Holiday Hike Chicago-Style: Festive Food & Walking tour in Chicago booking from $84.99

Holiday Hike Chicago-Style: Festive Food & Walking tour

Overview

There’s nothing more magical than downtown Chicago during the holiday season. Bobby’s Holiday Hike is a 3hr guided walking and food tour through the Chicago Loop, brought to you by Bobby's Bike Hike, internationally recognized for their tours. You’ll get to sample the Windy City’s favorite winter treats; including a slice of deep dish pizza, Chicago-style hot dog, Italian Beef, chocolate brownie, and hot apple cider. Upon arrival, you can add a VIP holiday craft beer package for $19.99/person. Our entertaining guides will get your holiday spirit primed with plenty of food and knowledge. Did you know Rudolph the red-nosed reindeer was a story created in Chicago? You’ll see the Christmas window displays at the original Marshall Field’s department store, Chicago's city Christmas tree, the ice skating rink at Millennium Park, and the legendary Christkindlmarket, a traditional German Christmas Market. No other tour offers such an all-inclusive experience of Chicago during the holidays!

City: Chicago

Sun 18 May

Other dates

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Starting at $84.99

Make a reservation

Sun 18 May

Starting at $84.99

Make a reservation

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What's Included

Food samples

Holiday attractions

Holiday Cocoa or Cider

Local tour guide

Additional Info

Wheelchair accessible
Public transportation options are available nearby
Suitable for all physical fitness levels
If you have dietary restrictions, please add a note in the special requirements section when booking, and email to [email protected] after booking to confirm they can accommodate.
Tour Operator can accommodate vegetarians or those who don’t eat beef or pork but can’t cater for gluten-free (limited options) or vegan (extremely limited options) diets.
VIP Adult Beverage upgrade (3 samples) available upon arrival for $19.99 per person extra (Ages 21+)
TripAdvisor rated this tour its highest-level Traveler’s Choice Award each year since 2002.
Our groups have exclusive VIP access to locations we visit.
Operates in all weather conditions, please dress appropriately
Minimum numbers apply. There is a possibility of cancellation after confirmation if there are not enough guests to meet requirements. In the event of this occurring, you will be offered an alternative or full refund.

What To Expect

Christkindlemarket

Enjoy a hot cider at this outdoor german christmas market

Palmer House Hilton Historic Lobby

Stroll down State Street where the lights, decorations and window displays dazzle. Throughout your tour, you'll make stops for a variety of tasty treats, including a brownie sample at the Palmer House Hotel, where the chocolatey treat was invented! While inside the historic building, your guide shows you the magnificent interior architecture of this grand old hotel, where many famous guests have stayed since it opened in 1875.

Macy's on State Street

Enjoy the Holiday decor

Millennium Park

Get a full tour of Millennium Park and gaze over the large outdoor ice-skating rink, flanked by the some of the most iconic buildings on the Chicago skyline. Watch hundreds of skaters twirl as they enjoy the free attraction. See the city’s official Christmas tree, loaded with spectacular ornaments and lights.

Cloud Gate

Iconic Chicago attraction

Jay Pritzker Pavilion

Gorgeous open air amphitheater

Daley Bicentennial Plaza

Enjoy Christkindlmarkt in Chicago

Wrigley Building

Visit one of Chicago's iconic buildings

Palmer House Hilton Historic Lobby

Visit the iconic Palmer House Hotel lobby and enjoy the original recipe brownie, invented here at the hotel for the 1893 Chicago's Worlds Fair.

The Art Institute of Chicago

Amazing collections

Show 7 more stops

Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Traveler Photos

Reviews (64)

H2OMan624

Jan 2025

We learned so much about the rich history of Chicago, the people who started the restaurants, the history of Chicago’s iconic foods: pizza, hot dogs, Italian beef sandwiches, this fires that destroyed Chicago and how the Chicago people rebuilt it time and time again. If you like good food, entertaining/educational presentations, this is definitely your kind of day trip! As I said our guide was Jeff who is a gifted storyteller with an endless vault of Chicago history. Ask for Jeff when you book your food adventure. He is an A+ guide.

Pat_P

Jan 2025

If you're here in the city during the winter (especially if it's your first time), this is a great way to stay your trip! See all the biggest sights and taste the signature tastes. Is your starting longer than the day, this is great way to get your bearings off the city before deciding where and what you want to do

Justin_D

Dec 2024

Today I found out it was a FBA woman named Alice Mae Redmond who created the deep dish pizza in Chicago! She gets no recognition for it in Chicago but that’s nothing new. Enjoy!

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Holiday Hike Chicago-Style: Festive Food & Walking tour

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