Are You Smarter Than a Drag Queen?

Monday morning pickup for art you've purchased. Swing by to collect your pieces and support local artists.

A Monday morning gathering for the leather and bootblack community to connect, share skills, and celebrate the craft. Whether you're experienced or just curious about the scene, this is a welcoming space to learn, polish, and build community with people who understand the culture.

A safe, confidential space for people in the leather community navigating recovery from addiction. This weekly Monday gathering offers peer support, shared experience, and the kind of judgment-free community that gets what leather life means. Whether you're early in recovery or supporting someone who is, you'll find people who understand both sides of your story.

Fifty-plus vendors fill 28,000 square feet of the Congress Plaza Hotel with everything from fashion and art to crafts, jewelry, and local makers. Whether you're hunting for something specific or just browsing what the queer and allied small business community is creating, this is the kind of market where you'll find something you didn't know you needed. Ticketed event.

A leather community celebration where bootblacks showcase their craft and artistry. This midday gathering brings together leather enthusiasts to appreciate the skill, tradition, and creativity that goes into bootblacking — from polishing techniques to custom designs. It's the kind of niche community event that reminds you how deep the leather world really goes.

Memorial Day afternoon takeover of Jackhammer's legendary subterranean space by Vespertine Chicago, a queer women's, trans, and non-binary community focused on education and exploration in fetish and BDSM. Interactive hands-on learning, safe scene play, and a strict fetish dress code (leather, PVC, uniforms, goth, rope, neoprene — no latex). Toy bags welcome, complimentary bag check available. 21+ with valid ID required. $30 advance tickets only.