Our sexy, 70s inspired subterranean cocktail lounge is a beautiful haven for live music, especially live jazz. Our new Velvet Underground series highlights queer jazz musicians for a night of easy listening, the perfect date destination and a lovely background to our exceptional lounge and cocktail program.

On May 11th we welcome in Millie Ahearn with Alvin Santner & Marion Mallard - playing from 8-11pm.

Millie Ahearn's music houses the experiences of a transgender musician navigating expressions of queerness and neurodivergence through jazz, focusing largely on transformation and the coming of the self into new life. It is gentle and exploratory, prioritizing heartfelt communication as it moves through cycles of light and dark, life and death. She has released two studio albums, ‘Octagyn’ (World Heart Beat Records, 2022) and ‘Theyness: Volume I’ (2026), with a third planned for release this summer.

Millie‘s original work, arranging work, and playing can be found on the albums of numerous artists across the city, and she has presented original music at the Chicago Jazz Festival, the Jazz Showcase, Andy’s Jazz Club, Evanston SPACE, and many other Chicago venues. Since June 2024, her biweekly jam session and concert series at Clara has given space for close to fifty Female, Non-Binary, and Gender Non-Conforming artists to present original music in an environment centered around community and love.

Doors at 6pm. A $5 cover starts at 7:30pm.

RSVPs are free and serve as calendar reminders for guests. RSVPs do not guarentee entry and are not in lieu of the cover charge at the door if entering after 7:30pm.

Dorothy is 21+ and requires physical or mobile ID for all to enter. Dorothy is also ADA accessible with elevator access on Campbell Ave. If you are a guest who requires elevator access, please wait by the black door with our logo in the window and call our staff to assist: 773-770-3799