Holiday Hike Chicago-Style: Festive Food & Walking tour

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From $79.99

27 reviews   (4.89)

Price varies by group size

Lowest Price Guarantee

Pricing Info: Per Person

Duration: 3 hours

Departs: Chicago, Chicago

Ticket Type: Mobile or paper ticket accepted

Free cancellation

Up to 24 hours in advance.

Learn more


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!

What's Included

Food samples

Holiday attractions

Holiday Cocoa or Cider

Local tour guide

What's Not Included

$10 per person (or more) suggested guide gratuity. (via Cash, Venmo and PayPal)

Alcoholic Beverages

Hotel pickup and drop-off

Traveler Information

  • INFANT: Age: 0 - 3
  • YOUTH: Age: 4 - 11
  • ADULT: Age: 12 - 99

Additional Info

  • Hand sanitiser available to travellers and staff
  • Operates in all weather conditions, please dress appropriately
  • Social distancing enforced throughout experience
  • Wheelchair accessible
  • 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 thing
  • If you have dietary restrictions, please add a note in the special requirements section when booking, and email to after booking to confirm they can accommodate
  • Public transportation options are available nearby
  • Travelers should have at least a moderate level of physical fitness

Cancellation Policy

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

  • For a full refund, you must cancel at least 24 hours before the experience’s start time.
  • If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
  • Experience may be cancelled due to Insufficient travelers

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.

60 minutes • Admission Ticket Free

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.

15 minutes • Admission Ticket Free

Macy's on State Street
Enjoy the Holiday decor

10 minutes • Admission Ticket Free

Daley Bicentennial Plaza
Enjoy Christkindlmarkt in Chicago

20 minutes • Admission Ticket Free

Cloud Gate
Iconic Chicago attraction

5 minutes • Admission Ticket Free

Jay Pritzker Pavilion
Gorgeous open air amphitheater

5 minutes • Admission Ticket Free

The Art Institute of Chicago
Amazing collections

• Admission Ticket Free

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