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It is that time of year again when Milwaukee and Chicago’s friendly rivalry spills down I-94 and onto the festival grounds at Grant Park. Just 90 miles south, our neighbors put on one of the biggest music festivals in the country. While we are still partial to the lakefront stages of Summerfest, Lollapalooza has once again proved why it draws fans from all over the world.
The first two days of the festival brought a mix of high energy rock, massive pop moments, country music history and genre bending performances that made for an unforgettable start to the weekend. Thousands of music lovers flooded the Windy City’s downtown for a lineup that felt like a who’s who of the modern music scene. We braved the summer heat, massive crowds and even a few questionable sports jerseys to capture some of the best moments.
From chart-topping headliners to rising stars making their mark, here are our favorite photos from the first half of Lollapalooza 2025.
Cage The Elephant
High energy does not even begin to cover it. From soaring jumps into the air to climbing down into the pit and wading through the crowd, Cage The Elephant made Thursday feel like a nonstop adrenaline rush.
Role Model
Pulling one of the biggest crowds of the entire festival, Role Model joked about speeding through his set so fans could rush over to see Gracie Abrams, grinning as he said, “I am not stupid.” His star power was impossible to ignore. Bo Staloch The young up and comer filled the BMI Stage with an impressive crowd, proving he is one of those acts you will be glad you saw before he hits the main stages.
Matt Champion
The former Brockhampton member showed he is more than just part of the now defunct group. His solo work had fans hooked from the first track to the last.
Luke Combs
History was made as Luke Combs became the first country headliner in the history of Lollapalooza. Fans from across the Midwest packed the park to see him prove that country belongs on the big festival stage.
Gigi Perez
Fresh off her Summerfest appearance opening for Hozier at the American Family Insurance Amphitheater, Gigi Perez brought soulful vocals and sharp stage presence to Grant Park.
Olivia Rodrigo
Friday night’s headliner turned the park into one massive singalong. The energy was as electric as her stop at Milwaukee’s Fiserv Forum just last year. Complete with a surprise appearance from Weezer, this wasn’t a set to miss.
Djo
Back in Chicago, Djo, or as some may know him, Joe Keery from Netflix’s “Stranger Things,” brought a massive replica of Cloud Gate (“The Bean”) for his backdrop and had the crowd cheering from start to finish.
Bleachers
With Jack Antonoff leading the charge, Swifties mixed in with Korn fans who were ready for the stage’s headlining set; in one of the most unique and oddly perfect crowd combinations of the weekend.
Amaarae
With her colorful style and genre blending sound, Amaarae delivered an energetic set that had her audience completely engaged.
Ravyn Lanae
Dressed in a stunning red gown, Ravyn Lanae delivered a performance that was every bit as elegant as it was captivating.
The Dare
The Dare kept the party going with his infectious dance ready sound. Fans also loved seeing him the day prior as Role Model’s “Sally” for his performance of “Sally, When the Wine Runs Out”.
Sierra Ferrell
Sierra Ferrell brought her signature Americana charm to Lollapalooza and even pulled out a train whistle during her performance, adding a playful twist that had the crowd grinning.
T-Pain
Fresh from his Wiscansin Fest in Milwaukee just a month ago, T-Pain brought his unmatched charisma and kept the crowd moving from beginning to end.
Wallows
Even with Dylan Minnette wearing a Cubs shirt, Wallows won us and the crowd over with their bright indie rock sound and undeniable energy.
