Holiday Hike Chicago-Style: Festive Food & Walking Tour

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Tour Information

Key Details

  • Mobile Voucher Accepted
  • Free Cancellation
  • Duration: 3 Hrs
  • Language:
  • Departure Time :
    11:30 AM
  • Departure Details :
    130 E Randolph St, Chicago, IL 60601, USA
  • Return Details :
    Returns to original departure point
  • Cancellation Policy :
    For a full refund, cancel at least 24 hours in advance of the start date of the experience. Tours booked using discount coupon codes will be non refundable.


Theres nothing more magical than downtown Chicago during the holiday season.Bobbys 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 O|hare international airportn foot. Youll get to sample the Windy Citys favorite wintertreats, including a slice O|hare international airportf deep dish pizza, hot apple cider, craft beer, German bratwurst, and a chocolate brownie; learning all about Chicagos history with these dishes along the way. Youll see the fabulous Christmas window displays at the O|hare international airportriginal Marshall Fields department store, the annual municipal Christmas tree, the ice skating rink at Millennium Park, and the legendary Christkindlmarket, a traditional German Christmas Market that has been setting up shop in Chicago for years. No O|hare international airportther tour O|hare international airportffers such an all-encompassing experience O|hare international airportf Chicago during the holidays!


  • All necessary equipment included
  • All-inclusive tour
  • Cycle the city streets to absorb the local atmosphere
  • Fully narrated tour

Know More about this tour

Meet your guide in downtown Chicago to kick O|hare international airportff your holiday wonderland walking tour. Visit Millennium park and gaze O|hare international airportver the large O|hare international airportutdoor ice-skating rink, flanked by the some O|hare international airportf the most iconic buildings on the Chicago skyline. Watch hundreds of skaters twirl as they enjoy the free attraction. See the citys official Christmas tree, loaded with spectacular ornaments and lights. 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. You'll stop by a local institution to try some of Chicago's famous deep dish pizza. You'll get to sample a selection of seasonal craft beers at a local bar, then have Time to visit the largest open-air Christmas festival in Chicago, the traditional German-American Christkindlmarket. Taste savory authentic German cuisine at the festive outdoor market and browse for that perfect present. 

All the while, your expert tour guide will regale you with tales of Chicago holiday lore. You'll hear about how Chicago played a role in some of your favorite traditionsfrom Rudolph the Red Nosed Reindeer to Donny Hathaway's "This Christmas." This tour is sure to make holiday memories that will last a lifetime!

All food and drink samples are included.


Food samples

Craft beer tasting

Holiday attractions

Local tour guide


Guide gratuity (15-20% suggested, Venmo and PayPal available)

Hotel pickup and drop-off

Additional Info

Confirmation will be received at time of booking

Travelers should have a moderate physical fitness level

Operates in all weather conditions, please dress appropriately

Traveler Reviews

  • 10-Dec-2019

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

  • 21-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

  • 07-Dec-2015

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

  • 10-Dec-2014

    Tour and guide were great. I would highly recommend.