Guided tour

Chicago: Guided Walking Tour and Food Sampling

Guided tour

Chicago: Guided Walking Tour and Food Sampling

From US$ 69.99 per person

Experience the magic and tradition that brings Chicago to life during the holidays on this walking tour through the Loop’s iconic holiday destinations. Join in the fun with some holiday food, sweets & beverages that make winter in Chicago so delicious!

About this activity

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Duration 3 hours
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Skip the ticket line
Live tour guide


  • Explore Millennium Park's Christmas tree and ice-skating rink
  • Warm up during the brisk walk with hot apple cider
  • Sample the original brownie at the historic Palmer House Hotel
  • Taste Chicago's famous pizza and hot dogs
  • Enjoy a VIP Christmas craft beer/cocktail sampling package (for an additional fee)
  • Visit the State Street holiday shopping districts and the Christkindlmarket
Full description
From shimmering lights to decadent bites, Chicago puts its best foot forward for the holidays.   Experience the city come to life during this special time of year on a walking tour through the Loop’s iconic holiday destinations. Pass by Millennium Park's ice skating rink and massive Christmas tree, admire the shimmering holiday lights on State Street, and behold Macy's dazzling holiday decor and window displays. Treat yourself with some brownies at the historic Palmer House Hotel, where brownies were invented, taste the famous Chicago deep-dish pizza and hot dog, and tuck into the city's largest open-air Christmas festival, Christkindlemarket, for some seasonal shopping. For an additional fee you can also enjoy a VIP Christmas cocktail sampling package.
  • Food
  • Non-alcoholic drinks
  • Guide
  • VIP drink package (if option selected)
  • Gratuity for guide

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Meeting point

Lou Malnati's Pizzeria, 410 N. Michigan Avenue, Chicago, IL 60611 Meet your guide at Lou Malnati's Pizzeria-Wrigley Building Northside, ground level. The guide will be holding a Bobby's Bike Hike sign and company shirt.

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Important information

What to bring

  • Passport or ID card

Know before you go

  • Be sure to wear comfortable clothing and shoes. Bring a camera and enter your best picture in the tour operator’s photo contest!
  • Note that tours run rain or shine.
  • A 15-20% gratuity for the guide is suggested.
Customer reviews

Overall rating

4.9 /5

based on 9 reviews

Review summary

  • Guide
  • Value for money
  • Service
  • Organization

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First and foremost Nate our tour guide is why this tour was amazing! Within 5 minutes we were all family having a blast walking, eating, laughing and learning some cool things about Chicago. I've lived in the Chicago area for 40+ years and have taken a number of tours, and thought I knew it all, but Nate amazed me with new tales. Then there's the food. You can't go wrong with Chicago's iconic staples. Take the tour! You'll love it!!

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March 22, 2023

Julia was an excellent guide, who gave us lots of fun information about Chicago! The food was wonderful at all 3 locations, including the dessert as well! It was fun to see the beautiful Macy’s store and the Christkind market. I would highly recommend the tour to anyone visiting during the holiday season.

March 22, 2023

Once again it paid for us to use GetYourGuide to book activities on the back of a hotel reservation.This walking tour was the highlight of our brief stay in downtown Chicago. Our guide Sarah was not only nice and knowledgable - she was enthusastic, approachable and genuine. We learned SO much we didn't know about Chicago! The walking pace was just right for exploring and talking together AND eating the amazing local snacks and specialties Sarah had organized for the group. I loved the cheddar and caramel popcorn mix while discovering the Pedway and the original-recipe brownie while soaking up the Palmer House. And we were especially pleased to have a slice of deep dish pizza waiting for us at Giordano's. (No need to spend the rest of our evening waiting 45 minutes to try it!) We highly recommend this tour.

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March 22, 2023

Product ID: 42344