Lollapalooza 2025: Day Three Highlights

Clairo - Bobby Talamine (c) 2025

Chance the Rapper - Bobby Talamine (c) 2025

Photography by Bobby Talamine
Writing and Editing by Fiza Javid

Grant Park - Chicago, IL
Saturday - August 2, 2025

What a wild ride it has been entering day THREE of Lollapalooza 2025. We were reeling from the joy of Olivia Rodrigo and Korn and preparing for the surprises in store for the day.

Holy crap – Winnetka Bowling League, Kickflip, Daniel Allan, LAYZ, Flux Pavilion, Clairo, Chicago Youth Symphony, and freakin' Damiano David.

As the sun hit peak scorch, LAYZ and Flux Pavilion tag-teamed with thunderous sets, proving that bass isn't just something you hear — it’s something you survive. Daniel Allan spun a more emotional set, perfect for that golden hour introspection we didn’t know we needed.

Clairo came in like a breeze — soft, wistful, and somehow commanding. Her live version of “Amoeba” felt like a collective exhale from a crowd that had just been through several sonic rollercoasters.
And then there was the Chicago Youth Symphony — a surprise and deeply moving interlude in the middle of the madness. Hearing strings fill the air over Grant Park felt like a reset. A reminder of the talent this city cultivates and the versatility this festival offers.

And just when we thought the day had peaked...
Out came Chance the Rapper. The energy erupted. Nobody saw it coming, and yet it made perfect sense — his city, his people, his legacy. He performed a medley of classics from Acid Rap and Coloring Book, and brought out Jamila Woods for a quick but electric duet. It was the kind of hometown lovefest that reminds you why live music still matters.

Earlier in the day, nestled between the explosive sets and bass drops, the Chicago Youth Symphony Orchestra took the stage — and what a stunning pivot it was. It wasn’t just a performance, it was a moment. In a weekend built on hype and chaos, their presence brought a calm, reverent energy to Grant Park that rippled through the crowd like a hush in a cathedral.

The violins soared, the timpani thundered, and for a second, Lollapalooza became a cinematic dreamscape. You could see festival-goers who had clearly stumbled onto their set by accident slowly stop, listen, and stay. Phones went down. Eyes widened. People laid in the grass, completely still, taking it in.

But the best part? Watching these insanely talented young musicians — many of them from right here in Chicago — hold their own on a stage usually reserved for global headliners. It was a beautiful reminder that music festivals can be about more than hype. They can be about heart, artistry, and investing in the next generation.
And speaking of heart…

Winnetka Bowling League brought theirs in spades.

The day wasted no time in delivering energy. Winnetka Bowling League opened their set with “CVS,” and it felt like a perfectly sarcastic love letter to the mundane, sung from the middle of a mosh pit. Kickflip followed with a set that was equal parts chaotic and cathartic — it’s always a good sign when the crowd knows every word to a song that dropped two months ago.

You could feel the shift the second they walked out. There’s something deeply charming about their stage presence — no posturing, no gimmicks — just pure, clever indie pop played with sincerity and a little smirk. They kicked things off with “On the 5”, which instantly turned the crowd into a chorus. It was like hanging out in a coming-of-age movie — one of those late-summer scenes where everything feels nostalgic while it’s still happening.

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Chance the Rapper - Bobby Talamine (c) 2025

Clairo - Bobby Talamine (c) 2025

Winnetka Bowling League - Bobby Talamine (c) 2025

Chicago Youth Symphony - Bobby Talamine (c) 2025

Flux Pavillion - Bobby Talamine (c) 2025

LAYZ - Bobby Talamine (c) 2025

Kickflip - Bobby Talamine (c) 2025

By the time Damiano David took the stage, the sun had dipped just enough to cast a cinematic glow over Grant Park. And then he arrived — shirtless, draped in glitter, leather pants clinging to his every movement, exuding that signature mix of Italian swagger and unapologetic glam rock chaos.
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This wasn’t Damiano from Måneskin — this was Damiano unleashed. His solo debut at Lolla was a masterclass in reinvention. With his new material, he’s leaning fully into his theatrical instincts, balancing dark, sultry ballads with explosive punk-fueled anthems that had the crowd gripping the barricades.

The band behind him? Tight. Loud. Dangerous. At one point, he pulled a fan on stage, danced with them, and kissed their hand like a gothic prince in a fever dream. The crowd was all his — hypnotized, screaming, filming, living.

What made it electric wasn’t just the performance — it was how much he owned the moment. Lolla has seen its fair share of solo breakouts, but this felt different. This felt like the birth of something bigger.
Damiano David didn’t just close out the day — he scorched it into our memory.

Lolla Day 3 was a fever dream — one that kept peaking, kept surprising, and somehow still left us wanting more.

See you tomorrow for the final chapter!  Fiza Javid - JBTV Music Television

Lollapalooza 2025, Grant Park, Chicago, Illinois, Bobby Talamine, Rüfus Du Sol, Twice, Jerry Bryant, Perry Farrell, JBTV Music Television, Bobby Talamine, Fiza Javid