Sapphic Serenade: Dorothy's Karaoke Night hosted by E.

The leather community's biggest night of the year — watch as competitors from around the world vie for the titles of International Mr. Leather and International Mr. Bootblack. This is the final round of one of the most prestigious contests in the leather world, drawing an audience of leather enthusiasts, community members, and supporters ready to celebrate excellence, artistry, and the values that define the community.

Sunday night poker at Meeting House Tavern — a regular gathering for players of all skill levels. Low-key, social, and a great reason to show up for cards, drinks, and the kind of crowd that actually knows how to have a good time.

Head to Jackhammer for Leather Slut, a bi/pan-focused kinky techno rave that brings Berlin's underground energy straight to Rogers Park. This is your chance to dance, express yourself freely, and connect with a community that celebrates leather, alternative style, and unapologetic sexuality in a judgment-free space. From 9 PM to 4 AM, you'll experience pulsing techno beats, a packed dance floor, and the kind of inclusive vibe that's made Jackhammer a Chicago institution for over 20 years.

Grab your friends and get ready to belt out your favorite tunes at Bearaoke IML, hosted by the charismatic Rhett Butlah at The SoFo Tap in Andersonville. This is your chance to shine on the mic in a fun, welcoming space where bears and their admirers come together to celebrate—whether you're belting out power ballads or having a laugh with your crew. With craft beers, creative cocktails, and a patio vibe, it's the perfect Sunday night to let loose and connect with your community.

The celebration Chicago's leather community has earned—a victory party for International Mr. Leather Big Bear, bringing together the leather and bear communities for an evening of pride, camaraderie, and good people. This is the night the community gathers to honor the winner and revel in what makes this community special.

Come celebrate unapologetically at Xtasy Leather Slut, where Jackhammer's legendary Sunday night energy brings together folks who love leather, attitude, and good times without judgment. This is your space to express yourself freely—whether you're into the scene or just curious—surrounded by a welcoming community that's been thriving in Rogers Park for over two decades. Expect a packed dance floor, killer vibes, and a crowd that knows how to have fun, all in a judgment-free zone that actually means it.