Breaking And Entering is in Chicago for Lollapalooza 2021! Be sure to stay tuned all weekend for recaps from the event, and subscribe to B&E on Patreon for exclusive interviews from the festival!

One of the crown jewels of the Midwest festival season returned on Thursday, as thousands flocked to Grant Park in Chicago for Lollapalooza 2021. The four-day event is known for big names, big crowds, and big performances, and after a year off due to the pandemic, Grant Park was ready to explode from early on in the day.

With a year away from stages, younger artists that were app-savvy made big impressions. Early in the day, MAX drew a big crowd to the Lake Shore stage, getting fans moving to hits like “Butterflies” and “Lights Down Low”. Over at the GrubHub Stage, indie rockers Almost Monday were another younger act pulling fans in with a catchy sound and lively stage presence. It was clear that in the past year and a half, new names were finding a way to make themselves heard, and fans were eager to finally see their music live again.

The first truly big feeling moment of the day happened around 4:00, when a massive crowd packed the GrubHub Stage for rapper Flo Milli. With every use of her signature “Flo Milli shit” drop, fans got louder, and a full on dance party broke out as she unleashed track after track from her “Ho, Why Is You Here?” project. Fans climbed trees for a better view, and it truly looked like a glimpse at one of hip hop’s next big stars.

On the other side of the street, rock up and comer LP was drawing a crowd of their own in, with a crunchy guitar-driven set that would put a smile on the face of the shrewdest rock purest. In the vein of bands like Led Zeppelin or, for modern comparative purposes Greta Van Fleet, the band had a swagger about themselves that made you feel like they knew what is in the cards for them. Their growing discography is drawing some big attention lately, and the set at the Tito’s Vodka stage showed fans exactly why it won’t be long before they’ll be playing the biggest stages.

As the sun began to blare down on Chicago, the crowds only became more energized in the heat. R&B/hip hop hybrid Saint Jhn felt the need to explore that on his own, getting into the crowd during his set at the Lake Shore stage. After insisting on opening up a hole for him to ignite the crowd, he was mobbed by fans, who would ultimately lift him up for part of his performance. His set was full of big songs from 2020’s “While The World Was Burning”, but also included a preview of a new song, as well as multiple versions of hit “Roses”, including the Imanbek remix that unexpectedly catapulted him to the top of viral fame.

There was always a feeling that when Playboi Carti‘s name was on the Thursday schedule on one of the main stages, a large crowd was sure to follow. That was the case, as tens of thousands were filling up the T-Mobile stage, partially in anticipation of Miley Cyrus’ set, and partially for Carti. The mob bounced and screamed with every bass drop, as Carti likely had one of the loudest sets of the festival so far. The energy was constant, and Carti reciprocated the fans with a smattering of hits, punctuated by adlibs so loud that his microphone was distorting on the biggest sound system in Grant Park.

Thursday night, however, belonged to Miley Cyrus, who made sure to make her Lollapalooza set a spectacle that wouldn’t be forgotten. Early on, a surprise cameo from Billy Idol for a cover of “White Wedding”, followed by appearances from Chicago’s own G-Herbo, and shortly after Juicy J, Wiz Khalifa, and the Bulls’ mascot Benny during “23” made the night extra memorable. The massive crowd stretched all the way to the Lake Shore stage, with a rough estimate of 50-60,000 people clinging to Cyrus’ every word. Miley did take time to thank the fans during her set, and made it a point to drive home that without the fans, concerts are nothing, as found out in the past year. There were certainly plenty of fans to hear and applaud that sentiment, and more and more will fill up Grant Park in the days to come.