Daddy Pop: Halloween Edition brings the Wilton Manors party to Jackhammer's basement in Chicago, a rugged, sexy night built for dancing with a Halloween twist. Dress up, get on the floor, and let the costumes do the talking. It runs Saturday, October 17 from 9 PM to 4 AM, hosted by The Hole, so you've got plenty of time to make an entrance.

Party

Fuzzed

Sunday, October 18th, 2026

6:00 PM

Chicago's premier furry party is back at Jackhammer for a night of live energy, good music, and plenty of local furries to meet and party with. Fursuits and furry gear are encouraged but not required, so come exactly as you are. It's a space built for community first, costume second. Tickets are pay-what-you-can, with proceeds going to support the production of the party and its talent.

Karaoke

Lip Service Karaoke

Wednesday, October 21st, 2026

9:00 PM

Chicago's kinkiest karaoke night happens every Wednesday at Jackhammer, hosted by Tim Bell. Step up to the mic and let it out, or settle in and watch the beautiful chaos unfold — this is a midweek release where bold performances, uninhibited energy, and a no-judgment crowd take over. Free to attend, first-come first-served; sign-ups happen on-site, so arrive early if you want the mic.

Happy Hour

Bear Happy Hour

Thursday, October 22nd, 2026

6:00 PM

Bear Happy Hour is a monthly social built for bears, friends, and admirers to connect, unwind, and ease into the night. Expect a relaxed, welcoming atmosphere at Jackhammer on the fourth Thursday of the month, with plenty of room to meet new people and catch up with familiar faces. It's a low-pressure, high-vibe space centered on community and conversation, and it's free to attend.

fetish

Fetish Friday: Gear

Friday, October 23rd, 2026

9:00 PM

The fourth Friday of every month, Jackhammer turns its floor over to leather, rubber, harnesses, hoods, and everything in between. Whether you're building a collection or wearing your first piece, this 9PM to 4AM night is about showing up, exploring, and getting into the energy of a packed room of people who understand the assignment. Entry is free before 10PM, and dressing to the theme is strongly encouraged.

Dance Floor

Diaper Up: Jurassic Playground

Saturday, October 24th, 2026

9:00 PM

The gates are open at Jackhammer's Jurassic Playground, a Diaper Up event for the Chicago leather and alternative crowd. Expect a prehistoric-themed playful night in one of the neighborhood's most welcoming, no-judgment bars, with the pool tables, darts, dance floor, and patio that make Jackhammer a longtime favorite.

More LGBTQ+ Events in Chicago

Discover more events happening around Chicago

dog-friendly

Doggy Days

Saturday, October 17th, 2026

12:00 PM

The SoFo Tap

A weekly dog-friendly hangout at The SoFo Tap where pups and their people gather for easy vibes, cheap drinks, and free treats for the dogs. From noon to 3pm every Saturday, this neighborhood bar's patio fills up with a relaxed, welcoming crowd that knows the best company comes with fur and a tail. No pretense, just good drinks and genuine community.

Video Bar

Post Brunch Fun

Saturday, October 17th, 2026

1:00 PM

Sidetrack

The Saturday afternoon shift at Sidetrack — when brunch hangs on and the dance floor starts calling. Grab a drink, catch up with friends, and ease into the weekend vibe before things really heat up. It's that sweet spot between lazy brunch energy and full-on nightlife, with good music, good people, and a rooftop if you need air.

Gaming Community

Pokémon Raid Social

Saturday, October 17th, 2026

2:00 PM

Meeting House Tavern

Free monthly Pokémon GO hangout at Meeting House Tavern where trainers team up for raids, trade Pokémon, and meet fellow players. Hosted by Flops, this laid-back Saturday afternoon combines gaming, drinks, and community energy — perfect for longtime players, competitive trainers, and newcomers alike.

fetish

BearUnion Play Party

Saturday, October 17th, 2026

3:00 PM

Cell Block Chicago

BearUnion Play Party is a Saturday afternoon play party in the back bar at Cell Block Chicago, the kinky side of Boystown. Tickets are required for the backroom and can be bought online or at the door. Everyone entering must be 21+ with valid ID, and it runs 3:00 to 7:30 p.m.

Tea Dance

Daddy Disco Party

Saturday, October 17th, 2026

4:00 PM

Sidetrack

Daddy Disco is back for a Saturday afternoon tea dance at Sidetrack — dance hits from the 80s, 90s, and 2000s with hosts Michael and Jeremy keeping the energy up. It's the kind of daytime dance party that hits different, with a crowd that knows how to have a good time and a sound system that makes you remember why you love these songs.

Community Focused

National Coming Out Day Sk8 The Rainbow

Saturday, October 17th, 2026

8:30 PM

LGBTQ+ Center Lake County

Lace up and celebrate National Coming Out Day at the roller rink — a free, all-ages event where skating, community, and self-expression come together. Whether you're hitting the floor or cheering from the sidelines, there's something for everyone. Registration is recommended to secure your spot.