• Location: Chicago, Illinois
  • Duration: 3 hours (approx.)
From USD $ 55.35 View price calendar

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Stroll through Chicago's winter streets, lit up for the holidays, on this 3-hour walking tour. Learn about Chicago's celebrated holiday traditions like the European-inspired Christkindlmarket, the beautiful decor and windows at Macy's, and ice skating at Millennium Park. Follow your local guide on a walk down festively decorated State Street and sample generous tastes of classic Chicago foods and holiday treats. Seasonal craft beer tastings will help you stay warm and toasty; please note this tour operates in all weather conditions, so dress appropriately.


  • 3-hour food and walking holiday tour of downtown Chicago
  • Visit the German-style Christkindlmarket, a festive outdoor market with warming cider and holiday shops
  • Stop at a local bar to taste seasonal craft brews
  • Head to the historic Palmer House Hotel, where brownies were invented, to try the popular chocolate treat
  • Admire the outdoor ice skating rink and magnificent architecture at Millennium Park
  • Sample Chicago's famous deep dish pizza at a festive restaurant
  • See Chicago's most majestic Christmas tree display at Millennium Park and the holiday windows at Macy's
  • Taste the famous Chicago-style hot dog

What You Can Expect

Chicago Holiday Stroll and Food Tour

Holiday Stroll and Food Tour

Meet your friendly local guide at the Chicago Cultural Center to get started on your tour of Chicago's holiday traditions.

Head for Millennium Park, the location of a large outdoor ice rink sitting smack among the famous landmark buildings of downtown Chicago. See the city's official Christmas tree, lit up for the season, and watch hundreds of skaters enjoy the free recreational activity.
As you walk, stop a brownie sample at the Palmer House Hotel, where the classic dessert was invented. See the magnificent interior architecture of this famous hotel, where many notable people have slept since its founding in 1875. Stop by a local bar to warm up and sip a unique Chicago craft beer. Stop by a local institution to try some of Chicago's famous deep dish pizza.

Visit the traditional German-American Christkindlmarket, a large open-air Christmas festival. Taste authentic hot apple cider and browse the handicrafts and traditional European products for the perfect gift or souvenir. You may come across model trains, a Santa house or a Christmas choir during your exploration.

Follow your guide into the iconic Macy’s building (formerly Marshall Field’s) to see the beautiful Tiffany mosaic ceiling and then smile at the charming holiday window displays. You'll also stop at a local shop to try the famous Chicago-style hot dog.

After 3 hours, your tour concludes, and you are free to explore Chicago's festive streets on your own.

Customer Reviews

kathleen e

5 star rating: Highly Recommended December 2015

Robby our New Zealand native guide was very knowledgable and fun. He was always very engaging and made sure we were treated very special. How he remembered our names I do not know. It was my husband 60 th and he made us feel very special. Great itinerary Great food tour Robby was wonderful. 5 stars


5 star rating: Highly Recommended December 2015

Not our first time doing a Chicago Food Tour...LOVED it again.

Sharon O

4 star rating: Recommended December 2014

Tour and guide were great. I would highly recommend.

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