Silent Book Club ft. Proud City by Block Club Chicago

Venus brings tarot readings infused with mediumship and spell work to Dorothy's underground speakeasy. An intimate evening for anyone curious about divination, energy work, or just looking for a different kind of magic on a Wednesday night. 6-10pm.

Sharp, unfiltered comedy from Chicago's most vicious alternative comedians. BARK BARK BITE brings the kind of standup that doesn't pull punches — expect smart material, weird energy, and a room full of people who actually get it. This is for comedy nerds and anyone who appreciates comedians willing to go there.

Ca$h Era takes over the decks on the second Friday of every month at Dorothy, spinning the kind of sets that keep this underground lesbian bar packed and moving. If you've caught her before, you know what's coming — if you haven't, it's time to find out why she's Dorothy's resident favorite.

Dark music, dancing, and real community for the sapphic and lesbian members of Chicago's goth scene. Dorothy's underground vibe is the perfect home for a night that celebrates who you are and the music you love.

The 2002 musical Chicago gets the full treatment — sing along to every number, test your Queen Latifah knowledge during intermission trivia, and stick around for raffle prizes and a sneak peek at She's the He. It's the kind of Monday night that actually gives you a reason to show up.

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.