Jim's 13th Birthday Trip: Lollapalooza

Jim & Sam went to Chicago in July of 2026 for Jim's 13th birthday trip. Jim has gotten really into music over the last few years, so it’s not too surprising that he chose to go to Lollapalooza, a 4-day long music festival in Grant Park in downtown Chicago. The map doesn’t really capture how huge Grant Park is. It was well over a mile from one end of the festival to the other.

Here was the lineup: 

Jim and Sam left out of the Columbia Regional Airport the morning before the festival started to give them some time to hang out in Chicago.

Sam, being the planner he is, secured a hotel right across the street from Grant Park before tickets were even on sale when prices were still closer to reasonable. This is a photo of the hotel at night.

The room was nice and bright and wasn’t too loud.

This shows people headed away from the festival and into downtown Chicago after a long day.

Jim and Sam’s first stop after taking the “L” from the airport was to walk to Willis Tower. They bought the City Pass, which turned out to be a great value and gave them express entrances to some of the attractions.

Afterward, they walked to take an architectural boat tour. Jim was super impressed with a building he recognized from a Wilco album cover.

Here is Jim enjoying the boat ride (and he talked Sam into buying him a Shirley Temple)

The next day, they had a very full day of music and walking. Sam took a photo of every band they saw. Some artists had a few dozen people in the audience, while others had tens of thousands.

Kim Theory (the first of the punky/riot girl sets we went to)

Know Good (the only DJ set we went to)

Bad Nerves (a punky band from England)

SB19 (a fun boy band from the Philippines)

Between Friends (a pop band)

Chalk (a really good industrial band that we were lucky enough to get center barricade for)

Sombr (a really good pop/funk artist who put on a great show. This was the first of the huge crowds we were a part of).

Lord (she put on a great show to close out the night)

According to Jim’s phone, they walked over 10 miles on the first day. They were a little sore, but luckily got a good night’s rest and were ready to start day two.

They started their day with a free Ferris Wheel ride.

After that, it was another full day of music.

Ben-O (kind of generic pop rock)

Party of Two (a good rap group)

Jim enjoying their set.

Slayyyter (a mostly pop act with elements of heavy metal).

Mother Mother (a great rock band that Jim and Sam and Amelie have seen before in St. Louis)

Zara Larsson (a pop act with lots of dancing)

Smashing Pumpkins (they had most of their original members and sounded great)

They brought out Olivia Rodrigo for one song!

The next morning, it was raining quite a bit, so the start time of the festival got pushed back a few hours. This gave Jim and Sam the opportunity to visit the Chicago Museum of Art, which was also very close to the hotel.

The day started a little late, but they still got to see most of the acts Jim was looking forward to.

Die Spitz (a punk/riot girl band)

Wolf Alice (a pop/rock band)

Clipse (a rap group that Jim was really into)

Jim and Sam before Clipse played

Frost Children (a pop/dance band)

Ethel Cain (we could only hear her and see her on the video screen while we were waiting on another artist to play)

BBNO$ (a rapper who put on a very energetic performance)

Jennie (a pop star from South Korea)

For the last morning of the festival, we walked to the Adler Planetarium before the music started.

Jim enjoyed seeing Lake Michigan

Water in Your Eyes (an artsy punk/riot girl band)

Winderhorse (a good punk band)

Yoasobi (a really fun popish group from Japan)

Turnstile (A hardcore band that we managed to get a really good spot for)

Ado (an amazing singer from Japan who does not allow photography. She only shows her silhouette, but you could see her band members).

The next morning, Jim and Sam went to the Shedd Aquarium before getting back on the “L” to head for airport.

Shedd aquarium:

Jim got to pet a shark: 

Souvenir hat:

Overall, it was an amazing trip! Four days of music was a whole lot, but Jim and Sam made some amazing memories in Chicago.