In August I decided to fly out to Chicago for the first time to visit my friend Sydney who had just moved there. Plus, we snagged tickets to Lollapalooza, a festival I’d been wanting to attend for the last few years.
Day 1
My first stop in the city was Bar Siena in the West Loop neighborhood to check out their happy hour and grab a drink with an old friend. I loved the view of the Sears Tower.
Afterwards Sydney and I went on an architecture river tour of the city. I’m super glad we sent it on this activity as it was a fantastic way to see the city and learn more about the history of such a cool place. We found a good deal on Groupon for less than $50 each, I definitely recommend booking this way!
Later in the evening we were wandering around Grant Park when a photographer asked to take our photos. He asked if we were sisters (we get that a lot!)
Day 2
The following day we headed out in the evening to grab some dinner at Umai and enjoyed some champagne and delicious sushi.
Next up it was time for some karaoke - going out with Sydney, who is a theater girl through and through, always means some performance antics are a must. We enjoyed some cocktails and renditions of Sabrina Carpenter at Elements.
After a few ballads we walked a block to Carbon, a club that was hosting a NYX influencer event that my friend had invited us to. I was super excited to attend the party, some influencers from Love Island were coming as well as Chase Infiniti who I loved in One Battle After Another. Plus, we got a bunch of free makeup from the NYX promo!
I loved the DJ’s that played the event and the free cosmos didn’t hurt either. One lesson learned though - influencer events don’t have much of a dance floor. I probably should have expected this honestly, but we made our own dance floor a vibe.
Day 3
Saturday was our first day at Lolla. Unfortunately the day got off to a rough start, with heavy rains flooding the park and delaying the festival start time by a couple hours. Sydney and I are not ones to be deterred, so we snagged some waterproof ponchos and made our way to Grant Park.
The weather cleared up by the time we arrived and we grabbed some drinks and camped out at the EDM stage for the remainder of the night.
I will say, this was the first 18+ festival I’ve been to and I could really feel the difference between that and 21+ festivals. Talk about a lack of concert etiquette! By the end of the night I was exhausted from being pushed around and surrounded by drunk teenagers.
Thankfully we were able to catch a bit of Olivia Dean’s set at the main stage, which had a much more relaxed energy.
Day 4
Our last day of the festival was easily the best. The sun was out, the skies were blue, and we found a much better spot in the crowd to dance it out. Plus, we found a great spot to grab drinks and get some down time that was 21+ and much less crowded.
We met up with one of my friends who was also visiting from Seattle for the festival and joined their group for some more EDM sets. The winning move for this day was dancing at the back instead of trying to get up close and get pushed around.
This trip was a chaotic one but full of fun and was a great opportunity for me to see my friend’s new city and visit somewhere I’d never been. Next time I’m coming back for a deeper dive on the museums, art, nightlife, and food.
Til next time Chicago!
