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Chicago-Style Holiday Hike: Festive Food and Walking Tour

icon 3 hours Mobile ticket Free Cancellation
Tickets from € 78.00

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

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.

  • Christkindlemarket, Chicago, Illinois, United States
    Enjoy a hot cider at this outdoor german christmas market
    10 minutes
  • Palmer House Hilton Historic Lobby, Chicago, Illinois, United States
    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, Chicago, Illinois, United States
    Enjoy the Holiday decor
    10 minutes
  • Millennium Park, Chicago, Illinois, United States
    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, Chicago, Illinois, United States
    Iconic Chicago attraction
    5 minutes
  • Jay Pritzker Pavilion, Chicago, Illinois, United States
    Gorgeous open air amphitheater
    5 minutes
  • Daley Bicentennial Plaza, Chicago, Illinois, United States
    Enjoy Christkindlmarkt in Chicago
    20 minutes
  • Chicago, IL 60601, USA
    Visit Chicago's Christmas Tree
    5 minutes
  • Wrigley Building, Chicago, Illinois, United States
    Visit one of Chicago's iconic buildings
    5 minutes
  • 410 N Michigan Ave, Chicago, IL 60611, USA
    Enjoy Chicago-style deep dish pizza
    15 minutes
  • 11 N Michigan Ave, Chicago, IL 60602, USA
    Enjoy a Chicago style hot dog or Italian Beef
    10 minutes
  • Palmer House Hilton Historic Lobby, Chicago, Illinois, United States
    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
  • 226 S Wabash Ave, Chicago, IL 60604, USA
    Enjoy an italian beef sandwich.
    10 minutes
  • The Art Institute of Chicago, Chicago, Illinois, United States
    Amazing collections
  • 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 [email protected] 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.
You can cancel up to 24 hours in advance of the experience for a full refund.
  • For a full refund, cancel at least 24 hours before the scheduled departure time.
  • If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the experience’s start time will not be accepted.
  • Cut-off times are based on the experience’s local time.
  • This experience requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund.
formorrie4
21 Dec 2023
Such a fun tour. Julia was AMAZING and so knowledgeable. A great way to sample Chicago’s most popular culinary delights while learning about the city and its history. A must do tour!!
960becb
20 Dec 2023
Great tour. The food and drink were delicious and Our tour guide Mickey was fun and knowledgable! Would recommend.
Shanta_C
18 Dec 2023
This was my husband and I first time visiting Chicago. I'm so happy I decided to do the tour and enjoyed every second of it. Our tour guide was Brooke, whom was very knowledgable of the entire city. I would definitely recommend this tour when visiting Chicago and ask for Brooke, she was amazing.
This tour in Chicago is organized by Bobby's Bike Hike - Chicago

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We always double-check the availability with our local partners for each booking. Even though this is usually a swift process, it can take up to 24 hours. Once this process is completed you will receive your voucher or ticket by email. If our local partner is not able to confirm your booking we will offer you the best possible alternative. If the new date and/or time doesn’t fit your itinerary, we will reimburse the full amount paid.
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