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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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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)

Mary M

Dec 2017

Sarah, our guide, provided a fascinating behind-the-scenes glimpse of Chicago landmarks and food hot spots. Sarah’s historical knowledge of Chicago and engaging her delivery made this holiday stroll the highlight of our Christmas holiday. We loved visiting popular sites, as well as places off the beaten track. Our plan is to return to Chicago and take the bike tour. Sarah’s interest in people and places made this tour fantastic! Our family highly recommends Bobby’s Bike/Hike Tour in Chicago!

nett10

Dec 2017

The walking tour with Adarius really provided a great taste of Chicago! My husband and I came for the third year and were looking for something new to do on Sunday afternoon. Our walking tour guide Adarius was full of interesting facts and his pleasant personality made it a most enjoyable afternoon! Slice of Deep Dish Pizza, Bratwurst from the Christkindlmarket and Hot Apple Cider. A slight negative - the market was so, so crowded that unfortunately we weren't able to look around much, and the lines were very long. We stopped at Macy's and another beautiful stop at the Palmer House for a bit of history and a chocolate brownie! Ended the tour, stopping where well known gangster/mobster frequented often! The historic story telling was entertaining and the stops festive and full of holiday cheer!

kathleen e

Dec 2015

Robby our New Zealand native guide was very knowledgable and fun. He was always very engaging and made sure we were treated very special. How he remembered our names I do not know. It was my husband 60 th and he made us feel very special. Great itinerary Great food tour Robby was wonderful. 5 stars