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Chicago-Style Holiday Hike: Festive Food and Walking Tour

5 (54)
Chicago, US
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Chicago-Style Holiday Hike: Festive Food and Walking Tour

5 (54)
Chicago, US
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Experience the magic of downtown Chicago during the holiday season with Bobby's Holiday Hike. This 3-hour guided walking and food tour takes you through the Chicago Loop, allowing you to sample the Windy City's favorite winter treats. Indulge in a slice of deep dish pizza, a Chicago-style hot dog, Italian Beef, chocolate brownie, and hot apple cider. Your knowledgeable guides will keep you entertained with fun facts about the city, including the origin of Rudolph the red-nosed reindeer. Explore the Christmas window displays at the original Marshall Field's department store, admire Chicago's city Christmas tree, and visit the legendary Christkindlmarket, a traditional German Christmas Market. No other tour offers such an all-inclusive experience of Chicago during the holidays. Don't miss out on this festive and delicious adventure!

About this experience

  • Free Cancellation For a full refund cancel at least before the start of your booking
  • Admission Included
  • 3 hours
  • Suitable for 1-15 Participants
  • Private Tour, Small Group Tour
  • Guided Experience
  • Sample delicious Chicago-style deep dish pizza
  • Indulge in a Chicago-style hot dog or Italian Beef
  • Experience the magical Christkindlemarket
  • Admire the beautiful Christmas window displays at Marshall Field's
  • Explore Millennium Park and see the iconic Cloud Gate sculpture
  • Food samples
  • Holiday attractions
  • Holiday Cocoa or Cider
  • Local tour guide
  • Alcoholic beverages
  • $10 per person (or more) suggested guide gratuity. (via Cash, Venmo and PayPal)
  • Hotel pickup and drop-off

Popular Hotels Closeby

More about this experience

Introduction

Step into the enchanting holiday season in downtown Chicago with Bobby's Holiday Hike. This 3-hour guided walking and food tour will take you through the vibrant Chicago Loop, giving you a taste of the city's festive food and showcasing its captivating holiday attractions. Bobby's Bike Hike, internationally recognized for their tours, brings you this magical experience that will leave you with unforgettable memories.

What to Expect?

During the Holiday Hike Chicago-Style tour, you can expect to indulge in the Windy City's favorite winter treats. Sample a slice of deep dish pizza, savor the flavors of a Chicago-style hot dog and Italian Beef, indulge in a chocolate brownie, and warm up with a cup of hot apple cider. For an added touch of luxury, you can enhance your experience by adding a VIP holiday craft beer package.

Who is this for?

This tour is perfect for anyone looking to immerse themselves in the holiday spirit while exploring the heart of downtown Chicago. Whether you're a local or a visitor, this experience is designed to captivate and enchant. The tour caters to all ages and interests, providing a delightful adventure for families, couples, and solo travelers alike.

Why Book This?

Bobby's Holiday Hike offers a unique and all-inclusive experience of Chicago during the holidays. Not only will you get to sample the city's iconic food, but you'll also discover fascinating insights about Chicago's holiday traditions and history. From admiring the Christmas window displays at the original Marshall Field's department store to witnessing the vibrant ice skating rink at Millennium Park and exploring the legendary Christkindlmarket, this tour combines delicious food, captivating sights, and local expertise.

Good to Know

When booking the Holiday Hike Chicago-Style tour, keep in mind that a suggested guide gratuity of $10 per person (or more) is recommended. Hotel pickup and drop-off are not included, so plan your transportation accordingly. While food samples are included, alcoholic beverages are not part of the package. So, get ready to embark on a delightful adventure and immerse yourself in the holiday spirit of downtown Chicago.

Reviews

Customers who have experienced Bobby's Holiday Hike rave about the magical atmosphere and the knowledgeable guides who bring the city to life during the holiday season. They appreciate the opportunity to indulge in Chicago's iconic winter treats and explore the city's festive attractions. The tour has received high praise for its unique blend of food, history, and holiday magic, making it a must-do experience for anyone visiting or living in Chicago.

How long before the event do I need to book?

  • You can book at any time before the event

Vouchers accepted in the following formats

  • Mobile

Is an adult required for the booking?

  • At least one adult or senior required per booking

Your Itinerary

Christkindlemarket

Enjoy a hot cider at this outdoor german christmas market

Admission Included

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.

Macy's on State Street

Enjoy the Holiday decor

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.

Cloud Gate

Iconic Chicago attraction

Jay Pritzker Pavilion

Gorgeous open air amphitheater

Daley Bicentennial Plaza

Enjoy Christkindlmarkt in Chicago

Chicago Christmas Tree

Visit Chicago's Christmas Tree

Wrigley Building

Visit one of Chicago's iconic buildings

Lou Malnati's Pizzeria

Enjoy Chicago-style deep dish pizza

Admission Included

Millennium Hall

Enjoy a Chicago style hot dog or Italian Beef

Admission Included

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.

Admission Included

Exchequer Restaurant & Pub

Enjoy an italian beef sandwich.

Admission Included

The Art Institute of Chicago

(Pass by)

Amazing collections

Reviews

(54)

5 (54)

formorrie4

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

Great tour. The food and drink were delicious and Our tour guide Mickey was fun and knowledgable! Would recommend.

Shanta_C

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.

Melissa_G

We enjoyed the tour. It was great way to see and learn different things about the city. Fun trying true Chicago food. Mickey the tour guide was great!

K4483BKtimm

Absolutely wonderful! Our your guide, Mickey Jordan, was fantastic. So knowledgeable and fun. The tour itself was great. Hit several Chicago landmarks along with sampling of great food.

Angelique_B

Mickey was great! We really enjoyed his jokes and personal touch. He made the tour very comfortable and funny!

Shelton_J

We really loved this tour. Brooke was knowledgeable with great energy. Loved her! One suggestion. During holidays when kriskrindlmarket cups are available, serve last stop hot chocolate in them for people taking tour.

Heather_C

This was mine and my husband's first time visiting Chicago together. I came to visit the Christkindlmarket, and I chose the Holiday Hike tour for its combination of food tastings and tour of the city. The food was full servings so quite filling after visiting three restaurants. We visited some key points of interest along the way, and our tour guide, Mickey, did a great job of educating us on the history of each location/meal we tried. There were 12 of us in our party, and Mickey helped to break the ice amongst the group. My only "disappointment" was thinking the samples would be from the Christkindlmarket since it said "seasonal samples" and had the photo of the market. Did get a Belgian Chocolate at the market, but would have loved a brat or pretzel. Still would highly recommend. Worth the investment.

Donna_W

We loved our guide Greg. He had great stories that I had not heard before even though I have visited Chicago several times.

Breann_Y

Super fun guide Hannah, great organization and stops! We had a blast! Nice to get express access to the Christmas Market.
Collected by Evendo, Tripadvisor & Viator
2024-05-04 01:06