Girlboss Guide to Festivals: Lollapalooza, a Retrospective


This year, Lollapalooza celebrated its 25th anniversary with a 4-day long festival in the heart of Chicago. It also marked the third time I've been able to go to the festival, and it gets better every year—mostly because I learn a little more and figure out how to make things much easier for myself. Being smack in the middle of a city makes Lolla pretty different from other festivals where you typically trek out into the wilderness and camp for a weekend, so it presents some unique hurdles. From one girlboss to another, here are my tried and true tips for planning ahead and having a great time at a music festival:

Pack It Up

The two biggies: Sunscreen and hydration. It's so important! If you're burnt to a crisp on Friday, you'll be out of commission for the rest of the weekend, and you definitely don't want that. Also, it gets hot out there, and drinking water is your best bet to keep cool and continually energized.

It's really important to make sure you look at the festival's website before you pack, too! Not all concerts are created equal. At Lollapalooza for example, your sunscreen will get taken away if it’s in an aerosol can. Outside food is also off limits (a bummer, I know), and so are any unopened bottles of water. So, if you have a camelbak, bring it empty and fill it at the festival. You gotta do your research!

Don't Rain On My Parade

This is one of those things where you don’t need it…UNTIL YOU NEED IT.
I bring a rain jacket, but one of those emergency ponchos works just as well too, and as an added bonus, it's big enough to drape over your backpack while you're wearing it. It might drizzle, or it might be a torrential downpour, in which case you don’t want to end up like these little boys I saw a couple years ago:

I'm betting their parents had an awesome time taking them home that night.

I'm betting their parents had an awesome time taking them home that night.

Call Me, Beep Me

When you enter a hugely packed music festival like this, it turns into a weird twilight zone where you’re surrounded by hundreds of thousands of people, yet you’re still totally off the grid. Cell reception is terrible—your texts won’t go through, or will take hours to send and be received, and your internet connection will be spotty at best—so plan ahead. You know how when you were little you made those plans with your parents like, "if we get separated, meet at this light pole"? You gotta do that here too. Coordinate with your crew and if something goes awry, you all know to meet back at the water tent by the entrance, for example.


Look, we're girls, and unlike boys, the reality is....we have to wipe every time. So when the toilet paper runs out in the portapottys on the first day, three hours after gates open, you want to be sure you're not caught—literally or figuratively—with your pants down. So, make sure you bring your own. I can't tell you how many times I have walked out of portapottys, personal roll of cushy toilet paper in hand, and received jealous stares from every man and woman who knew they were about to step into a hellish stink box that is TP-free; it is a powerful feeling. Bring a roll from home in a gallon-size zip bag. The gallon bag is crucial, too. If your water bottle leaks or it rains, you've still got an intact and dry roll of TP, and you won't be cleaning papery chunks out of your bag for the next week. And while you’re at it, hand sanitizer or baby wipes are a nice addition too, and help keep you feeling fresh, even though you’re spending all weekend in the elements.

Breezy Buns

There are a lot of factors working against your comfort at a festival: the heat; the rain; the crowds. This seems so small, but the degree to which keeping your whole downstairs situation dry and aerated is immensely important to your overall happiness. Get yourself a couple nice pairs of micro modal underwear. Modal wicks moisture 50% better than cotton and is super soft. MeUndies makes cute ones, and Girlboss Radio listeners can get a discount. ;)

Plug it in, Plug it in

If you go to enough concerts in your life without hearing protection, you’re bound to end up like this poor woman...

Let this video be a warning to you

Women live longer than men, so you might as well make sure you can still hear when you live to be a badass old lady. I know what you're thinking: Earplugs look totally dorky! Well, I'm here to tell you that times have changed. They make super low key ones, which preserve audio quality without distortion, so say goodbye to the ugly, fat, orange foam ones you've grown used to seeing. I have Earpeace ear plugs, which come in three different shades to match your skintone, but there are tons of other options on Amazon.

Chow Down

"The Caprese" from Cheesie's Pub & Grub

"The Caprese" from Cheesie's Pub & Grub

Chicago is an AMAZING city for food. Aside from all the great music you'll get to see live, some of the Windy City's best restaurants set up shop at Lollapalooza. Here are some of my top faves: 

Cheesie's Pub & Grub — Loaded grilled cheese sandwiches on cushy Texas toast bread. Is there anything better in life??

Edzo's — They make all their ground beef in-house, fresh every day, so the burgers are extra tasty.

Chicago-style Hot Dogs! — Just don't put any ketchup on it. I never figured out exactly why, but I'm pretty sure you can go to jail for that within Chicago city limits.

High brow + Low brow = DELICIOUS

High brow + Low brow = DELICIOUS

Harold's Chicken Shack — this is the first year I remembered seeing Harold's come to Lolla, but they're a South Side institution. If you're into fried chicken, this is the spot for sure.

Lobster Corn Dog from Graham Elliot Bistro — It's is a little pricy, and definitely extravagant, but you gotta treat yo' self to it at least once...

Chill the F**k Out

You should totally go see all the artists you want to see, but at a certain point, scheduling out your whole day to be somewhere at a certain time is more trouble than it's worth. Park it on a hilly spot—ideally between two stages—and have a snack, drink some wine, and hang with your friends. You'll still hear and see the music and you won't be squashed in with a hundred other sweaty people jabbing you in the ribs. That's what they make the jumbotrons for, after all. Also, just go walk around and check out something new. If you've got a gap in your schedule, walk over to a stage to see someone you've never heard of. And who knows? They might blow up within the next year and then you can claim massive street cred for seeing them ~before they were cool~. 

Swim Upstream

The day is over, you’ve had a wonderful time, and you're headed home! Unfortunately, so are literally hundreds of thousands of other people. If you can still bear it, try to walk a couple stops upstream, opposite of the direction you're headed. It's more work, but it'll guarantee you can sit and stay comfy on the ride home while everyone else is packed in, standing like sardines.

This could be you on the train. It doesn't have to be.

This could be you on the train. It doesn't have to be.

Alternatively, if you're taking a ride-sharing app home, use a surge-finding app like SurgeProtector to find a place to walk to where it's cheaper. The couple blocks surrounding the festival might be 3x but if you're willing to trek a little farther you can probably take it down to 1.5x. I saved about $20 every night by doing this…and hey, let’s be honest, that’s two extra beers' worth of money that you’re getting to keep for the next day. 

Keeping all that in mind, you're bound to have an amazing time. Think ahead, think smart, and just remember to keep it casual when you get there. You'll be a seasoned pro in no time.

— Tori Borengasser
Twittter: @toriborengasser