H4H Travels: My first trip to Chicago and Lollapalooza

August 11, 2015

I’ve never been to Chicago. And I’ve never been to Lollapalooza. I can now check both of those items off my bucket list.

Last week I headed to the Windy City for my first (and hopefully not last) Lolla experience. It was an incredible 5 days and I definitely made the most of it. Here are some of the highlights…

Day One: Exploration Day

My first thoughts driving into downtown Chicago from the airport was “Wow. This city is huge.” I am a native Houstonian, so big cities aren’t new to me. But this was different. I was definitely in awe.


The first stop was heading to my temporary home for the next few days, the Loews Downtown Chicago hotel. It should be noted that this is a brand new addition to Chicago. And boy was it beautiful. The lobby was a gorgeous mix of an industrial and chic looks. My favorite part was the Chicago skyline made out of wood.

I could see the Chicago River from my room, which was pretty cool. They did a great job of making their rooms comfortable. I slept really well every night…which was nice because I am usually a terrible sleeper. The bathrooms were larger than I was expecting from a hotel, too. And the walk-in shower was my best friend after a day of walking around and being outside.

After checking in at the Loews, I headed up to Ravenswood (I learned that Chicago is navigated by neighborhoods) to the Foundations of Music office. They recently moved into a sweet new office…an old warehouse turned into commercial/retail spaces. It was awesome to meet the team. I was so glad I was able to do that while I was in town. They also gave me some amazing recommendations of places to see and eat at while I was in town.


To get back to the hotel, my friend and I took the “L” train to get a real Chicago transit experience. I’m not gonna lie, it was kinda fun. In Texas we drive ourselves everywhere, so it was cool to do something a little different to get around town.

That night, we kicked off our weekend of music by heading to Lincoln Park to get some local food and see Cold War Kids play their Lolla warm up show. It was an awesome show. The venue was small, so there wasn’t a bad seat in the house. The opening band, Coasts, is also my new favorite band.

Day Two, Three and Four: Lollapalooza

It was finally here.  I’ve been to Austin City Limits Music Festival (ACL Fest) so many times, I am now an ACL vet. But I have never been to Lollapalooza. I can’t describe how excited I was about going to Lolla. The next 3 days were jam packed with great music, sun, meeting new people…and walking. Lots of walking. For my fellow Fitbiters, I was walking between 17,000-20,000 steps a day.


My first impression of Grant Park was similar to my first impression of Chicago…it was huge. The interesting thing to me was that the size of the park is actually smaller than Zilker Park (where ACL is held) but it was longer, so it felt so much bigger. I loved that it was right in downtown Chicago, so there was a beautiful skyline in the background.

We got out there pretty early on Friday to scope things out before checking out some bands. My favorites of the day were Coasts, James Bay, St. Paul and Broken Bones, Hot Chip, Alabama Shakes and the legendary Sir. Paul McCartney. Side note: I did not bring sunscreen the first day…that was a big mistake. By the end of the day, I had a lovely sunburn.


On Saturday we explored Chicago a little before heading back to Grant Park for round two. The sun was still blazing, but I was smart and brought sunscreen. My favorites of the day were the Tallest Man on Earth, Elle King and Sam Smith. We were able to get really close for Elle King and that was so so cool. She killed it.

By the time Sunday rolled around, it was a little cooler. But that meant rain was coming. We got out there early to see fellow Austinite (and KING supporter) Shakey Graves play…but towards the end of his set they started to evacuate the park due to bad weather. We jumped in a cab and headed up north to check out the John Hancock building to get a birds eye view of the city. About an hour and a half later, the weather had passed and they reopened the park. The really cool thing was that they didn’t cancel anyone. Instead they just moved set times back a little and everyone played a shorter set. That was awesome. Favorites from Sunday were Julia and Angus Stone, Of Monsters and Men and Florence and the Machine.

Day Five: Back to Austin

It went by so so fast. But it was such an awesome experience. I didn’t want to head home. After grabbing breakfast, we quickly checked out out Navy Pier. Then it was time to say goodbye to the Windy City and head back to Texas.

11356627_398630743659041_1154602465_nWhile we totally underestimated the security lines and missed our first flight, we had a surprise while waiting for the next one. We heard a bunch of cheering and folks chanting “U-S-A” towards one of the gates. It turns out it was some of the athletes returning home from the Special Olympics World Games in Los Angeles. They held up their medals proudly as they passed by everyone cheering for them.

That was a very special thing to see. We work with Special Olympics Texas and we know how hard they work to get to the World Games.

Thanks for such an amazing time Lollapalooza and Chicago. Until we meet again…