Teddy's Ice Cream
About
A small, family-owned ice cream shop on Montrose with a giant pink inflatable bear on the roof and unusually rich soft serve.
What to order: A soft-serve sundae, the Poseidon swirl, or a Greek-inspired sundae with visinada, figs and walnuts
You'll spot Teddy's by the giant pink inflatable bear on its roof. Ted Pirpiris opened the shop in 2022 in a strip mall his family has owned since 1968. The draw is the soft serve, made with a higher butterfat than most, so it's noticeably smooth and rich. There are more than ten sundaes, a candy-loaded Poseidon swirl, and Greek-inspired toppings like visinada (sour cherry), figs and walnuts, plus plenty of hand-dipped flavors. Every treat comes with a Teddy Graham on top, and the patio is a good place to linger on a summer night.
Address: 2000 W Montrose Ave, Chicago, IL 60618
Neighborhood: Lincoln Square
Recognized by: Infatuation.