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Click here for photos from day one and two of Lollapalooza 2025.
Milwaukee might be just 90 miles north of Chicago, but it is a whole different world when it comes to music festivals. We have Summerfest, the “Big Gig”, right on our lakefront. Chicago has Lollapalooza, a four day party in the middle of Grant Park that pulls in some of the biggest names in music. Every summer we make the short drive down I-94 to see if our southern neighbors can hold their own against the energy we bring to our own festival grounds.
The first two days of Lolla brought some memorable sets and surprises, but the second half of the weekend turned the excitement up even higher. Saturday and Sunday delivered everything from massive headliners to unexpected cameos to rising stars playing their biggest stages yet. For every moment that had the crowd dancing, there was another that left jaws on the ground.
From dramatic entrances to rowdy mosh pits to the kind of surprises that only happen when tens of thousands of fans are locked in for hours, the last two days of Lollapalooza 2025 were packed with unforgettable highlights.
Here are some of our favorite shots and moments from the second half of Chicago’s biggest music weekend.
Charlotte Lawrence
The rising pop singer brought a cool and easygoing vibe to her Saturday set, proving she is ready for bigger festival slots in the near future.
Young Miko
Puerto Rican trap star Young Miko kept the energy high with her confident stage presence and rapid fire delivery, making sure Saturday’s crowd did not get too comfortable.
Naomi Scott
The actress turned singer dazzled with a set that showcased her powerful vocals and reminded everyone she is just as much a force in music as she is on screen.
Chance The Rapper
In one of the weekend’s most unexpected moments, Chance popped up on the Perry’s Stage for a 15 minute set, teasing his upcoming album and sending the crowd into a frenzy.
Clairo
Dreamy indie pop and a perfect golden hour slot made Clairo’s set one of Saturday’s most picture perfect performances.
JPEGMAFIA
The ever unpredictable JPEGMAFIA brought a massive and engaged crowd and had them hanging on every beat, lyric, and chaotic moment.
Twice
K-pop royalty lit up Lolla with a high energy performance that had fans singing, screaming, and waving light sticks from start to finish.
A$AP Rocky
His set started late and ended abruptly at 10:01 but the dramatic entrance, descending on a giant helicopter prop, made every second worth it.
Ian
Things got so rowdy during Ian’s set that security had to pause the show until the crowd stepped back. This was easily one of the most intense mosh pits of the weekend.
Mariah The Scientist
Already a crowd favorite, Mariah stunned fans when she brought out Young Thug for “Walked In,” making for one of Sunday’s biggest surprise cameos.
Katseye
Formed on the Netflix reality competition series Dream Academy, Katseye may have just played their most important show yet ahead of their first headlining tour.
Rebecca Black (DJ Set)
Rebecca Black proved she could command a festival stage as a DJ, keeping Perry’s Stage moving with seamless transitions and crowd favorites.
The Marías
Smooth, stylish, and effortlessly cool, The Marías treated fans to favorites like “Paranoia” and “No One Noticed.”
Remi Wolf
The queen of quirky funk pop got the crowd dancing with “Photo ID” and “Disco Man” and even pulled off a playful cover of Tom Cochrane’s “Life Is a Highway.”
Dominic Fike
Returning to Lolla with a much larger audience than his last visit, Fike delivered a confident and polished set that felt like a victory lap.
Rebecca Black
Later in the night she surprised again with one of the most unexpectedly fun and energetic sets of the weekend.
Isaiah Rashad
Making use of headliner Sabrina Carpenter’s catwalk, Rashad brought his set right to the fans in the front rows.
BOYNEXTDOOR
Kicking off early on Sunday, the K-pop boy group still pulled a massive crowd at the Lakeshore Stage for an energetic afternoon performance.
