Chicago-Style Holiday Hike: Festive Food and Walking Tour
Chicago, US
98% of travellers recommend this
Highlights
- Sample delicious Chicago-style deep dish pizza
- Indulge in a Chicago-style hot dog or Italian Beef
- Experience the magical Christkindlemarket
- Admire the beautiful Christmas window displays at Marshall Field's
- Explore Millennium Park and see the iconic Cloud Gate sculpture
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Duration 3 hours
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Food samples included
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Local tour guide
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VIP craft beer upgrade
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Accessible for all fitness levels
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Operates in all weather
Experience the magic of downtown Chicago during the holiday season with Bobby's Holiday Hike. This 3-hour guided walking and food tour takes you through the Chicago Loop, allowing you to sample the Windy City's favorite winter treats. Indulge in a slice of deep dish pizza, a Chicago-style hot dog, Italian Beef, chocolate brownie, and hot apple cider. Your knowledgeable guides will keep you entertained with fun facts about the city, including the origin of Rudolph the red-nosed reindeer. Explore the Christmas window displays at the original Marshall Field's department store, admire Chicago's city Christmas tree, and visit the legendary Christkindlmarket, a traditional German Christmas Market. No other tour offers such an all-inclusive experience of Chicago during the holidays. Don't miss out on this festive and delicious adventure!
At a Glance
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Free cancellation
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3 hours
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Instant Confirmation
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Available in English
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Wheelchair accessible
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Mobile voucher
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Small Group tour
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Guided
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Family friendly
Featured Reviews
Explore the festive flavors of Chicago with a guided walking tour featuring iconic holiday treats and attractions in the heart of the city.
Included
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Food samples -
Holiday attractions
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Holiday cocoa or cider
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Local tour guide
Excluded
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$10 per person (or more) suggested guide gratuity. (via cash, venmo and paypal) -
Hotel pickup and drop-off
Meeting 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.
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What to expect
Christkindlemarket
Enjoy a hot cider at this outdoor german christmas market
10 minutes
Admission Included
Palmer House Hilton Historic Lobby
Stroll down State Street where the lights, decorations and window displays dazzle. Throughout your tour, you'll make stops for a variety of tasty treats, including a brownie sample at the Palmer House Hotel, where the chocolatey treat was invented! While inside the historic building, your guide shows you the magnificent interior architecture of this grand old hotel, where many famous guests have stayed since it opened in 1875.
15 minutes
Macy's on State Street
Enjoy the Holiday decor
10 minutes
Millennium Park
Get a full tour of Millennium Park and gaze over the large outdoor ice-skating rink, flanked by the some of the most iconic buildings on the Chicago skyline. Watch hundreds of skaters twirl as they enjoy the free attraction. See the city’s official Christmas tree, loaded with spectacular ornaments and lights.
60 minutes
Cloud Gate
Iconic Chicago attraction
5 minutes
Jay Pritzker Pavilion
Gorgeous open air amphitheater
5 minutes
Daley Bicentennial Plaza
Enjoy Christkindlmarkt in Chicago
20 minutes
Chicago Christmas Tree
Visit Chicago's Christmas Tree
5 minutes
Wrigley Building
Visit one of Chicago's iconic buildings
5 minutes
Lou Malnati's Pizzeria
Enjoy Chicago-style deep dish pizza
15 minutes
Admission Included
Millennium Hall
Enjoy a Chicago style hot dog or Italian Beef
10 minutes
Admission Included
Palmer House Hilton Historic Lobby
Visit the iconic Palmer House Hotel lobby and enjoy the original recipe brownie, invented here at the hotel for the 1893 Chicago's Worlds Fair.
10 minutes
Admission Included
Exchequer Restaurant & Pub
Enjoy an italian beef sandwich.
10 minutes
Admission Included
The Art Institute of Chicago
Amazing collections
The experience can be subject to change due to bad weather or unforseen circumstances. We always endeavour to give you the best possible experience.
Additional Information
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Wheelchair accessible -
Public transportation options are available nearby
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Suitable for all physical fitness levels
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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.
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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.
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VIP Adult Beverage upgrade (3 samples) available upon arrival for $19.99 per person extra (Ages 21+)
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TripAdvisor rated this tour its highest-level Traveler’s Choice Award each year since 2002.
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Our groups have exclusive VIP access to locations we visit.
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Operates in all weather conditions, please dress appropriately
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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.
What our experts say
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Try the deep dish at Lou Malnati's! -
Visit the Christkindlmarket for unique gifts.
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Take photos at Cloud Gate for great memories.
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Dress warm; it can get chilly outside.
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Check out nearby restaurants for dinner.
More About this Experience
Introduction
Step into the enchanting holiday season in downtown Chicago with Bobby's Holiday Hike. This 3-hour guided walking and food tour will take you through the vibrant Chicago Loop, giving you a taste of the city's festive food and showcasing its captivating holiday attractions. Bobby's Bike Hike, internationally recognized for their tours, brings you this magical experience that will leave you with unforgettable memories.What to Expect?
During the Holiday Hike Chicago-Style tour, you can expect to indulge in the Windy City's favorite winter treats. Sample a slice of deep dish pizza, savor the flavors of a Chicago-style hot dog and Italian Beef, indulge in a chocolate brownie, and warm up with a cup of hot apple cider. For an added touch of luxury, you can enhance your experience by adding a VIP holiday craft beer package.Who is this for?
This tour is perfect for anyone looking to immerse themselves in the holiday spirit while exploring the heart of downtown Chicago. Whether you're a local or a visitor, this experience is designed to captivate and enchant. The tour caters to all ages and interests, providing a delightful adventure for families, couples, and solo travelers alike.Why Book This?
Bobby's Holiday Hike offers a unique and all-inclusive experience of Chicago during the holidays. Not only will you get to sample the city's iconic food, but you'll also discover fascinating insights about Chicago's holiday traditions and history. From admiring the Christmas window displays at the original Marshall Field's department store to witnessing the vibrant ice skating rink at Millennium Park and exploring the legendary Christkindlmarket, this tour combines delicious food, captivating sights, and local expertise.Good to Know
When booking the Holiday Hike Chicago-Style tour, keep in mind that a suggested guide gratuity of $10 per person (or more) is recommended. Hotel pickup and drop-off are not included, so plan your transportation accordingly. While food samples are included, alcoholic beverages are not part of the package. So, get ready to embark on a delightful adventure and immerse yourself in the holiday spirit of downtown Chicago.Reviews
Customers who have experienced Bobby's Holiday Hike rave about the magical atmosphere and the knowledgeable guides who bring the city to life during the holiday season. They appreciate the opportunity to indulge in Chicago's iconic winter treats and explore the city's festive attractions. The tour has received high praise for its unique blend of food, history, and holiday magic, making it a must-do experience for anyone visiting or living in Chicago.
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