Chicago Cupcakes
Great Places for Tiny Cakes

It’s a question that’s been debated by the likes of The Washington Post and on NPR: Why are cupcakes so popular? While the paper’s recipe editor theorizes that the cakes’ small size appeals to those seeking portion control, the radio pundits believe that the boutique cupcakes feel like affordable luxury in a time of recession. Perhaps the answer is simply that they’re delicious—especially those made inside Chicago’s dozens of noteworthy bakeries.
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Lincoln Park: Sprinkles Come Standard

Hobbyist-turned-professional-baker Cindy’s pastel-hued cupcakes aren’t ready to eat until they’ve been topped with sprinkles. The cutesy creations embody the vibe at Sweet Mandy B’s, described by Centerstage Chicago as “the happiest, warmest, most delicious old-fashioned comfort shop in Chicago.”

Lakeview: Artisan Ingredients

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.”

University Village: Mobile Bake Shop

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.

Lincoln Park: Chicago Magazine’s Best Red Velvet

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.

River North & The Loop: Financier Turned Confectioner

After spending years building a career in finance, Teresa Ging made a radical move — she spent eight months perfecting cupcake recipes, then opened Sugar Bliss Cake Boutique in 2007. Today, the shop features 21 flavors that rotate daily, including chocolate peppermint and orange creamsicle.

Lincoln Park: Vegan and Gluten-Free

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.

Gold Coast: Avant Garde Flavors

More’s slick glass-and-chrome shelving system makes Patty Rothman’s cupcakes look like the modern art that they are — according to The New York Times Style Magazine: “[her] cupcakes skew more Ferran Adría than June Cleaver.” Flavors have included foie gras sour cherry and twice-baked potato.

Ukranian Village: Cupcake Happy Hour

The staff at Sweet Cakes Bakery use their Twitter page to announce their cupcake happy hour, a two-hour window during which customers can get the desserts—which come in vegan and gluten-free varieties—at a discounted price.

Wicker Park: Raspberry Confit- and Caramel-Filled Cupcakes

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.

Andersonville: Moon Pie and Malted Milk Ball

Everything on the menu at A Taste of Heaven is cooked in house and from scratch, according to Metromix Chicago. That includes the shop’s 13 cupcake flavors, such as moon pie, malted milk ball, lemon meringue, and orange creamsicle.

Lakeview: Neighborhood Institution

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.

Jefferson Park: Cupcake Towers

The staff at Beautiful Cakes builds cupcake towers, which mimic the shape of a traditional tiered cake. Customers can opt for the desserts in their traditional form as well, in flavors such as turtle, cookies and cream, and lemon.

University Village: For Cravings of All Sizes

Skinnie Piggy’s cupcakes come in three sizes—hog, skinnie, or piglet. The menu juxtaposes classic flavors, including birthday cake and german chocolate, with seasonal selections such as the piña colada, a coconut-infused cake topped with pineapple-and-coconut buttercream.

Lakeview: Hand Pies

Chefs at Fritz Pastry fold as many locally sourced ingredients into their pastries and desserts as possible. Alongside traditional cupcakes, they churn out hand pies, tiny, palm-sized sweets filled with fruit.

Noble Square: Cozy Coffee Shop

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.