Guided tour

Chicago Holiday Season: Guided Walking Tour and Samples

Chicago Holiday Season: Guided Walking Tour and Samples

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

Free cancellation
Cancel up to 24 hours in advance to receive a full refund
Covid-19 precautions
Special health and safety measures apply. Learn more
Mobile ticketing
Use your phone or print your voucher
Duration 3 hours
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Skip the ticket line
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Live tour guide
English, Estonian


  • 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 cocktail sampling package (for an addtional fee)
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
Covid-19 precautions
Safety measures in place
  • All areas that customers touch are frequently cleaned
  • The number of visitors is limited to reduce crowds
Traveler requirements
  • You are required to bring and wear a mask

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Prepare for the activity

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

5 /5

based on 4 reviews

Review summary

  • Guide
  • Value for money
  • Service
  • Organization

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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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January 23, 2018

Better than anticipated

Sara was an absolute delight. Knowledgeable and shared personal stories of places we stopped. Food was wow! Couldn’t eat the rest of the day. Would do another walk.

December 9, 2017

Great time

Well done. Awesome guide

December 18, 2016

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Product ID: 42344