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.
Merchant List Map

Sweet Mandy B’s 1208 W. Webster

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.”


Flirty Cupcakes 1030 W. Taylor

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.


Molly’s Cupcakes 2536 N. Clark

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.


Sugar Bliss Cake Boutique 115 N. Wabash

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.


Swirlz Cupcakes 705 W. Belden

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.


More 1 E. Delaware

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.


Sweet Cakes Bakery 901 N. Damen

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.


Alliance Bakery & Café 1736 W. Division

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.


A Taste of Heaven 5401 N. Clark

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.

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.”


Beautiful Cakes 5814 W. Higgins

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.


Skinnie Piggy 1214 W. Taylor

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.

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.

At Phoebe’s Bakery and Espresso Bar, trained pastry chefs swirl Italian buttercream frosting over cakes to create such signature flavors as salted caramel and pancake and bacon. Each week, the staff chooses 15 flavors to showcase from an [arsenal of 200.


Bennison’s Bakery 1000 Davis St.

Evanston: Suburban Staple since 1938

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 4945 N. Milwaukee

Jefferson Park: Cupcakes and Italian Espresso

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.


Dinkel’s Bakery 3329 N. Lincoln

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.


Cupcakes for Courage 110 W Park Ave

Multiple Locations: For a Good Cause

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 3216 W. North

Humboldt Park: 100-Year-Old Bakery

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.


Lovely: A Bake Shop 1130 N. Milwaukee

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.


TipsyCake 1944 N. Damen

Bucktown: Order Sweets Online

Naomi Levine started TipsyCake as a web-based business for custom cakes. Though she now has a storefront in Bucktown, she still sells her cupcakes online. She and her staff custom-design and ice each batch after customers choose from flavors like coconut, flourless chocolate, and orange.

Deal or no deal, our editors strongly recommend these businesses based on their reputation, popularity, and quality of service.

Keep Exploring Chicago

Related Deals