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Chicago-Style Holiday Hike: Festive Food and Walking Tour
Badge of ExcellenceChicago, USA
- 3 hours
- Mobile ticket
- Offered in: English
Explore our promoted experiences
Overview
Stroll through Chicago's winter streets, lit up for the holidays, on this gourmet walking tour. Learn about Chicago's celebrated holiday traditions like the European-inspired Christkindlmarket, the beautiful decor and windows on State Street, and ice skating at Millennium Park. Sample generous tastes of classic Chicago foods and holiday treats as you walk. Seasonal craft beer tastings help you stay warm and toasty; please note this tour operates in all weather conditions, so dress appropriately.
- Food and walking holiday tour of downtown Chicago
- Visit the German-style Christkindlmarket, a festive outdoor market with warming cider and holiday shops
- Stop at a local bar to taste seasonal craft brews
- Head to the historic Palmer House Hotel, where brownies were invented, to try the popular chocolate treat
- Admire the outdoor ice skating rink and magnificent architecture at Millennium Park
- Sample Chicago's famous deep dish pizza at a festive restaurant
- See Chicago's most majestic Christmas tree display at Millennium Park
- Taste the famous Chicago-style hot dog
What's Included
- Food samples
- Holiday attractions
- Local tour guide
- $10 per person (or more) suggested guide gratuity. (via Cash, Venmo and PayPal)
- Hotel pickup and drop-off
- Alcoholic Beverages
Meeting and Pickup
Meeting point
- 410 N Michigan Ave, Chicago, IL 60611, USA
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.
Start time
11:30 AM
End point
- Christkindlmarket Chicago50 W Washington St, Chicago, IL 60602, USA
What To Expect
Meet your friendly local guide in central Chicago to get started on your tour of holiday traditions in the city.
Head to Millennium Park, the location of a large outdoor ice rink sitting smack among the famous landmark buildings of downtown Chicago. See the city's official Christmas tree, lit up for the season, and watch hundreds of skaters enjoy the free recreational activity.
As you walk, stop for a brownie sample at the Palmer House Hotel, where the classic dessert was invented. See the magnificent interior architecture of this famous hotel, where many notable people have slept since its founding in 1875. Stop by a local bar to warm up and sip a unique Chicago craft beer. Stop by a local institution to try some of Chicago's famous deep-dish pizza.
Visit the traditional German-American Christkindlmarket, a large open-air Christmas festival. Taste authentic hot apple cider and browse the handicrafts and traditional European products for the perfect gift or souvenir. You may come across model trains, a Santa house or a Christmas choir during your exploration.
Follow your guide to State Street where the lights, decorations, and window displays dazzle. You'll also stop at a local shop to try the famous Chicago-style hot dog.
After your tour concludes, and you are free to explore Chicago's festive streets on your own.
Head to Millennium Park, the location of a large outdoor ice rink sitting smack among the famous landmark buildings of downtown Chicago. See the city's official Christmas tree, lit up for the season, and watch hundreds of skaters enjoy the free recreational activity.
As you walk, stop for a brownie sample at the Palmer House Hotel, where the classic dessert was invented. See the magnificent interior architecture of this famous hotel, where many notable people have slept since its founding in 1875. Stop by a local bar to warm up and sip a unique Chicago craft beer. Stop by a local institution to try some of Chicago's famous deep-dish pizza.
Visit the traditional German-American Christkindlmarket, a large open-air Christmas festival. Taste authentic hot apple cider and browse the handicrafts and traditional European products for the perfect gift or souvenir. You may come across model trains, a Santa house or a Christmas choir during your exploration.
Follow your guide to State Street where the lights, decorations, and window displays dazzle. You'll also stop at a local shop to try the famous Chicago-style hot dog.
After your tour concludes, and you are free to explore Chicago's festive streets on your own.
Christkindlemarket
10 minutes • Admission Ticket Included
Palmer House Hilton Historic Lobby
15 minutes • Admission Ticket Free
Macy's on State Street
10 minutes • Admission Ticket Free
Millennium Park
1 hour • Admission Ticket Free
Cloud Gate
5 minutes • Admission Ticket Free
Jay Pritzker Pavilion
5 minutes • Admission Ticket Free
Daley Bicentennial Plaza
20 minutes • Admission Ticket Free
Chicago Christmas Tree
5 minutes • Admission Ticket Free
Wrigley Building
5 minutes • Admission Ticket Free
Lou Malnati's Pizzeria - Michigan Ave
15 minutes • Admission Ticket Included
Millennium Hall
10 minutes • Admission Ticket Included
Palmer House Hilton Historic Lobby
10 minutes • Admission Ticket Included
Exchequer Restaurant & Pub
10 minutes • Admission Ticket Included
The Art Institute of Chicago (Pass By)
Additional Info
- Confirmation will be received at time of booking
- 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.
- Wheelchair accessible
- 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.
Cancellation Policy
You can cancel up to 24 hours in advance of the experience for a full refund.
- For a full refund, you must cancel at least 24 hours before the experience’s start time.
- If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
- Any changes made less than 24 hours before the experience’s start time will not be accepted.
- Cut-off times are based on the experience’s local time.
- This experience requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund.
Traveler Photos
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Reviews
5.0
54 reviews
Shanta_C, Dec 2023
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.
Melissa_G, Dec 2023
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!
Angelique_B, Dec 2023
Mickey was great! We really enjoyed his jokes and personal touch. He made the tour very comfortable and funny!
Shelton_J, Dec 2023
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.
Heather_C, Dec 2023
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.
Donna_W, Dec 2023
We loved our guide Greg. He had great stories that I had not heard before even though I have visited Chicago several times.
Breann_Y, Dec 2023
Super fun guide Hannah, great organization and stops! We had a blast! Nice to get express access to the Christmas Market.
David_B, Dec 2023
Julia was great. Made the walking tour so fun. Food was great Got into the Market so fast and easy!!
Michael_M, Nov 2023
A lot of fun, even if you have lived in Chicago all your life.
Brooke was a great guide. Knowledgeable, funny, dramatic in historical information, concerned for our safety.
Particularly at the holiday time of the year.
Look forward for doing this again with other family members and friends.
Ly_D, 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.
From $79.99
up to 24 hours before the experience starts (local time)
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Chicago-Style Holiday Hike: Festive Food and Walking Tour
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