Attending Lollapalooza 2021 was exactly what I needed after nearly two years without festivals and live music.

Grant Park is one of the most beautiful outdoor spaces, and it’s right in the heart of downtown Chicago. So seeing over eight stages, countless show-stopping surprises, and headliners Foo Fighters, Post Malone, Tyler, the Creator, and Miley Cyrus, light up the backdrop of an unrivaled skyline was the experience of a lifetime.

This year, Lolla celebrated its 30th anniversary amid the ongoing pandemic and did everything to make this event the safest and most memorable weekend of all time. Complimentary masks were available at the gates, hand sanitizing stations covered the festival, and attendees were required to show proof of vaccination or a negative test result within the last three days to enter. It was comforting knowing at least 90% were vaccinated while others met admission requirements.

Upon entering the main festival gate, I hit the stunning Buckingham Fountain and garden. There was a Lollapalooza sign for photos with your crew, and there was a Tito’s cocktail garden, Lolla merch store, and installations for photo opps. This year, a Golf store pop-up nestled a corner for Tyler, the Creator fans, as did a Bumble lounge for app users, and a spray-painted Modest Mouse hearse appeared another day. The fountain is the heart of the festival, and it was amazing to see it thriving with people zooming around to catch sets, flaunting fresh festival fits in group photos, and exploring everything offered within the garden.

The careful curation organizers have placed extends beyond the lineup and is clear as you venture through Lolla. Each year, Chicago’s busiest downtown streets are closed off to create an expansive haven for music, food, culture, and art, and it’s incredible to get lost in the details. Like venturing through the park and finding DJs spinning at shaded eateries and beer gardens, art installations, a T-Mobile photo booth, or one of the three stages that provided intimate sets and unique experiences.

Toyota Music Den, Bonus Tracks stage, and Bud Light Seltzer Sessions were the places to be in between sets. For years, Toyota has provided a great festival stage for intimate sets, and Lolla was no exception, with Absofacto, Riz La Vie, Phem, and Neal Francis, being just a few of the artists that played a 30-minute set. In addition to a surprise LUNAY set, the Toyota Music Den also hosted a listening session and Q&A with Emotional Oranges.

Surprise sets and guests during performances were a recurrent theme throughout the weekend, a special treat for every fan. Miley’s set was littered with guests (more on Miley here), iann dior and 24kGoldn performed “Mood,” Grandson was joined by Vic Mensa and Jessie Reyez, Surfaces x Tai Verdes, and the list goes on. However, one of the weekend’s best moments arrived in the form of a surprise set by Machine Gun Kelly at the Bud Light Seltzer Sessions. Billed as a surprise guest on the lineup, fans received an MGK notification minutes before, causing a mass exodus to a stage that could not fit the rowdy crowd it attracted.

MGK’s energy superseded the pandemonium his sudden appearance caused – exactly what you’d hope to get from a surprise set of this magnitude. Megan Fox was also spotted taking in the glorious spectacle that ensued, making this moment even more epic.

Just one of the artists to deliver an unforgettable performance, Lollapalooza was also a special weekend because it provided many artists with their first opportunity to perform live (as Peach Tree Rascal shared during their set), to perform full projects released during the pandemic, and to join their artist friends onstage for unforgettable Lolla moments. More on the music below. 

I tasted some of Chicago’s best eats throughout the weekend, though just a portion of the 35+ eateries serving up the city’s best. From Lou Malnati’s tasty deep-dish pizza to Harold’s Chicken’s 3-piece tenders, and of course, Wow Bao’s delicious teriyaki chicken bao buns, Chicago’s vast palette was on well display. Xurro was also on-site with a much-needed churro sundae, and the weekend would’ve been incomplete without a cheeseburger from Billy Goat Tavern. Grubhub also dished out meals from local spots at Chow Town Delivered and offered an on-site perk of $10 off delivery orders over $12.

Throughout the weekend, the festival ran its Rock and Recycle Program and partnered with multiple organizations to benefit the local community, educate festival-goers, and support sustainability efforts. This year, REVERB supported Lolla’s efforts to build a more sustainable music industry through the Divert It! Composting program. While onsite, REVERB volunteers educated and engaged fans in the fight to reduce food waste, an often-overlooked driver of climate change.

The festival also partnered with Musically Fed this year. Musically Fed works with artists, promoters, management, and venues nationwide to donate unused backstage meals to community organizations that feed the homeless, hungry, and food insecure.

THURSDAY

Arriving on Thursday felt surreal, but I quickly rushed to Christian French‘s set to see my first concert in over a year. I’ve seen French in concert once before, and it doesn’t compare to the energy and performance he gave on Thursday. The crowd, which grew quickly throughout his set, knew all of his songs and sang even louder for his latest single, “avalanche.” Some even knew his unreleased songs. Shortly after, I connected with Christian French about his next chapter. Read more here.

As Jill Conway notes in her Day 1 Recap, Aly & AJ opened the T-Mobile stage on Thursday, and like many, I couldn’t wait for my chance to hear “Potential Breakup Song.” The sister duo also recently shared an ambitious new album that features “Pretty Places,” a great guitar-led track that felt as breezy as the day, and “Break Yourself,” one of the best songs I saw them perform.

During the set, I also checked out the nearby T-Mobile Club Magenta, which offered T-Mobile members (+1) a premium viewing deck near the T-Mobile mainstage, charging stations, a full-service bar, and lounge seating to hide out from the sun.

Mickey Pierre-Louis for Lollapalooza 2021

Highlights included seeing MAX perform his incredible Colour Vision album, my first time seeing Orville Peck live, and finally hearing Olivia O’Brien sing “NOW.” One of my favorite sets of the day was Flo Milli! Milli was on fire, and the massive crowd she drew to the GrubHub stage could not get enough of her.

Saint JHN delivered an unforgettable set moments later, including jumping into the crowd, and Tchami kept the energy surging at Perry’s stage. Kim Petras took over the Lake Shore stage in head-to-toe Chanel. She played all of her hits, which had her fans screaming and dancing. She also played her unreleased disco-infused track “The Future Starts Now,” an absolute hit waiting to happen, and the bass-heavy unreleased bop “Somber.” All signs her next chapter will be unmissable.

Playing at the same time as Kim was Puerto Rican artist LUNAY, a last-minute lineup addition that brought Latin flavor to the weekend. He just released the music video for his song “TODO O NADA,” featuring Anitta, which he performed during his set. He also played his international hit “Soltera” while the crowd roared. Another major moment for Latin urban music after J. Balvin became the festival’s first Latin headliner in 2019.

Thursday, of course, ended with a party in the U.S.A. and Miley Cyrus. Sparkling in Gucci, she delivered an unreal show. Her voice was flawless, her execution was award-worthy, and she brought the best energy while playing a career-spanning set and bringing out so many artist friends to perform with her throughout the night. See more about Miley’s set here.

Lollapalooza’s first day was perfect. Whether you watched on Hulu or were lucky enough to attend, it proved that festival season is back in the best way. Thursday included performances by Ant Clemons, Ashe, Jimmy Eat World, Justin Jay, Kaytranada, Playboi Carti, Illenium, Oliver Tree, Steve Aoki, and more.

FRIDAY

Friday started with the sweet indie sounds of Gus Dapperton and his latest album Orca. Gus always puts on a great show, and his return to the stage was the perfect set to kick off the day. Chicago’s own Njomza took over the GrubHub stage shortly after, and I couldn’t miss it after hearing her new EP, LIMBO.

Grandson took over the T-Mobile stage to perform tracks from his album, Death Of An Optimist. Surprise guest Vic Mensa joined to perform “Oh No!!!” and Jessie Reyez hit the stage for “Rain.” Both songs appear on The Suicide Squad soundtrack, which I got to ask Jessie about shortly after she got off the stage with Grandson. See more here.

As Jill notes in her Day 2 Recap, Riot Ten and Subtronics threw down on the Solana x Perry’s stage. Polo G drew in one of the largest crowds of the afternoon, appropriate for the “RAPSTAR” chart-topper, and Brownies & Lemonade All-Stars and Friends brought out YehMe2, among other moments that further proved B&L knows how to throw a party.

Roddy Ricch, Jack Harlow, and Tyler, the Creator, closed out a stunning second Lollapalooza day. Roddy Ricch’s “The Box” is so damn popular; I think he played it twice. He could’ve played it five times, and I think Lolla would’ve turned up. Jack Harlow also brought a ton of energy. I’m admittedly new to his music but enjoyed what I heard before “What’s Poppin.”

While Marshmello tore Perry’s stage to shreds with an elevated stage and pyro (see here), I locked in for Tyler, the Creator. Tyler is so captivating on stage, and his album eras are so distinct and creative, it’s impossible not to love. The IGOR era provided some of my favorite shows, and his CALL ME IF YOU GET LOST era is delivering in spades with an entirely new show and setlist.

Friday included performances by Arizona Zervas, Emotional Oranges, Tai Verdes, Tobi Lou, Lauv, Omar Apollo, and $uicideboy$.

My Friday ended with Elohim‘s aftershow at Lincoln Hall. One of over fifty aftershows hosted over the weekend. See more here.

SATURDAY

As Lolla’s third day kicked off, so did another opportunity to catch new talent. JESSIA, the Canadian artist who had a breakout moment this year with “I’m not Pretty,” kicked the day off with a fun pop set. The Backseat Lovers dominated the T-Mobile stage with a great set that included their big hit “Kilby Girl.”

Saturday was also such a vibe because I got to see BIA, who has been making a “WHOLE LOTTA MONEY” since delivering her 2020 EP, FOR CERTAIN. Her artistry on stage, attitude, and music will make her an even bigger star this year.

Cautious Clay took the Lake Shore stage as one of the weekend’s most diverse lineup days unfolded. Whether basking in the sun to sweet saxophone sounds or dancing to his latest album, Deadpan Love, the singer-songwriter always puts on a fun set worth catching. Simultaneously, the GrubHub stage lit up with Chicago duo DRAMA, who has made a splash with releases like the slow-burning “Years” and collabs “You’ve Done Enough” and “Nobody” with Gorgon City.

One of the major Saturday highlights was Trippie Redd‘s set, which started shortly after and drew a staggering crowd. He opened with “Dark Knight Dummo,” which immediately sent the crowd into a frenzy that never seemed to die down. The rest of his set was led by moshpits and fans screaming every single word to his songs. Trippie played some of his biggest hits like “Taking a Walk,” “Miss The Rage,” his XXXTENTATION collab “Fuck Love,” “Topanga,” and even his Diplo collab “Wish.”

Toward the end of Trippie’s set, Lolla notified fans that MGK would be hitting the Bud Light Seltzer Sessions. Within minutes, the stage was overflowing with a crowd buzzing in anticipation. As fans waited for MGK, I caught Canadian pop star, Tate McRae. Over the last few years, Tate has dished out hits like “One Day,” “stupid,” and “that way,” but “you broke me first” exploded globally during the pandemic and swiftly placed her on a new echelon.

Her Lolla set confirmed what the world should know; Tate McRae is a pop phenom. Her performance included “bad ones,” which Tate shared she’s most excited to perform live, her Khalid collab “Working,” and the underrated “slower.” She closed with “you broke me first,” which had every person singing and cell phone recording. I met Tate ahead of her set – see my interview here.

After MGK, the night only got better with the one and only Megan Thee Stallion taking the T-Mobile stage. As Jill notes in her Day 3 Recap, Megan delivered the set fans needed, with her hits “Cash Shit,” “WAP,” “Body,” and “Cry Baby” making the cut.

Saturday featured Journey, Slander, and headliner Post Malone. While I managed to catch Journey play “Don’t Stop Believin'” and Slander brought The Eye concept to Lolla, there’s something about a Posty festival set that is unmissable. He opened with “Wow.” and “Better Now,” songs with over one billion Spotify streams each, and then unleashed a set of hits.

Saturday also included sets by CID, Kid Quill, Limp Bizkit, Michigander, Oliver Heldens, Young the Giant, and more.

SUNDAY

With Lollapalooza’s 30th anniversary wrapping, Sunday started with a house-infused revival from LP Giobbi. LP has the best on-stage persona. She’s vibrant, a wizard behind the decks, and always rocking as hard as her fans. Princess Nokia had on a beaded rave fit, crowd surfed, obliterated Lolla with the bass on “Tomboy,” and delivered a fun set. RMR hit the stage for his first-ever live performance in one of the day’s best fits paired with red Balenciagas. His set included cuts of his viral release “Rascal” and other songs from his debut EP. I got a chance to connect with RMR after his set. Read the interview here.

Toosi released his new album, Thank You For Believing (The Manifestation), and hit the Lolla stage two days later. He opened with his new song “what it cost,” which hooked me immediately and followed up with “Right Now.” Sunday afternoon was also led by memorable performances by Dr. Fresch, Jxdn, and Sullivan King. See more about their sets in our Day 4 Recap.

I caught a little of Surfaces, who brought out Tai Verdes at one point, and I finally got to hear “Wave of You” live. I also saw Rico Nasty performing an insane unreleased song called “Buss” and later “Key Lime OG.” I wish I had seen more.

BROCKHAMPTON hit the Bud Light Seltzer stage as Sunday closed. I got to hear the classic “1999 WILDFIRE” while waiting to catch my first NEZ set. NEZ has produced hits for A$AP Rocky and ScHoolboy Q and just dropped his debut solo EP. His set was pure energy from the moment it started and never let up. It was just what I needed as I ventured toward my final Lolla doubleheader of the weekend – Foo Fighters and Alison Wonderland. How can you miss either?

Alison Wonderland made her intentions clear from the minute she stepped on stage and did not disappoint. She delivered one of the best sets of the weekend. See more on Alison’s incredible set and setlist here.

I got to Foo Fighters as Taylor Hawkins performed a Queen cover and Dave Grohl obliterated the drums. I got pretty lucky because the band then played “All My Life” and “This Is a Call.” Dave wished his daughter Ophelia a happy birthday, and then Dave’s daughter Violet joined for a cover of “Nausea” by X. I left as the timeless “Best of You” blasted Grant Park.

Though I went to Foo Fighters, I made it back to Alison Wonderland for two of my all-time favorites, “Church” and “Bad Things.” Alison sang “Bad Things” live, which is always a special moment, before taking over the decks again to close out Lollapalooza’s spectacular 30th anniversary weekend. See Lollapalooza coverage HERE.