Iconic Windy City Sweets Rings In The Big Game & Valentine’s Day With The Ultimate Treats!

Think special sweets are only for Valentine’s Day? Think again.

“They’re for any special occasion,” said John Manchester, co-owner of Windy City Sweets in Chicago’s Lakeview neighborhood.

“We make our own custom handmade chocolates, fudge and molded chocolates,” Manchester said, including full-size footballs and basketballs [which weigh in at 3 to 3.5 pounds] to celebrate the Super Bowl and March Madness.

And for such occasions, there’s more: Manchester said Windy City puts together special platters filled with such items as bear claws – pecan, cashew and caramel clusters coated in chocolate – cookies with team logos and little foil-wrapped candies.

As Nebraska alums, Manchester and his wife, Jill, sent a chocolate football to associate athletic director Matt Davison and basketball to play by play announcer Kent Pavelka. Former Chicago Bulls head coach Fred Hoiberg also was a recipient of a chocolate basketball.

It was actually Jill who steered the former construction site engineer toward the candy business in 2011. She has worked for such giant candy empires as Brach’s, Farley and Lifesavers.

“This was really her thing. We were looking for something to buy. She had her favorites and I had mine. This was one of the ones we liked. We walked around and asked people what were their favorites and it was the s’more,” he said. So, they bought two.

“Man it was good,” Manchester said, adding, “And it’s still our best seller,” cut into wedges and covered in chocolate.

Manchester learned to craft specialty chocolates from the store’s former owner. Windy City also sells nuts, ice cream, gummies and licorice [“We have 45-plus kinds from all over the world.”].

One of the store’s specialties is an English toffee, “made from my great grandmother’s recipe. We found it in an old recipe book and sell it as Manchester’s English toffee.”

Aside from the sports themed chocolates and platters, Windy City creates special items for Valentine’s Day, Easter, the Fourth of July, Christmas, Hanukkah and New Year’s – and anything else customers want.

For Valentine’s, not only are there heart-shaped candies and truffles, but a chocolate box in which to package them.

“The whole thing is edible!” said Manchester, who adds he’s out to put the fun in candy.

For Easter, there are chocolate rabbits in varying sizes. After the holiday? “We break off the ears of any leftovers and package them as lucky rabbit’s ears,” he said.

One of the more unusual items is chocolate-covered bacon bits. The confection was the result of a suggestion from his dentist, who was extolling his friend’s annual bacon party. The treat comes in a cup as a mixture of milk and dark chocolate-covered pieces.

After a bout with bacon, chocolate-covered Twinkies or Rice Krispie Treats, Windy City needs to clean its equipment so it can be recertified Kosher to continue to service the synagogues with which it does business.

Not everything is sold locally. Windy City also does a robust commercial business and ships nationally and internationally.

But not all of Manchester’s efforts have been successful. He was once contacted by Lay-z-Boy, which wanted a chocolate chair for a promotion. He tried to make a miniature chair frame and cover it in chocolate. That didn’t work. Then they tried slabs of chocolate that could be assembled. That didn’t do it either.

“They went in a different direction,” Manchester lamented. He said they also tried to do a Kosher version of the bacon bits using turkey and soy-based bacon-flavored bits, but that also was a no-go.

The candy-maker said he wants his double storefront retail store to be a destination. He also said he’s a big believer in giving back to the community, citing the financial support the candy store has given to such entities as the Dignity Diner, The Greater Chicago Food Depository and LGBTQ+ organizations, like Center On Halsted. Windy City Sweets enjoys a collaborative charitable partnership with Dolphin Rose Music & Media.

How does Manchester keep from eating all the profits?

“I have two or three pieces of dark chocolate-covered almonds every day. That satisfies me,” he said.

Windy City confections range in price from $15 per pound for gummies, $18 to $21 for chocolate-covered fruit and nuts and $32 for handmade chocolates. Licorice is $16 per pound.

Windy City is open seven days a week from 11 a.m. to 9 p.m., with extended hours during the summer for ice cream lovers and closes only for Thanksgiving, Christmas and New Year’s.

“We also close early three days a year: Christmas Eve, New Year’s Eve and Super Bowl Sunday. Everybody’s home watching the game! Therefore, I invite our fans and customers to be sure to stop by the store soon or get your online orders in prior to the big game!”

Windy City Sweets is at 3308 Broadway, Chicago, and can be reached at (773) 477-6100.