Day three of Lollapalooza 2026 was dominated by weather issues, but that didn’t stop thousands and thousands of fans from filling up Grant Park to play in the rain and the mud.

Heavy rains overnight sent crews to Grant Park to repair flooded fields, and the repair efforts ultimately pushed the doors to the festival opening back by three hours. The delayed opening also cancelled over a dozen sets, and pushed start times around as well. The adjusted lineup would send some fans scrambling to find their next favorite show, but it ultimately didn’t affect the night’s headlining slots.

Once the rain finally slowed down, and fans got into Grant Park, there were still plenty of major acts set to play. One of the first to make an impact were Clipse on the Bud Light Stage, still riding their momentum of 2025’s “Let God Sort Em Out.” With a big crowd that only grew as the set went on, the combination of Pusha T and Malice didn’t rely on gimmicks to get a response from the crowd. Instead, they brought a flow and live show that was as pure as the substances they rap about. Armed with visuals of Black cultural icons behind them, the duo kept things tight for the duration of their set, with a very direct delivery that had fans screaming along with every quotable bar.

The rain turned the area near the T-Mobile main stage and the Allianz stage across from it into a gigantic mud pit, but that didn’t stop fans from flooding the field (in this case, literally,) to see their favorite acts. The Neighbourhood drew a frankly surprisingly big crowd to the T-Mobile stage, with fans screaming along at every opportunity to get a glimpse at frontman Jesse Rutherford. In the back of the field, though, the mud pit became a prime location for mud wrestling, which was also happening at the same time during the set, thanks to some eager festival goers and willing combatants.

Post-wrestling match, buzzy indie rockers Geese took the Allianz stage with a big crowd that filled every bit of available mulched-over space. “Getting Killed” was one of the biggest albums of 2025, and you could see it by the amount of people that were ready to damage shoes and clothing to get in close to the band. With an hour-long set, the band made the absolute most of their time, even with the rain starting to sprinkle once again.

The night, however, belonged to first-time headliner Olivia Dean. Sure, set closer “Man I Need” is a smash, but material from last year’s  “The Art Of Loving” had the crowd of mud-drenched festival goers singing along at full voice. With naturally soulful vocals and an already-polished stage presence, Dean is a superstar in the making, and it felt like this was her coming out party. It also felt like her headlining set at the end of a frankly chaotic day was pure catharsis for the Chicago crowd, who had endured rain and mud and probably lost a pair of shoes for the moment. This is Olivia Dean’s first headlining slot at Lollapalooza, but it certainly won’t be her last.

That’s the latest from a muddy Chicago Loop. With one more day to go, the festival crowd will hope to stay drier on Sunday. Stay tuned to Breaking And Entering for more and be sure to follow along on social as well.