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Chicago Holiday Theme Tour

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, the Millennium Park ice skating rink and Christmas tree, enjoy a warm and filling deep dish pizza, experience the German-inspired festivities of Christkindlmarket, and toast to a joyful season over a seasonal beverage! 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 & non-alcoholic 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 Chicago-style hot dog is unlike any sausage creation you’ve had before—all beef frank, mustard, tomato, pickle, relish, onion, sport pepper, celery salt… But never ketchup! Have one and change the way you eat this Chicago favorite.

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.

Deluxe Hot cocoa is one of the most popular treats enjoyed around the holidays every season.  We’ll enjoy one of the best seasonal concoctions that we’ve found….anywhere!

Traditional German food is a favorite holiday sample in this sausage-loving town. We’ll get to taste some of the best-selling dishes Christkindlmarket has to offer.

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. With an added fee, you can taste some of the most refined and refreshing pours as you learn about Chicago’s rich brewing history.  With the VIP package, guests over 21 will also enjoy a gingerbread rum infused spiked hot apple cider to help warm your soul.

  • Traditional German Christmas Market
  • Millennium Park Christmas Tree
  • Deep-Dish Pizza
  • Chicago-Style Hot Dog
  • Marshall Fields Holiday Window Displays
  • Hot Cocoa

Lou Malnati’s Pizzeria has been a Chicagoland favorite since 1971, and was voted Best Pizza by Chicago Magazine’s Readers Choice in 2021.

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.

Park Grill is Chicago’s award-winning destination restaurant, at the gateway to Millennium Park and along Chicago’s world-class Michigan Avenue.  Executive Chef, Alfredo Sandoval, brings his interpretation to contemporary American cuisine, infusing it with unique Chicago flavor.

Goddess and the Baker is a spin-off concept of the ultra-successful Goddess and the Grocer restaurants, which opened its first store in 2004. From the very start, the colorful Chicago storefront was bustling with high energy and bold flavors.

With an added fee ($19.99), you can taste some of the most refined and refreshing pours of craft beer as you learn about Chicago’s rich brewing history. With the VIP package upgrade, guests over 21 will also enjoy a gingerbread rum infused spiked hot apple cider to help warm the soul.

Lou Malnati’s Pizzeria: (located on the northside of Wrigley Building, ground level)

410 N. Michigan Avenue,
Chicago, IL 60611

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

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 to 3 hours
Length: 1.25 mile
Level: Festively Easy
Age: 1+

(Discount Online Rate includes Food Samples.)

Price: Fri-Sun Mon-Thurs
Adults $69.99 $64.99
Youth (Ages: 4-11) $64.99 $59.99
Infants (Ages: 0-3) when sharing w/ Adult $10.99 $9.99
Squad Price (Private groups up to 9 people) $549.99 $549.99
VIP Holiday Cocktail/Beer Tasting Upgrade $19.99

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Private Tour
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