entertainment travel What To Expect

Going To Lollapalooza? What to Expect!

Ahh, Lollapalooza. What a great time! 


Thanks Pepsi!

First of all, I should say, that I was only able to go to Lollapalooza with my dear friend, Whitney, because I won a sweepstakes from Pepsi! After you win one trip, you never expect to win another so I was ultimately shocked to receive a call that I would be able to attend! The contest included airfare, 3 nights hotel stay at the Hyatt Centric Loop in downtown Chicago, $300 (+$500 for opting to drive vs. fly) spending cash, and two 3 day general admission tickets to Lollapalooza. I had never been to Lollapalooza before, or a major music festival, so had no clue what to expect! I did a little googling before I went, but didn’t find a whole lot of helpful information! A lot of the stuff I did find was in relation to what to wear! I thought I’d create a post to help anyone in future years who are planning on attending for the first time. 

PicMonkey Collage

Boots and backpack both from DSW!

Buy a backpack. I strongly suggest getting a backpack. I could never imagine carrying around a purse or anything else all day! A backpack was so convenient and I felt safe wearing it. Not to mention it can hold souvenirs with decent room! 3 weeks later and I’m still wearing a backpack – maybe I am in denial that Lollapalooza is over? 


I could have lived in this comfy romper and Teva sandals all week!

Wear comfy shoes & clothes! Yes, do it! Do you really want to be walking through thousands of drunk people with uncomfortable shoes? There are plenty of cute, comfy options, so do your research. Please don’t be that person wearing stilettos at a music festival. I’m pretty sure we saw a couple of those! I totally understand the desire to look cute, but by day two we had totally opted for comfort versus hip. July/August is super hot and you will most likely be sweating, so remember that! 

This photo does not do justice as to how many were there.

Buy souvenirs on DAY ONE. Both Whitney and I bought T-Shirts and a water bottle on day one and two. By day three, the Camelback water bottles were gone and the selection of souvenirs was lame.  We even had some girl come up to us and offer $30 to purchase Whitney’s water bottle. T-shirts were averaging $30 each and the water bottles, which we thought were a steal, were only $15 and are all limited edition! 

Double check what is prohibited and allowed before going. On Lollapalooza’s website, they clearly state what is allowed and what is not! The two things we saw get confiscated the most during the entering phase were food, sunscreen, and water bottles. You are allowed to bring in water bottles (and my friend even suggests two) but they must be empty, which makes sense, because they don’t want underage kids sneaking in alcohol, I’m assuming.

There are TONS and TONS and TONS and TONS of people. No surprise, right? I’ll admit I was a little taken aback how difficult it was too walk at some points, and that’s saying a lot considering how big Grant Park is and how much they blocked off for us.


Moments before Tove Lo.

You have to have patience which is ultimately very hard when you have a 200 pound drunk teenager running into you with his sweaty body and hot pizza. Honestly though, it’s hard to complain, because what do you expect going to such a huge music festival? Expect long and slow lines for the ATM (bring cash to avoid) and once again remember to be patient


Happy in our little bubble! 🙂

You don’t need to be in the crowd to experience the music. On day one we decided to really go all in – wake up early, stand in the crowds, listen to the music, fend off the people – rock out, you know. Half way through day one though, we realized – we’re old. I say that because we’re no longer in that stage of our lives where we are carefree and encompass that “do anything” attitude. Thankfully, we stumbled upon a lovely area on day one where there was a giant screen that gave us amazing views of the performances! Not to mention SHADE and some relaxing blue chairs! Seriously, you could not get it any better. Sure, we weren’t experiencing it like a concert goer would, but more of how the concert goer’s parents would. The main point is that we were happy and comfortable! I honestly don’t think I would have gotten to experience the music as good in the mix if it wasn’t for this shaded grassy area. 

Wear sunglasses to judge people easier. (Jk?)

Wear sunglasses to judge people easier. (Jk?)

It’s pricey. Absolutely not a surprise here – things are expensive at any huge event where mass amounts of people go! One of our favorite dishes from Chubby Wieners was their cheesy fries that rang in at $7! Beer was anywhere between $6-$8, and wine was $7 (yes, there is a wine tent). In one weekend, between two people, we managed to blow $500 – that included all meals, a couple souvenirs, 2 movies, and transportation! Insane how it all adds up! 


About to eat a delicious cheesy fry from Chubby Wieners.

A few tidbits…Drink water, your friends and family will kindly remind you as you begin to post photos on social media…those wristbands are SUPER hard to get off once they are in place, so don’t be an idiot and cut of your best friend’s circulation by going crazy and not realizing that…You’ll constantly get solicited to sell your wristbands after each day from hagglers on the street, don’t make eye contact…bring hand sanitizer – the porta potties aren’t fresh and are pitch black at nighttime…but most importantly have fun because no matter how hot, crowded and how many times you tell yourself “you’re over it” you end up missing it terribly when it’s over. 




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