Chicago-Style Holiday Hike: Festive Food and Walking Tour | 3 hours

64 Reviews | Chicago
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You can select up to 15 travelers in total.
Adult (12-99) Minimum: 1, Maximum: 15
2
Youth (4-11) Minimum: 0, Maximum: 15
0
Infant (0-3) Minimum: 0, Maximum: 15
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Free Cancellation For a full refund, cancel at least 24 hours before the scheduled departure time.
Holiday Hike: Festive Chicago Food and Walking Tour
2 Adults x $84.99
$169.98
Approx Total
$169.98

Inclusions / Exclusions

  • Mobile ticket
  • Offered in: English
  • 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

Overview

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!

Meeting points

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

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Itinerary

  • Christkindlemarket

    Enjoy a hot cider at this outdoor german christmas market

    10 minutes

  • 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 minutes

  • Macy's on State Street

    Enjoy the Holiday decor

    10 minutes

  • 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 hour

  • Cloud Gate

    Iconic Chicago attraction

    5 minutes

  • Jay Pritzker Pavilion

    Gorgeous open air amphitheater

    5 minutes

  • Daley Bicentennial Plaza

    Enjoy Christkindlmarkt in Chicago

    20 minutes

  • N/A

    Visit Chicago's Christmas Tree

    5 minutes

  • Wrigley Building

    Visit one of Chicago's iconic buildings

    5 minutes

  • N/A

    Enjoy Chicago-style deep dish pizza

    15 minutes

  • N/A

    Enjoy a Chicago style hot dog or Italian Beef

    10 minutes

  • 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 minutes

  • N/A

    Enjoy an italian beef sandwich.

    10 minutes

  • The Art Institute of Chicago (Pass By)

    Amazing collections

Sample Menu

Additional Info

  • 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.

Free Cancellation

November 20100% refund
November 21No refund

You can cancel up to 24 hours in advance of the experience for a full refund.

  • For a full refund, you must cancel at least 24 hours before the experience’s start 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 good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.
Traveler Photos
Reviews

4.9

64 reviews

Total review count and overall rating based on Viator and Tripadvisor reviews
  • 5 stars
    60
  • 4 stars
    3
  • 3 stars
    0
  • 2 stars
    1
  • 1 star
    0

Reviews by TravelOne travelers

Showing 1-5 of 60 reviews with 5 stars

Educational, entertaining, and lots of walking, but really fun.

Published on Jan, 2025

We learned so much about the rich history of Chicago, the people who started the restaurants, the history of Chicago’s iconic foods: pizza, hot dogs, Italian beef sandwiches, this fires that destroyed Chicago and how the Chicago people rebuilt it time and time again. If you like good food, entertaining/educational presentations, this is definitely your kind of day trip! As I said our guide was Jeff who is a gifted storyteller with an endless vault of Chicago history. Ask for Jeff when you book your food adventure. He is an A+ guide.

Delicious essentials of the city!

Published on Jan, 2025

If you're here in the city during the winter (especially if it's your first time), this is a great way to stay your trip! See all the biggest sights and taste the signature tastes. Is your starting longer than the day, this is great way to get your bearings off the city before deciding where and what you want to do

FBA created deep dish pizza

Published on Dec, 2024

Today I found out it was a FBA woman named Alice Mae Redmond who created the deep dish pizza in Chicago! She gets no recognition for it in Chicago but that’s nothing new. Enjoy!

I had an amazing time on...

Published on Dec, 2024

I had an amazing time on this tour! Jamal was my tour guide. He was so nice and had great information about the restaurants and the city. I tried a lot of food I wouldn't have gotten on my own, and was able to see a lot of the city in only 3 hours. My only suggestion would be for the tour to arrange our apple cider in a souvenir mug!

We had Mickey as our...

Published on Dec, 2024

We had Mickey as our guide and he was absolutely amazing!!! Super informative, friendly and funny! He did an amazing job and took us to some really cool spots.

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