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Chicago Cupcake Graduating From Food Truck to Wicker Park This Month

It'll offer more than cupcakes along Milwaukee Avenue.

Chicago Cupcake
Chicago Cupcake
Brendan Bolger

Though its popularity has peaks and valleys, there always seems to be room for the sweet and reliable cupcake. The owner of Chicago Cupcake hopes to tap into that sentimentality when the food truck graduates into a brick and mortar spot in Wicker Park. The new space, inside the former Bar Bar Black Sheep on Milwaukee Avenue, will give owner Brendan Bolger room to bake and offer new items. He's gunning to open before Thanksgiving Day.

"It was always my goal," Bolger said, of transitioning from food truck to restaurant. "My background is in finance, but I had a pension for baking, ever since college."

When Bolger created Chicago Cupcake, cupcakes were at the height of trendiness. Though that popularity has dipped, as other sweet things like doughnuts, cake pops, pies and cronuts gained popularity, Bolger says cupcakes are a convenient treat that will always have a place in a grab-and-go society.

The shop, at 1415 N. Milwaukee Ave., has about 30 seats inside, a service counter and will eventually have a sidewalk patio. Bolger also wants to offer brunch, but that won't start until spring at the earliest. Bolger, whose cupcakes can be purchased at Mariano's stores and at Coalfire Pizza, says his cakes differ because they're richer than other offerings and have special crusts.

As for those new items? They're planning to serve Leige waffles, which are popular in Belgium. A crisp exterior from pearl sugar provides a caramelized glaze, while the insides have a brioche-like texture, and Bolger said it's one of the best things he's "ever put in his mouth." The bakery will also have a toppings bar for said waffles.

Chicago Cupcake will also pour Sparrow coffee, and will open early mornings so commuters can grab something before work. Don't worry, Chicago Cupcake's two food trucks, one that sticks around the city and the other in the suburbs, will remain in operation.

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