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Chicago-Style Holiday Hike: Festive Food and Walking Tour

Chicago, USA
3 hours
4.9
(68)
Food & Drinks
|
Family Friendly
|
Walking Tours
|
City Highlights
|
Seasonal & Special Occasions
Date
Friday
November 21, 2025
Change date
Time
11:30 am
Options
Holiday Hike: Festive Chicago Food and Walking Tour
Infant
Ages: 0-3 years old
0
Youth
Ages: 4-11 years old
0
Adult
Ages: 12-99 years old
2
Checking availability

What You Will Do

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!

What's Included?

  • Food samples
  • Holiday attractions
  • Holiday Cocoa or Cider
  • Local tour guide

What's Not Included?

  • $10 per person (or more) suggested guide gratuity. (via Cash, Venmo and PayPal)
  • Hotel pickup and drop-off
  • Alcoholic beverages

Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Itinerary

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.

1

Christkindlemarket

10 minutes

Enjoy a hot cider at this outdoor german christmas market

Show 13 more stops

Additional Information

This activity is operated by Bobby's Bike Hike - Chicago
  • 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.

Guide Options

  • Guide - English

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