Lollapalooza 2025 rumors and lineup predictions

If you’re experiencing a bit of “deja vu” while looking at summer festival lineups, it’s probably because pop-punk singer-songwriter Olivia Rodrigo is present on most of them. She’s playing Governors Ball, Glastonbury, nearly every international edition of Lollapalooza and the Osheaga Festival in Montreal. Her presence as a headliner at no less than four other Lollas and her spot on the Osheaga lineup (which shares a weekend and often some headliners with Lolla in Chicago) makes her a virtual lock for a mainstage set in Grant Park.

Probability: 100 percent
Past Lollas: None

Every Lolla lineup needs an EDM headliner, and Aussie trio Rüfüs Du Sol seem likely to receive the mainstage treatment in Chicago this summer. The group’s latest tour in support of its 2024 release Inhale / Exhale is skipping Chicago, but Lolla weekend is suspiciously devoid of confirmed shows—save for a gig in nearby Indianapolis on August 3. Coupled with the fact that Rüfüs is playing all three South American editions of Lolla, we’re pretty sure you’ll be grooving to “Innerbloom” in Grant Park.

Probability: 90 percent
Past Lollas: 2016, 2019

Following up a stint as an opening act on the Eras Tour, pop singer-songwriter Gracie Abrams is playing arenas, ampitheaters and festivals across the globe this summer, including Glastonbury, Lollapalooza Berlin and Madison Square Garden. The “I Love You, I’m Sorry” singer isn’t booked anywhere in the Midwest this summer, but her presence on the Osheaga lineup (the same weekend as Lolla) and an otherwise open schedule over the weekend leads us to believe that she’ll be belting out “That’s So True” in Grant Park.

Probability: 85 percent
Past Lollas: 2022

It’s been three years since English rockers Glass Animals graced a stage at Lolla and the heat waves are still fakin’ us out. The group is sticking to the festival circuit this summer, with confirmed dates at Bonnaroo, Governors Ball, and Osheaga. The latter fest takes place in Montreal during the same weekend as Lolla, so it’s likely that these animals will migrate to Grant Park, serenading the sweaty crowds with their ubiquitous tune about the middle of June.

Probability: 80 percent
Past Lollas: 2022

Country singer-songwriter Shaboozey has seen his star rise over the past year, thanks to an inescapable single (“A Bar Song (Tipsy)”) and his collaboration with Beyoncé on her Cowboy Carter album. His summer schedule is sparse, but he’s confirmed to perform at Lollapalooza Paris and Osheaga in Montreal. The latter date places Shaboozey in North America (just a flight away from Chicago) during Lolla weekend—coupled with his breakout status, we think there’s a good chance he’ll be on the lineup.

Probability: 75 percent
Past Lollas: 2022

When Stranger Things star (and former Chicagoan) Joe Keery’s band Djo performed at Lollapalooza back in 2022, the group’s track “End of Beginning” hadn’t yet achieved TikTok montage ubiquity. We don’t think that Keery is going to miss an opportunity to belt out the lyrics, “When I’m back in Chicago, I feel it” against the backdrop of the aforementioned city’s skyline—and Djo’s tour in support of its new album The Crux is missing a date in the Windy City. The band will be coming off a string of festival dates in Europe just ahead of Lolla weekend, but a bit of jet lag only adds to the poignancy of a nostalgic Midwest anthem.

Probability: 70 percent
Past Lollas: 2022

Before she became synonymous with the earworm single “Espresso,” Sabrina Carpenter turned in a set at Lollapalooza in 2023 that featured an ABBA cover. Now the former Disney Channel star is commanding huge crowds and is scheduled to play a series of shows at Madison Square Garden and Crypto.com Arena this fall. But Carpenter didn't announce a Chicago date when she extended her Short n' Sweet Tour this year, which feels like a sign that she’s been tapped to headline Lolla—consume your caffeinated beverage of choice to fuel up for the inevitable sing-along. 

Probability: 65 percent
Past Lollas: 2023

The past few months have been huge for LA rapper Doechii, between her Tiny Desk Concert, the release of her acclaimed mixtape Alligator Bites Never Heal and a subsequent Best Rap Album win at the Grammys. Considering all of her success, Doechii’s summer touring schedule is remarkably quiet—just a few festivals in Europe and an appearance at Osheaga in Montreal. If she’s going to play just one US festival this summer, Lolla would make the most sense, considering its proximity to Osheaga (and the fact that the two fests frequently share acts). 

Probability: 60 percent
Past Lollas: None

If Pitchfork Music Festival hadn’t been canceled, reunited and reinvigorated indie rockers TV on the Radio would have been a shoo-in as a headlining act. The group hasn’t played a single show in Chicago since their revival in late 2024 (celebrating the 20th anniversary of Desperate Youth, Blood Thirsty Babes) and there’s no Windy City date on their current summer itinerary, which means that they’re likely holding out for a festival. While they’ve played Lolla in the (distant) past and will be performing at Osheaga in early August, there’s a decent chance that they’ll join the lineup at Riot Fest, instead.

Probability: 45 percent
Past Lollas: 2007, 2009, 2015

Lollapalooza embraced K-pop when BTS member J-Hope headlined the festival in 2022, and South Korean artists have had a presence on the lineup ever since. Most K-pop acts make one-off appearances in Grant Park that aren’t part of larger U.S. tours, so it’s difficult to predict who might join this year’s lineup. But Lollapalooza largely books acts associated with the two largest South Korean entertainment companies: HYBE and JYPE. That’s why the JYPE-affiliated girl group Twice’s recent announcement of a world tour could point toward an appearance at Lolla—potentially as part of a larger U.S. tour.

Probability: 35 percent
Past Lollas: None

This blues-rock duo from Ohio was once a fixture of Lolla, performing at the festival every other year (and making a rare consecutive appearance in 2007 and 2008). It’s been more than a decade since the pair last took the stage in Grant Park (outside of a performance at the 2024 NASCAR Chicago Street Race), but 2025 could mark their return—their current tour notably skips Chicago and they’ve been transparent about taking gigs to make ends meet after a canceled arena tour last year. Aside from a spot on the Shaky Knees lineup in Septemeber, their U.S. festival schedule is pretty much nonexistent, which means they might show up at Lolla … if they’re not already booked for Riot Fest.

Probability: 25 percent
Past Lollas: 2005, 2007, 2008, 2010, 2012

Jenny Lewis has performed at Lollapalooza solo (2014) and with the reunited Postal Service (2013), but the seminal indie rock outfit she fronted has never made the festival’s lineup. Even though Rilo Kiley recent reunited, the group doesn’t look like it will be making its way to Grant Park this summer. Both legs of the band’s summer tour are skipping Chicago, but there’s a gap in the itinerary between dates in Nebraska and Florida that’s perfectly situated during Riot Fest weekend (September 19-21). Considering Riot Fest’s penchant for nostalgic reunions, we’re nearly positive that Rilo Kiley will be headlining Chicago’s other big fest.

Probability: 0 percent
Past Lollas: None