Summary

Each night of Lollapalooza offers four competing headliners, and oftentimes it’s difficult to choose where to land at the end of the night. The second night of the 2026 edition in Chicago’s Grant Park was no exception, with the evening offering Charli XCX , the Smashing Pumpkins , Major Lazer, and Freddie Gibbs as its top line. If there was a night this year for headlining FOMO, it was this one. And even the rain that steadily fell through the day and evening couldn’t dampen that feeling.

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