With the sun beating down on Chicago, tens of thousands of fans converged once again on Grant Park for day one of Lollapalooza, ready to party from the moment the gates opened. Day one of the festival brought some full-circle moments, as well as some buzzing festival debuts.

It doesn’t take much to get the Lolla crowds fired up, especially on the Perry’s Stage. Up-and-comer MPH, however, worked the afternoon crowd into a frenzy, with a mixture of drum-and-bass and house that got crowds bouncing along. Even as the temperatures reached their high for the day, he managed to pull tons of people over his way, with everyone looking to rage on day one of the festival. 

Part of what makes the festival so special is when you see acts get to embrace the moment. That was especially true for British rapper Little Simz, who made her Lollapalooza debut on the Tito’s Stage with a band in tow. Over the course of her 45-minute set, she not only brought her brand of energetic grime to the stage, but midway through, brought out turntables to turn the stage into her own DJ set. At one point, she stopped to look out at the crowd, who broke out in spontaneous applause for her. It was certainly a moment for an artist that has already been bubbling, and now is getting to fully hit her stride. 

Immediately afterwards on the Bud Light Stage, Empire of the Sun drew one of the biggest crowds of the day, and certainly the largest for a non-headliner. With the Chicago skyline behind them and the sun starting to finally subside, the Australian duo brought a stage show complete with Kabuki-style dancers and Luke Steele running out into the Lollapalooza crowd to greet as many people as possible. It’s entirely possible that Empire of the Sun is a future Lollapalooza headliner, and Thursday afternoon’s set certainly had the crowd to make you a believer.

Following that, on the other end of the grounds, Wet Leg took over the Allianz Stage, fresh off of the release of the deluxe edition of 2025’s “Moisturizer.” The duo packed 15 songs into an hour-long set with the sun now fully resting behind the cityscape. With the heat calming down, it made for ideal festival conditions, and the ever-rising duo set the tone for the main portion of the night.

On the T-Mobile stage, Lorde made her return to Lollapalooza for the first time since being rained out in 2017. She not only addressed that previous show, where she only managed to play two songs before things were halted, but more than made up for it, with 90-minutes of pure alt-pop spectacle. At one point, the New Zealander admitted that the world looks much darker to her now than it did when she was a fresh-faced star playing Lollapalooza for the first time in 2014. For as dark as that moment felt, she rebounded with a bright spot, bringing out Friday night headliner Charli XCX for “Girl, So Confusing.” Lorde is embracing all of the facets of herself as a performer, and for a festival that has literally watched her grow up, it felt good to see her rightfully get the shine of a main stage headlining spot.

Meanwhile, nestled in the trees of the Airbnb Stage, funk-punks Viagra Boys delivered a show that felt as grimy as Lollapalooza could get. With a wall of amps behind them and a barrage of near-constant strobes, the band ripped through an hour-long headlining set for a decent crowd, which would eventually break out into mosh pits and ultimately crowd surf percussionist Elias Jungqvist over the barricade. While more polished headlining sets were happening elsewhere, the fireworks in the distance felt like just the right addition to the Swedish band’s barrage of post-punk and the message of “endless anxiety” which they flashed on the screen behind them repeatedly. 

There’s already been a ton of big moments coming out of Lollapalooza 2026, and we’re only 25% done with the four-day festival. Stay tuned to Breaking And Entering for more from Grant Park in Chicago all weekend long.