Chicago-Style Holiday Hike: Festive Food and Walking Tour

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Summary
Experience Details
What You’ll Experience
Where to Meet
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Duration
3 hours
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Number of Guests
1 - 15 guests
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Language
English
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Digital Ticket
Mobile or paper ticket accepted

Discover Chicago's festive charm on a 3-hour walking tour. Indulge in local treats like deep-dish pizza and hot dogs. Explore iconic holiday sights and enjoy optional craft beer tasting.

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For each guest that attends this experience, byFood will donate
10 meals

Experience Details

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 You Get

Food samples
Holiday attractions
Holiday Cocoa or Cider
$10 per person (or more) suggested guide gratuity. (via Cash, Venmo and PayPal)
Hotel pickup and drop-off
Alcoholic beverages
Alcoholic Beverages

Good To Know

  • 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.
  • 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.
  • Operates in all weather conditions, please dress appropriately

What You’ll Experience

1

Christkindlemarket

Enjoy a hot cider at this outdoor german christmas market
10 minutesAdmission Ticket Included
2

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 minutesAdmission Ticket Free
3

Macy's on State Street

Enjoy the Holiday decor
10 minutesAdmission Ticket Free
4

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.
1 hourAdmission Ticket Free
5

Cloud Gate

Iconic Chicago attraction
5 minutesAdmission Ticket Free
6

Jay Pritzker Pavilion

Gorgeous open air amphitheater
5 minutesAdmission Ticket Free
7

Daley Bicentennial Plaza

Enjoy Christkindlmarkt in Chicago
20 minutesAdmission Ticket Free
8

Chicago Christmas Tree

Visit Chicago's Christmas Tree
5 minutesAdmission Ticket Free
9

Wrigley Building

Visit one of Chicago's iconic buildings
5 minutesAdmission Ticket Free
10

Lou Malnati's Pizzeria

Enjoy Chicago-style deep dish pizza
15 minutesAdmission Ticket Included
11

Millennium Hall Restaurant

Enjoy a Chicago style hot dog or Italian Beef
10 minutesAdmission Ticket Included
12

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 minutesAdmission Ticket Included
13

Exchequer Restaurant & Pub

Enjoy an italian beef sandwich.
10 minutesAdmission Ticket Included

The Art Institute of Chicago (Pass By)

Amazing collections

Meeting & Pickup

Meeting Point

410 N Michigan Ave, North Michigan Avenue, Cook County Illinois, United States, US, 60611

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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.
End Point

Christkindlmarket Chicago, West Washington Street, Cook County Illinois, United States, US, 60602

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Cancellation Policy

Cancel your booking at least 24 hours before the experience start time to receive a full refund minus a 3.2% transaction fee.

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from  $77.27 
Book Now
Please note that the time is in Central Time.
Free cancellation (24 hours notice)
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INSTANT CONFIRMATION
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Earliest available date: November 21, 2025
from  $77.27  per guest
Book Now
Please note that the time is in Central Time.
Free cancellation (24 hours notice)
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For each guest that attends this experience, byFood will donate
10 meals
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