story / Bri Ng Schwartz
photos/ Lauren Nakao Winn
Chicago’s Lollapalooza 2025 brought fans across genres and generations together for this weekend to remember. LADYGUNN caught up with pop-girls on the rise and K-POP idols that dominated the festival lineup, and enjoyed sets from viral artists and friends of the magazine whose stars are shining brighter than ever before.
Day 1
We began our weekend with friend of LADYGUNN Jade LeMac, who we met in November. Lollapalooza marks her US festival debut, as she prepares to head out on the road with Marren Morris on her upcoming The Dreamsicle Tour. We talked about what she’s been up to since we last spoke.
Jade LeMac
“I did my first mini headline tour in May, and I’ve been working really hard on this new EP that’s going to come out in the Fall. My first single off of it, ‘Running Home’ comes out on August 15th. It’s been one of my favorite songs to perform live. It’s so upbeat and gets the crowd’s hands up.”
On the topic of other songs she enjoys performing live, Jade says: “Watching how the crowd sings my biggest song, ‘Constellations’ is always such a mind blowing experience.”
Jade’s Chicago debut was marked with three performances: opening the Tito’s Vodka stage, an afternoon at the Toyota Den, and opening for another friend of LADYGUNN, Role Model at his sold-out aftershow at Pilsen’s Thalia Hall.
Role Model by Chad Wadsworth, Lollapalooza
Tucker proved that he’s come a long way from the boy-next-door we met in 2022. The “Sally, When The Wine Runs Out” singer has festival-goers packed like sardines – far too crowded for Tito’s Vodka Stage alone, proving he may be ready to headline the festival in the near future.
Following ROLE MODEL’s set, fans ran to the T-Mobile stage for starlet GRACIE ABRAMS. The whole festival could hear fans singing her dance hit “Close To You” and leapt with excitement upon bridging Robyn out as a special guest for 2010 classic “Dancing On My Own.”
South Korean rock band XDINARY HEROES headlined The Grove stage in the evening, proving that Korean musical influence extends beyond pop. Watching members Gunil, Jungsu, Gaon, O.de, Jun Han, and Jooyeon brought me back to my days of watching bands like Mayday Parade, A Day To Remember and Pierce the Veil play Warped Tour.
Tyler the Creator by Roger Ho, Lollapalooza
Also closing out night one on the T-Mobile stage was Tyler The Creator. Fresh off his Chromokopia tour, debuting his new dance album Don’t Tap The Glass, he’s the only artist on the festival lineup to have his own merch booth and installation. I look forward to his continued artistic longevity and impact.
Day 2
Day 2 kicked off with Top Dawg’s newest signing, Alemeda. Her pop-rock R&B fusion started the day at a ten, with “Alemeda Army” bringing the energy to the Tito’s Vodka stage. We got the chance to meet this rising star following her performance and talk about her recent tour with another pop-rock divaRachel Chinouriri,her signing with Top Dawg, and her upcoming run of festival dates.
“Rachel’s tour was my first ever real tour, the first time I’ve performed that many times consistently. Rachel has such an accepting, loving fanbase. Top Dawg has brought me so many opportunities to tour and do these festivals. Everyone on that roster inspires me. I’ve collabed with a lot of people and we’re just one big happy family.”
Alemeda
When asked where she’s most excited to travel on this run of festival dates, her answer was a no-brainer: “Paris for Rock En Seine. I have to go straight to Cafe Charlot when we get there. I don’t even want to go to my hotel. I’ll take the bags.”
Alemeda, with her unique sound and already dedicated fanbase, is sure to follow in the footsteps of her Top Dawg family members.
Later in the afternoon, The Dare brought electricity to The Grove stage. His viral hit “Girls” had the crowd on the ground bouncing beneath me. His presence alone behind sunglasses had us captivated, and in Chicago fashion he closed his set with a shot of Malort.
Being back in Chicago, we felt it at sunset for Djo’s set at the T-Mobile stage. Having spent his college years in the city, followed by his Stranger Things stint, he had the audience of natives, transplants, and visitors alike nostalgic for other versions of themselves with “End of Beginning,” made popular from FX/Hulu’s The Bear.
Closing out the Friday at the T-Mobile stage was our favorite pop-rock princess Olivia Rodrigo. Keeping to her GUTS Tour and festival run tradition of bringing out musical legends as special guests, Weezer joined her onstage for a duet of crowd favorites “Say It Ain’t So” and “Buddy Holly,” making it a night to remember for the Gen-Z and Millennial audience members.
Olivia Rodrigo by Kirby Gladstein, Lollapalooza
Day 3
Starting the day off at the Bud Light stage was JYP Entertainment’s fresh-faced KickFlip. The self proclaimed “little brothers” of TWICE prepped K-Pop fans camping out at the Bud Light stage for their seniors by putting their own spin on TWICE hits “Feel Special” and “Like OOH-AHH.” We got to know Kyehoon, Amaru, Donghwa, Juwang, Minje, Keiju, and Donghyeon for what was a majority of the members’ first times in Chicago. After months of prep for this performance, they reflected on the experience with us.
“It still feels a bit surreal,” says Minje. “We practiced a lot, and we’ve always wanted to perform on this kind of stage. We finally succeeded in that goal, so I really want to say thank you to Lollapalooza.”
Building on that, Kyehoon paid homage to their labelmates and got us excited for TWICE later in the evening.
KickFlip
“It’s truly an honor for us to be here at Lollapalooza Chicago as one of the teams representing JYP. It’s such a huge moment, and we know it was only made possible thanks to the amazing artists who came before us and paved the way. We’re really looking forward to watching the stage of TWICE sunbae-nim later and learning as much as we can from their stage.”
Later in the afternoon, a diverse crowd of festival-goers agreed after Doechii’s intricately staged set, it was her weekend. Creating a storyline with her jumbotron visuals, everyone in the audience got a show regardless of their proximity to the stage. She brought out JT for their song “Alter Ego,” made a callback to her viral umbrella moment pre-Met Gala, and brought elaborate choreography throughout. Her set also marked the official announcement for her upcoming tour, Live From The Swamp. She proved to us that she is more than a YouTube actor and has been set free from making TikTok music alone. Her upcoming tour is sure to be historic.
Doechii by Roger Ho, Lollapalooza
The highly anticipated TWICE headlining set on the Bud Light stage was a fireworks show in more than one sense of the word. With booming vocals from all, the power in their performance shined through with high-notes, ad-libbing, and synchronicity in their choreography.
TWICE
In some ways, it felt like the whole weekend was leading up to this moment, from TWICE ads taking over bus stops, limited-edition desserts from Magnolia Bakery, and a K-POP Demon Hunters activation where TWICE fans could sing songs from the hit Billboard charting soundtrack on a double-decker bus. One thing is for sure: TWICE walked away from their set stealing the hearts of an all new, American fanbase.
Day 4
Bringing the energy to the final opening performance on the Bud Light stage was UK rising pop-princess flowerovlove. Starting the day with the campiest of energy, she emerged from a yellow purse. Enamored with this choice, reminiscent of Chappell Roan emerging from an Apple bong for her 2024 Govball performance, I asked her how this choice came to be:
“It’s about what the history of bags mean for women.” She says. “It’s not just a cutesy accessory. You carry your whole life in your purse. It’s about me, my whole life. I’m in my bag!”
Having opened for festival headliner Olivia Rodrigo and Halsey on their UK tour dates, floweroflove shares what she’s learned from these respective artists:
“Watching Halsey inspired me to have dancers in my set. I’ve always wished to be in a band. I want friends on-stage! They hype you up. Halsey had her dancers dance around her in a ring, and I did that in my set as well. With Olivia, I learned more about crowd interaction. She’s so good at it.”
flowerovlove
What’s next for floweroflove? She left me with three words:
“Get a seatbelt.”
Consider us strapped in!
It would be impossible to discuss rising pop-princesses without talking about KATSEYE, the global girl group taking the world by storm. The group consists of femme powerhouses Daniela, Lara, Manon, Megan, Sophia, and Yoonchae, who represent various countries from across the globe. We asked them what it means to be a global girl group in 2025, and they were quick to leave us with words of inspiration.
KATSEYE
Daniella shared, “I think it’s an honor to represent each of our own distinctive countries.”
“Being a global girl group in 2025 is what the music world and world at large needs.” Sophia added. “A lot of people these days, especially us as women outside of KATSEYE, love to see that kind of representation. We love to see women be successful and create something beautiful and inspiring to young girls. To be the ones doing it is the highest honor.”
Their mid-day set pulled one of the largest crowds of the weekend. They stole Sunday with their debut performance of their newest hit single “Gabriella” which brought the heat with a new arrangement featuring cuban-tones and choreography. Daniella closed the song thanking the audience for allowing her to share her culture through this performance, which brought proud tears to our eyes. The set was sure to be a career defining moment for the group.
Friends of LADYGUNN Remi Wolf and Rebecca Black also helped close out the magical weekend, with Rebecca doing both a DJ set and vocal performance, stapling herself as a queer club pop hybrid here to stay. Remi’s trippy visuals and cover of Rascal Flatts’ “Life is A Highway” brought the energy up for the mid-day crowd, gracing us with her upbeat bops and quippy audience interactions.
Sabrina Carpenter, Lollapalooza
Our favorite “pint-sized princess” Sabrina Carpenter closed out the weekend with her 1960s Cable TV inspired set. Our favorite TWICE girls made an appearance for Sabrina’s tour tradition of handcuffing celebrity audience members before performing “Juno.” She also brought out legendary Chicago act Earth Wind and Fire collaborating on hits like “Let’s Groove” and “September.” This surprise performance defines what it means to have hits that remain viral for decades and across generations
We look forward to seeing how Lollapalooza will build on the success of this year’s K-Pop takeover, and which upcoming artists continue to rise to fame following their 2025 debuts. We’re sure our friends from past features will continue to dominate the charts and prepare to headline future festival lineups.