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The Best Drag Shows in Chicago

Posted on March 28, 2023   |   Updated on September 30, 2025
Sidney Madden

Sidney Madden

Muffy Fishbasket at drag bingo in Evanston. (Courtesy of Muffy Fishbasket)

Muffy Fishbasket at drag bingo in Evanston. (Courtesy of Muffy Fishbasket)

Anti-drag show laws are passing in red states across the country and Illinois is not immune: Drag events in Illinois were among the most threatened and targeted in the country last year, according to GLAAD.We tapped drag queen Muffy Fishbasket, aka Jacob Green, to help us identify some of the best drag shows in Chicagoland.

Best drag dining: Lips in South Loop

“OF COURSE LIPS is going to be on this list. With regular performers like Vivian Dejour, Ruff N’ Stuff, Batty Davis, and Demi Sexton, you’re in for a glamorously good time.”

“With a new home at Women and Children First, performers travel to schools, museums, hospitals and events to promote diversity, inclusivity, representation, empathy, literacy, and creativity.”

Best drag king–produced show: Highwood Pride’s Slay the Cabaret“Almost 20 years ago, Sebastian and the Chicago Boi Toiz RULED the Boystown bars. Today, he produces at the rotating quarterly show.”

Best queer/drag variety: Peek-Easy in Wrigleyville

“This place hits different drag genres — in almost every show! Many of the shows’ cast members are transgender, queer, and non-binary. Talk about the beauty of representation. Willy LaQueue is a standout emcee.”

Best dragaret (drag cabaret): Lip Service in various locations

“Mrs. Yuka Layme is back with her singing dragaret. She’s a stage-ready tenor, has witty banter, loves musical theater, and has talented singers.”

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