The Good, The Bad, and The Spicy Secrets of Running Food Pop-Ups in Chicago

How Creativity, Hustle, and a Little Heat Shape Chicago’s Food Pop-Up Scene

Running a food pop-up is exciting—it’s a mix of chaos, creativity, and yes, a little heat! In a city like Chicago, where people expect bold flavors and unforgettable experiences, every pop-up feels like a performance. My journey started in 2016 with Sobremesa Chicago, where we always brought BBQ, sazón, and our secret sauce: Ají Sobremesa. While the sauce got people talking, it was consistency that kept them coming back. But here’s the spicy truth: running a pop-up isn’t just about great food. It’s about sweating it out—carrying all the equipment, finding the right venue, and making it work, even when there’s no kitchen. That’s where the real magic (and madness) happens.

The Good: Creativity Unleashed

Pop-ups are great for creativity. Chefs get to break free from the usual restaurant setting, where menus and costs control everything. With pop-ups, you can try new dishes, mix bold flavors, and give people something they’ve never tasted before. At Sobremesa Chicago, we packed every plate with tropical, happy vibes and spicy Latin flavors. From the kick of our Ají Sobremesa to the sazón from chefs like Gabriel Moya, José Zayas, and sous chef Efrén Candelaria (best rice cooker😉) we wanted each bite to bring the heat.

Pop-ups let you surprise people. In Chicago, diners crave not just food but the experience. Pop-ups let them in on the secret, the spicy adventure. Whether you’re serving from a back alley in Pilsen or a patio at SleepingVillage, every dish tells a story.

The Bad: The Hustle is Real

Now for the hard (and sweaty) part: the grind. Running a pop-up will make you sweat—literally. It’s not just about cooking. You have to find a venue, figure out where to cook (and hope there’s a kitchen), and carry everything—tables, grills, propane—across the city. Sometimes you’re lucky and have a good setup, but most of the time, you make it work with whatever you have. That’s the hustle diners don’t see, but it’s what makes pop-ups special. The grind is spicy and real.

Finding new customers is tough too. But word of mouth? That’s gold. Consistency and people talking about you—that’s the key. For Sobremesa, it wasn’t just about serving good food once. It was about showing up every time and bringing the heat. Pop-ups grow when people say, “You have to try this.”

The Ugly: Burnout and Unpredictability

Running a pop-up is exhausting—and can be a total burn-out if you’re not careful. The unpredictability can make you sweat even more. Sometimes the perfect venue falls apart last minute, or you run out of food too early because the crowd was way bigger than expected. And when there’s no kitchen—ay ay ay! It’s hot, messy, and pure chaos.

But here’s the spicy truth: even with all that heat, the most beautiful moments happen when it works. The regulars who show up, the friends who help, the strangers who come for the food but stay for the experience—these are the connections that keep you going. I’ll never forget when I’d visit other restaurants and hear, “Are you part of the yellow sauce crew? What’s in that sauce?” That’s when you know your food has left a lasting mark.

The Chicago Factor: A City That Loves Its Food

Chicago is the perfect city for pop-ups. People here love good food, but they also want something different—something with a bit of spice. Pop-ups work because they break the norms. Every neighborhood—from Logan Square to Pilsen—gives a unique backdrop for creative food experiences. It’s not just about the food; it’s about building a community.

For Sobremesa Chicago, it wasn’t just about serving Latin-inspired dishes. It was about the vibe. Our pop-ups were tropical, warm, and full of shared meals with a spicy kick. Every dish had a story, and that’s what people loved—not just the food, but the feeling of being part of something bigger.

The Memorable Moments: The Heart of Pop-Ups

Anyone who’s worked in pop-ups will tell you: the little moments make it all worth it. Anytime tío Efren took the mic, the energy in the room lit up. And every 4th of July party? Pure magic 🪄✨ (viva PR 🇵🇷 libre thou’). These events weren’t just about food—they were gatherings where strangers became friends, and friends became family. We found hidden gems in Chicago’s food scene, learned from farm-to-table experiences, and built connections that last (special s/o Farm Butcher Tables 🐖)

These moments—where everything makes sense—are why pop-ups, with all their spice and chaos, leave such a lasting impact.

Conclusion: Embrace the Madness (and the Spice)

Running a pop-up is not easy. It’s chaotic, spicy, and unpredictable. But it’s also exciting. For anyone thinking of starting a pop-up, my advice is simple: enjoy the process. It goes by fast, and in a world where eating out can be expensive, creating a community through food is priceless.

The pop-up world is wild, messy, and full of heat—but that’s exactly what makes it beautiful.

Besiss🥰
Génesis ❤️‍🔥🔥