Saturday, Oct 02 2021

10:00AM

Boozy Brunch
D.S. Tequila Co.

11:00AM

Chicago Pride Fest 2021
Halsted St. from Addison to Grace

Kit Kat Pride Brunch with Kinley Preston
Kit Kat Lounge & Supper Club

Divalicious Drag Brunch (Saturday)
Kit Kat Lounge & Supper Club

12:00PM

Doggy Days
The Sofo Tap

2:30PM

Chicago Pride Fest: Shangela
Halsted St. from Addison to Grace

3:00PM

Spring Awakening: Autumn Equinox
Addams/Medill Park, 1301 W. 14th Street

3:15PM

Chicago Pride Fest 2021: Katie Kadan
Halsted St. from Addison to Grace

5:30PM

Chicago Pride Fest 2021: Brooke Eden

6:00PM

Kit Kat Pride Dinner with Yeisa Jovovich
Kit Kat Lounge & Supper Club

7:00PM

Country Line Dance Lessons
Charlie's Chicago

7:30PM

The Golden Girls: The Lost Episodes, Vol. 5- SEX! A Handbag Parody
Leather Archives & Museum

8:00PM

Chicago Pride Fest: St. Panther
Halsted St. from Addison to Grace

Draglicious Saturday Night Drag Review
Hydrate Nightclub

Cameron Esposito
The Den Theatre, 1331 N. Milwaukee, 2nd Fl.

Power Hour: Britney and Madonna (DJ Cashera, late)
Scarlet Bar

Pride Fest Dance Party
Sidetrack

Pride Fest at Progress
Progress Bar

9:00PM

Chicago Pride Fest 2021: Mya
Halsted St. from Addison to Grace

10:00PM

DJ Abel at Hydrate (Pride Fest Weekend)
Hydrate Nightclub

DJ Brryce Fersher at Scarlet
Scarlet Bar

Saturday Night Main Event
Charlie's Chicago

11:00PM

Sashay: Pride Fest Standup Comedy Showcase
The Laugh Factory Chicago

Sunday, Oct 03 2021

10:00AM

Boozy Brunch
D.S. Tequila Co.

11:00AM

Chicago Pride Fest 2021
Halsted St. from Addison to Grace

Kit Kat Pride Brunch with Kinley Preston
Kit Kat Lounge & Supper Club

Divalicious Drag Brunch (Sunday)
Kit Kat Lounge & Supper Club

12:00PM

Chicago Pride Fest 2021: Pet Parade
North Halsted and Grace

Chicago Pride Parade 2021 (CANCELED)
Lakeview and Uptown neighborhoods

1:00PM

Bear Beer Blast
The Sofo Tap

2:00PM

Sunday Social with Chamilla Foxx & DJ RONS
Meeting House Tavern

Pride Fest at Progress
Progress Bar

2:30PM

Chicago Pride Fest: Debbie Gibson
Halsted St. from Addison to Grace

3:00PM

Spring Awakening: Autumn Equinox
Addams/Medill Park, 1301 W. 14th Street

The Golden Girls: The Lost Episodes, Vol. 5- SEX! A Handbag Parody
Leather Archives & Museum

4:00PM

Sunday Funday Show Tunes
Sidetrack

5:30PM

Queeriod! A Drag Hype Show
Charlie's Chicago

6:00PM

Kit Kat Pride Dinner with Yeisa Jovovich
Kit Kat Lounge & Supper Club

6:30PM

Chicago Pride Fest 2021: Mila Jam
Halsted St. from Addison to Grace

7:00PM

Scarlet Pride: DJs Cashera and Kirk
Scarlet Bar

8:00PM

Chicago Pride Fest 2021: Crystal Waters
Halsted St. from Addison to Grace

9:00PM

Chicago Pride Fest 2021: Nina Sky
Halsted St. from Addison to Grace

Anthems
Berlin Nightclub

Bearaoke with Pat Da Bear
The Sofo Tap

10:00PM

House Collective ft. Ethan Cole and Joe Pacheco (Pride Fest Edition)
Hydrate Nightclub

House Collective
Hydrate Nightclub

11:00PM

Mas Leche
Charlie's Chicago

Monday, Oct 04 2021

8:00PM

Musical Monday Show Tunes
Sidetrack

10:30PM

Lipstick and Mascara
Hydrate Nightclub

Tuesday, Oct 05 2021

5:00PM

D.S. Tequila Wing Night
D.S. Tequila Co.

7:00PM

OUTspoken! LGBTQ+ Storytelling
Sidetrack

8:00PM

Pop En Español
Hydrate Nightclub

Tune Up Tuesdays
Charlie's Chicago

10:00PM

Tag Team Tuesdays
Charlie's Chicago

Wednesday, Oct 06 2021

7:00PM

Bitchy Bingo
Lips Chicago

Country Line Dance Lessons
Charlie's Chicago

7:30PM

Roscoe’s Dinner & Disney Musical Bingo
Roscoe's Tavern

9:00PM

Men's Room Wednesday
Sidetrack

Karaoke Wednesdays
Replay Lakeview

11:00PM

Sapphire's Secret Shadows
Charlie's Chicago

Thursday, Oct 07 2021

7:00PM

The Divas hosted by Ruff N' Stuff
Lips Chicago

RuPaul’s Drag Race UK Viewing Party
Roscoe's Tavern

Chicago's RuPaul's Drag Race UK Viewing Party
Sidetrack

9:00PM

Boys and 90s Beats
Lucky Horseshoe Lounge

Thirsty Thursday Karaoke
Meeting House Tavern

9:30PM

Bubble Pop
Hydrate Nightclub

10:00PM

Frat Night with DJ Kirk
Scarlet Bar

Friday, Oct 08 2021

3:00PM

TGIF Show Tunes
Sidetrack

Milwaukee Pride: PridetoberFest
Henry W. Maier Festival Park, Milwaukee

6:30PM

Glitz and Glam Fridays
Lips Chicago

7:30PM

The Golden Girls: The Lost Episodes, Vol. 5- SEX! A Handbag Parody
Leather Archives & Museum

8:00PM

Flannel Friday
The Bird Cage

8:30PM

No Skips: 'Come on Over' by Shania Twain

9:00PM

GRRR at The Sofo Tap

FACES: A Drag Show by the Couleé Sisters
Hydrate Nightclub

10:00PM

ROSABEL - Ralphi Rosario's Chicago LGBT Hall of Fame Induction *Extended Set*
Le Nocturne Chicago

Fierce Fridays
Charlie's Chicago

11:00PM

Social House ft. DJ Ron Carroll
Hydrate Nightclub

Saturday, Oct 09 2021

10:00AM

Boozy Brunch
D.S. Tequila Co.

11:00AM

Divalicious Drag Brunch (Saturday)
Kit Kat Lounge & Supper Club

12:00PM

Milwaukee Pride: PridetoberFest
Henry W. Maier Festival Park, Milwaukee

Doggy Days
The Sofo Tap

1:00PM

Dog Day Saturday Afternoon
Sidetrack

7:00PM

Country Line Dance Lessons
Charlie's Chicago

CODE Night October
Cell Block

7:30PM

The Golden Girls: The Lost Episodes, Vol. 5- SEX! A Handbag Parody
Leather Archives & Museum

8:00PM

Power Hour: Throwback 2007 followed by DJ Cashera
Scarlet Bar

Draglicious Saturday Night Drag Review
Hydrate Nightclub

10:00PM

DJ Brryce Fersher at Scarlet
Scarlet Bar

Saturday Night Main Event
Charlie's Chicago

11:00PM

Deanne at Hydrate
Hydrate Nightclub