Windy City Sweets creates niche with nostalgia, neighborhood connection
Chicago sweet shop forges connection through quality, giving back.
John and Jill Manchester weren’t looking to buy a candy store when they sought a new business opportunity in 2011, but it was a match made in heaven.
John has a background in engineering, which he can apply to just about any field. Jill, meanwhile, has worked in the candy industry for years and eats candy “night and day,” John said.
So, when the Manchesters walked into Windy City Sweets, the then-28-year-old candy shop in Chicago’s Lakeview neighborhood, they were delighted.
“The visual of all the colors, the smell of the candy — it’s magical. It’s back in time. It’s a simpler time,” John said. “When we walked in, we looked around to see all the different candies, the nostalgia, the memories that it brought back.”
Jill asked to try the store’s specialty — homemade s’mores — and that was it.
“As soon as she bit into it, she said, ‘We’re buying this store. This store is ours,’” John said. “And we did.”
Over the next six years, with help from the original owner, the Manchesters have grown Windy City Sweets in size (it doubled from 750 sq. ft to 1,500 sq. ft.), in product lines and in its community footprint.
Those s’mores that hooked the Manchesters from the beginning? They’re now available with peanut butter and caramel fillings. The Manchesters have also expanded Windy City’s line of crunch cups, which have crunchy inclusions mounded in chocolate. John said they’ve added milk and dark chocolate bacon cups and white chocolate jalapeño cups for customers in search of a sweet and spicy treat.
The store is also known for its hand-poured chocolate Easter rabbits. John said he and employees poured more than 3,000 for the 2017 season. The rabbits that didn’t make it into Easter baskets had their best parts — their ears — lopped off and repackaged for customers needing a post-Easter pick-me-up.
“We’re always thinking and trying to dream up something new,” John said.
Apart from sweets made onsite, Windy City offers a variety of bulk and pre-packaged nostalgic treats. One whole wall is covered with individually wrapped pick-and-mix candies, and shelves at the center of the store feature items such as Wax Lips, Pixie Stix, Smarties and Candy Buttons.
John said Windy City Sweets sources from up to 90 different suppliers with a focus on smaller, mom-and-pop shops like theirs. He also pointed to Windy City’s efforts to give back to its North Side neighborhood. Windy City hires employees from the area, and the store often makes donations to school and community functions. And since Windy City offers 32 flavors of ice cream, it also sponsors socials for community and religious organizations.
In fact, Windy City’s neighborhood mentality caught the attention of American Express, which has featured the store a few times for Small Business Saturday, an annual event emphasizing support of local businesses.
“We try to be whatever we can be to the neighborhood,” he said.
That goes for greater Chicago as well. Given its size, Windy City Sweets has the flexibility to create custom gift baskets and items. John said the store dipped special pumpkin-flavored pretzel rods for the Chicago Bears and filled up a metal container with $500 of product for a thank-you gift one downtown corporation gave to another.
While Windy City Sweets has developed a strong connection to its community over the last three decades, the Manchesters have no plans to stop there.
John said he’s building Windy City’s wholesale business, noting the store’s products are available at the SoHo House Chicago, Theatre Wit and smaller, independent grocery stores. He hopes to get into more grocery stores and Chicago’s two airports in the future.
The Manchesters also have plans to brand their traditional English toffee, but they’ve been studying the best way to execute that, John said.
“We want to do it right. We don’t want to stumble out,” he said. “We’re at the point where I believe we can do that.”
The Manchesters have also weighed developing bakery items and expanding back-of-store space for building custom baskets and fulfilling online orders.
No matter where the future takes Windy City Sweets, the Manchesters will stick to the principles that have made the store a North Side staple.
“We’re looking at quality versus quantity or size,” John said. “Where life is a little bit sweeter, a little simpler, a little better, a little old school.”