Craziest Cupcakes In Chicago

Craziest Cupcakes In Chicago

Chicago is no stranger to the glory of cupcakes. With a new specialty store popping up on every corner, it’s not hard to find a great cupcake. The cupcakes featured on this list aren’t just your average chocolate, vanilla, and red velvet. The bakeries featured below have everything from bacon to marshmallows.

Here are some of the craziest cupcake flavors in Chicago. Have a favorite we missed? Leave a comment, and tell us below.


2536 N. Clark St., Chicago
(773) 883-7220

Located in the Lincoln Park neighborhood, Molly’s was named after the founder’s third-grade teacher who always baked tasty cupcakes for students’ birthdays. At Molly’s, you can indulge your sweet tooth for a good cause. A portion of the profits are donated directly to community schools.

Featured ‘Crazy Cakes’:
1) The Ron Bennington (chocolate cake, peanut butter filling, chocolate ganache, crushed butterscotch topping)

2) Cookie Monster (Vanilla chocolate chip cake, raw cookie dough center, buttercream, mini chocolate chip cookie)

3) Minty Mash-Up (chocolate cake, mint chocolate chip filling, mint buttercream, chocolate bar)

4) Peach Cobbler

5) Carrie’s Campfire (chocolate cake, marshmallow fluff, hot fudge, graham cracker crumbs, chocolate bar chunks)



Phoebe’s Cupcakes

613 West Briar Place, Chicago
(773) 525-0817

Phoebe’s Cupcakes typically has 15 cupcake flavors available each week, which are rotated from more than 200 total flavors. Check their website for the ever changing menu and cupcake flavors.

Featured ‘Crazy Cakes’:
1) Breakfast Cupcakes (Maple soaked Buttermilk Cake with a Maple Butter Frosting topped with Crispy Bacon)

2) Orange Bourbon Pecan (Orange cake with orange bourbon sugar cream topped with bourbon candied pecans)

3) Banana Mocha (Chocolate espresso cake with banana Italian butter cream topped with a chocolate covered espresso bean)

Sugar Bliss

115 N. Wabash, Chicago
(312) 845-9669

Located in the Loop, Sugar Bliss cake boutique has a variety of unique cupcakes. Flavors change daily, so check their website for the latest variety. Prices range from $1.50 per mini-cupcake or $15 for a dozen, to $3.50 for a regular size cupcake, or purchase a dozen for $40.

Featured ‘Crazy Cakes’:
1) Chocolate Peanut Butter

2) Orange Creamsicle (Madagascar bourbon vanilla cake with orange vanilla zest buttercream)

3) Chai Latte Cupcake (Vanilla cake with chai buttercream topped with cinnamon dust)

4) Strawberry Dream (Fresh strawberry cake with strawberry cream cheese frosting)

5) Pumpkin Patch (Pumpkin spice cake with cream cheese frosting)


705 W. Belden Ave., Chicago
(773) 404-2253

Located in Lincoln Park, Swirlz cupcakes are baked fresh daily. This local favorite has something for everyone. Gluten-free and vegan cupcakes are also available.

Featured ‘Crazy Cakes’:
1) S’mores

2) Tiramisu

3) Pumpkin Cheesecake

4) Twixie (Chocolate cake, vanilla shortbread cookie, caramel butter cream)


50 E. Walton Street, Chicago
(312) 573-1600

Located in the Gold Coast, Sprinkles bakery began in Beverly Hills, and most recently expanded to Chicago. Always packed with eager cupcake lovers, this has become the go-to cupcake spot for locals and tourists alike. Cupcakes are $3.25 each, $36 for a dozen.

Featured ‘Crazy Cakes’:
1) Chai Latte

2) Orange Cranberry

3) Chocolate Marshmallow

4) Ginger Lemon

The Cupcake Counter

229 W. Madison St., Chicago
(312) 422-0800

Located in the Loop, The Cupcake Counter features daily surprises, and everyday favorites. For a bonus treat, add a scoop of ice cream to your favorite cupcake for $4. Cupcakes are $3 each, $33 for a dozen. Check their website or store for daily specials.

Featured ‘Crazy Cake’:
1) Ice Cream Sandwich (A scoop of ice cream sandwiched between your favorite cupcake)

Have a favorite we missed? Leave a comment, and tell us below.–Lauren Wulf, CBS Local Chicago

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