Holiday Hike: Chicago's Festive Food and Sights

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: 24 hours
Highlights
  • 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…

Location
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
4.9
(68 Ratings)
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H2oman624
Jan 8, 2025
Educational, entertaining, and lots of walking, but really fun. - We learned so much about the rich history of Chicago, the people who started the restaurants, the history of Chicago’s iconic foods: pizza, hot dogs, Italian beef sandwiches, this fires that destroyed Chicago and how the Chicago people rebuilt it time and time again. If you like good food, entertaining/educational presentations, this is definitely your kind of day trip! As I said our guide was Jeff who is a gifted storyteller with an endless vault of Chicago history. Ask for Jeff when you book your food adventure. He is an A+ guide.
Review provided by Tripadvisor
Pat_p
Jan 2, 2025
Delicious essentials of the city! - If you're here in the city during the winter (especially if it's your first time), this is a great way to stay your trip! See all the biggest sights and taste the signature tastes. Is your starting longer than the day, this is great way to get your bearings off the city before deciding where and what you want to do
Review provided by Viator
Justin_d
Dec 24, 2024
FBA created deep dish pizza - Today I found out it was a FBA woman named Alice Mae Redmond who created the deep dish pizza in Chicago! She gets no recognition for it in Chicago but that’s nothing new. Enjoy!
Review provided by Viator
Kasey_e
Dec 16, 2024
I had an amazing time on... - I had an amazing time on this tour! Jamal was my tour guide. He was so nice and had great information about the restaurants and the city. I tried a lot of food I wouldn't have gotten on my own, and was able to see a lot of the city in only 3 hours. My only suggestion would be for the tour to arrange our apple cider in a souvenir mug!
Review provided by Viator
Steve_g
Dec 15, 2024
We had Mickey as our... - We had Mickey as our guide and he was absolutely amazing!!! Super informative, friendly and funny! He did an amazing job and took us to some really cool spots.
Review provided by Viator
Wendy_w
Dec 8, 2024
Chicago Holiday - Hi, I had Lilian for our group leader. I know I didn’t spell her name right but she was wonderful. I loved hearing about the history and everything of Chicago. I have been to Chicago in 2008 but had not taken this tour before obviously cause this was a holiday hike got to see like Christmas stuff and everything. The only thing I wish is that I thought we were gonna go inside the Palmer house so I’m gonna make an effort to go by today. I haven’t tried my brownie yet, but I wanna go in there and just look around because of the history other than that everything else was wonderful on the trip
Review provided by Viator
Michelle_l
Dec 7, 2024
Holiday city/food tour - We loved our tour!!! Learned so much about the city and got to eat some delicious food!! Would definitely recommend doing!! Lillian was our tour guide. She was great!!
Review provided by Viator
Jane_n
Dec 4, 2024
3 informative & delicious hours in Chicago - Best pizza I ever had in my life—78 yrs old. Guide had fun w us, gave us lots of info & let us contribute info. The group was very open, young, energetic. We got along so well—several international visitors. Two others I was traveling w didn’t go and after hearing of my tour experience, were wishing they had gone. Don’t miss it, especially if you like to eat—they have the food ready when you arrive!
Review provided by Viator
Islandtraveler19
Dec 1, 2024
Fantastic tour, don’t let the cold deter you - Jeanine wea a great guide! Lots of good food from deep dish pizza, beef sandwich, Garrett’s popcorn, Chicago dog, and the Palmer brownie. Every stop was well organize, and we stayed on track for the 3 hour time limit. Our guide was very entertaining.
Review provided by Tripadvisor
Osterholz
Dec 1, 2024
Excellent way to see Chicago! - Even though it was 28°, we had a blast on this tour. Our guide, Jeff was informative, entertaining, and enthusiastic! Plenty to eat too, complete with snacks. Would highly recommend!
Review provided by Tripadvisor