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

64 Reviews | Chicago
From $84.99 per person Lowest Price Guarantee
Select Date and Travelers
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
0
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

Open in Google Maps

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.

Compare Similar Experiences

Current

Chicago-Style Holiday Hike: Festive Food ...
3332HOLIHIKE
time

3 hours

time Free Cancellation
64
From
$85 /   Person
Chicago: Gangsters and Ghosts Walking To ...
61552P8
time

2 hours

time Free Cancellation
7,121
From
$35 /   Person
Chicago Walking Food Tour With Secret Fo ...
Special Offer
7812P19
time

3 hours

time Free Cancellation
649
From
$80 /   Person
Chicago Private Architecture Walking Tou ...
177345P25
time

3 hours

time Free Cancellation
4
From
$211 /   Person
Chicago Seasonal Stroll Walking Tour of ...
3332P22
time

2 hours

time Free Cancellation
4
From
$45 /   Person
Chicago Favorites Ultimate Food and Walk ...
3332BITEWALK
time

3 hours

time Free Cancellation
1,447
From
$85 /   Person
Chicago Walking Tour: Historic Treasures ...
3173P10
time

2 hours

time Free Cancellation
345
From
$30 /   Person
Customers Who Bought This Tour Also Bought
Chicago Architecture River Cruise
5580ARC
time

1 hour

time Free Cancellation
14,058
From
$49 /   Person
Chicago: Gangsters and Ghosts Walking To ...
61552P8
time

2 hours

time Free Cancellation
7,121
From
$35 /   Person
Big Bus Chicago: Hop-On Hop-Off Sightsee ...
5096CHICAGO
time

2 hours

time Free Cancellation
1,953
From
$50 /   Person
Skydeck Chicago Admission Ticket
5671SKYDECK
time

1 hour 30 minutes to 2 hours

time Free Cancellation
1,538
From
$44 /   Person
Chicago in a Day: Food, History and Arch ...
5713P139
time

5 hours

time Free Cancellation
927
From
$132 /   Person
Chicago River Architecture Tour with Sma ...
Likely To Sell Out
92538P1
time

1 hour 30 minutes

time Free Cancellation
817
From
$49 /   Person
Lake Michigan Skyline Cruise in Chicago
5580SKY
time

30 minutes

time Free Cancellation
761
From
$33 /   Person
Chicago Walking Food Tour With Secret Fo ...
Special Offer
7812P19
time

3 hours

time Free Cancellation
649
From
$80 /   Person
Chicago's Secret Interiors Architectural ...
92538P4
time

2 hours

time Free Cancellation
613
From
$29 /   Person
Chicago Gangster and Food Walking Tour
61552P17
time

2 hours

time Free Cancellation
472
From
$75 /   Person
2-Hour Guided Segway Tour of Chicago
85696P1
time

2 hours

time Free Cancellation
422
From
$65 /   Person
Chicago Buffet Dinner Cruise on Lake Mic ...
5042CHISUN
time

2 hours to 3 hours

time Non Refundable
347
From
$122 /   Person
Recently Viewed
24ft Pontoon Boat Rental
New On TravelOne
220142P3
time

4 hours to 10 hours

time Free Cancellation
34
From
$253 /   Group
Classic Cotswolds Online Road Trip Trave ...
New On TravelOne
470950P7
time

72 hours

time Non Refundable
0
From
$16 /   Group
Lake Nakuru National Park; Admission Tic ...
44482P72
time

8 hours

time Non Refundable
1
From
$75 /   Person
2D1N Buffalo trek by Hmong Sister House ...
259598P15
time

48 hours

time Free Cancellation
81
From
$110 /   Person
3 New York Neighborhoods Semi-Private To ...
Likely To Sell Out
31003P2
time

2 hours

time Free Cancellation
168
From
$39 /   Person
Wormsloe Historic Site & Bonaventure Cem ...
3902P10
time

6 hours

time Free Cancellation
689
From
$74 /   Person
Connect with TravelOne
Louise Berg
Destination Expert
Plan your Next Trip
TravelOne Subscribe
We organise unforgettable vacations.
Subscribe for trending deals.
© Copyright 2025 TravelOne Technologies Inc. | All Rights Reserved.
Visa Card Mastercard Maestro Amex Discover

TravelOne uses cookies to give you the best possible service. If you continue browsing, you agree to the use of cookies. More details can be found in our privacy policy.

Do you have a destination in mind, or would you like TravelOne AI to suggest one?

What is your destination?

Are you visiting Japan for the first time?

Travel Date

What is your general interest for this trip?

City Breakup


Travelers Details


Adults
Ages 12 or above
Child
Ages 8-12
Child
Ages 3-7
Infant
Ages 0-2
Adults
Ages 12 or above
Child
Ages 8-12
Child
Ages 3-7
Infant
Ages 0-2

Accommodation Preferences

Preferred Star Rating?

Property Preference?

Property Location?

Preferred Hotel Chain?

Meal At The Hotel?

Dining Preferences

Which meal package would you like to choose?

What are your meal preferences?

Dining Style Preferences?

Cuisine Preferences?

Dining Atmosphere Preferences?

Preferred Meal Times?

Transportation

What are your preferences for Arrival/Departure Airport Transfers?

What are your preferences for internal transfers?

Guide Support

What kind of guide support do you prefer during your trip?

Preferred Language for Guide?

Preferred Type of Guide?

Group Size for Tours with Guides?

Desired Role of the Guide?

Specific Guide Personality/Style Preference?

Do you need dining recommendations/reservations support from the guide?

Flights Preferences

What are your preferences for onward and return flights?

Cabin Class

Preferred Departure Time

Preferred Arrival Time

Preferred Airlines

What are your preferences for internal flight?

Cabin Class

Preferred Departure Time

Preferred Arrival Time

Preferred Airlines

What type of experiences do you seek while traveling?

    Air & Water-Powered Thrill Rides
    Airboat Tours Flyboarding Jet Boat Rentals Jetpacks
    Climbing & Vertical Challenges
    Caving Climbing Ice Climbing Rock Climbing Sea Caving
    High-Adrenaline Aerial Adventures
    Air Tours Hang Gliding Heli-Hiking Helicopter Tours Helicopter Transfers Paragliding Parasailing Skydiving Ziplining
    Land-Based Extreme Driving
    4WD Tours ATV Tours Buggy Rentals Dune Bashing Go Kart Hummer Tours Motor Sports Motorcycle Tours Off-Road Tours Performance Car Driving Road Trip Vespa Rentals
    Sand & Desert Adventures
    Camel Rides Sandboarding
    Snow & Ice Adventures
    Dog Sledding/Mushing Husky Dog Tours Ice Fishing Ice Skating Snowboarding Snowmobiling Snowshoeing
    Unique & Unconventional Challenges
    Bungee Jumping Escape Rooms Flight Simulator Fun & Games Scavenger Hunts Shooting Shooting Ranges Tubing Zorbing
    Water & Surf Sports
    Freediving Kitesurfing Rafting Scuba Diving Surfing Lessons Wakeboarding Waterskiing White Water Rafting
    Classic & Scenic Cruises
    Canal Cruises Catamaran Cruises Dhow Cruises Gondola Cruises Sightseeing Cruises Water Tours
    Multi-Day & Extended Water Journeys
    Multi-day Cruises Ports of Call Tours Shore Excursions Worry-Free Shore Excursion
    Private & Adventure Boating
    Boat Rentals Power Boats Sailing
    Themed & Specialized Cruises
    Dinner Cruises Night Cruises Submarine Tours
    Unique & Alternative Water Travel
    Duck Boat Tours Ferry Services Pack Animal Tours Water Equipment Rentals Water Parks Water Transfers
    Cycling & Eco-Friendly Transport
    Bike Rentals Bike Tours Cycling Cycling Classes E-Bike Tours
    Land-Based Exploration
    Hiking Tours Nature Walks Self-guided Tours Walking Tours
    Nature & Wildlife Conservation
    Eco Tours Nature and Wildlife Tours Wildlife Encounters Wildlife Watching
    Protected Natural Areas
    Involves Animals Involves Poverty Stricken Communities National Parks Nature Parks
    Sustainable & Responsible Travel
    Sustainable Tours Volunteer Tours
    Culinary Classes and Workshops
    Candy Making Classes Chocolate Tours Cocktail Tastings Mixology Classes Olive Oil Tasting Paella Making Classes Pasta Making Classes Pizza Making Classes Wine Making Workshops
    Dining Experiences and Meals
    Breakfast Brunch Dinner Dinner and Show Tickets Lunch Restaurants
    Food & Beverage Tours
    Beer & Brewery Tours Chocolate Tours Coffee & Tea Tours Culinary Tours Pastry Tours Sake Brewery Tour Sake Tasting Street Food Tours Taco Tours Wine Tours
    Food Tastings and Sampling
    Cocktail Tastings High Tea Olive Oil Tasting Sake Tasting Wine Tastings
    Food-Related Cruises
    Brunch Cruises Coffee Cruises Dinner Cruises Lunch Cruises
    Specialized Food Events
    Dining Experiences Dinner and Show Tickets
    Thematic Food Events & Experiences
    Donut Walking Tour Markets
    Classic & General History Tours
    Archaeology Tours Architecture Tours City Tours Cultural Tours Historical Tours
    Historical Landmarks & Sites
    Ancient Ruins Castles Tours Monuments and Memorials Religious Sites
    Industrial & Commercial History
    Factory Tours Plantation Tours
    Literature, TV & Film-Based Tours
    Game of Thrones Tours Harry Potter Tours Literary Tours TV Tours
    Museum & Cultural Institutions
    Attractions & Museums Museum Tickets & Passes Museums Planetariums
    Mystery & Dark History Tours
    Crime Tours Ghost Tours Underground Tours
    Observation & Structural History
    Classic Car Tours Observation Decks Skyscrapers & Towers
    Art & Creative Workshops
    Art Classes Craft Classes Painting Classes Photography Tours Pottery Classes
    City Exploration
    Hop on Hop Off Buses Trolley Tours Tuk Tuk Tours
    Cultural & Heritage Experiences
    Costume Dress Up Experiences Cultural Tours Culture Fashion Shows Fashion Tours Lantern Festival
    Dance & Music Participation
    Dance Lessons Dance Shows
    Historical & Traditional Skills
    Archery Classes Swordsmanship Classes
    Language & Cultural Learning
    Language Classes Spanish Lessons
    Performing Arts & Live Shows
    Acoustic Concerts Ballet Tickets Ballroom Dance Shows Belly Dance Shows Broadway Shows Cirque du Soleil Shows Classical Concerts Classical Music Flamenco Performance Live Concerts Musicals Opera Performances Sufi Whirling Shows Tango Dance Shows Theater Shows Traditional Dance Performances
    Exclusive & VIP Experiences
    Once in a Lifetime Experiences Private and Luxury Viator Exclusive Tours Viator Experience Award 2022 Viator Experience Award 2023 Viator Experience Award 2024 Viator VIP Tours
    Private & Personalized Travel
    Private Day Trips Private Drivers Private Sightseeing Tours
    Romantic & Scenic Experiences
    Helicopter Tours Limousine Tours Luxury Car Tours Photo Shoots Romantic Tours Sunset Cruises
    Weddings & Special Celebrations
    Photo Shoots Wedding Ceremonies Wedding Packages Weddings & Celebrations
    Adventure & Sports in Nature
    Horseback Riding Mountain Bike Rentals Mountain Bike Tours Sandboarding
    Boating & Cruises
    Glass Bottom Boat Tours Gondola Cruises Sailing
    Camping & Outdoor Stays
    Camping Honeymoon Packages
    Fishing & Marine Experiences
    Eco Tours Fishing Charters
    Hiking & Exploration
    Glacier Walks Hiking Tours National Parks Natural Attractions Nature Parks Nature Walks Outback Tours Parks
    Paddle & Active Water Sports
    Jet Ski Rentals Kayaking Tours Stand Up Paddleboarding
    Sky & Aerial Nature Experiences
    Hot Air Balloon Rides Northern Lights
    Underwater Exploration
    Scuba Diving Shark Diving Snorkeling Swim with Dolphins
    Wildlife Observation & Encounters
    Aquariums Bird Watching Dolphin Watching Safaris Shark Diving Swim with Dolphins Whale Watching Wildlife Encounters Wildlife Watching Zoos & Wildlife Parks
    Dance & Cultural Party Experiences
    Disco Dance Shows Luaus Samba Dance Shows
    Festivals & Seasonal Celebrations
    Carnival Christmas Festivals Halloween Mardi Gras Oktoberfest Packages & Special Events
    Live Music & Performances
    Concerts Jazz Shows Live Concerts Music Tours Musical Shows Opera Performances R&B/Soul Concerts Rap & Hip-Hop Concerts Samba Dance Shows Theater Shows
    Nightlife & Entertainment
    Adults-only Shows Bar Tours Burlesque Shows Cabaret Casino Tours Comedy Shows Night Cruises Night Tours Nightlife Pub Tours
    Spectacle & Family-Friendly Entertainment
    Children’s Shows & Concerts Circus Shows Family-friendly Shows Fireworks Shows Shows
    Unique & Themed Experiences
    LGBT Friendly Tours Street Art Tour Theme Parks Universal Theme Parks
    Travel by Season
    Autumn / Fall Spring Spring Break Summer Winter Winter Sports
    Healing & Wellness Experiences
    Spas Thermal Spas & Hot Springs Yoga Classes
    Immersive Spiritual Experiences
    Light & Sound Shows
    Sacred & Religious Sites
    Religious Sites Religious Tours
    Spiritual & Cultural Rituals
    Easter Lunar New Year Sufi Whirling Shows
    Traditional & Cultural Bathing Practices
    Arab Baths Hammams & Turkish Baths Onsens
    Ball Sports
    Golf Tours & Tee Times Lacrosse Classes Softball Classes Tennis
    Combat & Tactical Sports
    Martial Arts Classes Paintball
    Extreme & Challenge-Based Sports
    Obstacle Courses
    Spectator Sports & Events
    Baseball Tickets Horse Racing Rugby Soccer Sporting Event Tickets & Passes
    Sports Training & Lessons
    Cycling Cycling Classes Sports Lessons
    Winter Sports
    Skiing Skiing Classes

    Loading questions for you...! Please wait...!

    Loading questions for you...! Please wait...!