Saving Chicago's Street Festivals: A Vendor's Perspective

As a locally owned Chicago design studio and retailer, Transit Tees has proudly participated in the city's most iconic neighborhood festivals for over 20 years. From Wicker Park Fest to Midsommarfest and Taste of Randolph, these vibrant events aren’t just calendar highlights, they’re the heartbeat of our neighborhoods and essential for small businesses like ours.

But this summer, that heartbeat is at risk.

As reported by WGN, a coalition of nearly two dozen Chicago festival organizers has sounded the alarm: skyrocketing costs and record-low donations are putting the future of our beloved street festivals in jeopardy. Even with record-breaking attendance at events like the 2024 Wicker Park Fest, public donations have plummeted. “There’s a misconception that the city pays for these festivals,” says Transit Tees owner Tim Gillengerten. “The reality is that it’s gate donations and the mom-and-pop shops, the bars, and the independent vendors like us that fund and power these events.”

Transit Tees is deeply rooted in Wicker Park and Andersonville, where everything we design, produce, and screen-print is made right here in Chicago. Our presence at these festivals is about more than selling, it’s about celebrating the culture of our city and connecting with the community face-to-face. Whether you discover our Chicago Handshake LED Light, our Chicago Style Eats Puzzle, or our newest Old Style Tavern Light Box at one of these festivals, the energy and conversation around our booth is part of what keeps Chicago’s creative scene thriving.

But festivals don’t run on magic. City ordinances require free admission, so funding relies on voluntary gate donations, local sponsorships, and vendor fees. With rising expenses like permits, sanitation, entertainment, and security, many organizers can no longer cover costs. Without immediate community support, these events may disappear.                   

These festivals are vital platforms. They’re where tourists find their favorite Chicago-themed gear for the first time. They’re where locals come back year after year for our best-selling El Board Game, Windy City Socks, or Chicago Flag Hat. And they’re where artists, musicians, and small brands like Transit Tees grow.

Losing them would be a loss for us all.

We live and breathe these festivals, and we’re asking you to do the same. When you attend, donate at the gate. Shop from neighborhood vendors. Follow and share our story on Instagram, Facebook, TikTok, and YouTube. Every post, every purchase, and every dollar helps keep the spirit of summer in Chicago alive.

We believe in these festivals because they reflect who we are: Locally Designed. Chicago Inspired.

Visit SaveOurStreetFests.org for more info.

The Transit Tees Team