Olivia, Sabrina, Gracie lead Lollapalooza’s pop girl summer, plus hip-hop, country, alt-rock
Photos by Andy Argyrakis and Daniel DeSlover
If there’s a loose theme to tie together the fully loaded 2025 edition of Chicago’s Lollapalooza, it’s the pop girl summer being lead by the superstar likes of Olivia Rodrigo, Sabrina Carpenter and Grace Abrams.
However, with over 170 acts populating eight stages throughout four days, practically nothing is off limits, including the experimental hip-hop of Tyler, The Creator, country chart-topper Luke Combs and local alt-rock hero DJO.
In other words, Grant Park is the place to be from Thursday, July 31 through Sunday, August 3 to see all of the above, plus any of these mega headliners or undercard essentials, while expanding upon a tradition that firmly planted its roots in the Windy City exactly 20 years ago.
1. Olivia Rodrigo (Friday)
Hands down the hugest currently active pop star on the planet, who’s known just as much for rocking out, Olivia Rodrigo is poised to have her “GUTS (spilled)” on an adoring audience. Add in a “Sour” yet spectacular “Driver’s License” start, and it’s going to be as “Good 4 U” as it gets.
2. Tyler, The Creator (Thursday)
Tickets sold out so fast to Tyler, The Creator’s pair of United Center shows, those shut out can thankfully breathe a sigh of relief over this bonus opportunity. This time through, the theatrical, alternative hip-hop hero is focused on the ambitious “Chromakopia” project, which revisits his occasional exploration of soul and jazz.
3. Sabrina Carpenter (Sunday)
The momentum of Sabrina Carpenter’s blockbuster “Short N’ Sweet” era would’ve been enough to keep fans excited about encountering the “Expresso” icon. However, the announcement of its follow-up, “Man’s Best Friend,” has faithful wondering if she’ll perform “Man Child” or more cheeky previews.
4. Luke Combs (Thursday)
Country always maintained somewhat of a presence at Lollapalooza, at least as of late, but up until Luke Combs, no one primarily associated with the genre ever headlined the festival. It turns out the singer/guitar slinger is an excellent choice based on a multi-platinum discography dating back almost a decade, including helping revive Tracy Chapman’s iconic “Fast Car.”
5. Doechii (Saturday)
What started out on TikTok blossomed into a full-fledged recording and touring career for Doechii, the red hot rapper who dropped “Denial Is A River,” “Anxiety” and “What It Is (Block Boy).” Her second mixtape, “Alligator Bites Never Heal,” continues exploding everywhere and it won’t be long before she lands on the schedule’s top line.
6. T-Pain (Friday)
The amount of individual or collaborative singles T-Pain stocked up since the early 2000s is staggering, so much so there’s no way he’ll be able to fit all them into a mere hour. However, it’s guaranteed he’ll bring the hip-hop and R&B-fueled party, plus possibly a few “On Top Of The Covers” tunes in the spirit of “The Masked Singer.”
7. Grace Abrams (Thursday)
Going from a support act for Rodrigo to Taylor Swift only accelerated an ascent that was already brewing as Gracie Abrams transitioned from her debut record, “Good Riddance,” to the enormous sophomore offering, “The Secret Of Us.” Arrive early in case of a Chappell Roan-like crowd and prepare for the folk-flavored troubadour to kick up her emotive relatability another notch.
8. DJO (Friday)
Chicago certainly knew the name of hometowner Joe Keery prior to finding fame on “Stranger Things” and “Fargo,” although musical alter ego DJO is quickly becoming as prominent. In fact, his quirky indie rock, neo-psychedelia and synth-pop combination is amongst the catchiest around, supported by the singles “End Of Beginning” and “Basic Being Basic.”
9. Finneas (Sunday)
The super producer behind his sister Billie Eilish, alongside several others, is similarly unpredictable and innovative as a solo artist. “For Cryin’ Out Loud!” marks Finneas’ latest long player and a conscious decision to steer his typically bedroom-derived creations towards a standard studio environment.
10. Marina (Saturday)
“Princess Of Power” may simply be the moniker of Marina’s sixth album, but it’s also a fitting description for the pop singer/songwriter latest euphoric chapter in general. That’s because she’s turning inward for a soundtrack of self-reclamation and is destined to empower an entire field in the process.
Lollapalooza comes to Grant Park from Thursday, July 31 through Sunday, August 3. For additional details, visit Lollapalooza.com.







