A monthly pop dance party for lesbians and sapphics at Dorothy's subterranean lesbian bar. Scissor hosts with DJ Memoirs spinning feel-good pop hits, followed by performances from Scissor, Irregular Girl, and Siichele starting at 10:30pm, then a cover-free DJ set by El Gato from midnight to 2am. $10 cover from 8:30pm–midnight; free before 8:30pm and after midnight. 21+.

Karaoke

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

Monday, October 26th, 2026

7:00 PM

Costume on, babe: it's Halloweek karaoke at Dorothy in Chicago's West Town, and this one's called Sapphic Serenade. Grab the mic, claim your big number and let E. keep the night rolling from 7:00 PM to 11:00 PM on Monday, October 26, 2026. Dress to match the season and bring your loudest voice to this lesbian bar's intimate underground room.

musical

Buffy the Vampire Slayer: Once More with Feeling Sing Along

Tuesday, October 27th, 2026

7:00 PM

Dorothy is turning its screen into a stage for a Buffy the Vampire Slayer sing-along, streaming the legendary "Once More with Feeling" musical episode during Halloweek in Chicago's West Town. Bring your best demon-slaying voice and join the crowd belting every number together. It kicks off at 7pm on Tuesday, October 27, and it's the perfect way to start your Halloween week.

Cabaret

Coochies From The Crypt: a 90s Horror Hoochie Cabaret & Freaknik For Lesbians & Sapphics

Thursday, October 29th, 2026

7:30 PM

The crypt is back for its one-year anniversary, and this sapphic celebration is pulling out all the haunts. Expect a night of 90s horror-inspired cabaret performances, a dress code that demands drama (think Scream Queen meets Hoochie nostalgia), and an afterparty where DJ Khalimelon spins Freaknik classics and 90s hits until Dorothy closes. Unfiltered, unapologetically sapphic, and always packed—grab tickets early.

Lesbian

Lesbian & Sapphic Goth Night

Friday, October 30th, 2026

8:00 PM

Lesbian & Sapphic Goth Night at Dorothy in Chicago's West Town is back to kick off Halloween weekend, and you'll want to dress the part. After a packed debut, this dark, vampy, sapphic night is all black lace, moody music and late-night dancing from 8 PM to 2 AM, so grab your most dramatic look and come ready to haunt the dance floor.

Lesbian

Halloween Night at Dorothy with MobeeThicc

Saturday, October 31st, 2026

6:00 PM

Spend some or all of your Halloween night at Dorothy, Chicago's lesbian bar, with music by MobeeThicc. It's a 70s-inspired speakeasy in West Town, so dress up and dance the night away with the whole crowd. Doors open at 6:00 PM and the party runs until 2:00 AM, so you can come early for a drink or stay late as the night heats up.

More LGBTQ+ Events in Chicago

Discover more events happening around Chicago

Community Hub

Saturday Morning Coffee Hangout

Saturday, October 24th, 2026

9:00 AM

LGBTQ+ Center Lake County

Start your Saturday right with the community — free coffee and tea, open wifi, and a room full of people who get it. Whether you're looking to connect with regulars or meet someone new, this is the kind of low-pressure hangout that actually works. Staff around if you need anything.

Community Center

Care Navigator Services

Saturday, October 24th, 2026

9:00 AM

Center on Halsted

Connect with a Care Navigator at Center on Halsted in Chicago for resource navigation, referrals and case management support. Services are open to everyone, regardless of HIV status, with specialized support for people living with HIV. Stop by on Saturday morning, October 24, and get pointed to the help you need, no judgment, just answers.

Neighborhood Bar

Northalsted Halloween Pup Crawl

Saturday, October 24th, 2026

10:00 AM

Chicago IL

The 12th annual Halloween Pup Crawl turns Northalsted into a trick-or-treat paradise for dogs and their people. Walk the neighborhood from Aldine to Cornelia, collect swag and treats from local vendors, snap photos with Miss Foozie, and cap off the morning with an after-party brunch at the Lark Patio at 2pm. Costumes encouraged—for you and your pup. $5 advance registration includes a tote bag, raffle entry, and pup swag.

Community Center

Golden Diners Hot Meals

Saturday, October 24th, 2026

10:30 AM

Center on Halsted

Golden Diners Hot Meals is a free lunch and conversation program for adults 60 and older at Center on Halsted in Chicago, running every Tuesday, Thursday and Saturday in partnership with the City of Chicago's Golden Diners Program. Grab a warm meal, pull up a chair and catch up with neighbors and friends over lunch.

Drag Brunch

Drop Dead Beauties Bottomless Drag Brunch

Saturday, October 24th, 2026

11:00 AM

Kit Kat Club

The Kit Kat Divas bring the heat to this legendary bottomless brunch — choreographed themed drag shows, incredible costumes, and two hours of free-flowing mimosas, bellinis, sangria, and signature cocktails. Two-course prix fixe brunch included. Book your table or walk in; expect pumping music, personal interaction with the divas, and the kind of high-energy performance that's made Kit Kat Chicago's best venue for drag.

dog-friendly

Doggy Days

Saturday, October 24th, 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.