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Celebrate LGBTQ Pride at Chicago Pride Fest 2023

by | Jun 21, 2023

Chicago Pride Fest, June 17-18, 2023, was welcomed by thousands. The 22nd annual, all-ages event was a celebration of LGBTQ life, culture, and community. The sight of a 60,000+ person crowd so big that it stretched half-a-mile was an exciting and fun for many as they witnessed history being made once again.

Chicago Pride Fest banner hanging over the 2023 festival entrance.

The two-day street festival in the Northalsted neighborhood, from Addison to Grace St, features live music on three stages. The $20 suggested donation for entry helped pays performers and festival workers, and funds community programs. Generous public donations paid for the Chicago Pride Crosswalks; 14 rainbow paved intersections installed in 2019 that make up the longest installation of its kind in the world.

Massive crows attend the 2023 Chicago Pride Fest.

What is Chicago Pride Fest?

The Chicago Pride Fest is a weekend long live music street festival celebrating the community in Chicago’s landmark Northalsted/Lakeview district. The half-mile-long summer festival features all-day line-ups of live music on three different stages, 100+ vendors, food and drinks, DJs, dancing, and entertainment. An estimated 60,000 attended the event, from near and far, representing all colors of the rainbow.

A group of friends showing their Pride at Chicago Pride Fest 2023.

Chicago Pride Fest’s South Stage Saturday lineup showcases local favorites: Sixteen Candles, Too Much Molly, Hello Weekend, and more. Sunday programming by Peach Presents features BbyMutha, Cookiee Kawaii, The Vixen’s Black Girl Magic and others. Performance schedules below.

Two friends in colorful outfits at Chicago Pride Fest 2023.

Additional attractions include the Waveland DJ Stage, a Youth Pride Space for teens, Proud Pet Parade with Miss Foozie, Firebrand country western dance and Servin’ Fysh dance company, Chicago Gay Men’s Chorus, Rainbow Run, guest speakers, and over 150 merchandise and food vendors.

A vendor selling Pride flags and accessories at Chicago Pride Fest 2023.

The Youth Pride Space debuted last year and returns for both days of Chicago Pride Fest at Broadway and Waveland. The dedicated safe space for LGBTQ+ teens and teen allies (age 12-18). Programming includes speakers, entertainment, activities, dance area, food and beverages, and counseling resources. 

A drag performer walking through the crowd at Chicago Pride Fest 2023.

The event celebrated community to uplift each other in the struggle for equality and human rights…Outright attacks, especially on transgender and BIPOC members of our community, are ongoing. 

The event takes place the weekend before the 53rd annual Chicago Pride Parade (June 25th, organized independently).

A group of people watching a performance at Chicago Pride Fest 2023.

“We come together in June to celebrate community and uplift each other in the struggle for equality and human rights,” said Northalsted Vice-President and lead event organizer, Mark Liberson. “Despite decades of progress, the need for Pride has not lessened, as outright attacks, especially on transgender and BIPOC members of our community, are ongoing.”

Performers at Chicago Pride Fest 2023

There was a strong line-up of fabulous entertainers for Northalsted Market Days 2022, with both local, national, and international talent. From cabaret to comedy, drag to DJ, the variety of entertainment was eclectic and fun. 

Massive crowds making their way through Chicago Pride Fest 2023.

Here is a look at the headline acts that graced the stages:

Eureka O’Hara 

Eureka, known by various names such as Eureka O’Hara and Eureka!, is the stage persona of Eureka D. Huggard, an immensely talented American drag queen and a captivating figure in the realm of reality television. 

Eureka O'Hara performing on stage at Chicago Pride Fest 2023 in Chicago, Illinois.

During the ninth season of RuPaul’s drag race, fate dealt Eureka an unfortunate twist when a knee injury forced her to leave the competition prematurely. This made her the first contestant in the show’s history to be sent home due to an injury. 

Eureka O'Hara performing on stage at Chicago Pride Fest 2023 in Chicago, Illinois.

However, her remarkable talent and undeniable charisma caught the attention of the show’s producers, who granted her an automatic spot on the following season, the tenth. Eureka seized the opportunity with unwavering determination and went on to secure the position of runner-up in that highly competitive season.

Eureka O'Hara performing on the main stage at Chicago Pride Fest 2023.

Eureka slayed the stage for 30 mins and performed many of her best-known hits. She was accompanied by a quadruplet of back-up dancers. 

Eureka O'Hara performing on stage at Chicago Pride Fest 2023 in Chicago, Illinois.

Ultra Nate 

Ultra Naté Wyche, born on March 20, 1968, is an immensely talented American singer, songwriter, record producer, DJ, and promoter. Her contributions to the music industry have propelled her to success on the pop charts, earning her a prominent place among notable artists.

Ultra Nate performing on the main stage at Chicago Pride Fest 2023.

Ultra Naté’s discography boasts several chart-topping hits that have made a significant impact on the music scene. Her songs, such as “Free,” “If You Could Read My Mind” (as part of Stars on 54), and “Automatic,” have resonated with audiences and achieved remarkable success on the pop charts.

Ultra Nate performing on the main stage at Chicago Pride Fest 2023.

A distinguishing feature of Ultra Naté’s career is her remarkable consistency in dominating the US Hot Dance Club Play chart. Virtually all of her singles have soared into the Top 10 of this influential charts Notable tracks that have captured the hearts of fans and dominated dancefloors include “Show Me,” “Free,” “Desire,” “Get It Up (the Feeling),” “Love’s the Only Drug,” as well as her number-one hits, “Automatic,” “Give it All You Got” featuring Chris Willis, “Waiting On You,” and “Everybody Loves the Night.”

Ultra Nate performing on the main stage at Chicago Pride Fest 2023.

In recognition of her achievements and enduring impact, Billboard magazine honored Ultra Naté in December 2016, ranking her as the 12th most successful dance artist of all time. This prestigious accolade solidifies her status as a powerhouse in the dance music genre and acknowledges her profound influence on the music industry.

Ultra Nate performing on the main stage at Chicago Pride Fest 2023.

Heather Small

Heather Margarita Small, born on January 20, 1965, is an exceptional soul singer from the United Kingdom. She is widely recognized as the former lead vocalist of the renowned band M People, contributing her powerful vocals to their chart-topping hits. Following her time with the band, Heather embarked on a successful solo career, leaving an indelible mark on the music industry.

Heather’s journey began in Ladbroke Grove, West London, where she was born and raised in a council estate. As a teenager, her immense talent shone through, and she joined the group Hot House as their lead singer. During this time, Heather’s remarkable voice was featured as the studio singer on the re-recorded version of “Ride on Time” by Black Box, further showcasing her vocal prowess.

A crowd gathers to watch a live performance on the main stage at Chicago Pride Fest 2023.

A turning point in Heather’s career occurred when she serendipitously crossed paths with Manchester DJ Mike Pickering, formerly of Quando Quango. This encounter led to the formation of the iconic group M People. With Heather’s soulful vocals as the centerpiece, M People went on to achieve extraordinary success, selling over 10 million albums worldwide. Their distinctive sound resonated with audiences, and songs like “Moving On Up,” “One Night In Heaven,” and “Search for the Hero” became massive hits.


Slayyyter, also known as Catherine Grace Garner, is an American pop singer and songwriter originally from Kirkwood, Missouri, and currently based in Los Angeles. She made her entry into the music scene independently through SoundCloud, showcasing her distinctive style. Her single “Mine” achieved notable success, reaching number 38 on the iTunes pop chart. This track was featured on her self-titled debut mixtape, which was released in 2019. Slayyyter’s debut studio album, “Troubled Paradise,” arrived in June 2021 under the Fader label.

Known for her captivating pop sound, Slayyyter’s music has drawn comparisons to iconic artists like Britney Spears, Lindsay Lohan, and Paris Hilton. Her musical influences include an eclectic mix of artists such as Fergie, Timbaland, Nelly Furtado, Lady Gaga, Taylor Swift, Justin Timberlake, Madonna, Heidi Montag, Janet Jackson, and Whitney Houston. These artists played a significant role in shaping her own unique style and musical direction.

A crowd gathers to watch a live performance on the main stage at Chicago Pride Fest 2023.

In addition to her musical talent, Slayyyter’s visual style is often described as “distinct MySpace-era,” and she frequently collaborates with the artist Glitchmood for single artworks.

With her infectious energy and creative approach, Slayyyter continues to make waves in the industry, amassing a growing fanbase. Her debut album, along with her successful mixtape and charting single, solidifies her position as a rising star in pop music. 

As she forges ahead, Slayyyter’s artistry promises to leave a lasting impact on the ever-evolving pop music landscape.

Other notable performers included Jordy, Meet Me @ The Alter, Nick Osin, Sixteen Candles, Sasha Love, and Chomper. 

A DJ spins on stage for the crowds at Chicago Pride Fest 2023.

Community Involvement

Community involvement is a very important part of the Chicago Pride Fest experience. People came out to have fun, see their friends and family, and to support local businesses. While there were plenty of vendors for Chicago Pride Fest, many Northalsted businesses offered special promotions, hosted events, and brought in additional talent for the weekend. 

A male go-go dancer performs at a local restaurant during drag brunch at Chicago Pride Fest 2023.

Virgin Hotel Chicago, the host hotel for Chicago Pride Fest, offered special accommodation packages and proceeds from specific beverages at their participating restaurants were donated to The Center on Halstead as part of the Virgin Hotel Gives Back program. 

The Virgin Hotel Chicago with a Pride flag hanging out front.

Many people come to Chicago Pride Fest, not just for the amazing street party and music festival, but also to attend other events that took place each night and into the early hours of the morning. 

Go go dancers on a bar top in a local gay bar during Chicago Pride Fest 2023.

 History of Chicago Pride Fest  

The Chicago Pride Festival had humble beginnings, rooted in a pivotal moment of resistance. It all started on a fateful night, June 28, 1969, when a small bar in New York’s Greenwich Village, the Stonewall Inn, became the site of a transformative event. 

At that time, it was customary for a few police officers to enter LGBTQ+ bars, subjecting patrons to degrading treatment and arrests. However, on this night, the patrons refused to comply with the usual harassment. 

A crowd gathered outside the Stonewall Inn, and the drag queens and others who had endured such mistreatment fought back, unwilling to accept the status quo any longer.

The following day, thousands took to the streets surrounding the bar, signaling a powerful message that LGBTQ+ individuals would no longer tolerate being treated as second-class citizens. 

A group of friends enjoying the sun and fun times at Chicago Pride Fest 2023.

Stonewall Uprisings That Led to Chicago Pride Fest

This uprising, known as the Stonewall Riots, left a considerable mark on New York City, becoming a catalyst for change far beyond its immediate vicinity. One year later, LGBTQ+ activists in Chicago and Los Angeles marched in commemoration of the Stonewall uprising, asserting their demand for equal treatment and rights.

This historic event gave birth to a tradition that has been celebrated annually in Chicago on the last weekend of June ever since. While the nature of the celebration has evolved over the years, the essence of Pride remains unchanged. 

The early Pride parades in Chicago were not merely processions; they served as defiant political statements, boldly asserting the rights and visibility of the LGBTQ+ community. The number of participants and spectators has grown exponentially, from a few hundred to hundreds of thousands, reflecting the widespread support for the cause.

A group of friends wearing colorful outfits at Chicago Pride Fest 2023.

Pride has become a multifaceted expression of LGBTQ+ political, cultural, and social identity, declaring that every individual within the community deserves full equality and respect. The accomplishments of early LGBTQ+ activists and their tireless efforts to dismantle discrimination have paved the way for significant progress, but the journey towards true equality is ongoing.

Chicago Pride Fest is Monumental For The Gay Community

Beyond the main festivities, the celebration extends throughout the entire month of June in Chicago. Pride-related events such as concerts, readings, films, and plays abound, providing a rich tapestry of diverse activities that honor and commemorate the LGBTQ+ community. One can immerse themselves in the spirit of Pride every day, participating in various events and engaging with the vibrant community.

A large group wearing puppy hoods, dog masks, and other fetish gear at Chicago Pride Fest 2023.

As we approach Chicago’s annual Pride Parade, it is a time to join in the collective celebration and remembrance. Let us not forget the words of Sylvia Rivera, a courageous transgender activist who stood up to the police that first night at the Stonewall Inn. She proclaimed, “I’m not missing a minute of this. It’s the revolution.” 

A lady wearing a jewelled cap at Chicago Pride Fest 2023.

Even today, Pride remains a testament to the ongoing revolution for LGBTQ+ rights, a testament to the progress achieved, and a call to continue the work that lies ahead.

Chicago Pride Fest 2024 

Chicago Pride Fest is one of the best weekends of the gay agenda in Chicago during the summer months, attracting people from across North America. The variety of entertainment and atmosphere of the event is fantastic. 

A group of friends enjoying the sun and fun times at Chicago Pride Fest 2023.

In addition to a massive outdoor gay music festival, you can enjoy one of the oldest gay villages in North America, attend parties, and visit the must-do attractions in Chicago, like The Bean, a river architecture cruise, and get deep dish pizza. If you haven’t been, haven’t been in a while, or are a regular attendee, it’s time to put Chicago Pride Fest on your calendar for 2024.

A dancer performing on stage at Chicago Pride Fest 2023.

Choose Chicago as Your LGBTQ Travel Destination

Chicago has a way of making everyone feel welcome. The LGBTQ+ communities, friendly residents, diverse nightlife, and year-long Pride celebrations make Chicago one of the most inclusive cities in the country. Come explore the historic landmarks, welcoming neighbourhoods and thriving nightlife scene. 

An excited crowd cheers during a performance on the main stage at Chicago Pride Fest 2023.

Pride is in Chicago’s DNA and they are excited to welcome you. Visit Chicago and discover why Condé Nast Traveler readers voted Chicago the Best Big City in the U.S. for a historic sixth year in a row!

Two friends posing in front of the iconic silver bean in Millennium Park, Chicago.

For more information, visit www.choosechicago.com and follow @choosechicago on Facebook, Instagram and Twitter. #ChicaGOandKNOW

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Brian Webb

Brian Webb


Brian Webb is the founder and editor-in-chief of HomoCulture, a celebrated content creator, and winner of the prestigious Mr. Gay Canada – People’s Choice award.An avid traveler, Brian attends Pride events, festivals, street fairs, and LGBTQ friendly destinations through the HomoCulture Tour. He has developed a passion for discovering and sharing authentic lived experiences, educating about the LGBTQ community, and using both his photography and storytelling to produce inspiring content.Originally from the beautiful Okanagan Valley in the southern interior of British Columbia, Brian now lives in Vancouver, British Columbia. His personal interests include travel, photography, physical fitness, mixology, drag shows.

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