Chicago Pride Fest is back for the first time since 2019; full entertainment schedule just released

Mon. September 20, 2021 10:54 AM by News Staff

vincint headlines chicago pride fest on october 1

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First look at Chicago Pride Fest entertainment schedule

After a year away due to COVID-19 constraints, an in-person Chicago Pride Fest returns to the Northalsted neighborhood, commonly referred to as 'Boystown', on October 1 - 3.

Festival organizers recently announced the addition of Sunday, October 3, following the cancellation of the 2021 Chicago Pride Parade. With the added day comes even more live music and entertainment. 

The complete schedule for the three-day festival was released Monday with additional headliners Debbie Gibson, Jamila Woods, Katie Kadan, Nina Sky, and Mila Jam.

Mýa, Shangela, VINCINT, Crystal Waters, Kristine W, Brooke Eden, and St. Panther are among the previously announced acts.

Also included in the 2021 line-up are local favorites Black Girl Magic with The Vixen and other artists produced for Sunday by Peach Presents, Dancing Queen: ABBA Salute, Sixteen Candles, Boy Band Review with special guest Toxic feat. Garek, Rod Tuffcurls & the Bench Press, CATFIGHT, iPop, and Bev Rage & the Drinks.

COVID-19, which forced the cancellation of the 2020 event, is still playing a part.

Organizers said the same protocols in place for Northalsted Market Days in August will be repeated for the Pride festival, which includes the recommendation that attendees be fully vaccinated or wear a mask.

“We're grateful that vaccinations have enabled the return of events this year, allowing LGBTQ+ people and allies from all over the midwest and beyond a meaningful opportunity to celebrate life and community together,” said Northalsted Business Alliance Vice-President and festival organizer Mark Liberson.

The majority of bars and restaurants along N. Halsted St. continue to require proof of vaccination, or a recent negative test, for entry.

Free COVID testing and vaccinations from Northshore Clinical Labs will be available at both the north (Halsted and Addison) and south (Halsted and Grace) gates.

A $15 suggested donation helps pay performers, festival workers, and funds community programs in the north side neighborhood.

2021 Chicago Pride Fest Entertainment Schedule

Friday, October 1    

North Stage    

5:00 PM    DJ Laura B

6:00 PM    Pride Drag Show

7:00 PM    Kristine W

7:45 PM    Drag Show

8:45 PM    VINCINT

Waveland Stage

5:00 PM    DJ Zel

6:30 PM    VJ Bryan 

8:30 PM    Avi Sic

T-Mobile South Stage


7:45 PM    Spirit Brigade

8:15 PM    Rod Tuffcurls

Saturday,  October 2    

North Stage    

12:00 PM    DJ Laura B

1:00 PM    Pride Drag Show

2:30 PM    Shangela

3:15 PM    Katie Kadan

4:15 PM    Pride Drag Show

5:30 PM    Brooke Eden

6:30 PM    Pride Drag Show

8:00 PM    St. Panther

9:00 PM    Mýa

Waveland Stage

11:00 AM    DJ Vlad 

1:00 PM    Spencer Huff

2:30 PM    ArianaDJ 

4:00 PM    Ethan Cole 

5:30 PM    DJ Ca$h Era 

7:00 PM    Diox

8:30 PM    Miss DJ Meg 

T-Mobile South Stage

12:45 PM    Chicago Gay Mens Chorus

1:30 PM    Chicago Spirit Brigade

2:00 PM    iPop

4:30 PM    Boy Band Review w/special guest TOXIC ft. Garek

6:45 PM    Bev Rage & The Drinks

8:15 PM    Sixteen Candles

Sunday,  October 3    

North Stage    

12:00 PM    Miss Foozies Pet Parade Start

12:00 PM    DJ Laura B

1:00 PM    Pride Drag Show

2:30 PM    Debbie Gibson

3:15 PM    Pride Drag Show

4:30 PM    Dancing Queen

5:30 PM    Pride Drag Show

6:30 PM    Mila Jam

7:00 PM    Pride Drag Show

8:10 PM    Crystal Waters

9:00 PM    Nina Sky

Waveland Stage

12:00 PM    DJ Martin 

2:00 PM    Rae Chardonnay 

3:30 PM    Janky

5:00 PM    Jesus Montanez 

6:30 PM    DJ X-tasy 

8:00 PM    Apollo X

T-Mobile South Stage

12:30 PM    Chicago Pride Brigade

1:00 PM    Miss Foozies Pet Parade Awards

1:30 PM    Peach Presents Takeover w/Supes Base

3:00 PM    TBA

4:00 PM    Jamila Woods

4:45 PM    TBA

6:00 PM    Orisun

7:00 PM    Roy Kinsey & Friends

8:00 PM    Peach Presents Takeover w/Supes Base

8:45 PM    The Vixen Presents Black Girl Magic