Lollapalooza: Chicago, Illinois

There’s something about a summer road trip that feels like freedom. If you know me, then you know I love road trips—mostly because whittling down my packing to fit into one carry-on and one checked bag is nearly impossible. I need an entire bag for my shoes alone. This road trip was a little spontaneous, a little chaotic, and exactly what I needed. It was a hot girl summer kind of trip. This summer was all about spending time with my friends.

Lollapalooza was the biggest festival I had been to to date. This time, I was not making the trip to Chicago by myself. My best friend Lauren came with me, and we turned it into a full experience. We drove into Chicago the night before the festival on July 30th, checked into our hotel, and from that point on, everything unfolded naturally. No strict schedule—except the lineup. We stayed at SpringHill Suites by Marriott Chicago Downtown / River North. I had stayed at the same hotel during my Saint Patrick’s Day trip, and I chose it again for the included breakfast, the parking garage for my car, and the location. It was a short walk to the festival grounds, which made everything so much easier, especially after long days of walking, dancing, and standing in crowds. It also sits right in the middle of the city, so when we needed a break from the festival, we could easily explore Chicago without going out of our way. It felt like the perfect balance between convenience and comfort.

Where we stayed:

SpringHill Suites by Marriott Chicago Downtown / River North

410 North Dearborn Street

Chicago, Illinois, USA 60654

One of my favorite things about Lollapalooza is that we didn’t have to plan every second of our day. Some days we were running between stages trying to catch specific artists, checking the lineup constantly. Other days, we slowed down. We found a spot, sat in the grass, and listened to whoever was playing until it was time for our favorites. The festival grounds were huge—there was always a new corner we hadn’t explored yet. It was the kind of weekend where some mornings started slow and some nights ended late, and somehow that mix made it even better.

There were so many artists throughout the weekend, but a few stood out. On Thursday, we saw Alex Warren, Tyler, the Creator, and Cage the Elephant. Friday brought Olivia Rodrigo and T-Pain, which felt like such a fun mix of completely different vibes. Saturday, we caught Max McNown and Doechii, and by Sunday, we were fully in the rhythm of the festival, seeing Graham Barham, Landon Barker, and finally Sabrina Carpenter.

Out of everything, Sabrina Carpenter was the moment. The energy, the performance, the way the crowd moved with her—it felt electric. It was one of those sets where you stop thinking about everything else and just exist in the moment. It ended up being the perfect way to close out the festival, and honestly, I don’t think anything could have topped it.

What made this trip even more special was having Lauren there with me. There’s something different about experiencing a festival with your best friend. We had mornings where we took our time getting ready, nights where we stayed out way too late, and moments in between where we were just laughing, walking, and figuring things out as we went. It wasn’t structured or perfectly planned, but that’s what made it feel real. It felt like one of those weekends you wish you could replay.

Most of our meals ended up being festival food, which honestly just comes with the experience, but we did have a couple standout moments. One of my favorites was at The Smith, where we sat down for a real meal and ordered pasta and gnocchi that were rich, comforting, and exactly what we needed after being on our feet all day. We also grabbed sushi one night—something lighter but still so satisfying. Those small breaks from the festival chaos felt just as important as the festival itself.

The Smith Chicago

400 N Clark St.

Chicago, Illinois, USA 60654

We stayed in Chicago a couple extra days after the festival because Lauren’s birthday was on August 4th, and I knew I wanted to make it special. I found the cutest black-and-white cake with the words “a tiny bit older” written across it, which felt very us—simple, slightly edgy, and a little funny. It was the perfect way to end the trip and slow things down before heading back home.

Outfit-wise, I leaned into what I always feel best in—something a little edgy, a little feminine, and still comfortable enough for long days. Flowy black skirts, bralettes, statement jewelry, and of course, my cowboy boots. I will always choose closed-toe shoes for festivals. Between walking to and from the venue, moving between stages, and exploring the city, comfort matters more than anything else.

There were a few things I brought that made a huge difference. LMNT hydration packs were non-negotiable, especially with how hot it was. Staying hydrated completely changes your energy throughout the day. Comfortable shoes are a must, and keeping your bag light makes everything easier. I also always bring my tripod—it’s one of those things I never regret having.

If I had to give advice to anyone going to Lollapalooza, it would be simple. Wake up early enough to eat breakfast, even if you don’t feel like it. Drink more water than you think you need. Wear comfortable shoes. And most importantly, don’t over-plan your entire weekend. Some of the best moments happen when you’re not rushing, when you’re just sitting, listening, and taking everything in.

This trip wasn’t about perfection. It was about saying yes to the moment, spending time with my best friend, and letting everything unfold naturally. It was chaotic, carefree, and a little messy in the best way—and honestly, that’s what made it unforgettable.

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