All Articles Conquering Chicago’s Pitchfork music festival on a solo trip

Conquering Chicago’s Pitchfork music festival on a solo trip

You’re never really alone in a crowd.

By Emily Reily29 Sept 2023 4 minutes read
Black Belt Eagle Scout performing at the Pitchfork Music Festival
Black Belt Eagle Scout performing at the Pitchfork Music Festival
Image: Courtesy of Pitchfork Music Festival

My trip at a glance:

Hometown: Dover, NH

Destination: Chicago

Number of nights: Four

Biggest fear was: Not being able to find my way around

Most excited for: Going to my first multi-day music festival

Why I wanted to go:

I’m a huge music fan, as well as a music writer, and I’ve always wanted to experience a multi-day music festival. I went to Lollapalooza in 1992 when it was touring around the country, but that was a local, one-day experience. This time around, my husband Tim picked the destination for me as a surprise Christmas gift. He knew that I really wanted to go to Pitchfork, but also knew I was afraid to go because it would have to be alone: None of my friends were interested in coming, and he would have to stay home to work and take care of our school-age daughter.

How I balanced spontaneity with planning:

To maximize my trip, I arrived the afternoon before opening day to see Hamilton Live at the CIBC Theater. Pitchfork is a three-day music festival that runs from 11 a.m. until about 10 p.m., so I spent most of my time there, with the exception of a visit to a record store and a leisurely morning spent reading a local diner.

I did make one snap decision: On the way to the airport, I took an Uber detour to the Art Institute of Chicago. I’m pretty sure I was the last person to board the flight home. I don’t recommend cutting it that close, but being able to do exactly what you want on your timetable—especially as a busy work-from-home mom—was luxurious.

The people I met:

On the third day, I met up with a friend—another music writer and Chicago native—to chat about the festival. After a couple of days alone, it was a nice change of pace to bounce around ideas and hear someone else’s perspective about acts that still had yet to perform but were absolute must-sees. If we chose to go to different stages, we met up in between to check in.

If I have only one solo-travel tip, it's this:

This is your trip, so try new food and take some fun risks—always with safety in mind. Let family and friends know your itinerary. Also: Portable cell phone chargers are a must.

How I kept costs at bay:

Earl Sweatshirt performing at the Pitchfork Music Festival
Earl Sweatshirt performing at the Pitchfork Music Festival
Image: Pooneh Ghana

This was a bucket-list trip for me, so budgeting wasn’t the biggest focus. But I still found ways to save. The festival took place during a July heat wave; instead of purchasing single-use plastic water bottles, I made use of the free refill stations throughout the festival grounds. There were also free bottles of Bai juice everywhere, so I grabbed those whenever I could. I also saved on airfare by choosing an early flight.

The times when I felt safe/unsafe:

I had never used Uber before this trip—there were times when I felt unsafe using the service, especially in the evening. But I was somewhat familiar with the app and how it worked, which helped. For extra security, I always chose private rides.

The second day of Pitchfork also brought some unease, when thunderstorms closed the venue for a few hours. Everyone had to leave the field and find their way back to wherever they were going. I was soaked and stuck in a downpour under the L train with a whole bunch of people I didn’t know. The crowds made the cell service spotty, so I had to walk a few blocks to get an Uber back to my hotel. Later, the sun—and heat—came back and I returned, only having missed a few acts.

What I learned about myself:

Crowd at the Pitchfork Music Festival
Crowd at the Pitchfork Music Festival
Crowd at the Pitchfork Music Festival
Image: Daniel Cavazos

This trip taught me that I should have done this a long time ago. It was scary, but exhilarating, to know that I could accomplish this on my own. I learned to take some things in stride and became more clear about my personal limitations. It turns out I don’t mind spending time by myself at a show or small concert venue if I feel safe. If I felt at all uneasy—whether due to large crowds or waiting in an unknown corner for an Uber pick-up—I would just find another place to be. I didn’t stay out late at night attending festival after-parties; I made sure to be back in my room by 10 or 11 p.m.

My Chicago cheat sheet:

Eat

  • The menu at Breakfast House takes a range of influences; you’ll find everything from chicken and waffles to huevos rancheros. Post-meal, wander the surrounding tree-lined streets of West Town.

Play

  • Union Park has more than 13 acres full of playgrounds, a pool, a garden, pickleball courts, and more. You can also take in a great view of Sears Tower from the field.
  • Reckless Records has stacks of indie, alternative, punk, and post-punk records from music labels like Matador, Sub Pop, Kill Rock Stars, Drag City, and Dead Oceans.
  • The interior of CIBC Theater is bathed in warm tones and glittery lights and the performance seating here is cozy and comfortable. Don’t skip grabbing a pre-show cocktail.
  • Art Institute of Chicago is worth even a short visit—there’s a place to store luggage while you browse. There are classics by Monet and Van Gogh, along with some of Picasso’s most famous works.

Stay

  • La Quinta by Wyndham is within walking distance of convenience stores, the L train, and The Bean—plus the included breakfast is served with incredible city views. Pro tip: The lobby doors are operable only by key card at night, which makes it feel extra secure for solo visitors.

The solo traveller's playbook

Tips, trip ideas, and essential info for getting out there on your own
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Emily Reily
Emily Reily is a New Hampshire-based freelance journalist and music critic. A former newspaper photojournalist, copy editor and page designer, Emily has been published in New York Times for Kids and the Washington Post Magazine; as well as online sites Paste, Vice, Treble, Riot Fest, New York Observer, Thrillist and others.