Olivia Rodrigo delivered a powerful performance Friday night as she made her Lollapalooza Chicago debut, headlining Day Two of the annual music festival in Grant Park. Rodrigo, currently on her GUTS World Tour, performed a mix of fan favorites from her Grammy-winning debut album SOUR and her chart-topping follow-up GUTS.

Olivia Rodrigo delivered alongside surprising guests Weezer as Lollapalooza continued in Chicago with performances by T-Pain, Flipturn, Gigi Perez, Bo Staloch and more.

Olivia Rodrigo was joined by surprise guest Weezer during her headlining set at Lollapalooza 2025. On Friday (Aug. 1), the 22-year-old pop superstar made her debut on the second day of the Chicago music festival at Grant Park. Toward the end of her evening set, she surprised the crowd by inviting Weezer to join her on stage.