It’s hard not to love Chicago’s food scene. If comforting deep-dish pizza and Anthony Bourdain’s favorite hot dogs weren’t enough, the Windy City has also brought us a puppet-operated ice cream parlor. Yes, you read that right. The Sugar Hole, a whimsical ice cream shop in Northwest Chicago, serves up classic soft serve — chocolate or vanilla, cup or cone, rainbow or chocolate sprinkles — from a “puppet-powered” walk-up window.
The soft serve (which isn’t just melted ice cream) is tasty, but that’s just the cherry on top; the true star of the show is the ordering experience. The Sugar Hole is staffed by a cast of hand puppets, including Moolisa, Eggbert, and Puddles, all of whom are wonderfully chatty and humorous. Here’s how it works: customers walk up to a charming blue “hobbit door,” and then (to the unending delight of children and children at heart), the puppet on duty pops out of a large curtain-covered hole to take their order and payment, plus crack a few jokes and answer any burning questions. Since the puppets lack opposable thumbs, human staff members safely deliver the ice cream to patrons.
The history of The Sugar Hole
The Sugar Hole started in the summer of 2024 as a pop-up shop at the Color Club, an event space and arts venue in Chicago’s Irving Park neighborhood. In a 2024 interview, owners Abby Monroe and Josh Dihle told Block Club Chicago that the idea originated as a way to cater to the many families in the neighborhood with a kid-friendly treat stop. Inspired by their young son’s love of hand puppets, they started joking that the shop should be puppet-operated, and the rest is history.
Unsurprisingly, the one-of-a-kind ice cream parlor was an instant hit. After two successful seasons dishing out soft serve with a side of entertainment (or entertainment with a side of soft serve), the puppet-operated operation is set to return around Memorial Day 2026. In addition to classic soft serve, the menu has expanded to include beer and cold brew coffee for the adults, dairy-free Blue Moon ice cream pops, and seasonally flavored hand pies from Chicago’s Bang Bang Pie & Biscuits. The sweet pop-up shop is only open on weekends in the summer (Labor Day through September), and lines can get pretty long, but the unique opportunity to order a nostalgic ice cream treat from a charismatic puppet is well worth the wait…