Holiday Hike Chicago-Style: Festive Food & Walking tour

  • Operates Seasonal - 3 hours
  • Refundable
  • Printed Voucher/E-Voucher
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Operates Seasonal
Activity Highlights
This is a typical itinerary for this product

Stop At: Millennium Park, 201 East Randolph Street, Chicago, IL 60601-6530

Meet your guide at 11:30 am at the world-famous Giordano's Pizzeria, where you will taste Chicago's unique and delectable stuffed pizza to kick off your holiday wonderland walking tour. Visit 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.

Duration: 1 hour

Stop At: Palmer House Hilton Historic Lobby, 17 E Monroe St, Chicago, IL 60603-5608

Next, 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.

Duration: 15 minutes

Stop At: Macy's on State Street, 111 N State St, Chicago, IL 60602-1659

Enjoy the Holiday decor

Duration: 10 minutes

Stop At: Daley Bicentennial Plaza, 337 E Randolph Dr, Chicago, IL 60602-1305

Enjoy Christkindlmarkt in Chicago

Duration: 20 minutes

Stop At: Cloud Gate, 201 E. Randolph St. Millenium Park, Chicago, IL 60601-6530

Iconic Chicago attraction

Duration: 5 minutes

Stop At: Jay Pritzker Pavilion, Millennium Park, Chicago, IL

Gorgeous open air amphitheater

Duration: 5 minutes

Pass By: The Art Institute of Chicago, 111 S Michigan Ave 159 East Monroe Street, Chicago, IL 60603-6110

Amazing collections

Activity Details
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, hot apple cider or cocoa, German bratwurst, and the original chocolate brownie recipe. Add a VIP cocktail to boot. 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!
Departure & Return
Departure Point130 E Randolph St, Chicago, IL 60601, USA Departure Time11:30 AM
ReturnReturns to original departure point
What's Included
  • Food samples
  • Holiday attractions
  • Local tour guide
  • Holiday Cocoa or Cider
  • Guide gratuity (15-20% suggested, Venmo and PayPal available)
  • Hotel pickup and drop-off
  • Alcoholic Beverages
Additional Information
  • Confirmation will be received at time of booking
  • Operates in all weather conditions, please dress appropriately
  • Wheelchair accessible
  • Near public transportation
  • 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.
  • Travelers should have a moderate physical fitness level
  • This experience requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund
  • This tour/activity will have a maximum of 15 travelers
  • Face masks required for travelers in public areas
  • Face masks required for guides in public areas
  • Hand sanitizer available to travelers and staff
  • Social distancing enforced throughout experience
Cancellation Policy
For a full refund, cancel at least 24 hours in advance of the start date of the experience.
Traveler Reviews

Average based on 5 reviews.

5 Star
4 Star
3 Star
2 Star
1 Star

  • Noah, our guide, was informative, entertaining and a pleasure to hang with! The food stops were perfect and the day was fun!

  • 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

  • Not our first time doing a Chicago Food Tour...LOVED it again.

  • Tour and guide were great. I would highly recommend.

5 reviews
$69.99 USD
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Adult(s) upto 9 passengers
  • Activity Highlights
  • Activity Details
  • What's Included
  • Additional Information
  • Cancellation Policy
  • Traveler Reviews