Walk, Eat & Celebrate the Season
Experience Chicago’s favorite seasonal food and walking tour, featuring deep-dish pizza, hot chocolate, festive lights, and stops at the city’s top holiday landmarks.
-
$80 USD
-
All Ages
-
3 hours
-
Illinois, United States
-
Chicago
-
- Deep-Dish Pizza Tasting
- Christkindlmarket Visit
- Millennium Park Lights
- Italian Beef & Brownie Samples
- VIP Beer/Cocktail Option
- Family-Friendly Walking Tour
- Holiday History & Fun
- Iconic Chicago Landmarks
-
- Guided 3-hour holiday walking tour with food and beverage tastings at multiple stops.
-
- Wear warm, comfortable clothing and walking shoes.
Chicago Holiday Hike & Festive Food Tour Features
Festive Food Adventure
Savor Chicago’s iconic eats like deep-dish pizza, Italian beef, and brownies on a guided holiday walk through the city’s most cheerful spots.
Chicago Holiday Landmarks
See Millennium Park’s Christmas tree, Magnificent Mile lights, and the Christkindlmarket all in one festive afternoon.
Chicago Holiday Hike & Festive Food Tour Details
- Highlights
- Description
- Itinerary
- Price & Availability
- Food & Drink
- Instructions
- Restrictions
- Transportation
Highlights
-
Deep-Dish Pizza Tasting
-
Christkindlmarket Visit
-
Millennium Park Lights
-
Italian Beef & Brownie Samples
-
VIP Beer/Cocktail Option
-
Family-Friendly Walking Tour
-
Holiday History & Fun
-
Iconic Chicago Landmarks
Description
Step into Chicago’s winter wonderland with Bobby’s Bike Hike on the Holiday Hike: Season Sampling Food & Walking Tour. This 3-hour guided experience blends the city’s top holiday attractions with classic Chicago cuisine. Guests enjoy deep-dish pizza at Lou Malnati’s, Italian beef sandwiches, and desserts like the original Palmer House brownie. Along the way, the tour explores Millennium Park, the Magnificent Mile, Marshall Field’s holiday windows, and the German-inspired Christkindlmarket. Add the VIP upgrade for festive beer and cocktail tastings. Perfect for food lovers, families, and visitors eager to celebrate the Windy City’s holiday cheer.
Itinerary
- 11:15 AM – Check in at Lou Malnati’s Pizzeria, 410 N. Michigan Ave
- 11:30 AM – Begin guided walking tour
- 12:00 PM – Deep
- 12:45 PM – Visit Millennium Park Christmas Tree and lights
- 1:30 PM – Stop at Christkindlmarket for festive treats
- 2:30 PM – Tour ends near Daley Plaza
Price & Availability
$79.99 adults, $69.99 youth, $9.99 infants. VIP upgrade $19.99 for beer/cocktail tasting. Runs daily late Nov–Dec 24.
Food & Drink
VIP option adds 3 local craft beers or cocktails for guests 21+.
Instructions
Arrive 15 minutes early for check-in; tour runs rain or shine.
Restrictions
Event operates in winter weather; bring gloves and layers.
Transportation
Guests meet at Lou Malnati’s Pizzeria, 410 N. Michigan Ave.
Frequently Asked Questions
More Holiday Experiences
-
Chicago Seasonal Stroll Holiday Walking Tour
Explore Chicago’s holiday landmarks, lights, and festive... More
- 2-Hour Guided Holiday Walk
- Includes Top City Attractions
- Family & Group Friendly
- Chicago Winter Lights Experience
-
Chicago Christmas Tree Crawl Tour
Guests exploring Chicago’s indoor Christmas trees during the... More
- Holiday Walking Tour
- Architectural Interiors
- Christkindlmarkt Visit
- Festive City Landmarks
Contact Us
-
Christmas Holiday Tours
Fort Collins, CO 80526 -
Meeting locations vary for each tour: You will be sent a meeting location after you book
