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Chicago-style ‘Holiday’ Hike: Season Sampling Walking Tour

Taste your way through the holiday season on this food and beverage walking tour…Chicago-style! This holiday-themed tour begins at the end of November and runs through Christmas Eve. Bobby’s Holiday Hike is a great way to experience all that Chicago has to offer during the winter holidays in a single afternoon stroll! See the lights of the Magnificent Mile, enjoy a warm and filling deep dish pizza, experience the German-inspired festivities of Christkindlmarket, and toast to a joyful season over local craft beer! This three-hour Chicago holiday tour is perfect for families, friends, holiday parties, and anyone looking to celebrate the season in an exciting new way.  All Food & Beverage Samples included in Ticket Price.

What To Expect

Deep-dish pizza is one of Chicago’s most famous recipes, and lures pizza enthusiasts from all over the world. Learn the history of this epic pie and taste some of the best for yourself!

Cloud Gate, known affectionately as “The Bean” debuted in Millennium Park in 2006. Designed by famed Indian artist, Anish Kapoor, this giant, stainless steel masterpiece has become one of the most famous symbols of Chicago arts and culture.

The Chicago municipal Christmas tree has been a Windy City tradition since 1913. The tree is locally grown and decorated with thousands of lights, lit for the first time in an annual lighting ceremony.

The Marshall Field’s Christmas Windows have been cheering up the sidewalks of State Street since the 1940s. These playful, holiday-themed displays draw crowds from all over the midwest with their elaborate theming and animatronics.

The Loop is Chicago’s bustling business district, named for its location within the rectangular convergence of multiple “El” train tracks.

Hot apple cider is one of the most popular treats enjoyed at the Christkindlmarket every season. Spiced and soothing, this drink is the perfect way to warm up on chilly a Chicago afternoon!

Traditional german bratwurst is a favorite holiday food in this sausage-loving town. Served two-to-a-bun, this sandwich a Christkindlmarket bestseller.
Fun fact: Chicago is home to the world’s first brownie! Served as a portable dessert during the 1893 World’s Fair, the brownie has been pleasing Chicagoans and visitors alike for generations. Taste the original recipe—with walnuts and an apricot glaze—at the Palmer House Hilton today!

The Magnificent Mile lights are a twinkling sensation in the downtown shopping district. The illumination kicks off with an annual festival and parade, with thousands of lights lining Michigan Avenue and beyond.

Chicago is making a name for itself as an American craft beer capital. We’re home to some of America’s favorite breweries, with new microbreweries appearing every year. Taste some of the most refined and refreshing pours as you learn about Chicago’s rich brewing history.

marshall field and company in chicagogiordanos pizza in chicago on food tour

Our Vendors

Giordano’s has been serving up their original “stuffed pizza” since 1974, and has been named “Chicago’s Best Pizza” by NBC, CBS Chicago, New York Times, Concierge Preferred, and more!

Christkindlmarket is Chicago’s largest open-air holiday market and is well-known for its vendors’ high quality gifts and food, holiday cheer, and for being the ideal place for families to create their own holiday traditions.

The Lockwood is an upscale restaurant located within the historic Palmer House Hilton, famous for their extravagant Christmas dinners and their original-recipe chocolate brownie.

Exchequer Pub has existed in various iterations since the 1920s. Famous for their baby back ribs, deep dish pizza, and Exchequer Amber lager, the pub is a financial-district favorite for locals and visitors around the Holidays.

What Our Customers Are Saying“We did the Holiday Hike walking tour and our guide was extremely knowledgeable and friendly. We learned a lot about the history of Chicago and some fun holiday-specific history. It was a great way to see and taste your way through Chicago!”

– Gretchen P.  Arlington, Virginia

Chicago-style ‘Holiday’ Hike: Season Sampling Walking & Food Tour

Duration: 2.5 hours
Length: 1.25 mile
Level: Festively Easy

(Discount Online Rate includes Food & Beverage Samples)

Price: Fri-Sun Mon-Thurs
Adults $57.75 $54.75
Students $52.75 $49.75
Military $52.75 $49.75
Senior $52.75 $49.75
Kids (under 4) $11.75 $10.75



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