A Week in Chicago + Lollapalooza

Last week, four of my friends and I crammed into my car and set off for Chicago to enjoy what is probably the best week of my whole year. Lollapalooza is a four day long music festival full of huge artists, great food, and a ton of people. This was my first time back in Chicago since I visited in 2019, so I was excited to be back and get to see more of the city.

Day One

We got to Chicago the day before the festival started, giving us plenty of time to settle into the hotel and enjoy some of the city before we had no more energy left to. We went over the weekend of my friend Lauren's birthday, so we spent this day celebrating her...obviously.


We had dinner at The Smith, which had excellent food, service, and one of the best espresso martini's I've ever tasted. After dinner we stumbled across a country karaoke bar, and if you know me or my friends this is totally not the place for us-- but we had a blast.


The night ended with a walk back to our hotel on Ohio street (Chicago's prized possession,) along the way we stopped at McDonalds for some food and a strawberry shake, then relaxed on the grass hill outside to countdown Lauren's birthday.


Day Two

Day two was day one of Lollapalooza, we woke up relatively early to rotate through the shower and get ready for the day. This day was Lauren's actual birthday, so we stopped at Wake-N-Bakery for some THC-infused breakfast (don't come at me, it's legal there.) After breakfast we caught a Lyft back to the hotel and started walking to the festival.


At the festival, we saw The Wombats, Still Woozy, Tove Lo, Remi Wolf, Ashnikko and Lil Baby. Between the concerts we grabbed some of the best food, churro sundaes, grilled cheese sandwiches with macaroni inside and some seltzers.


When the day of live music was done, we walked back to our hotel and stopped for food along the way. The plan was to hit the hotel, change and go out, but we were all exhausted by the time we made it home so we opted for a good night of rest instead.


Day Three

This day started with a quick hotel relocation, we were only able to have our first hotel for two nights and booked a different one for the rest of the trip. So we packed up, checked out, and hit the road for a quick drive to our new location.


After everyone was ready to go, we headed to Verilife to pick up some goodies and were met with an even bigger surprise. The dispensary was running one of the best PR moves I've ever seen-- if you made a purchase or signed up for their email newsletter you could enjoy a free pre-roll on their sesh bus, stocked with snacks, freebies and water, then head over to a free shuttle that took us to the festival. Of course we jumped at this opportunity to avoid the 30-minute walk there.


To be honest, the bus was terrifying the first day. There was no music, nobody was talking, and we realized we would be extremely easy to kindap and had no clue if this bus was actually taking us to the festival. Spoiler alert, it was.


We got off the bus just three blocks from Grant Park and found a McDonald's for Logan to get his daily strawberry shake. In true McDonald's fashion, their ice cream machine was broken so we headed straight to the venue.


On day three we saw Tinashe, Don Toliver, and MGK, we also heard Dua Lipa preforming past her set on the way out which was a great touch on an amazing night. We walked back home laughing at the water and tee shirt salesmen.


Day Four

After two days of live music, energy was low, so we started the day with a walk to Dunkin' and some light shopping. We hit up Sephora and ZARA, both had wide selections and it was exciting to be able to shop ZARA in person for the first time.


Once we had our caffeine fix, we walked back to the hotel to get ready for our day. We walked back to Verilife to snag our free pre-roll and ride to Grant Park. This trip on the shuttle was much more tolerable than the last, our group was the only one on the shuttle and the driver let us connect to the Bluetooth so that we didn't have to have a silent ride.


Once we got off the shuttle we stopped by McDonald's for another daily strawberry shake, but of course their ice cream machine was still broken. So on we went.


We saw Surf Mesa, Lil Durk, Wallows, YG, Big Sean, Kygo and J. Cole. J. Cole's concert was by far my favorite, and honestly the one artist on the lineup that made me buy my ticket.


Day Five

At this point it felt like we were re-living the same day over and over. We walked to Dunkin' again for breakfast and coffee, then walked back to the hotel to get ready for our last day at Lollapalooza.


We walked our usual route to Verilife for one last ride and avoided the McDonald's after multiple failed attempts to hunt down a strawberry shake.


On the last day we saw Kenny Hoopla, Charli XCX, PinkPantheress, Dominic Fike, Green Day and Denzel Curry. My favorite show from that day was Denzel Curry, even though I had never heard one of his songs prior to the concert. My friends and I sat down at his set to eat and ended up enjoying the music so much that we ditched our food and headed into the crowd.


We walked back to the hotel one last time and gathered some of our things to make checkout easier the next morning.


Day Six

On the last day we woke up early enough to enjoy the free hotel breakfast and pack up the rest of our things. We were all extremely tired by this point and got a late checkout so that we could hangout and relax for a bit longer.


After we checked out we stopped at Ēma, a Mediterranean restaurant, for lunch. They had amazing food and the outdoor seating was nice, clean and relatively quiet. Once we ate we drove out of the city, stopped for gas and food then drove back home.


Want to see more about my trip? Head to my Instagram for photos and videos of my time in Chicago.