Adventure Collective
Chicago Sweets and Treats Dessert Tour: A Delectable Urban Adventure - Chicago

Chicago Sweets and Treats Dessert Tour: A Delectable Urban Adventure

Chicagoeasy

Difficulty

easy

Duration

2–3 hours

Fitness Level

Suitable for most fitness levels; involves walking urban streets over a few miles.

Overview

Taste your way through Chicago’s top dessert spots on a walking tour that blends sweet indulgence with urban exploration. Discover local gems and meet passionate artisans in the heart of the city.

Chicago, Illinois

Chicago Sweets and Treats Dessert Tour

2.5 Hours • Ages 7+ • Sweet Treats

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Adventure Photos

Chicago Sweets and Treats Dessert Tour photo 1

About This Adventure

Embark on a delightful 2.5-hour journey through Chicago's West Loop, sampling an array of decadent desserts from mochi donuts to classic cannolis. Led by a local food expert, discover the neighborhood's rich culinary history while enjoying treats from renowned spots like Molly's Cupcakes and JoJo's Shake Bar. Indulge your sweet tooth!

Satisfy your sweet tooth with decadent desserts in Chicago's West Loop neighborhood

Duration

2.5 Hours

About

  • You'll sample everything from a modern mochi donut, to a classic fresh-filled cannoli, with a stop for a salty snack in the middle.
  • Your local food expert will regale you with the tales and traditions tied to some of our favorite goodies.
  • The perfect experience for that person in your life who always asks to see the dessert menu.

What to Expect

On our Chicago Sweets and Treats Dessert tour, you'll experience an all-out decadent journey through the West Loop's renowned and extensive dining scene. With a hot chocolate in hand, you'll stroll down Restaurant Row to visit a modern food hall, cute bakeries, and other dessert destinations. You'll learn about how the area transformed from a working-class neighborhood in the 1900's to the trendy foodie hot spot that it is now.

On your journey, you'll sample full-size tastings of desserts that have been around for centuries along with newer creations offering modern spins on the classics. We challenge you to finish off every morsel, but you'll have the opportunity to take some snacks back with you if you hit your sugar limit.

Whether you're vacationing in Chicago for the first time or are a seasoned local - we guarantee you'll walk away from this tour with a greater appreciation for the last and arguably best course in a meal - and perhaps a sugar buzz. Join us on our Chicago Sweets and Treats Dessert tour for a dessert course that keeps on going.

Where We'll Eat

Gaijin Chicago's first Japanese okonomiyaki restaurant helmed by chef Paul Virant and listed as one of Chicago's best Japanese restaurants in the 2021 Michelin Guide.

JoJo's Shake Bar at TimeOut Market Classic diner-feel with a dose of 80's and 90's nostalgia known for the monster shakes and hot chocolates.

Luella's Southern Kitchen at TimeOut Market Chef Darnell Reed's homage to his great grandmother's Southern cooking.

PB&J (Pizza, Beer, and Jukebox) A family-friendly hangout with music, beer, and a menu that includes a $350 peanut butter and jelly sandwich.

J.P. Graziano's Iconic family-run Italian sub shop and grocer that's been in business since 1933.

Molly's Cupcakes Winners of the first season of 'Cupcake Wars,' their cupcakes are inspired by the owner's third grade teacher and in her honor, a portion of their proceeds go to local schools.

Adventure Tips

Bring an appetite

Wear comfortable shoes and come hungry—this tour features multiple dessert stops that will leave you pleasantly full.

Stay hydrated

Carry a water bottle to balance out the sweets and stay refreshed throughout the walk.

Inform about dietary restrictions

Notify the tour operators in advance if you have allergies or dietary needs to ensure a safe and enjoyable experience.

Weather-appropriate clothing

Chicago’s weather can be unpredictable, so dress in layers to stay comfortable during the walk.

Local Insights

Wildlife

  • Urban pigeons
  • City-dwelling squirrels

History

Chicago’s dessert scene reflects its rich immigrant heritage combined with modern innovations, growing especially vibrant since the late 20th century.

Conservation

Tour operators emphasize supporting local businesses that source ingredients sustainably and maintain eco-friendly practices.

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Frequently Asked Questions

Recommended Gear

Comfortable walking shoes

Essential

Essential for covering multiple stops on city streets without discomfort.

Reusable water bottle

Essential

Keeps you hydrated as you stroll between dessert locations.

Light jacket or layers

Essential

To stay comfortable amid varying weather conditions in Chicago.

all specific

Small backpack or tote

Handy for carrying purchases or personal items during the tour.