High demand for Flirty Cupcakes, which once operated exclusively out of a food truck, required the staff to open a permanent location. The University Village café, called the Dessert Garage, doles out the same oreo cupcake, banana-chocolate, and pineapple rum cupcakes as the baby-blue truck, which continues to circle the city on a weekly schedule.
Though their red velvet had a Chicago Magazine reviewer “waxing nostalgic about dessert tables in the Deep South,” Molly’s Cupcakes is not a one-trick pony. The staff churns out classic cupcakes alongside those that hide a tasty filling — such as mousse, Boston cream, and peach cobbler — in their center.
The creativity of the flavors on the Swirlz cupcake calendar—including pumpkin chocolate chip, brownie batter, taffy apple, cinnamon honey bun—might distract from the fact that almost half of them are gluten-free or vegan and gluten-free. Each is also topped with a two-tone tuft of the shop’s signature Italian butter cream frosting.
Though his cake designs have been featured on TLC’s “Amazing Cakes,” Alliance Bakery & Café’s pastry chef Peter Rios deserves equal recognition for what’s inside of his cupcakes. Indulgent fillings, such as a red-raspberry confit, salted caramel, and passionfruit, burst forth from five of his 15 flavors.
Locally made butter. Nielsen Massey pure vanilla extract. Zingerman’s goat cheese. The cupcakes at Southport Grocery & Café come in simple flavors—red velvet, chocolate, vanilla—but these rich ingredients, according to CS Magazine, render them “big enough to share but addictive enough that you won’t want to.”
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Bennison’s Bakery opened in 1938, and the staff’s allegiance to high-quality ingredients—cream, real butter, fresh buttermilk, and eggs—hasn’t changed since then. Two master bakers oversee the large-scale production of cupcakes and pupcakes, which feature puffs of chocolate buttercream and fudge shaped into the face of a smiley pooch.
It may seem that artists moonlighting as pastry chefs staff Luscious Layers Bakery. Their portfolio of cupcake designs includes three-dimensional sleeping babies, jungle animals, and bookworms. Beneath the frosting and fondant art lie cupcake flavors such as French toast and chocolate with peanut-butter mousse.
Café Soroni’s staff is equally as proud of their classic cupcakes—vanilla, red velvet, and chocolate cake swirled with cream-cheese-and-butter icing—as they are of their carefully curated hot-beverage selection. After indulging in dessert, customers can sip an Italian espresso or nurse a mug of organic tea from Austria.
Third-generation owner Norm Dinkel told the Redeye that he has nothing but confidence in Dinkel’s Bakery’s ability to compete with the city’s new crop of cupcakeries: “We’ve been making cupcakes since 1922.” Each cupcake comes with a generous dollop of frosting, and the bakery staff can customize designs for holidays or parties.
After her sister was diagnosed with Hodgkin’s Lymphoma in 2010, Laura Pekarik defrayed the cost of medical bills by selling cupcakes in flavors she invented herself. Her creations were such a hit that she turned them into a business that’s garnered a sweet reputation—she even competed on Food Network’s Cupcake Wars in 2012.
At Panaderia Nuevo Leon, customers grab pair of tongs to help themselves to the shelves of fresh bread, pastries, and desserts that line the 30-year-old shop. Nestled among the selection are chocolate cupcakes served with an extra-large swirl of frosting.
Roeser’s Bakery is such a Chicago tradition that the city council recognizes one block of North Avenue as “Honorary John C. Roeser Avenue” in memory of the shop’s founder. Metromix Chicago says it’s the oldest family-owned bakery in all of Chicagoland, and like the shop itself, the red velvet cupcakes remain a favorite.
Inside Lovely, customers perch on barstools, pore over computers, and catch up over lattes; this is exactly the welcoming vibe that owners Bob and Gina Hartwig had in mind before opening the shop. The menu features sandwiches and coffee, as well as four cupcake flavors: chocolate, vanilla, red velvet, and carrot.
Deal or no deal, our editors strongly recommend these businesses based on their reputation, popularity, and quality of service.