My Lollapalooza Travel Diary

I’ve been hitting up music festivals for over a decade. As a music festival veteran, and on the brink of 30, I thought it was about time to hang up my festival fringe… but not without one last hooray. And OK I still might go to Coachella if the situation presents itself… but I’ve spent enough time / energy / money / footsteps at music festivals.

So, Cassondra and I decided to pack our bags and head to Chicago for Lollapalooza. This festival crossed off a lot of firsts: my first time to Chicago, to the Mid West, and to a four day festival. FOUR DAYS. It was a lot. The festival started on a Thursday and went through Sunday. We arrived Thursday mid afternoon and made it to our hotel and out the door just in time to catch Lana Del Rey.


The beauty of Lolla, compared to other festivals, is that you don’t have to commit to the festival all day. In fact, we used the mornings and afternoons to explore the city, and reserved our early evenings for the festival. Most of the artists we wanted to see started around 6pm, which gave us a full day to do things like the beach or the museum. Also, they allow up to 3 in-an-outs each day, so you have the option to check out an early band, leave for the afternoon, and come back at dusk. The headliners each night have to end by 10pm (otherwise, they get a $10,000+ fine) so we even had time to grab a late dinner and/ or drink in the city afterwards. Although I will note that Radiohead said FU to the rules and went into overtime past 10pm to play “Creep.” It was awesome.

I must say, I wish I had discovered this festival years ago. It’s much more laid back and not nearly as scene-y. And despite the sheer size of Lollapalooza — 400,000 people!— there was a surprising amount of space. We had no problem scouting out an area to sit and listen with a view of the stage!

OK, so let’s get into the highlights of the festival, my style diary, and a few of my must-see and dos in Chicago!




The Skyline

Hands down the best view I’ve ever had while listening to my favorite bands!



The Booze

They serve wine by the bottle in a plastic jug. I’ll let you in on a secret — I actually slipped one into my suitcase for wine nights at the park back home! Bars are scattered aplenty throughout the fairgrounds, so no hand should be empty.

The Food

Holy cow! I thought the VIP area at Coachella had the best food, but the GA food at Lolla trumps even the finest food at other festivals. Do not miss the deep dish by the slice, a Chicago dog, or a honey fried chicken sandwich.

The Fashion

While the people watching isn’t nearly as good as a Coachella (no Riri or Leo DiCaprio in the crowd, sadly,) the fashion is fun and less trite. Sure, there was enough fringe to go around, but for the most part comfort was king and people had fun with their outfits, rain or shine!

The Bands

Everyone we saw was stellar. My highlights were Radiohead (omg,) Flume, Grimes, and Two Door Cinema Club. You really can’t go wrong with a line-up as great as Lolla’s!


The weather in Chicago is highly unpredictable, so I went with easy dresses that wouldn’t RIP if they got a little wet. 




 Red dress-1






Outfit 1: H&M dress, H&M shoes, DIY choker, Vita Fede bracelets, Guess bag. Outfit 2: XX dress, TiVa sandals, DIY choker, Guess bag, Paul Smith sunglasses. Outfit 3: Jumpsuit from Thailand, H&M sandals, Backpack from Tulum, Perverse sunglasses. 


Lou Malnati’s

I’m more of a thin crust gal, but if you head to Chicago, you have to make sure you stop at Lou Malnati’s for some classic Chicago deep dish. The best in the city, and the Malnati salad was pretty stellar too!


Au Cheval

Au Cheval was hands down the best meal we had. The burger was insane, and they delivered a unique spin on a cobb salad, which was my personal favorite. Think pork belly instead of bacon with a little cilantro mixed in the ranch. I’m still salivating.



Want a classic Chicago dog? Check out standing room only for some of the best dogs in town.


Soho House: Chicago

If you get the chance, check out Soho House for a late dinner. And if you’re up for it, stay for dancing under the disco ball into the wee hours. Don’t forget to check out the pool on the rooftop!

3 Arts Cafe

We didn’t do a meal here because of the 2 hour wait, but we did spend some time drinking our coffee in the garden. Worth it, if even only for the view!

3 Arts Cafe Restaurant

Big Star

We washed down our long weekend in Chicago with some good ‘ol tex mex. Delicious!



Architectural Boat Tour

I’m such a tourist, and I don’t even care. I love learning about the cities I travel to, and there is no better way to see all of the beautiful high rises in Chicago than on the water! The tour is about 1.5 hours and it’s totally worth it. A must do!


Beach Day!

Who knew Chicago had a beach? Not me! We headed to Lake Michigan to go paddle boarding and jump in the lake, and it was so worth it! A mega perk… it’s fresh water. We stopped for lunch at Castaways, which had pretty great food for a diner on the beach.



Art Institute of Chicago

If you’re a museum junkie like me, you won’t want to miss the Art Institute of Chicago! We went in the late afternoon and spent two hours looking at their vast collection of impressionist art.



All in all, I absolutely loved Chicago and can’t wait to go back! The food was delicious, the views were epic, and I’m still dreaming about Radiohead. I hope you enjoyed this post!

To shop my festival looks, check out the gallery below. xx

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