In '91, Jane's Addiction, Nine Inch Nails and Ice-T Lollapalooza-ed in Arizona during the now-established festival's debut tour. Five years later I was born, and while I’ve learned so much from going to shows like Mad Decent Block Party, Okeechobee and Sunset Music Festival, among countless others, there's nothing like legally being able to tip back as much Cupcake wine as possible while turning 21 at Lollapalooza, now an annual single-city tradition in Chicago.

CL'S LOVE LETTER TO CHICAGO

This year, popular artists like the Windy City hometown hero Chance the Rapper,The Killers and self-proclaimed weirdo Lorde headlined Lolla, which spoke to my tastes perfectly, but I still learned a lot on my first festival assignment (and final story as an intern) for CL. Here are some observations.

1. Take the "El." Just do it. Horrific traffic and hordes of humans shut down Michigan Avenue in front of the Grant Park festival grounds. Get yo' self a Ventra card!

2. Sneak alcohol in. Lolla is expensive, and if you stash booze well enough then you won’t have it confiscated by event security.

3. NM, buy the $27 bottles of Cupcake. One bartender highly urged me to skip $8 glasses of wine since I’d be drinking all day (or so she probably assumed because it was only 1:30 p.m, sorry mom and dad).

Tracy May



4. Migos doesn't care that you care that they're late. The rap group waltzed right onstage without missing a single beat, but they did miss an apology to the large crowd that waited more than 30 minutes to see them Thursday evening. No one seemed to care too much, however, and the set went on as if nothing happened.

5. Rockstar androgyny is alive and well. Thank you Mick Jagger! Lemon Twigs was reminiscent of the Rolling Stones singer mixed with Matty from The 1975 wearing dark lipstick and eyeshadow while crooning broodingly. Cage the Elephant's frontman wore a sequined dress with fishnets. See photos from The Lemon Twigs' set here.

6. Shaun White is a very supportive boyfriend. I was super bummed to see that Phantogram didn't have a lot of hype at their "fourth show at Lollapalooza," but it came out with red cups full of god knows what ready to "fuck shit up... in the nicest way possible." No one in the crowd knew the words or was really familiar with the band, but its biggest fan came in the form of frontwoman Sarah Barthel's carrot-topped gold medal-winning extreme-athlete BF. See photos from Phantogram's set here.

7. The ASL workers are super dedicated and having a great time. I've never really paid much attention to signers at concerts but Lolla's hand-magicians for the hearing impaired were almost as fun to watch as the performers themselves.

Tracy May



8. All festival crowds are not equal. In a crowd as big as Lolla's, you can count on encountering one or two people who are... too much. Everything isn't sunshine and rainbows at these things, especially with fights breaking out consistently. Just don't let it ruin your vibe, since amazing people are also out there ready to be your new BFF.

9. I'm a way bigger Killers fan than I ever knew that I was. The Vegas outfit played hit after hit on Friday as the sea of people sang along to seemingly every word. Consider me a lifer.

10. Stretch and, like, take care of yourself. The 21-year-old grandma in me says to drink water all day, too. Thank me for it later.

11. Get to your favorite sets early. Skip those "maybe I should see them" sets and be at the "I have to see them" ones. Crowds form early so it's worth it to be close to your faves when they finally come to rock.

12. Balance between electronic and live music. Skip a DJ once in a while in favor of the live sets with instruments. In smaller crowds — like that of reunited '90s alt-rock act Live — the vibe of live instruments is magical (no disrespect to DJs, but when I go to festivals I don't want to exclusively see dudes pushing buttons).

13. Chance the Rapper is a king who likes to share. Despite producer-payment snafoos, Chance is a loyal man of the people, dedicated to his fans and stayed on stage until 10:30 p.m. He even brought out longtime friend and rapper Vic Mensa for his own spotlight moment.

14. Sometimes the party starts really early. Rapper Machine Gun Kelly started the situation on Sunday at 2:30 p.m. in a metallic alligator-skin jacket. MGK did all of his most popular songs like "Wild Boy," and covered Linkin Park's "Numb" in tribute to Chester Bennington, whom he was supposed to tour with; the giant crowd went wild.

15. Lou Malnati's deep-dish pizza and Grahamwich lobster corn dog. Life-changing. See more must-eat Windy City restos here.

16. If you want to see some amazing music and Tove Lo's boobs, go see her live. The "PUSSY POWER" singer wears a mesh bodysuit and pasties and eventually flashes the crowd minus the pasties during "Body Talk." Real highlight, though: never-ending empowering vibes that should embolden anyone who has ever spent a morning singing into a hairbrush. Here are you boobies.

17. You must love Grouplove. The L.A. pop outfit puts on one of the best live shows I've ever seen, and its sunset performance for the Windy City felt like a love letter. See more photos from Grouplove's set here.

Tracy May



18. See the unknown bands your friends suggest. Euro-DJs Justice were a pleasant surprise, and so were Tove Lo, EDM wunderkind Jai Wolf, MGK and The Killers.

19. Don't let rain and an evacuation order ruin your night. Even when the downpour happens during a set by Porter Robinson, one of EDM's best live artists.

20. People are super weird and won't let you borrow their phones. That being said, don't lose your phone or your friends, but don't be afraid to see sets by yourself — just have a meet-up spot.

21. The bar to head to after a shower and an outfit change is Three Dots and a Dash. The hidden underground tiki bar serves up drinks that will get you drunk after a couple of sips.

In the end, nothing matters more than being around laid-back people that want you to have fun and doing whatever you think is necessary to let loose. It's not always about the music or the alcohol or how many likes you can get on your new #Lolla Facebook profile picture. Friends and family make everything better, and none of this would've been possible or close to fun without them.

Mady Dudley is a Florida State undergrad trying to graduate on time. Wanna do my senior year for me? Contact her here.