Chicago-Style Holiday Hike: Festive Food and Walking Tour
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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!
Reviews
Reviews and Rating (Tripadvisor)
5 stars
Reviews by Tripadvisor travelers
H2OMan624, 1/8/2025 5:28:27 PM
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.
Pat_P, 1/2/2025 6:31:28 PM
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
Justin_D, 12/24/2024 9:35:13 PM
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!
Kasey_E, 12/16/2024 10:08:06 AM
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!
Steve_G, 12/15/2024 2:28:50 PM
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.
Wendy_W, 12/8/2024 10:05:26 AM
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
Michelle_L, 12/7/2024 5:32:43 PM
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!!
Jane_N, 12/4/2024 12:58:03 PM
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!
Islandtraveler19, 12/1/2024 6:55:05 PM
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.
Osterholz, 12/1/2024 11:11:52 AM
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!
- Wheelchair accessible
- Public transportation options are available nearby
- Suitable for all physical fitness levels
- If you have dietary restrictions, please add a note in the special requirements section when booking, and email to reservations@bobbysbikehike.com 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.
Departure point
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.Redemption
Please arrive 15 minutes before scheduled tour time $10 per person (or more) suggested guide gratuity. (via Cash, Venmo and PayPal) Wear comfortable and seasonally appropriate clothing/shoes Please use the Restroom before your arrival. Bring a bottle of water. Tours run rain or shine If you have dietary restrictions, please contact local operator by reaching out via email to reservations@bobbysbikehike.com after booking to confirm they can accommodate.24 hours before travel date - 100% refund
Less than 24 hours before travel date - 0% refund