• Tour code: 5277CHICUP
  • Location: Chicago, Illinois
  • Duration: 2 hours (approx.)

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Taste the best cupcakes in Chicago on this 2-hour walking tour led by a local guide. Stroll along the Magnificent Mile, making stops at 6 artisanal bakeries, sweet shops and dessert boutiques for treats like Italian gelato and decadent gourmet cupcakes. See famous Chicago landmarks, like the Chicago Water Tower and the John Hancock Building, along the way for a dose of city sightseeing with your sugar.


  • 2-hour cupcake walking tour in Chicago
  • Follow your local guide on an easy walk along the Magnificent Mile
  • Visit several artisanal bakeries and shops to sample six sweet treats
  • Indulge in a variety of decadent gourmet cupcakes and gelato – all tastings included
  • See famous Chicago landmarks along the way including the John Hancock Building and Chicago Water Tower

Why Our Insiders Chose This Tour

What You Can Expect

Cupcake Walking Tour in Chicago

Take a cupcake break with a refreshing scoop of gelato

Meet in front of Leonidas Chocolate Café to begin your 2-hour cupcake walking tour with your guide and food-loving group. Step inside this historic chocolatier to treat your tastebuds to their first cupcake of the day.

Wander through the Goddess and Grocer, a food lover’s paradise run by Chicago-based food fanatics. Hit up More Cupcakes, a modern art museum-meets-cupcake bakery where you’ll enjoy a sophisticated, gourmet cupcake with an innovative twist.

Get a dose of pop culture at Sprinkles, founded by Candace Nelson, a featured judge on TLC’s 'Cupcake Wars'. Sprinkles is arguably the world's first cupcake bakery and the progenitor of the gourmet cupcake craze, and the cupcakes stand hold up to their reputation.
Step back in time as you visit one of the oldest and most famous Italian delis in Chicago, L'Appetito. Though this is a cupcake tour, it’s impossible to overlook the gelato here. At Crumbs Bake Shop, which bakes more than fifty delicious varieties of cupcakes daily, taste one of their famously decadent chocolate cupcakes. 

As you walk, your guide will point out iconic Chicago landmarks like the Chicago Water Tower and the John Hancock Building. You’ll leave this 2-hour tour with some knowledge about Chicago and a satisfied sweet tooth.

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