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 their set at T-Mobile Stage prior to Sombr’s performance. Sombr duetted with the Australian boy band for their hit “She Looks So Beautiful,” which reached No. 24 on the Billboard Hot 100. With Luke Hemmings dyeing his hair black, both looked as if they could’ve been cousins while sharing an embrace on stage.

charli xcx embodies everything we should want in our pop stars. The British singer-songwriter kicked off her grungy Music, Fashion, Film era with her first expansive performance where she affirmed headliner status on Friday night (July 31) and gave fans a taste of what’s to come on her upcoming tour. While Charli shows typically have all eyes on her, she brought out about 15 dancers to join her for tracks like “Girl, So Confusing” and turned the stage’s catwalk into a fashion show for “Card Declined.” The artist weaved in more Brat than expected (“Club Classics,” “Apple,” “365” and “360”) with some Wuthering Heights cuts like “House” and “Dying for You” (the transition from “Dying for You” into “Club Classics” was jarring in the best way possible). Instead of closing out with anthems such as “Vroom Vroom,” “Boom Clap,” or “I Love It,” Charli opted to see her latest album’s introspective narrative through with her gloomy MFF finisher “No One Lasts Forever.”

Zara Larsson first performed at Lollapalooza in 2017 and nine years later, she boasts one of the weekend’s most anticipated sets. After a two-hour delay following Lil Uzi Vert’s cancellation, Larsson took the stage to what she said was the largest American crowd of her career to date. However, it was a fan named London who stole the show when he joined her for “Lush Life” and perfectly executed exuberant dance moves with ease that served as a collective shot of dopamine for all present.

Olivia Rodrigo was spotted by eagle-eyed fans at a Chicago airport on Thursday night (July 30), leading up to her surprise appearance when she joined Smashing Pumpkins’ headlining set for an infectious performance of their top ’90s hit “33.”

Travel issues canceled Lil Uzi Vert’s Lolla set; however he still managed a guest appearance hours later during Major Lazer’s set where he performed hits like “Just Wanna Rock,” “Money Longer,” and “XO Tour Llif3.”

Slayyyterpalooza brought a taste of Missouri to Chicago. The singer wore waterproof hunting boots and fishing-themed belt featuring fishing gear that matched Friday’s overcast vibe (July 31). Slayyyter has been rising rapidly in popularity throughout 2026; her momentum led Lollapalooza organizers to move her up to perform on headliners stage where she drew a massive audience at her afternoon slot at 2:45 p.m. CT. It’s one thing seeing streaming stats but another experiencing thousands singing along live; Slayyyter’s ascension continues with another milestone she’ll fondly remember thanks to her performance at Lolla.