48 Hours As A VIP At Lollapalooza

Music festivals don’t get better than Lollapalooza, in my opinion. You’re not trapped in a million-degree desert like Coachella; you don’t have to spend all day on an international flight like Glastonbury; and you don’t have to pretend to like country music like Stagecoach. The Chicago-based concert weekend has always been my favorite music event of the year, and it raised the bar even higher in 2025 by giving me the full VIP experience. Here’s exactly how a VIP wristband can upgrade your Lollapalooza weekend, if you’re considering going for it next year.

After I first got a taste for Lolla’s VIP perks last year, I resolved that it was the only way I wanted to experience the festival from now on. It’s been a decade since I first attended Lollapalooza as a recent college grad in 2015, and although that chaotic experience was memorable, it was also way too much walking, crowding, and craning to try to catch a glimpse of the stage.

This year, Amazon gave me the much-needed upgrade so I could finally see my fave stars Doechii and Sabrina Carpenter in person for the first time. I also got early access to the new Alexa+ to help me plan my schedule, from which stages to travel between to the brand activations giving out the best swag.

In honor of Ms. Carpenter, here’s the short n’ sweet rundown of how my VIP weekend went.

Friday, Aug. 1

10:00 a.m.: Although Lolla technically started on Thursday, I only got passes for Saturday and Sunday, so I didn’t arrive at the airport for my flight to Chicago until Friday morning. This sadly meant I was missing Olivia Rodrigo and Gracie Abrams, but I was too busy focusing on the acts I would be seeing to feel too upset.

3:00 p.m.: I ended up arriving at the Palmer House hotel exactly in time for check-in. My wristbands and Alexa+ were waiting for me in my room, so I started making my plan for the next couple days by asking the powered-up virtual assistant about the show schedules and weather. She would also be my pre-game queen for playing all the artists I was planning to see before setting out each day.

7:00 p.m.: As Lolla was raging on just a couple blocks away from my hotel, I made my way to the nearby Peruvian restaurant Tanta for a rooftop dinner with the Alexa+ reps and other journalists and influencers on the trip. The courses kept coming for hours, but the ceviche was my personal favorite.

During the meal, we all chatted about who we were excited to see over the weekend, and the Amazon reps gave us some helpful tips on new ways to use Alexa+, like booking Uber rides or having her suggest substitutions when cooking recipes.

Saturday, Aug. 2

10:00 a.m.: It was finally Lolla time! An hour before festival gates officially opened, our Amazon reps got us in to get an early look at the Alexa+ activation, which lets visitors decide between entering a “Party” room or a “Chill” room. The party room is covered in mirrors, and bubbles fall as music plays, letting you snap pics while you dance with friends. The chill room offers a vibe reading from Alexa+, changing the room’s color to match your mood.

At the end, there’s a claw machine you can play to win artist merch, Uber rides, Ticketmaster gift cards, and more prizes. Since the lines can get incredibly long during peak Lolla hours, this early arrival gave us the perfect excuse to scope out this year’s layout without a crowd.

4:00 p.m.: There weren’t any acts I was too interested in early on Saturday, but later in the afternoon, I made sure to get a good spot for Marina (née and the Diamonds). The T-Mobile stage’s VIP area had reserved standing room next to the stage, just to the left.

Crucially, this area is also connected to VIP-only drink and food stands, where my friend and I could quickly grab some vodka lemonades between songs with barely any wait at all.

7:00 p.m.: The real reason I was so pumped for Saturday’s lineup had finally arrived. After a short food break, my friend and I hurried back to our spots at the T-Mobile stage for Doechii, who themed her whole set around a school aesthetic, breaking her set into various lessons in hip hop.

The highlight for me was when she referenced her Met Gala umbrella meme by having her dancers cover her in umbrellas, then they revealed JT in a surprise appearance, as the two launched into their collab “Alter Ego.”

As an extra special treat for the crowd, she finished her set by announcing her Live From The Swamp Tour, kicking off this fall.

8:00 p.m.: Here’s where I get to highlight the absolute best part of VIP access: the golf carts. Right after Doechii left the stage, my friend and I walked right over to the transportation line right next to the stage area, and after maybe a 10-minute wait, we were being driven all the way to the other side of the park, right next to my hotel. The perfectly non-stressful ending to a perfect first day of Lolla.

Sunday Aug. 3

11:00 a.m.: What’s a wild night without a brunch recap the next morning? Before hitting up the fest for round two, I met up with my fellow journalists and our Amazon rep at Cindy’s for plates of yogurt, potatoes, sausages, chilaquiles, and of course, mimosas. The rooftop spot had an incredible view overlooking Millennium Park.

Over the meal, I got the lowdown on some activations I missed, like the Tic Tac pop-up that allows concertgoers to customize a pack with their favorite flavors, or Venmo’s offering of charm bracelets you get to make yourself.

3:00 p.m.: I wandered around after brunch and caught a bit of Katseye’s main stage performance — though I didn’t employ my VIP status this time. After bopping around for a bit, I headed out to grab a meal and a shower to be fully prepared for what I knew was going to be the main event later on.

6:30 p.m.: Before hitting up our final shows, my friend and I spent some time chilling at the Jack Daniel’s activation, which had a karaoke stage set up. We entered our names to sing the 2006 classic “Lips of an Angel” by Hinder, but the roster was already incredibly long by the time we showed up in the early evening.

We gave up after about an hour since our next performance was about to start — only to later find out we had been called up just a few minutes after we left. Well, damn!

8:00 p.m.: The karaoke sacrifice was honestly worth it, because we arrived at the Tito’s stage just in time for Rebecca Black. In case you missed the last several years of her career, Black isn’t just the “Friday” girl anymore — she’s been pumping out some serious pop bangers, which her 2025 album Salvation is filled with.

She also loves a controversial aesthetic, taking the stage in a wedding dress while surrounded by faux protesters.

8:45 p.m.: This is when the VIP golf carts really came in clutch. Earlier in the day, we learned Sabrina Carpenter’s set had been pushed forward 15 minutes, so after a good chunk of Rebecca Black’s set on the complete other side of Grant Park, my friend and I beelined for the carts to get to Sabrina’s stage on time.

Thankfully, we didn’t miss a second.

As the sky darkened over Chicago, Sabrina lit Lolla up with silly newscaster and infomercial videos in between her hits. But the most unforgettable element was when Sabrina surprised us all by bringing out Earth, Wind & Fire for some truly party-starting performances of “Let’s Groove” and “September.”

As if having the ultimate dance party with thousands of fellow Carpenters wasn’t euphoric enough, Sabrina closed her set by giving us a little peek at her upcoming album Man’s Best Friend.

10:30 p.m.: The VIP golf carts did it again! We managed to catch the last of the vehicles back to the other side of the festival, and made it back to the hotel in just about a half hour. I used some of the energy I was still carrying from Sabrina’s show to start packing for my flight in the morning. And before I went to bed, I had one final request: “Alexa, set alarm for 7:00 a.m. Play ‘Espresso.’”