Chicago Holiday Tour
Holiday Hike – Festive Food & Walking
Taste your way through the holiday season on this food and beverage walking tour…Chicago-style! This holiday tour begins at the end of November and runs through Christmas Eve. Experience all that Chicago has to offer during the winter holidays in a single afternoon food and walking tour! 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.
The adventure begins at Lou Malnati’s Pizzeria in the Wrigley Building (410 N. Michigan Avenue) right on Chicago’s Magnificent Mile, which is Chicago’s largest holiday shopping district and hosts the unofficial start to the Christmas season each year with it’s Holiday parade down it’s cooridor. Here you’ll meet your fun-loving and enthusiastic tour guide who will introduce you to the beautiful city and our history of holiday cheer. Your group will share a hot, cheesy, deep dish pizza, one of Chicago’s favorite holiday meals—often shipped around the country as a gift! You’ll learn about the history of this Goliath pie and taste why it’s become a global phenomenon. Guests over 21 years will be able to upgrade their ticket to the VIP Christmas cocktail/Craft beer package to enjoy a locally crafted Chicago beer with their pizza.
After pizza, your guide will lead you on an amazing journey where we’ll see the Wrigley Building and it’s beautiful Christmas tree and holiday decor, then a beautiful walk over the Chicago Riverwalk to make a stop at the Chicago Theatre and it’s iconic Chicago marquee. By this point in the tour we’ve opened your appetite back up to enjoy a traditional Chicago-style hot dog at Billy Goat Tavern, a local favorite made famous by the famous SNL skit. Their Chicago-style hot dogs are served with all the traditional fixings as well as vienna beef, the preferred beef hot dogs of Chicago. Guests over 21 years will be able to upgrade their ticket to the VIP Christmas cocktail/Craft beer package to enjoy a locally sourced and seasoned craft beer sample or holiday cocktail.
Then we’re off to Millennium Park. Here you’ll get a full tour and catch a peek of some of our favorite (and most-heavily Instagrammed) works of public art such as Cloud Gate (aka ‘the Bean’), the Pritzker Pavilion, the Crown Fountain, and Chicago’s city Christmas Tree. You’ll learn about Chicago’s long history of Christmas tree distribution and see the annual city Christmas tree, donned with thousands of twinkling lights. Ample photo opportunities guaranteed!
The excitement of Millennium Park will work up your hunger and we’ll satisfy that craving with another Chicago staple, the Italian beef sandwich served with sweet or hot peppers and drenched with au juis.
Next, it’s on to try the Chicago brownie, invented right here in Chicago, where we’ll relax in the elegantly-decorated lobby of the Palmer House hotel. The Palmer House is the longest continually-operating hotel in North America, but is better known for its famous dessert invention: the brownie!
The tour will then head over to State Street for a glimpse of the Christmas window displays at the flagship Marshall Field’s department store (now a Macy’s). These narrative dioramas have been drawing crowds since their debut in the 1940s, and get more creative and elaborate every year.
The tour will conclude at Chicago’s legendary Christkindlmarket, a German and European-inspired open-air holiday bizarre. Dozens of vendors from around the world set up shop in Daley Plaza to sell some of the finest holiday foods and gifts available in the city. You’ll get to taste of some delicious German holiday fair and learn about other Bobby-approved holiday activities to enjoy during your stay in Chicago before being let go to discover the market and all it has to offer.
If you’d like to skip the holiday food and just enjoy the guided holiday stroll — Chicago’s Seasonal Stroll – Walking Tour. These two holiday tours are sure to get you in the Holiday spirit, so enjoy!
Hear about our Holiday Hike from Bobby’s Bike Hike Founder, Jeremy, on WGN Radio!
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.
Hot Apple Cider is one of the most popular treats enjoyed during the holidays every season. We’ll enjoy an old world version from one of the most popular German vendors at Christkindlmarket!
An Italian beef sandwich, originating in Chicago, composed of thin slices of seasoned roast beef, simmered and served au jus on a long Italian-style roll. Ours will be topped with sweet green Italian peppers. The sandwich’s history dates back to the 1930s.
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 three samples of Seasonal local craft beer 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 Cider
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 famous Billy Goat Tavern located right next to the world-famous Millennium Park, serves delicious Chicago-style hot dogs to Chicago locals and Millennium Park visitors every day of the week.
Bongiorno’s specializing in Italian Beef and thin-crust pizzas, is a family-run business and takes pride in providing you with the best home-cooked Italian food and service in Chicago. They have won many awards from the Hungry Hound, Chicago Magazine, and TripAdvisor speak well for their work.
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.
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
(Discount Online Rate includes Food Samples.)
|Youth (Ages: 4-11)||$64.99||$59.99|
|Infants (Ages: 0-3) when sharing w/ Adult||$10.99||$9.99|
|VIP Holiday Cocktail/Beer Tasting Upgrade $19.99|