Masquerade

Queer women, trans, and non-binary folks — this is your Pride celebration. Vespertine takes over The Hole for a four-hour daytime event that answers the question "Does kink belong at Pride?" with a resounding hell yes. Expect interactive hands-on learning, safe scene play, and a room full of people ready to express themselves through fetish and BDSM. Fetish dress code required (leather, PVC, uniform, goth, rope, neoprene — get creative). $30 tickets in advance; 21+.

The ultimate Pride bar crawl hits Chicago's Proudest Neighborhood on Saturday, June 27. Kick off at 1pm at Sidetrack, then hop your way through Northalsted's legendary venues with the community. Tickets available through Ticket Tailor — this is the neighborhood's biggest Pride celebration, and it's worth showing up for.

Saturday afternoons at Meeting House Tavern belong to the people who show up to decompress, connect, and be themselves without judgment. It's part social mixer, part chosen family gathering — the kind of space where you can actually talk and be heard. A low-key, welcoming afternoon that reminds you why community matters.

Hydrate's weekend afternoon party is the kind of event that turns a lazy Saturday into a full day out — early enough to start fresh, late enough to keep the energy going. Expect a packed dance floor, resident DJs spinning the hits, and a crowd that knows how to have a good time without taking itself too seriously.

The last Saturday of every month belongs to the women and sapphic community at Sidetrack. Five to nine pm is your window to dance, connect, and celebrate with folks who get it — a recurring gathering that's become a reliable highlight for anyone looking to spend their evening around their people.

A weekly celebration for the bear and masculine-presenting community at Hydrate. Expect a welcoming crowd, strong drinks, and the kind of vibe where everyone belongs. Perfect for connecting with your people in a space that gets what community means.