Lollapalooza took over Grant Park from 30 July to 2 August, with more than 170 acts and the sort of weekend that gets described afterwards as a turning point. The claim is doing a lot of lifting, but there is one genuinely unusual thing about this year’s bill, and it is at the very top of it.
Of the eight headliners — Lorde, John Summit, Charli XCX, the Smashing Pumpkins, Olivia Dean, Jennie, Tate McRae and the xx — five were women. According to Book More Women, which tracks gender equity in live music, this is the first time a major American multi-genre festival has put at least three women at the top of its bill since the organisation began collecting the data in 2018. For a format that spent two decades treating one female headliner as a gesture, that is the story of the weekend.
The clothes
The wardrobe rose to the occasion, in a way festival wardrobes generally do not. Olivia Rodrigo, appearing as a surprise guest rather than a booked act, wore an archival white babydoll dress from Balenciaga’s spring/summer 2006 collection with matching knee-high stockings and Jimmy Choo Mary Janes — a look that suggests she has read the ongoing commentary about her stage clothes and decided to keep going regardless.
Jennie went military and precise in a look from Ann Demeulemeester’s autumn 2026 collection. Sombr made a strong case for himself as the best-dressed man on the site, in a lace black top and feathered jacket from Alessandro Michele’s Valentino. Olivia Dean worked through a run of custom Versace, including a sequinned fringe minidress and a cream gown with ruffles running along the hem of an enormous, undulating skirt.
The sets people will be posting about
Charli XCX and Lorde ended their long public back-and-forth by performing “Girl, So Confusing” together, Charli appearing during Lorde’s Thursday set — the latter’s first Lollapalooza since 2017.
Rodrigo’s cameo came the following night, when she joined Billy Corgan and the Smashing Pumpkins for “Thirty-Three”; Yungblud turned up in the same set for “Luna”. That performance carried its own weight for Chicago: the Pumpkins had not played Lollapalooza since 1994, when the festival was still a touring operation, and had never played it in the two decades since it settled into Grant Park in 2005. They marked the return by building the whole thing out as Pumpkinpalooza.
Olivia Dean brought out Sam Fender to perform “Rein Me In”, marking the song becoming the longest-running number one in UK chart history. Sombr pulled 5 Seconds of Summer onstage during his set; 5SOS returned the favour in theirs with a Katy Perry cover. And Tate McRae closed the festival on Sunday by lowering herself into a vat of liquid gold, which is either the most or least subtle way to end four days, depending on your tolerance.
SB19 made history on the opening day as the first homegrown Filipino act and the first P-pop group on a Lollapalooza bill — a distinction worth stating precisely, since Filipino-British and Filipino-American artists including beabadoobee and Rodrigo have played the festival before.
What the booking says
The through-line is a festival that has been quietly reorganising itself. Lollapalooza began in 1991 as a travelling alternative showcase and made Chicago its home in 2005, and its recent years have leaned steadily further into pop. It is also paying close attention to two constituencies at once: the very new, like Adéla, who played her Lolla debut a month before her first album is even out, and Oklou; and the 2010s acts whose catalogues have been revived by TikTok, hence 5 Seconds of Summer and the Chainsmokers on a 2026 bill.
Add stormy weather, mud, and tens of thousands of people showing up for midday sets, and the case for Lollapalooza as the festival of the moment more or less makes itself — though Coachella has heard that before.
