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\n\tEach night of Lollapalooza<\/a> offers four competing headliners, and oftentimes it\u2019s difficult to choose where to land at the end of the night. The second night of the 2026 edition in Chicago\u2019s Grant Park was no exception, with the evening offering Charli XCX<\/a>, the Smashing Pumpkins<\/a>, Major Lazer, and Freddie Gibbs as its top line. If there was a night this year for headlining FOMO, it was this one. \u00a0\u00a0<\/p>\n \n\tThe two main stage spots belonged to Charli, whose return to Lolla also marked her first festival date following the release of her excellent Music, Fashion, Film<\/a><\/em>, and the Pumpkins, the hometown heroes who made their official Lollapalooza Chicago debut (they previously performed the OG traveling Lolla version back in 1994). Both rocked their respective sides of the park.<\/p>\n \n\tFor their set, Smashing Pumpkins leaned into material from Mellon Collie and the Infinite Sadness<\/em>, their third studio album that turned 30 last October, alongside classics from Siamese Dream<\/em> as well as songs from recent album Aghori Mhori Mei<\/em>, including \u201cEdin.\u201d<\/p>\n \n\tThey also surprised fans with a couple of guests<\/a> early on, including Yungblud<\/a>, who sang \u201cLuna\u201d from Siamese Dream<\/em>. Yungblud, who performed earlier<\/a> in the night, remarked the moment was \u201ca dream come true.\u201d A few songs later, Olivia Rodrigo<\/a> joined frontman Billy Corgan for an elegant, acoustic performance of \u201cThirty-Three.\u201d Their appearances highlighted Smashing Pumpkins\u2019 resonance over more than three decades, and their influence on the next generation of rock stars.<\/p>\n \n\tMeanwhile on the other side of the field, Charli XCX was holding court on the T-Mobile stage with her apt backing band and a bevy of dancers. Though she\u2019s played a couple intimate one-off shows<\/a> ahead of her appearance on Friday, Charli XCX officially kicked off her tour behind Music, Fashion, Film<\/em> in Chicago at Lollapalooza. It was a grand return for the star, who has taken the stage at Lolla in Chicago in previous years, including in 2015, 2017, and 2022 \u2014 each performance a showcase of her evolution. She kicked off her new era at the fest with \u201cRock Music.\u201d<\/p>\n \n\tCharli was in the midst of her last handful of songs when she confessed on \u201cCamera\u201d how it makes her feel. The audience was feeling it too, singing and dancing along as she delivered songs from her new album, such as \u201cSS26<\/a>\u201d and B-sides, like the ruminating \u201cIf You Take Away the Music Then What Has She Got?\u201d <\/p>\n