Christmas Activities

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Our most recommended Chicago Christmas Activities

Chicago: Guided Walking Tour and Food Sampling

1. Chicago: Guided Walking Tour and Food Sampling

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.

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Other Sightseeing Options in Chicago

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What people are saying about Chicago

Overall rating

5.0 / 5

based on 6 reviews

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.

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.

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.

Julia was a great guide! She was enthusiastic and knowledgeable about Chicago as she is a local with great tidbits.

Kevin was a fun, informative and all around great guide. Highly recommend the tour for some Chicago Holiday fun!