Lesbian · Chicago

Lesbian Holiday Film Series at Dorothy: Happiest Season

Name: Lesbian Holiday Film Series at Dorothy: Happiest Season
Start: 2026-12-21T19:00:00-06:00
Location: Dorothy

Dorothy

2500 W Chicago Ave, Chicago, IL 60622

directions(773) 770-3799website

Coming up

Mon, Dec 21 · 7:00 PM

Monday, December 21, 2026

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About

Dorothy's Lesbian Holiday Film Series kicks off with Happiest Season, a cozy night of queer holiday cinema in Chicago's West Town. Settle into the speakeasy's retro booths for a screening that proves the holidays can be gay, messy and full of heart. The series runs four lesbian-centered films this December, and Monday's 7 PM start is a perfect way to warm up the week.

Parenting & Queer Families

TV & Streaming

Film

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More Events at Dorothy

Showing 6 upcoming events

Live Music

Dusky Waters: The Mother Magnolia Tour Live

Friday, November 13th, 2026

7:00 PM

New Orleans singer-songwriter Dusky Waters brings her ancestral Americana to Chicago for an intimate trio night at Dorothy, the 70s-inspired lesbian speakeasy in West Town. Expect close-up storytelling and rich harmonies in a room built for listening. Doors open at 7pm and the set runs till 8:30pm, so you'll have time for a nightcap after.

Late Night

DJ Feature: Ca$h Era

Friday, November 13th, 2026

10:00 PM

Ca$h Era, Chicago's 2026 resident DJ, pops up at Dorothy every month in West Town, bringing the late-night energy to this 70s-inspired lesbian bar. Expect a set built for the dance floor, a sexy speakeasy atmosphere, and a crowd that's here to move. It starts at 10:00 PM and runs until 2:00 AM, so get there early to claim a spot.

Lesbian

The Vault

Saturday, November 14th, 2026

8:00 PM

The Vault is Dorothy's Saturday-night return to the speakeasy-style underground, with the red door as your ticket back in. Dorothy sits in Chicago's West Town at 2500 West Chicago Avenue, and this event runs Saturday, November 14, 2026 from 8:00 PM to 2:00 AM. It's a lesbian bar night with a 70s-inspired atmosphere, so come ready to settle in and stay a while.

retro

Queer Movie Monday: Stud Life

Monday, November 16th, 2026

7:00 PM

Queer Movie Monday at Dorothy in Chicago's West Town is your third-Monday ritual: host Shelli Nicole screens the best queer films in the retro, subterranean speakeasy, and you could walk out with a prize. Grab a seat, settle in and let the lights go down. It starts at 7:00 PM and runs until 9:30 PM.

Lesbian

Sapphic Songwriter Series

Wednesday, November 18th, 2026

7:00 PM

The Sapphic Songwriter Series at Dorothy in Chicago's West Town is a lesbian-focused night of original music from local artists, in an intimate speakeasy setting. Come for the songs, stay for the new favorite you discover. It kicks off Wednesday, November 18th at 7:00 PM.

Comedy

Wigs: Stand Up Comedy in Wigs

Thursday, November 19th, 2026

7:00 PM

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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Oops We Did It Again: Y2K Drag Dinner

Friday, November 13th, 2026

Times on venue site

Kit Kat Club

Oops We Did It Again is a Y2K-themed drag dinner at Kit Kat Club, Chicago's original drag show lounge in Lakeview on Halsted Street. Pull out your frosted tips and butterfly clips, settle in for an elevated dinner by Chef Chelsea Poe, and watch the Kit Kat Divas take the velvet stage. It kicks off Friday, November 13 at 7pm, so you'll want to book a table early.

Happy Hour

Queer Happy Hour @ Nightshade & Dark

Friday, November 13th, 2026

7:00 PM

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Are You Smarter Than a Drag Queen?

Friday, November 13th, 2026

7:00 PM

2Bears Tavern Uptown

High-energy drag trivia night hosted by Tia Pet at 2Bears Tavern Uptown. The questions are tricky, the host is shady, and the room is completely out of control—in the best way. Gather your team and test your wits over three hours of comedy, competition, and chaos. Free to play, no cover, drinks flowing, and the perfect way to kick off a Friday night at this neighborhood bar. Every Friday from 7pm to 10pm.

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Artemis Singers Karaoke Fundraiser Party

Friday, November 13th, 2026

7:00 PM

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Artemis Singers, Chicago's all-volunteer lesbian feminist chorus, is throwing a karaoke party at Whiskey Girl Tavern on Clark Street in Chicago's Edgewater neighborhood. Grab the mic, grab a drink, and support 46 years of community singing: 100% of net proceeds go straight to the chorus. All ages until 9 PM, 21+ after. Food and drinks are for purchase, and there are pay-what-you-wish baked goods.