Lollapalooza 2025 Was A Music Fan’s Dream

As a Chicago native, I’ve been to Lollapalooza several times — and even while braving August heat or a sudden downpour, I still had a blast seeing my favorite bands and musicians over the years.

However, I was always curious what it would be like to attend as an “insider” — someone who gets the VIP treatment and access to the artists on the lineup. Thanks to T-Mobile, I finally got to live out that dream. From attending meet-and-greets to getting side-stage access to one of Lolla’s biggest acts, this year’s fest — which hosted about 115,000 attendees per day — felt more intimate than any I’d been to before.

Below, 10 highlights from the music-filled weekend.

A Rooftop Happy Hour

I started the weekend at T-Mobile’s Creator Happy Hour event on the Nobu Hotel rooftop. The brand outfitted the space with an assortment of drinks, delicious bites, and goodies. During a tour of their Creator Suite, I got a peek at a fun lounge area where content creators can hang out, play pingpong, film videos, or dress up in vintage fare (courtesy of the Lost Girls shop).

Djo’s “Back In Chicago” Moment

First on my agenda was to check out Stranger Things star Joe Keery, aka Djo, who played to a massive crowd. Of course, once he started playing his viral hit “End of Beginning,” fans couldn’t help but sing along to his ode to Chi-Town.

Olivia Rodrigo Rocked Out

Olivia Rodrigo closed out Friday night with a roaring set list of her hits from Guts and Sour — and surprise guests Weezer. I danced and sang along to “Bad Idea, Right?” and “Drivers License” from Club Magenta — an elevated oasis for T-Mobile’s Magenta Status members where they can relax, sip a complimentary drink, grab exclusive merch, create a customized bandana necklace, and get an incredible view of one of the main stages.

Two Friends Meet & Greet

Between acts, Club Magenta also hosted several Q&A sessions and meet-and-greets with artists from this year’s lineup, like Charlotte Lawrence, Isaiah Rashad, and EDM duo Two Friends.

Two Friends tell me they were excited to partner with T-Mobile because of the chance to have these intimate encounters with fans. “We’ve had fans tell us they drove hours just to see us — and ended up making new friends while waiting in line, which is pretty wild. It’s moments like that that remind us this isn’t just about music, it’s about connection,” they say. “Sitting down and getting personal with fans in such a relaxed setting really makes it feel like we’re all just hanging out. That’s what makes it special.”

Up Close & Personal With Marina

One of the highlights from the weekend was getting side-stage access to Marina’s performance on Saturday. Seeing the indie-pop songstress strut along the stage and singing “Primadonna” and “Are You Satisfied?” against the backdrop of thousands of fans was unreal.

Chance The Rapper’s Surprise Set

After Marina’s performance, I dashed over to Chance the Rapper’s surprise performance. Promoting his upcoming album, Star Line, the Chicago native got fans moving in the summer heat by playing a mix of his hits and new songs. He concluded his performance by asking the crowd to mosh, making for a wild end to a whirlwind 15-minute appearance.

Doechii’s Show-Stopping Performance

One of the most anticipated performances of Lollapalooza lived up to the hype. Doechii proved she’s headliner material with a creative set that paid homage to ’90s hip-hop. She performed her viral hit “Anxiety” and brought out special guest JT for “Alter Ego.” (If you missed it, don’t fret: She announced her upcoming tour, Live From the Swamp, at the end of her performance.)

A Lucky Draw

Fan experiences are a major part of Lollapalooza. Between acts, most attendees will visit various fan activations for free swag, a chance to relax and recharge, or some more fun. Along with Club Magenta, and branded charging stations and lockers, T-Mobile also had a massive Gumball Machine. People lined up for a chance to win cool prizes, including exclusive merch, side-stage access, or aftershow tickets.

Katseye Fired Up The Crowd

A new girl group is in town, and they proved they can slay. Playing to one of the biggest crowds on Sunday, Katseye were red hot (literally). Along with their hit song “Gnarly,” they also performed their new single, “Gabriela,” for the first time live, making their first Lolla appearance a memorable one.

Sabrina Carpenter Closes The Fest

Lollapalooza ended on a high note with headliner Sabrina Carpenter bringing an abbreviated version of her Short ’n Sweet show to the festival for a 75-minute set. Her performance was full of her signature cheeky humor, an appearance by K-pop group Twice, and — most notably — a crowd-pleasing performance from Earth, Wind & Fire, who joined Carpenter on stage to sing “Let’s Groove” and “September.” For her grand finale, she sang last year’s song of summer, “Espresso,” and unleashed a vibrant fireworks display to cap off the fest.