Holiday Hike Chicago: Festive Food Walking Tour
54 Ratings
Experience the magic of downtown Chicago during the holiday season with Bobby's Holiday Hike. Sample the city's favorite winter treats and explore iconic holiday attractions on this festive food walking tour.
Duration: 3 hours
Cancellation: 1 day learn more
  • Christkindlemarket - Enjoy a hot cider at this outdoor german christmas market
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)
  • Hotel pickup and drop-off
  • Alcoholic Beverages
Additional Information

Experience the enchantment of Chicago’s city center during the festive period with Bobby’s Holiday Hike. This 3-hour walking cum food tour across the Chicago Loop is an offering from Bobby’s Bike Hike, a globally renowned tour operator. Enjoy sampling winter delicacies of the Windy City, from deep-dish pizza, Chicago-style hot dog, and Italian Beef, to chocolate brownie and hot apple cider. When you reach, there’s an option to avail a VIP holiday craft beer package at $19.99 per person. Our lively guides will set the right holiday mood with ample edibles and trivia. Did you happen to know that Chicago is the birthplace of the Rudolph the red-nosed reindeer story? The tour includes sights of the Christmas window displays at the erstwhile Marshall Field’s department store, the city’s Christmas tree, Millennium Park’s ice skating rink, and the famous Christkindlmarket - a characteristic German Christmas Market. No other tour provides such a comprehensive holiday experience of Chicago!

  • 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.
  • Tour Operator can accommodate vegetarians or those who don’t eat beef or pork but can’t cater for gluten-free (limited options) or vegan (extremely limited options) diets.
  • VIP Adult Beverage upgrade (3 samples) available upon arrival for $19.99 per person extra (Ages 21+)
  • TripAdvisor rated this tour its highest-level Traveler’s Choice Award each year since 2002.
  • Our groups have exclusive VIP access to locations we visit.
  • Operates in all weather conditions, please dress appropriately
  • Minimum numbers apply. There is a possibility of cancellation after confirmation if there are not enough guests to meet requirements. In the event of this occurring, you will be offered an alternative or full refund.
410 N Michigan Ave
North Michigan Avenue
Departure Point: Lou Malnati's Pizzeria - Wrigley Building Directions: Please note that the entrance is located on the Northside of the Wrigley Building - ground level. Your guide will be wearing a Bobby's Bike Hike shirt and paddle.
Cancellation Policy

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

Customer Ratings
(54 Ratings)
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Dec 21, 2023
A Must Do Tour!! - Such a fun tour. Julia was AMAZING and so knowledgeable. A great way to sample Chicago’s most popular culinary delights while learning about the city and its history. A must do tour!!
Review provided by Tripadvisor
Dec 20, 2023
Good one - Great tour. The food and drink were delicious and Our tour guide Mickey was fun and knowledgable! Would recommend.
Review provided by Tripadvisor
Dec 18, 2023
Do It! It was the BEST experience - This was my husband and I first time visiting Chicago. I'm so happy I decided to do the tour and enjoyed every second of it. Our tour guide was Brooke, whom was very knowledgable of the entire city. I would definitely recommend this tour when visiting Chicago and ask for Brooke, she was amazing.
Review provided by Viator
Dec 11, 2023
We enjoyed the tour.... - We enjoyed the tour. It was great way to see and learn different things about the city. Fun trying true Chicago food. Mickey the tour guide was great!
Review provided by Viator
Dec 10, 2023
A Definite Must Wgile in Chicago - Absolutely wonderful! Our your guide, Mickey Jordan, was fantastic. So knowledgeable and fun. The tour itself was great. Hit several Chicago landmarks along with sampling of great food.
Review provided by Tripadvisor
Dec 9, 2023
Mickey was great! - Mickey was great! We really enjoyed his jokes and personal touch. He made the tour very comfortable and funny!
Review provided by Viator
Dec 9, 2023
Happy Holiday Tour - We really loved this tour. Brooke was knowledgeable with great energy. Loved her! One suggestion. During holidays when kriskrindlmarket cups are available, serve last stop hot chocolate in them for people taking tour.
Review provided by Viator
Dec 9, 2023
Worth the trip! - This was mine and my husband's first time visiting Chicago together. I came to visit the Christkindlmarket, and I chose the Holiday Hike tour for its combination of food tastings and tour of the city. The food was full servings so quite filling after visiting three restaurants. We visited some key points of interest along the way, and our tour guide, Mickey, did a great job of educating us on the history of each location/meal we tried. There were 12 of us in our party, and Mickey helped to break the ice amongst the group. My only "disappointment" was thinking the samples would be from the Christkindlmarket since it said "seasonal samples" and had the photo of the market. Did get a Belgian Chocolate at the market, but would have loved a brat or pretzel. Still would highly recommend. Worth the investment.
Review provided by Viator
Dec 7, 2023
Great food, great tour! - We loved our guide Greg. He had great stories that I had not heard before even though I have visited Chicago several times.
Review provided by Viator
Dec 4, 2023
Super fun! - Super fun guide Hannah, great organization and stops! We had a blast! Nice to get express access to the Christmas Market.
Review provided by Viator