Every time I pass by Teddy’s Ice Cream in Ravenswood, I check to see if the giant pink inflatable bear is out on the roof. It turns out I’m not the only one.
“Teachers are always telling me that they’ve got all these kids coming into class and all they want to do is talk about the bear on my roof,” said owner Ted Pirpiris.
Well, I have some intel. They put the bear up on the roof when the wind speed is lower than 15 miles per hour.
And no, the crew of neighborhood teens who work there aren’t climbing onto the roof under the cover of night. Pirpiris confirmed they just flip a few switches in the back, and the bear inflates on its own.
Pirpiris opened the ice cream shop in 2022 in the strip mall his family has owned since 1968. He takes pride in the fact that thousands of kids will remember the shop as their childhood ice cream spot.
The store regularly partners with local elementary schools and sponsors youth sports leagues. Two years ago, Pirpiris even invited a group of about 40 preschoolers to come behind the counter and scoop their own ice cream.
“Seeing all the kids come in is always the best feeling,” Pirpiris said. “It was so funny watching them all pulling on and hanging off the soft serve handles trying to make their own cones.”
Every Teddy's treat comes with the shop's signature Teddy Graham on top. But don't sleep on the soft-serve: It's made with 10% butterfat instead of the 6% industry standard, and Pirpiris swears you can taste the difference.
The fun doesn’t stop in Ravenswood. This year, Teddy’s opened a second location in Lincolnwood at 3910 W. Touhy Ave.
“I love when we get the Greek music jamming at night and see people out on the patio dancing and just loving the vibe,” Pirpiris said. “It’s just a fun, family-friendly place to be.”
