Chicago Holiday Guided Walking Food Tour
Experience Holiday Magic on a 3 Hour Guided Food Tour in Downtown Chicago with Bobby's Bike Hike
IL
people
1 participant
hours
- • Explore Chicago's Holiday Wonders on a Guided Food Tour
- • Indulge in 3 Hours of Festive Delights and Local History
- • Experience the Most Comprehensive Holiday Tour in Chicago
Why We Love This Unique Experience
Experience the enchanting sights and tastes of Chicago during the most wonderful time of the year with the Chicago-Style Holiday Hike: Festive Food and Walking Tour! This delightful 3-hour guided journey through the heart of the city showcases the festive spirit that makes Chicago a magical destination during the holidays. Savor mouthwatering samples, enjoy the rich history of the area, and create long-lasting memories as you stroll through charming neighborhoods adorned with twinkling lights and holiday cheer.
As you wander through the vibrant streets, indulge in iconic Chicago winter treats. The tour includes tempting bites of deep dish pizza, classic Chicago-style hot dogs, and the delicious Italian beef sandwich. To warm up, a complimentary hot apple cider adds the perfect festive touch. Marvel at Chicago’s stunning holiday decorations while exploring popular attractions such as the legendary Christkindlmarket, the iconic city Christmas tree, and the bustling ice skating rink at Millennium Park. Knowledgeable guides will share fascinating stories, including the creation of Rudolph the Red-Nosed Reindeer right in Chicago, bringing extra holiday magic to the experience.
This unique tour not only offers a joyful outing for family and friends but also makes for a thoughtful gift! Whether as a surprise treat for loved ones or a fun corporate gift, the Chicago-Style Holiday Hike will delight anyone who craves festive joy and delicious food in an unforgettable setting. Create cherished memories this holiday season by sharing the gift of experience!
Check Availability & Book
Experience Overview:
Chicago-style Holiday Hike: Festive Food And Walking TourThere’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!
Meeting Point
410 N Michigan Ave
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.
What's included:
- Food samples
- Holiday attractions
- Holiday Cocoa or Cider
- Local tour guide
Not included:
- $10 per person (or more) suggested guide gratuity. (via Cash, Venmo and PayPal)
- Hotel pickup and drop-off
What to expect:
Duration: 3 hours
Christkindlemarket
50 W Washington St, Chicago, 60602-1305, Illinois
Enjoy a hot cider at this outdoor german christmas market
10 minutes • Admission Ticket Included
Palmer House Hilton Historic Lobby
17 E Monroe St, Chicago, 60603-5608, Illinois
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
111 N State St, , Chicago, 60602-1659, Illinois
Enjoy the Holiday decor
10 minutes
Millennium Park
Chicago, 60602, Illinois
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.
1 hour
Cloud Gate
201 E. Randolph St., Millenium Park, Chicago, 60602, Illinois
Iconic Chicago attraction
5 minutes
Jay Pritzker Pavilion
Millennium Park, Chicago, Illinois
Gorgeous open air amphitheater
5 minutes
Daley Bicentennial Plaza
337 E Randolph Dr, , Chicago, 60602-1305, Illinois
Enjoy Christkindlmarkt in Chicago
20 minutes
Chicago Christmas Tree
Chicago, IL 60601, USA
Visit Chicago's Christmas Tree
5 minutes
Wrigley Building
400-410 Michigan Ave, , Chicago, 60611-4213, Illinois
Visit one of Chicago's iconic buildings
5 minutes
Lou Malnati's Pizzeria
410 N Michigan Ave, Chicago, IL 60611, USA
Enjoy Chicago-style deep dish pizza
15 minutes • Admission Ticket Included
Millennium Hall
11 N Michigan Ave, Chicago, IL 60602, USA
Enjoy a Chicago style hot dog or Italian Beef
10 minutes • Admission Ticket Included
Palmer House Hilton Historic Lobby
17 E Monroe St, Chicago, 60603-5608, Illinois
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 Ticket Included
Exchequer Restaurant & Pub
226 S Wabash Ave, Chicago, IL 60604, USA
Enjoy an italian beef sandwich.
10 minutes • Admission Ticket Included
The Art Institute of Chicago
111 S Michigan Ave, Chicago, 60603-6110, Illinois
Amazing collections
Pass by without stopping
> More Experience Gifts in Chicago
Details & Important Info
Additional Experience Details & Important Information
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.
Cancellations & Refunds
Reservation Changes, Cancellations & Refunds
Changes to reservations for tickets can be made until 3 days prior to the date scheduled. Reservations may be re-scheduled by the operator of the activity due to reasons such as weather, minimum participation requirements, mechanical issues or other interruptions beyond their control.
Organized by
Bobby's Bike Hike - Chicago
Product SKU: US-4749-0005
Google Business Profile: Bobby's Bike Hike - Chicago
What People Are Saying
If you're considering a Chicago Food Tour, customers rave about the exceptional guides who bring the city’s rich history and delectable cuisine to life! Highlights include engaging, knowledgeable guides like Josie, Julia, and Robby, who not only share fascinating stories but also ensure a fun, welcoming atmosphere. Guests appreciate the generous food portions at iconic spots—like the famous deep-dish pizza and local brews—making it a filling and memorable experience. With a perfect blend of culture, food, and festive ambiance, this tour is a must-try for both locals and visitors looking for a delightful way to explore Chicago!
Experience Highlights
Knowledgeable Guides... Delicious Food... Engaging Experience... Great for Groups... Memorable City Insights... Fun and Interactive... Perfect for Families... Highly Recommended!
Chicago Holiday Food and Walking Tour
IL
people
1 participant
hours
- • Explore Chicago's Holiday Wonders on a Guided Food Tour
- • Indulge in 3 Hours of Festive Delights and Local History
- • Experience the Most Comprehensive Holiday Tour in Chicago
Best Experience Providers
Our Activity Partners are highly rated and experts in what they do, guaranteeing you an unforgettable experience.
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