Sabrina Carpenter, Martin Garrix, Katseye Close Lollapalooza 2025

The summer of 2025 has brought sweltering heat, pummeling humidity and the seemingly constant threat of storms to the city of Chicago. But all of that went on hiatus as Lollapalooza arrived in Chicago last week to celebrate its 20th year as a destination festival, with a mild weekend in the upper 70s providing fans the perfect weather in which to indulge in the American installment of what’s become arguably the strongest global brand in the festival sphere.

Argentinian guitarist Ivan Singh headed to Chicago just four years ago with little more than a cigar box guitar, racking up local gigs at iconic Windy City blues clubs like Rosa’s and Legends since.

Last week, Singh, 26, was joined on stage at Legends by venue owner and iconic Chicago bluesman Buddy Guy just a few days ahead of his 89th birthday and appeared in Grant Park throughout the weekend to perform as part of Hulu’s online livestream of Lollapalooza, showcasing his scorching guitar playing as both Hulu and Lolla embraced arguably Chicago’s most famous musical export: electrified blues music.

“I’m really grateful to the Hulu team. Because they wanted to include something representative of Chicago. And I was blessed enough to get the call,” said Singh, providing viewers of the stream live blues between each set. “Honestly, playing blues, being in Chicago and having the chance to share my own Latino way? My experience playing blues at Lolla has been great.”

For Singh, performing during the Hulu stream put an unprecedented amount of new eyeballs on his playing, showcasing his prowess to fandom across a variety of genres. Prepping the release of new music, he wears a number of hats as a versatile independent artist.

“I’m my own producer, my own manager and everything. And, you know, you’ve got to make things happen. I try to do the best I can,” said the guitarist of navigating life as an independent musician. “I’ve only been here for four years. This is also a different cultural language for me as well,” Singh said. “I actually just recorded three new songs. They’re done. I’m hoping to at least put them out before September or October.”

Amidst the rise of the internet, online streaming has quickly become the primary source of consumption for music fans, upending the sale of physical media over the course of the last 25 years.

As that’s made it harder and harder for artists to monetize recorded music, most have been forced to look to the road as the primary musical revenue stream.

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But emerging from pandemic, the ability to generate income via touring and live concerts has also become harder, with elements like inflation and venue merch cuts leaving a slimmer profit margin for artists out on tour.

While it was anathema for an artist to partner with a brand 20 or 30 years ago at the height of the major label system, today, such partnerships aren’t just common, in many cases they’re critical.

“You know, Crown Royal and I kind of have a little bit of history now. We’ve been together for about a year. I feel like we’re in a relationship,” said country singer songwriter Tanner Adell with a smile on her brand partnership with the whisky maker. “As an independent artist, they came in and said, ‘We want to support your first tour.’ This was my first headlining tour and it went amazing. Now we are renewing our vows and doing a second tour together.”

In addition to a set on the Lollapalooza main stage Friday night, Adell helped close up the festival late Sunday, appearing at the Ramova Theatre on the city’s south side as part of Crown Royal’s “Pancake Palace” pop-up, one which fed concertgoers whiskey driven appetizers as Sunday gave way to Monday while shining a spotlight on the company’s new apple, peach and blackberry flavorings.

A collaboration between Crown Royal and Juicy Couture on a branded tank top benefits Women In Music. And the unique parallels that exist in the creative approach to both songwriting and mixology were on full display throughout the event.

“It’s super cool. I think it’s the way in which they brought worlds together - you’ve got Tanner performing which is exciting. And I’m a big whiskey guy myself,” said reality star Miguel Harichi, who appeared in season six of Love Island USA and took part in Sunday’s pop-up alongside Adell. “I used to be a mixologist, used to be a barman. And now I’m still making cocktails. At parties, at functions, I’ll be throwing it down in the bar. So, I think it just made sense.”

Tour support is a crucial element for any artist, with corporate partnerships helping to foot the bill. For Adell, the collaborative endeavor continues to pay dividends.

“Being an independent artist makes so many things that are dreams and goals that you have very difficult to attain. And going on tour is really hard to do as an independent artist,” explained the singer, who released her debut full length album Buckle Bunny in 2023, appearing on Beyoncé’s Cowboy Carter album a year later. “For me, live shows are my favorite thing. Being on stage is the reason that I am here,” said Adell. “It makes me feel like, ‘OK. When it’s my turn to give back to a smaller artist, I’m going to remember these times and how someone took a chance on me.’”

Singer and rapper Isaiah Rashad took to the stage of the Riviera Theatre on the city’s north side for a Saturday night aftershow ahead of a one hour performance on the festival’s T-Mobile north main stage Sunday.

Partnering with the telecom giant, Rashad interacted with fans on site at T-Mobile’s “Club Magenta” installment during a Q&A session, a great example of the way corporate sponsors vie to provide concertgoers (and customers) a unique experience on site at festival activations across the country.

“The aftershow was fire,” said Rashad prior to his performance. “I’ve been in dad mode since yesterday. I’ve been kicking it with my baby. We’re excited to see Katseye and Sabrina Carpenter and Dominic Fike,” he said. “But this is one of my first corporate things, first corporate brandings, that I’ve done. It kind of validates me, makes me feel like I’m heading in the right direction.”

While some artists seek corporate partnerships as a way of financing and exposing their music to a wider audience, others continue to choose reality television.

New Jersey-born singer songwriter Carol Ades appeared in season five of NBC’s The Voice in 2013, releasing a pair of EPs after.

“When I was on The Voice, I was 17. I think when you’re 17, you’re just way more confident than you are at 29. You’re like delusionaly confident,” said Ades with a laugh. “So, I think it was really so valuable for me to have that experience then and be like, ‘Oh, I can do anything. Nothing’s real. Whatever. Just show up and try it.’ Especially now that I’m a little bit older and wiser - and dumber because I’m older, you know what I mean?” explained the songwriter with a smile. “But I have that to look back on and be like, ‘Yeah but you did that thing! You can do anything.’”

Last September, Ades released her debut full-length studio effort Late Start, recently embarking upon her first headlining tour, arriving in Chicago for a 40 minute set Friday night on the BMI stage.

Having recently collaborated with artists like Kesha, Ades is able to apply what she’s learned from the collaborative efforts as she hones more new music of her own.

“I think the main thing I learned from writing for other artists is just that no idea is bad. Just ideas, ideas, ideas,” she said. “Because it could be for me, for Kesha, for someone else - and the process is just so fun when you let it be fun and you don’t overthink it. They’re just songs. So, just have fun with it.”

Pennsylvania-born hip-hop duo Joey Valence & Brae took in Lollapalooza 2024 as fans but arrived in the Windy City as performers this year, rolling through a 45 minute set Sunday on the Grove stage.

“We got to Chicago last night and did the afterparty show at midnight - woke up, came here. We love Lollapalooza, love Chicago. It’s the best. Ready to party!” said Brae backstage prior to the duo’s set Sunday. “We’re gonna go see A$AP Rocky!” added Valence excitedly.

Following the release of their second studio album No Hands last summer, Joey Valence & Brae are set to drop their major label debut Hyperyouth August 25 via RCA.

“It’s just good,” said Brae with a smile. “It’s gonna be a dance album. You’re gonna laugh, you’re gonna cry, you’re gonna dance, you’re gonna bounce. That’s all. Get ready to party.”

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For fans looking to continue the party, aftershows take artists from the massive festival stage into the more intimate club environment of venues across the city, with headlining performances beginning somewhere around midnight.

While his set was a highlight on day four at Lollapalooza 2025, FINNEAS took advantage of his Saturday night aftershow, highlighting a special guest.

“So, Ashe and I, in secret the last two years, made an album together,” he said welcoming the singer songwriter to the House of Blues stage while setting up the pair’s new single “The Hudson.”

Ashe handled piano on “The Hudson” with the duo further offering up their 2021 collaboration “Till Forever Falls Apart,” with their new album The Dream due September 19.

Opening the aftershow solo on piano FINNEAS navigated “Starf–er,” picking up an electric guitar as the House of Blues floor began to shake soon after, with the five piece backing band joining in as fans hopped along in time during a spirited take on “Lotus Eater.”

“Chicago, thanks for staying up late with me. I appreciate you!” said FINNEAS detailing fond moments spent at House of Blues, like watching Sabrina Carpenter perform in 2023 and supporting his sister Billie Eilish on stage at the venue in 2013. “This is a long day! I appreciate you being up in the wee hours!”

17 year old Chicago rapper Star Bandz performed at Lollapalooza on Friday with the Chicago Youth Symphony Orchestra offering up an unparalleled Lollapalooza performance Saturday night. Lollapalooza’s spotlight upon young, local talent continued Sunday via the embrace of large ensemble The Happiness Club.

The Happiness Club offers a performing arts education program to Chicago youth between the ages of 8 and 18 free of charge, providing camaraderie, purpose and leadership while helping kids to embrace the idea of responsibility.

“It’s a really unique experience that, I think, changes their perspective on what’s possible for them,” said Artistic Director Tanji Harper, who’s been with Happiness Club for over 20 years. “We’re literally backstage at one of the biggest rock concerts that happens in all of the world. So, for them to be exposed to stuff like this at such a young age, it just brightens their whole world up to what’s possible for them later. And they don’t have boundaries or limitations on what they think they can do or what they think they can accomplish. They’re wide open now,” she said.

“We have great teachers. They learn rap, hip-hop, dancing, and singing. We have a vocal director. They write their own songs. All of that’s great,” added Maureen Schulman, board president of the not-for-profit. “But it also instills a lot of confidence and a strong work ethic. And I think that whether they go into the arts or not, it really helps them be successful after The Happiness Club.”

The Happiness Club offered up a pair of the weekend’s most resonant Lollapalooza performances Saturday and Sunday on the Kidzapalooza stage, collaborating with bassist Divinity Roxx (former bassist and musical director for Beyoncé), who took to Kidzapalooza prior to their set, encouraging the youth ensemble.

“We create songs about social issues that they go through. Mostly positive stuff: things that help them cope with stress or bullying at school or their self-confidence,” Harper explained. “A bunch of kids getting together to sort of talk about issues that they go through on a daily basis. And then we make the music. And then we go out and we tour the songs anywhere anybody will let us,” she said. “We try to keep it upbeat, a fun show - so that everybody is in on it. And we get complete buy in from the young people that hear it. It’s positive and it’s uplifting.”

K-pop adjacent L.A.-based pop group Katseye proved to be a hit during a highly-anticipated 45 minute performance on the festival’s north main stage Sunday, one delivering an equally uplifting message of connection during divisive times.

Touting American, South Korean, Swiss and Filipino members, Katseye sing primarily in English with a clear goal not just for their Lollapalooza performance but the path forward following the release of their second studio album Beautiful Chaos earlier this summer.

“We’ve been a girl group for only a little over a year. And hitting these milestones is insane,” said Manon backstage prior to the set. “It’s been a super exciting weekend so far. We’ve had lots of fun. And we are all super, super thrilled about [the set]. It’s going to be the biggest thing we’ve done in our career so far. I think we just want to inspire - especially young girls out there - to chase their dreams and put in the work and show that it really pays off,” she said.

“I think that we have always tried to have a touch in our music that can resonate with any age group, all different cultures and people from around the world,” added Lara. “Especially because we are all from different places, we try to incorporate a little bit of our individuality and cultures into everything. But, also, when it comes to ages and stuff like that, we really want Katseye to be a universally loved group rather than just for this demographic,” said the singer.

“We have been working so, so hard, rehearsing every single day for this moment,” added Daniela. “We’re going to be doing new things that people haven’t seen yet. So, we’re very excited to show that off.”

A quieted hush fell over the crowd Sunday as an introductory video rolled on screen, alerting fans to the imminent arrival of pop star Sabrina Carpenter, who would perform for over an hour opposite rapper A$AP Rocky and Dutch DJ and producer Martin Garrix as Lollapalooza 2025 drew to a close in Chicago.

“I feel so grateful and so honored to be here, Lollapalooza!” said Carpenter early in Sunday’s set. “Thank you for bringing me back. Make some noise for all of the artists that performed this weekend!”

Carpenter was the epitome of poise, delivering an energetic and entertaining performance on stage while controlling the moment with a quick wit between songs.

Carpenter conjured up images of Fleetwood Mac’s “Seven Wonders” via the rewarding pop rock feel at the heart of “Taste” second in the set, with a series of videos continually localizing the Lollapalooza performance for the Windy City faithful.

Acoustic guitar drove “Coincidence” as Carpenter crouched down with a tambourine early, with the video screens showing members of TWICE in attendance during “Juno” later.

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But the real surprise lay in Carpenter’s handpicked guests, as Chicago-born R&B/funk legends Earth, Wind & Fire arrived for a bit of a homecoming celebration alongside Carpenter on the Lollapalooza stage.

“Chicago, the first time I played here it was to a room of 300 people,” said Carpenter incredulously, looking back. “Now, because of you guys, we get to play this one,” she continued. “I just thought it would be fun if we could bring some friends out!” she exclaimed, introducing her iconic guests.

Moving from “Let’s Groove,” a funky, rollicking bassline soon drove “September,” with Philip Bailey smiling through a killer early vocal as the ensemble worked in a snippet of The Emotions’ 1977 hit “Best of my Love.”

Nearby, fireworks and pyro soared as Garrix worked up the crowd over 75 minutes on Perry’s stage.

“I played Ibiza Thursday night. Friday night and Saturday was Las Vegas and then today in Chicago. Tonight, I fly right after the show to Utah,” said Garrix, racking up frequent flyer miles in the run up to Lollapalooza. “I remember the first time I came here. And I was just mindblown by the size of the festival - by the energy, by the crowds. And just the skyline,” said the DJ, looking back upon Lolla Chicago sets in 2014 and 2016. “What I remember the most is that I walked on stage and it felt so surreal. You’ve got the crowd of people and then the skyline in the back. Really special.”

For Garrix, the process of collaboration is a rewarding one which found him working with songwriter and producer Lauv on “Mad” earlier this year while teaming with AFROJACK, David Guetta and Amél on “Our Time.”

Collaborating with Dutch DJ and producer Armin van Buuren and vocalist Libby Whitehouse, Garrix is set to release his latest single “Sleepless Nights” this Friday, August 8.

“Any collaboration, I’m learning so much from the people that I collaborate with - from the production point of view or the songwriting point of view,” said Garrix Sunday backstage at Lollapalooza 2025. “I love Armin. I’ve known him since forever. So, it was just a matter of time until we ended up doing a song together. And Libby was incredible,” he said. “We recorded with her in the studio. We wrote the bridge together. And just the whole song has been fun. It’s my first trance song ever. My first song at 138bpm,” Garrix explained. “So, I’m excited to play it tonight.”