Lollapalooza 2025 Through Fresh Eyes: A First-Timer’s Experience

After four straight days of attending Lolla this past weekend, all I have to say is it felt like a coming out of a dream and back into reality. Very bittersweet that all the fun had to come to end. Lolla this year had one of the best headliners in my opinion and went above and beyond seeing everyone geek out when they came out to perform. Lollapalooza is a major festival in Chicago has said you need to experience. As a first time, I didn’t know what to expect and after getting advice from folks that attend in the past more than once I needed their guidance. So here is my take on giving first-timers what Lolla 2025 was all about from fans, music and the crazy lines for interactive pop-ups worth the long wait.

Lolla Fans Look Out for Each Other

From outfits to mosh pits, the fans at Lolla didn’t surprise me. In fact, it confirmed my feeling that they come prepared for everything. Need help finding your phone on the ground? Taking a picture with your friends? Or getting water handed out by security? I noticed some fans at certain performances were really helpful.

I thought that if you went to Lolla alone, your chances of getting help would be slim, but that’s not really true. Even the performers checked in with the crowd and asked people to keep some distance while moshing, which is pretty normal at concerts these days.

I talked with a few people at the BMI and Bud Light stages who had been to Lolla before, and they said everyone looks out for the person next to them. If you feel uncomfortable, you can just walk over to the security guards posted near each stage to get help instead of running across the crowd.

I also chatted with a couple of fans of The Marias at the Bud Light stage. They all had clear bags filled with bandages, mini fans, gum, water, and extra socks. Each friend had a bag and shared whatever was needed with each other.

I loved how the performers and their fans dressed to match the vibes, like it was a fashion show. I’m a sucker for cute outfits because it shows they’re really dedicated to the moment.

From Up and Coming to Global Icons at Every Stage

Setting a plan to hit every stage during Lolla week was the most stressful part of the experience. As a die-hard music fan, I wanted to see every act, but I knew it was impossible. I laid out an outline of the artists I wanted to see, and the decisions weren’t the easiest to make. I tried to stick to my plan each day, but it was my curiosity that led me to check out artists I’d never listened to before.

I walked by the BMI stage after hearing catchy beats and discovered the artist performing was Rachel Grae. I’d never heard of her before, but I added one of her songs to my playlist to check out later. I know Lolla is designed to have tons of music playing all day, so I guess setting a plan can help ease the anxiety.

If I could go do it again, I would still outline a plan to see my all time favorite artists, but also room to wander around each day and catch music from artists I’d never heard of a bit more.

Interactive Brand Activations Were Worth the Wait

All the brand activations had a long line to access the experience and while there were a few I really enjoyed checking out, there were some I couldn’t wait too long in. Lolla had more than ten pop-ups all four days everything from photo op display by Popsockets, to rollerblading at Coca-Cola, and even a huge Tic Tac set up that had everyone attention to check out.

I loved the variety of options this year. My favorite was the American Apparel x Sentrock booth featuring a local Chicago artists who’s mural are all over the city. It was also fun seeing everyone geek out over the massive Tic Tac pop-up where everyone were grabbing handful of mints and lining up to snap a photo in the booth. The longer the line the more hyped pop-up everyone had their eyes on to experience.

It was a nice change of pace to take a break from the music and pop-up scene in Grant Park. It’s no joke how people had their friends bring them water and snacks while they waited in line. I didn’t get the chance to check out all the pop-ups since I was mostly interested in getting to check out the music performances. But if a pop-up caught my eye, I couldn’t help but stop and check it out.

Final Thoughts

Attending Lollapalooza for four days, I realized it is not for everyone— and that’s totally okay. If you are someone like me, who sees Lolla as a place to discover new and see iconic artists, you have to go at least once in your life. I spent years not going because I wasn’t prepared, and after going all four days, I still wasn’t prepared but I enjoyed going through it.

Not to burst your bubble, but if you’ve never been to Lolla before, you are never really prepared for it. I went with the mindset of checking out music, and it was so dope to see each artist treat their performance as an epic piece of art. Major love to their efforts, and it felt like a highlight of my summer to see each artist and be in the present, outside the screen, seeing acts like Olivia Rodrigo, Korn, Doechii, and the list goes on.

I can safely say Lolla wasn’t bad, you just need to double down on wearing comfy shoes and carry an extra pair of earplugs.

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