Photos by Dan Garcia
by Jay Cuzman
Lollapalooza 2025 reminded the world why it’s one of the crown jewels of the global festival circuit.
For four days, Chicago’s Grant Park was a melting pot of music, drawing hundreds of thousands of fans from around the world for a lineup that spanned rap, pop, country, R&B, K-pop, and everything in between. The energy was relentless, the surprise moments were plentiful, and the scope of performances felt like a flex, solid proof that Lolla can still set the standard for summer festivals.
Whether it was A$AP Rocky’s grand helicopter entrance or a surprise set from Chicago’s own, Chance The Rapper, every day delivered its own historic moments. Lollapalooza 2025 wasn’t just a festival, it was a four-day pop culture event that will be talked about for the rest of the summer and beyond.
A$AP Rocky Descends from the Skies
Closing out Sunday opposite Sabrina Carpenter, A$AP Rocky turned his entrance into an action movie, literally descending onto the stage from a massive prop helicopter. Even with a 15-minute delay, the crowd’s anticipation exploded when the bass hit. His set further cemented him as one of hip-hop’s most dynamic performers.
Chance the Rapper Surprises Fans
On Saturday, Chance the Rapper pulled one of the weekend’s most talked-about moves with a surprise 15-minute set at Perry’s Stage, using the moment to hype his upcoming album Star Line. Fans who stumbled upon it walked away with a story to tell, while die-hard Chano followers reveled in a classic hometown moment.
JPEGMAFIA Delivers a Weekend Highlight
It’s not easy to stand out in a lineup this stacked, but JPEGMAFIA’s chaotic, crowd-engaging performance was one of the most unforgettable sets of the weekend. From high-energy performances of some of his best tracks to his razor-sharp delivery, his set was pure catharsis for a crowd that never stopped moving.
Ian Turns Viral Freestyle into a Live Frenzy
One of the wildest scenes came courtesy of Ian, who performed a live version of his viral XXL Freshman Freestyle for the first time. The crowd got so wild that security had to briefly cut his mic and halt the show until fans stepped back. When the music resumed, the energy somehow went even higher.
Mariah the Scientist Brings Out Young Thug
Mariah the Scientist treated her fans to a special surprise, a guest appearance from her boyfriend, Young Thug. The moment sent a ripple of excitement through the crowd, blending her smooth, soulful delivery with Thug’s raw energy.
Twice Turns Saturday into a K-Pop Spectacle
Saturday night belonged to the K-pop group Twice, whose headlining set was a visual and sonic overload in the best way possible. With precision choreography, vibrant visuals, and fan chants echoing across Grant Park, the group’s presence proved Lolla’s global reach.
T-Pain Turns Nostalgia into a Dance Party
T-Pain brought his arsenal of hits, “Buy U a Drank,” “Bartender,” “All I Do Is Win” and the rest of his massive features, all against a custom Super Nintendo-inspired backdrop. It was a reminder that few can turn a festival set into a wall-to-wall singalong like T-Pain.
Olivia Rodrigo Brings In a Sea of Fans
By the time Olivia Rodrigo took the stage Friday night, Grant Park was a sea of people as far as the eye could see. Some called it the largest Lollapalooza crowd ever, and based on the wall of fans singing along to every word, it’s hard to argue. From “good 4 u” to “vampire,” Rodrigo commanded the moment with an emotional but confident performance that showed just how quickly she’s grown into one of pop’s biggest stars.
Luke Combs Makes Country History at Lolla
Thursday brought a first for the festival: a country music headliner. Luke Combs embraced the milestone with his trademark authenticity, delivering a set that blended chart-toppers like “Beer Never Broke My Heart” with heartfelt ballads. While Tyler, the Creator was pulling a massive crowd on the other side of the park, Combs proved country also has a place in Lolla history books.
Dominic Fike’s Bigger, Better Return
Returning to Lolla with an even bigger crowd than before, Dominic Fike radiated ease and cool as he breezed through songs like “Babydoll” and “Mama’s Boy.” It was the kind of set that felt tailor-made for a golden-hour summer evening.
Ravyn Lenae Shines for the Hometown
Chicago native Ravyn Lenae delivered a silky, vibrant set that showcased her vocal control and artistry. Fans vibed with every note, making it one of the weekend’s most soulful moments.
Amaarae Brings Global Grooves to Grant Park
Amaarae’s set was a colorful, genre-bending journey that pulled from R&B, Afropop, and alt-pop. Her vibrant stage presence and airy yet commanding vocals kept fans swaying from start to finish, proving she’s one of the most refreshing voices in the festival circuit right now.
Isaiah Rashad Connects with TDE Loyalists and New Fans Alike
On Sunday, Isaiah Rashad stepped into the spotlight with a set that felt personal yet expansive. TDE die-hards rapped every word, while Sabrina Carpenter fans who showed up early found themselves vibing to Rashad’s smooth flow and soulful beats. His performance balanced introspection with bounce, making it one of the sleeper highlights of the weekend.
Matt Champion Marks a New Era
Former Brockhampton member Matt Champion proved his artistry stands on its own with a solo set that felt like a fresh chapter. Mixing sleek production with a laid-back delivery,
Champion’s set had moments that hinted at Brockhampton’s high-energy past, but it was clear he’s carving his own lane now.
Montell Fish Brings Intimacy to a Massive Stage
In a festival full of big production and bombastic moments, Montell Fish’s performance stood out for its quiet power, blending gospel influences and raw emotion.