Conquering Chicago’s Pitchfork music festival on a solo trip
You’re never really alone in a crowd.


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:

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:


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.

