Comedy · Chicago

Wigs: Stand Up Comedy in Wigs

Name: Wigs: Stand Up Comedy in Wigs
Start: 2026-11-19T19:00:00-06:00
Location: Dorothy

Dorothy

2500 W Chicago Ave, Chicago, IL 60622

directions(773) 770-3799website

Coming up

Thu, Nov 19 · 7:00 PM

Thursday, November 19, 2026

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About

Wigs: Stand Up Comedy in Wigs is a comedy night at Dorothy, the sexy 70s-inspired lesbian speakeasy in Chicago's West Town. Your favorite stand-up comics take the mic in full wig glory, so expect big hair, bigger punchlines, and a room that's in on the joke. It's Thursday, November 19 at 7:00 PM, and it's exactly the kind of night you'll want to tell people about the next morning.

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More Events at Dorothy

Showing 6 upcoming events

Dance Party

Pop! x Strapped!

Saturday, October 24th, 2026

9:00 PM

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.

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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.

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