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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

Sun 22 Dec

Other dates

You can choose the date already on the booking website

Starting at $79.99

Make a reservation

Sun 22 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)

Ly_D

Dec 2022

Loved the option to have a beer tasting from the local brewery and our tour guide was awesome. The food was delicious and the pizza from Lou Malnati’s pizzeria was the best deep dish we’ve ever had.

Janelle_B

Dec 2022

This tour was wonderful and I would highly recommend it to anyone. Our tour guide, Julia, did an excellent job of telling us about Chicago’s history and taking us to the most popular spots in Chicago. One of my favorite things about the tour was being able to walk into restaurants and not have to wait to be seated or for our food and drinks. It was a very busy day in Chicago so this made it easy to see a lot more than doing it on your own.

Amy K

Dec 2022

A fun and informative way to experience Chicago’s famous non-foodie foods with a jovial and quick witted guide. Josie entertained us and expedited our feasting at several local establishments on a very busy December Saturday. As others may have already mentioned… do not eat much, if anything prior to this tour. We were served nearly full portions at each of the stops. Josie reeled off fun Chicago facts and kept us entertained as we made our way from one food stop to the next. Her upbeat vibe made the tour a hit for us.