Chicago: Guided Holiday Walking Tour and Food Sampling

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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!


  • 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 adult beverage sampling package (for an additional fee)


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. Upon arrival, for an additional fee you can also enjoy a VIP Christmas adult beverage sampling package.


Food Non-alcoholic drinks Guide VIP drink package upgrade (offered upon arrival)

Important Information

  • Be sure to wear comfortable clothing and shoes. Bring a camera and enter your best picture in the tour operator’s photo contest! Upon Arrival you will have the option to upgrade to a VIP adult drink package which includes 3 unique beverage pairings. This option is $19.99/per person (adults only) Note that tours run rain or shine. A 15-20% gratuity for the guide is suggested.

Easy cancellation

Cancel up to 24 hours in advance for a full refund


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