DOWNTOWN — Ideal weather and amazing performers continued to draw massive crowds as Lollapalooza capped off a successful weekend Sunday.
On the north end of Grant Park, rap legend A$AP Rocky had the crowd moshing as he opened inside a model helicopter dangling above the Bud Light stage. It was his first Lolla performance in exactly ten years, on the same stage.
The Harlem rapper’s fans couldn’t contain themselves as he performed with pyrotechnics and custom changes. At least a dozen young fans were seen wheeled or escorted out by security amid safety concerns, and screens shown a warning to fans to take three steps back from the stage prior to the show.
Rocky tore down the catwalk as he rapped his hits “Praise the Lord (Da Shine)” and “Riot (Rowdy Pipe’n).”
On the south end of the park, Sabrina Carpenter performed for a massive crowd from the T-Mobile stage — and brought out Chicago band Earth, Wind & Fire for renditions of “Let’s Groove” and “September.”
Back in 2023, Carpenter was performing on the Lakeshore stage nearby, she told the crowd as she pointed to it. She credited her fans for her ability to headline on a main stage this year.
Channeling her retro aesthetic, the pop sensation performed hits from her last two albums and “Manchild,” the single for her upcoming project “Man’s Best Friend” dropping Aug. 29.
The crowd went wild for songs like “Taste,” “Feather,” “Bed Chem,” “Please Please Please” and “Because I Liked a Boy.”
“Chicago, the first time I played here was for a room of 300 people,” Carpenter told the crowd. “When I wrote that last song, I could hardly picture anyone singing it, let alone so f—ing many of you, wow.”
And while Carpenter’s voice stands on its own, her performance was a full-blown theatrical production, complete with an elaborate stage set, masterful choreography, video skits, costume changes, props and fireworks.
Ahead of her song “Juno,” Carpenter “arrested” K-pop girl group and fellow Lolla headliners TWICE with fuzzy pink handcuffs for “being too hot” — a shtick she’s performed throughout her latest tour.
From the moments the gates opened Sunday at 11 a.m., it was clear Carpenter would be one of Lolla’s biggest acts as countless festgoers donned pastels, baby doll dresses, corsets, lace and Sabrina merch in her honor.
Although the crowds were packed as usual, especially as sets progressed over the weekend, veteran attendees didn’t notice anything out of the ordinary, just the usual Lolla massive gatherings as the fest stretched into its fourth and final day.
Rebecca Black’s Resurgence
Just an hour before headlining shows began, early 2010s YouTuber-turned-queer-icon Rebecca Black tore up the stage alongside two dancers dressed as missionaries in short plaid skirts. She performed a DJ set at the Perry’s stage as well on Sunday.
In her penultimate song Sunday night, she teased the crowd with an EDM rendition of her infamous 2011 hit “Friday.”
She reminisced on her memories at Lollapalooza, including a performance on the BMI stage years ago and being in the crowd in 2014 to see The 1975 and Childish Gambino.
“Ever since that night, I’ve been so excited to return to this city.”
“This is my heart, this is where I love to be, I’m so grateful for you all being here,” Black said. “And if there’s one thing that I know about most of you by now that I’ve been to the city a few times,”
“We’re all gay,” she said to raucous cheers.
And as The Marías performed “Back to Me” live on the Bud Light stage, friends Alex and Brit recorded an emotional rendition of themselves singing the song. Brit, overcome with emotion, soon crumpled to the ground and covered her face as María Zardoya sang the heartbreaking tune.
“I skipped [hearing] ‘Back to Me’ live because it reminds me of my least favorite person on this world, and I knew if I listened to it when it came out I would have contacted him again,” Brit said. “So I’m now at a state where I did not feel like reaching out to him and I could process the lyrics for the first time live, insane. I came here from California to do it.”
“It’s so freeing,” she said.
Local Art And Artists Take Stage
Up as one of the first performances of the day, rapper and Chicago native Kaicrewsade — born Makhi Miller — kicked off the final day of Lolla at noon on The Grove stage.
Dozens of fans gathered into a mighty audience that cheered him through each song.
It was his first time performing at the mega fest, he told the crowd.
Accompanied by a background singer, sax player and trumpeters, Kaicrewsade was a natural performer, delivering jazzy rap while directing the crowd to chant, two-step and wave their arms through his performance.
“I’m from this beautiful city right here,” he told the crowd at the beginning of his set.
Despite technical difficulties during his song “Preroll,” he carried on without hesitation.
“I’m sorry to my weed smokers,” he said before continuing to the next song.
The crowd got bigger as his set went on, and he wrapped it up with a performance of “Fukizutahmbout!”
And a couple hours later on the Tito’s stage, Chicago indie psych rock band Post Animal played for their hometown. They were added to the schedule this weekend as a last minute replacement for Wunderhouse, but they made the stage their own.
“Thanks for coming out early,” the band said on stage. “Hometown sh—.”
The band consists of Dalton Allison, Jake Hirshland, Javier Reyes, Wesley Toledo, Matt Williams and “Stranger Things” star Joe Keery, who played his own Lolla set on the T-Mobile stage as Djo on Friday.
As the band celebrates their latest album “Iron” — the band’s first project with Keery since 2017, the Sun-Times reports — they performed some of its biggest hits, including “Setting Sun,” “Last Goodbye” and “Pie in the Sky.”
“Anybody know that we put out a new album?” bassist Dalton Allison asked the crowd, which was met with loud roars of confirmation.
Over by the Buckingham Fountain, American Apparel did a clothing popup with Pilsen artist Sentrock. The self taught street artist — Joseph Anthony Perez — created designs for festgoers to have custom placed on a variety of shirts.
It wasn’t Perez’s first time at Lollapalooza for art’s sake, and his goal for this design was “to capture the essence of the city with Lollapalooza coming into town,” he said.
That design garnered a large line of festgoers snaking through and past a good part of the nearby plaza, competing in length with the general merch tent. He was “honored” to see such an extensive queue.
Sentrock’s creations for the collaboration feature vibrant designs including his iconic bird mask and an homage to Lolla and the city.
“it’s more of like … the essence of it, with the colors, the energy,” Perez said. “You look at the symbolism in there with the cars, and you look at the buildings in the background, the dice — just like elements of having fun enjoying you know, summertime in Chicago.”
“I want people to take away the energy of having fun,” he said. “It has a lot of inspiration from the community.”
A Wide Variety Of Fest Food
The midway section of the fest would get extremely crowded after 5 p.m. (aka dinnertime), as hundreds of hungry concertgoers swarmed the previously manageable food lines for local favorites like Lou Malnati’s, Kamehachi, Wow Bao and Joey G’s Mac and Cheese (there were was no shortage of options for lovers of pizza and cheese fries).
The fest’s vegan food court Plant Base, now in its second year, offered delicious alternatives in a less-crowded space, with plant-based versions of empanadas, gyros and orange chicken offered by restaurants like Soul Veg City and Lit Vegan Chicago. There was also a stand by local vegan ice cream window Vaca’s Creamery.
This year’s Vibe Village — which featured the new and popular Gangnam Market with grab-and-go Asian snacks — was also popular. Other food options in the area included Matcha City, Kong Dog, JoJo’s Shaker, Pink Mu, Taiyaki, Deep Purpl and more.
For beauty lovers, Ulta Beauty and Glam Suite pop-ups, a Lunairi Charm Bar, a hat bar and other activations were popular with attendees ready to add even more glitter and highlights to their already sparkly ensembles.
But for most, the music stages were the main draw, until the weary crowd swarmed the streets outside the gates late Sunday to head for home, bringing another four fabulous days of Lollapalooza to a close.
See more photos from day four:
Listen to the Block Club Chicago podcast:
