The Best Moments So Far From Lollapalooza 2026

All eyes in the music world are on Chicago this weekend, as Grant Park plays host to another year of Lollapalooza. With the weather looking uncertain for the festival’s later days, thousands flocked to the Chicago Riverwalk on a sun-kissed Thursday afternoon (July 30) to kick off Lolla. 

Performances began around noon CT across nine different stages and wrapped up with Lorde making her return to the Lolla stage for the first time since 2017 with Chicago’s own John Summit co-headlining on opposite ends of the park. 

The rest of the day saw performances from Filipino boy band SB19, who made history as the first P-pop group to perform at Lolla, as well as Bella Kay, Blood Orange, Little Simz, Boys Noize, Audrey Hobert, Sombr, 5 Seconds of Summer and Wet Leg.

A jam-packed weekend remains on tap, with anticipated headlining sets from Charli xcx, who made a guest appearance during Lorde’s performance, as well as Olivia Dean, Tate McRae, The xx, Smashing Pumpkins and Jennie.

There was chatter on the festival grounds from fans speculating that A-listers Olivia Rodrigo, who was allegedly spotted at Chicago’s O’Hare Airport, and Ariana Grande could be popping up. Ari’s Eternal Sunshine Tour comes to Chi-Town on Aug. 3. 

Lollapalooza has remained one of the premier U.S. festivals by mixing a range of superstars with upstarts and legacy acts spanning different generations. 2025’s Lolla saw headlining performances from Olivia Rodrigo, Tyler, the Creator, Sabrina Carpenter, A$AP Rocky and Doechii.

Thanks to the good folks at Dunkin’, Billboard is on the ground for Lollapalooza 2026. Here are the best moments from the festival so far. (This list will be updated daily.)

Katy Perry’s “Teenage Dream” has quite the lore with 5 Seconds of Summer fans. The Australian pop-rock band covered the 2010 Billboard Hot 100 No. 1 hit during performances like Summertime Ball in 2014, and at a SiriusXM visit that same year, leading to the cover holding a special place in fans’ hearts. A decade later, 5SOS revived the rockified cover of the glitzy turbo-pop anthem, which supplied a heavy dose of nostalgia to festivalgoers.

Charli xcx and Lorde working it out on the remix never gets old. Charli popped out for the “Girl, So Confusing” remix during the later stages of Lorde’s headlining set, and the immediate screeches from fans of the pop stars’ heartwarming reunion further cement it as one of pop’s signature moments in the 2020s. This time around, Charli kept things fresh by appearing on the Jumbotron while sipping from the functioning school water fountain Lorde had on stage. Perhaps Lorde will return the favor, and they’ll run it back on Friday (July 31) with Charli headlining.

When John Summit was making DJ tutorial YouTube videos and quit his CPA job in 2019, who knew what was in store seven years later for him? Summit, a Chicago native, went from attending Lolla in general admission to a night one headliner. He delivered one of his most expansive sets to date, featuring dancers in cubicles, Pitbull hits reimagined as EDM tracks and an appearance from British singer Absolutely to perform their “DON’T BELIEVE IT” collaboration.

It was a successful Chicago debut for SB19, who became the first P-pop group to perform at Lollapalooza. The five-man boy band was extremely grateful for the opportunity, which drew support from Filipinos from across the globe who made sure they were in attendance for the historic set. SB19 playfully joked about how they were still adjusting to the American diet filled with bread and pasta. They ran through various tracks in Filipino and English, while previewing a cover of Francis M.’s “Mga Kababayan” anthem and their newest track “Lawless,” which arrived on Friday (July 31).

Sombr’s Lollapalooza performance was a cathartic experience for the singer, as the 21-year-old admitted he’s been in a “dark” place in recent days, but was aided by the return to the stage. After telling the audience he was about to “turn this place upside down,” Sombr brought 5 Seconds of Summer back out, who played the set at the T-Mobile Stage prior to the “Homewrecker” singer-songwriter. Sombr duetted with the Australian boy band for 5SOS’ 2014 hit “She Looks So Beautiful,” which reached No. 24 on the Billboard Hot 100. With Luke Hemmings dyeing his hair black, the 5SOS lead singer and Sombr looked as if they could’ve been cousins while sharing an embrace on stage.