Holiday Hike Chicago-Style: Festive Food & Walking Tour

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Tour Information

Key Details

  • Mobile Voucher Accepted
  • Duration: 3 Hrs
  • Language:
  • Departure Time :
    11:30 AM
  • Departure Details :
    410 N Michigan Ave, Chicago, IL 60611, USA
  • Return Details :
    Christkindlmarket Chicago, 50 W Washington St, Chicago, IL 60602, USA
  • Cancellation Policy :
    This activity is non-refundable 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 on foot. Youll get to sample the Windy Citys favorite wintertreats; 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. O|hare international airport|hare international airport|hare international airport|hare international airport|hare international airport|hare international airportur 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? Youll see the fabulous Christmas window displays at the original Marshall Fields 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!


  • 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

Holiday attractions

Local tour guide

Holiday Cocoa or Cider


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

Hotel pickup and drop-off

Alcoholic Beverages

Additional Info

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.

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

Travelers should have a moderate physical fitness level

This experience requires a minimum number of travelers. If its canceled because the minimum isnt met, youll be offered a different date/experience or a full refund

This tour/activity will have a maximum of 15 travelers

Hand sanitizer available to travelers and staff

Social distancing enforced throughout experience

Traveler Reviews

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  • 14-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.

  • 11-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.

  • 05-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.

  • 04-Dec-2022

    Josie is a wonderful guide. She is funny, knowledgeable, and quite informative. She organized our time well and kept us moving.

  • 04-Dec-2022

    We had a great time. Josey was an amazing guide. We would recommend to anybody visiting the city of Chicago.

  • 03-Dec-2022

    It was a great experience! Josie did an excellent job leading us through the city and giving us all kinds of facts with a touch of humor. Would highly recommend this food tour!

  • 01-Dec-2022

    We had a fabulous time with Josie guiding us through some historical, beautiful and delicious sites in downtown Chicago. We came to appreciate some of the amazing history of the city and enjoyed some delicious and iconic flavors that Chicago is known for along the way. It was a fantastic activity to enjoy with family and I new friends met during the tour. Thank you Josie!

  • 01-Dec-2022

    This is a must do tour whilst in Chicago! Josie our guide was so knowledgeable and made the tour fun for everyone. The food stops were amazing and Josie was able to answer all our questions without any hesitation. This walking tour gives you a great insight to what Chicago offers. If you do just one tour do this one and upgrade to include the beers - you won’t regret it. Oh and also don’t eat too much before this walking tour as food portions are good sizes

  • 28-Nov-2022

    Learning the history around the food of Chicago was my favorite part. Tour guide Josie was knowledgeable and personable.

  • 27-Nov-2022

    The food was of much larger portions then thought they would be giving an much better experience. Our guide was knowledgeable and very nice

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