Rain that flooded Chicago overnight and continued to fall on Saturday delayed the third day of Lollapalooza 2026 and caused organizers to push back doors by about three hours for cleanup. The downpours caused pooling throughout Grant Park where the festival
is held. By the time it opened at 3 p.m., the grounds were understandably muddy, but navigable for attendees.
The delay also caused a shift in scheduling, with some performances canceled altogether, and others truncated. Fortunately, weather did not derail two of the day’s best performances, headliner Olivia Dean and rising star Sienna Spiro.
Dean’s ascent to the top spot has been a quick one. “This is so crazy,” she said as she took in the crowd, which stretched back to the end of her side of the park. She last played in 2024 on a smaller stage in the daytime and noted that last year her first headlining show in Chicago drew about 1,500 people. “To be headlining this year is just crazy and truthfully I’ve been crying all day because I just feel so privileged to do this,” she added.
It’s been a banner year for Dean, who kicked it off by winning the Grammy for Best New Artist in February and it’s been augmented by her making history. On Friday, Dean and Sam Fender set a new U.K. record for longest running Number One song on the singles chart. The duo’s song, “Rein Me In,” spent 19 weeks atop the U.K. singles chart. It surpassed Frankie Laine’s record for 1953’s “I Believe,” which spent 18 weeks at the top and held the record for more than 70 years.
To mark the occasion, Dean brought out Fender as a surprise guest during her headlining set on T-Mobile stage on Saturday to perform their hit.
It was one of the highlights from her elegant set, which featured songs from her debut album Messy (including “Dive”) and many of her songs from her breakout sophomore effort, 2025’s The Art of Loving.
Earlier in the day, rising star Sienna Spiro performed on the Airbnb stage, which was packed with fervent fans who sang along to her cuts from debut album, Visitor. Standouts included “Pure,” “He’s Not My Baby, I’m His,” “Great Expectation,” and closer “Die on This Hill.”
Similarly to fellow British singer Dean, the 20-year-old hearkened an other-era quality during her set, with orchestral arrangements that included live horn sections. Sounding both timeless and fresh, Dean and Spiro did so with panache on Day Three of Lollapalooza 2026.
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