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Holiday Hike Chicago-Style: Festive Food & Walking tour

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 3-hour guided walking and food tour through the Chicago Loop, brought to you by Bobby's Bike Hike, internationally recognized for tours by bike and on foot. 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. Add a VIP holiday craft beer package. 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 fabulous 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-encompassing experience of Chicago during the holidays!

City: Chicago

Mon 23 Dec

Other dates

You can choose the date already on the booking website

Starting at $79.99

Make a reservation

Mon 23 Dec

Starting at $79.99

Make a reservation

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Unique Activities (21) Transfers & Transportation (103) Tours, Sightseeing & Cruises (113) Entry Tickets (47) Sporting Events (1) Good for Small Groups (6) Seasonal & Holiday Tours (41) Walking Tours (697) Outdoor Activities (20) Limitied Availability Tours (6) LGBT Friendly Tours (4) Family-friendly Activities (7) Solo Travelers' Tours (147) Food & Drinks (27) Travelers recommend (73) Good for Groups (8) Top Activities (18) Guided Audio Tours (3) Art, Culture & History (135) Attractions to explore (38)

What's Included

Food samples

Holiday attractions

Holiday Cocoa or Cider

Local tour guide

Additional Info

Wheelchair accessible
Public transportation options are available nearby
Travelers should have at least a moderate level of physical fitness
Operates in all weather conditions, please dress appropriately
All of our walking tours at the present moment do allow for ADA compliant and wheelchair accessible. But please note that sometimes our restaurants change and we cannot guarantee every restaurant will not include stairs of some sort which might make things difficult. But a majority of our stops should be ADA compliant.
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
Hand sanitiser available to travellers and staff
Social distancing enforced throughout experience

What To Expect

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.

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

Daley Bicentennial Plaza

Enjoy Christkindlmarkt in Chicago

Cloud Gate

Iconic Chicago attraction

Jay Pritzker Pavilion

Gorgeous open air amphitheater

The Art Institute of Chicago

Amazing collections

Show 4 more stops

Cancellation Policy

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

Traveler Photos

Reviews (38)

shaz_aussie39

Dec 2019

Our guide Justin was very informative and friendly. We really enjoyed the food and drink we tried, would highly recommend this tour.

Kayla H

Dec 2018

Our tour guide Brittany was so awesome! She had so much knowledge on Chicago and we were very pleased with that! We had a blast.

alijohnson0201

Dec 2017

I've lived in the Chicago area my whole life and learned so many new, interesting facts about Chicago and its history. While doing so, we tried some great Chicago food and were able to see the city all dressed up for the holidays. We did this tour as a team building activity for work and we all had a blast! Our tour guide Sarah was very knowledgeable and fun and made this a wonderful experience.