The Whip

  • Shotgun: Stephanie
  • Riders: Alvaro, Bernadette, Thor
  • Hitchhikers: uber driver (guy), uber driver (girl), other Stephanie, all the high schoolers on the train, guy who really wanted to see Hardwell, young frat stars, Cubs fans

The Trip

Coachella, Bonnaroo, or Lollapalooza. That was the question.

After a quick look at the headliners (I don’t know smaller acts like that to let them factor in too much), I figured this was a year for Lolla. They won the lineup battle and it was their 25th anniversary. Sounded like the move to me. Coachy and Bon Bon would have to wait another year before my presence.

I got my friend Stephanie a ticket for her graduation (using one of my first big boyish paychecks irrationally wisely), handcuffing her into a commitment to go with me. Over the following months, we bought my ticket, flights, and planned our five day adventure into Frank Sinatra’s kind of town. With the festival being four days, we wanted an extra day to explore the city. Following some coordination with my friend Alvaro, we found our place to crash right outside the city in a town called Lisle. Before we knew it, we landed at the O’Hare International Airport, Alvaro scooped us, and we were bouncing around the city of Chicago.

Our first full day began with our uber driver giving us a ride into the city (swell guy). He gave us the lowdown of Chicago and how to make the most of our day. I don’t think we disappointed. We kicked things off with a boat tour where we saw the architect of the city (making Ted Mosby and Tom Hansen proud), and we learned about a cow who burnt the whole city to the ground back in the 1800’s.

After that, we ate some Chicago pizza that we couldn’t finish, went up on the Skydeck at the Sears Tower, and made it to the Cubs-Sox game (luck of the draw to be in Chicago for such a marquee series). I bought a Sox tank (declaring my allegiance to the South Side, feeling that the Cubs were too mainstream). Steph did the opposite and chose to be a Cubs fan. At the game, we saw the rivalry first hand, seeing people charging a dollar extra to Sox fans for Gatorade. I kept my Sox tank in my bag and cheered along when the Cubs won. The theme song was so catchy. “Go Cubs Go!”

Alvaro scooped us again after (we didn’t want to get lost in the Chi) and took us back to home base. We saw as much of the city as we could on our first day. The next four would be committed to Lollapalooza.

The next morning we bought a Kentucky Gentlemen bottle of whiskey, and Alvaro made us pancakes and eggs. Throw in toaster strudels and Redbull, and you have our pregame breakfast for each day.

We took the train into the city every morning (the move), filled with high schoolers and locals. Drinking was allowed on the train, so more pregaming was done there until we were in the heart of the city. Following an epic walk from the train and some stealth tactics to get through security (if you’re not sneaking stuff in, you’re not living), we were in the grounds of the beautiful Lollapalooza!

It was magical. Centering around Grant Park, a massive fountain rested in the middle (perfect for instas), and the city skylines were in the background of each stage.

Each day was an adventure. Each day brought it’s own experience and told it’s own story. Day 1 felt like a day to feel everything out. Day 2 was the day to lose your mind. Day 3 was a take-it-easy day. And Day 4 was the send off.

Over the course of each, we made set friends, five second friends, friends that wouldn’t leave us alone. First-timers and veterans. High schoolers and collegers. Little kids and adults. Locals and travelers like us. It was a melting pot of everyone. We saw Lana Del Ray spew good vibes, Red Hot Chili Peppers rock out like it was still the nineties, and Ellie Goulding send us home speechless (which I was happily surprised by). We ate Chicago-style hotdogs (when in Rome), more pizza, and on the final day this fantastic corn dog filled with lobster.

It wasn’t always easy. We had to split Lana and J. Cole down the middle, and RHCP with Disclosure. Stephanie and I nearly took each other’s head off each day. We even missed when  Flosstradamus brought out Chance the Rapper. But everything always ended with a happy ending. We may have missed Chance with Floss, but we were there when Future brought him out to sing “No Problems”. I nearly cried.

By the end of Day 4 (but really the end of Day 2), we couldn’t feel our legs, and wouldn’t feel em again for another week. We had given Lollapalooza and Chicago our all. We rolled each other back to the train station on the final night, sad it was over, but happy we could finally relax. After one last night in Lisle, we got dropped off at the airport the next morning and took our flight back to Florida. I edited our video the whole way back. If the upcoming years will feature Coachella or Bonnaroo, they’ll have quite the shoes to fill left by Lollapalooza.

Visiting Recs

  • Take a boat tour
  • Don’t call the Sears Tower anything, but the Sears Tower
  • Choose your Cubs-Sox allegiance wisely
  • Take a train and then drink on the train (it’s legal)
  • Stretch before, during, and after each day of Lollapalooza
  • Always be on the lookout for President’s daughters

Quotes of the Trip

  • “Try not to suck”
  • “Nice boobs”
  • “Pronounced Sears”
  • “Hey Chicagooo! What do you say?”
  • “Cheek.”

Top Tweets 

Top Instas

Next Trip


Hooperpalooza 4… Destination: Vegas!
(coming early September)
(follow along on Snapchat: @hoopertv)

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