell work to Dorothy's underground space — the kind of intimate, mystical evening that feels like a secret only your closest friends know about. Four hours to get a reading, connect with something deeper, and settle into the speakeasy's retro glow.