Chicago-Style Holiday Hike: Festive Food and Walking Tour

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based on 54 reviews
  • Duration:3 hours (approx.)
  • Location: Chicago, Illinois
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Upto 24 hours in Advance.
Mobile or paper ticket accepted
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There’s nothing more magical than downtown Chicago during the holiday season. Bobby’s Holiday Hike is a 3hr guided walking and food tour through the Chicago Loop, brought to you by Bobby's Bike Hike, internationally recognized for their tours. 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. Upon arrival, you can add a VIP holiday craft beer package for $19.99/person. 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 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-inclusive experience of Chicago during the holidays!


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Posted By : formorrie4
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!!
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Posted On : 2023-12-21 10:55:04 full ratings


Posted By : 960becb
Great tour. The food and drink were delicious and Our tour guide Mickey was fun and knowledgable! Would recommend.
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Posted On : 2023-12-20 16:05:52 full ratings


Posted By : Shanta_C
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.
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Posted On : 2023-12-18 12:24:44 full ratings


Posted By : Melissa_G
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!

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Posted On : 2023-12-11 16:17:07 full ratings


Posted By : K4483BKtimm
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.
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Posted On : 2023-12-10 20:09:22 full ratings


Posted By : Angelique_B
Mickey was great! We really enjoyed his jokes and personal touch. He made the tour very comfortable and funny!
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Posted On : 2023-12-09 16:37:24 full ratings


Posted By : Shelton_J
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.
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Posted On : 2023-12-09 14:31:35 full ratings


Posted By : Heather_C
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.
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Posted On : 2023-12-09 09:47:29 full ratings


Posted By : Donna_W
We loved our guide Greg. He had great stories that I had not heard before even though I have visited Chicago several times.
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Posted On : 2023-12-07 11:31:14 full ratings


Posted By : Breann_Y
Super fun guide Hannah, great organization and stops! We had a blast! Nice to get express access to the Christmas Market.
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Posted On : 2023-12-04 20:01:07 full ratings