Rain, Mud And Big Firsts Mark Lollapalooza’s 3rd Day

DOWNTOWN — Despite torrential downpour Saturday morning, delaying the third day of Lollapalooza, fans made the most of the time lost, cut set times and muddy festival grounds.

Lollapalooza opened its doors at 3 p.m., a four-hour delay, due to continued rain showers across the city and flooding in Grant Park. Videos circulating on social media showed crews at the park pumping water out. By the time the gates opened, the grounds were no longer underwater, with woodchips laid out across the entire park.

The evening’s scheduled headliners — including Olivia Dean, DJ Trixie Mattel and Jennie — as well as Geese and local DJ Whethan were still on the schedule, but the Sunday (1994), Chezile, Wisp, the Chicago Youth Symphony Orchestra and several others were among the acts that got cut. 

The Chicago Youth Symphony Orchestra, which was set to headline the Tito’s Stage, was specifically cut due to concerns of the damage that continued rain could do to the instruments, according to a statement from Lollapalooza. 

Impromptu Wrestling Makes Use of the Mud

Despite the shortened lineup, festivalgoers still found a way to make the third day memorable, particularly members of Chicago’s sapphic community, who answered an Instagram call to gather for an impromptu call for “Lesbian Mud Wrestling.”

Lindsay Perrin, an Indianapolis resident who organized the event, said the idea started as a joke after she saw videos showing how muddy Grant Park had become. Perrin posted the invitation on Instagram, where the video quickly drew more than 120,000 views.

“I’m a lesbian, and I’m all about planning community events,” Perrin said. “We have the muddy field, and I thought people would love it.”

At first, some festivalgoers lingered around the edge of the makeshift wrestling ring, unsure whether anyone would participate. Then the crowd suddenly converged, and women began jumping into the mud. Perrin said she was surprised by how many people showed up and were willing to wrestle.

Kylie Terpening, a 24-year-old Lakeview resident, said three friends sent her Perrin’s Instagram post, convincing her she needed to attend. She initially planned to take photos but ultimately joined the match after encouragement from a friend. She joked to Block Club that this was a  “great excuse to leave early,” to take care of her dog.

“It was so fun, and I’m so happy we all did this,” Terpening said. “We were a little nervous at first, and then we really got into it.”

Terpening said she was proud of everyone willing to get dirty in front of the crowd.

Jenna Salter, who lives in West Town, also learned about the gathering on Instagram. She initially planned to watch from the sidelines but decided to participate after having a few drinks. 

“I love making queer community in Chicago,” Salter said. “Everyone’s so welcome here.”

As pairs of women joined the wrestling circle one by one. Perrin acted as a ring leader, starting each match with a countdown and refereeing the spectacle, making sure no one got hurt.

“I’m always chasing adventure, and so this was just awesome. I love to be the center of attention … I got what I wanted,” Perrin said with a huge smile on her face, covered in mud.

Big Firsts Onstage And In The Crowd

By the time 8 p.m. rolled around, large crowds converged on opposite ends of the festival for Saturday’s headliners, Olivia Dean and K-pop sensation Jennie.

Olivia Dean took the stage in a sparkling, mermaid-style gown, opening her headlining set with “Nice to Each Other” as a live band filled out the sound behind her.

The stage itself resembled a flower caught mid-bloom, giving Dean a dramatic backdrop as she moved between vocals and tambourine. At one point, she joked that the humidity was going to make her hair double in size.

Dean also reflected on how quickly her relationship with Chicago had grown. In 2024, she played an afternoon Lollapalooza set to a much smaller crowd. She later returned for a Chicago show in front of about 1,500 people, she said, making Saturday’s headlining slot especially meaningful.

Before “So Easy (To Fall In Love),” Dean encouraged the crowd to pretend everyone around them fancied them so they could feel sexy.

She also performed hits like “Lady Lady” and brought out artist Sam Fender to perform their song “Rein Me In”, marking the first time the song has been played live in the U.S., Dean said. Overall, the London artist delivered a polished set that matched the scale of her rise from afternoon performer to Lollapalooza headliner.

On the opposite end of Lollapalooza, Jennie launched her headlining set with a burst of fire as red curtains dropped to reveal her rising from the center of the stage, flames burning around her. She opened with “Filter,” wearing a feathered crown, a cropped military-style jacket and baggy jeans.

Jennie, who was making her festival debut, is the first female solo K-pop star to headline Lollapalooza. The festival has consistently featured K-pop headliners and acts since BTS mega star J-hope headlined the Chicago festival in 2022.

Heart-shaped light sticks glowed throughout the crowd, which spanned generations, from young girls to older fans, as people danced along to the choreography-heavy set.

The performance moved into an R&B breakdown packed with dancing before Jennie launched into “Pretty Girl Mantra.”

“We’re just getting started,” she told the crowd.

Jennie paused later in the set to introduce each of her dancers, giving them their own moment before turning back to the audience.

“To see you all in front of my eyes feels like a dream,” she said.

During “Start a War,” fans threw their hands into the air for the chorus. The set also included the song “Handlebars,” as Jennie continued mixing fun choreography with more intimate moments with the crowd. She also spent a portion of her set introducing new music with songs like “Sweet Tooth” and “Lock It Down.”

My Block, My Hood, My City Heads to Lolla

While the festival marked several firsts for its headliners, it also offered a milestone experience for 14 Chicago teens attending Lollapalooza for the first time through a partnership between My Block, My Hood, My City and Airbnb.

The outing was part of the nonprofit’s Explorers program, which introduces young people to new neighborhoods, careers and experiences. Airbnb provided Saturday VIP tickets through its partnership with the organization, which has grown over the years, said Jonathan Buckner, public policy manager for Airbnb.

Brianna Matthews, My Block, My Hood, My City’s manager of youth development, said the goal was to give the teens access to an event in their own city that might otherwise feel out of reach.

“We hope that not only is this a core memory for them, but we hope that they are inspired by this,” Matthews said.

For 18-year-old Ayden Mahaffey, the outing was his first Lollapalooza and his first music festival. The South Side teen was especially excited to see Olivia Dean after his sister introduced him to her music.

Mahaffey also dressed for the occasion, experimenting with a festival look that included baggy pants, a cropped jacket and a silver necklace with a photo of his grandmother in it.

“I didn’t know how people dressed or anything, since I’m new to the experience,” he said. “I decided to try something different.”

Mahaffey said that many young people his age rarely get the chance to attend concerts or large events, while emphasizing the importance of the festival experience for him.

“Going out and seeing a new community of people is real cool to look at,” he said.

Tyrice Hunt, 18, also from the South Side, said he had wanted to attend Lollapalooza before but did not want to go alone. Joining the program gave him a chance to see Leon Thomas, spend time with friends and take a break from everyday pressures.

“I feel like Lollapalooza just takes it all away,” Hunt said. “It’s so many things to experience and see and do.”

Hunt said he also hoped the day would help him build stronger relationships with other teens in the program and make new connections as he works toward becoming an electrical engineer and starting businesses.

The group of teens headed to Buckingham Fountain to see the festival’s multiple activations before heading to the T-Mobile Stage to see Leon Thomas perform. The group danced, swaying side to side with their phone in the air, singing along to the song “Mutt.”

For Matthews, that kind of exposure is the point.

“When young people have access, they are inspired,” she said.

Lollapalooza concludes Sunday with headliners Tate McRae, The XX and The Chainsmokers. Check back here for dispatches and further festival updates.

See more photos from day three of Lollapalooza: