Category Chicago Holiday & Christmas Tours

Chicago · CHICAGO HOLIDAY & CHRISTMAS TOURS

The 7 Chicago Holiday & Christmas Tours to Book First

7 tours

Chicago-Style Holiday Hike: Festive Food and Walking Tour

Chicago-Style Holiday Hike: Festive Food and Walking Tour - Palmer House and State Street Windows: Brownies and Grand Lobbies

1.Style Holiday Hike: Festive Food and Walking Tour

★★★★★★★★★★5.0 · 68 reviews · from $84Our pick

A small-group Chicago holiday hike with Christkindlmarket cider, iconic winter sights, and full tastings like deep-dish pizza and hot dogs.

“This was mine and my husband's first time visiting Chicago together. I came to visit the Christkindlmarket, and I chose the Holiday Hike tour for its combination of food tastings and tour of the city. The food was full servings so quite filling after viRead more”

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The Christmas Tree Crawl Experience Chicago at the Holidays

The Christmas Tree Crawl Experience Chicago at the Holidays - The treasure-hunt format, and why the stories matter

Holiday Walking Tour: Underground Chicago via the Pedway

Holiday Walking Tour: Underground Chicago via the Pedway - Navigating the Pedway Underground, Then Popping Back Out

3.Holiday Walking Tour: Underground Chicago via the Pedway

★★★★★★★★★★5.0 · 27 reviews · 3 hours (approx.) · from $65

Walk Chicago’s Pedway on a small-group guided route, ride the L through the Loop, and end at Cloud Gate, including transit.

“Our guide Tom was a life long Chicago resident and extremely knowledgeable and personable. He catered the tour to fit the interests of our family. Our son had recently moved to Chicago and he gave him several ideas on how to further explore the area. We will definitely be doing another tour with him when we get back to Chicago.”

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Chicago: Guided Holiday Walking Tour and Food Sampling

Chicago: Guided Holiday Walking Tour and Food Sampling - Meeting at Lou Malnati’s, then getting moving right away

Chicago: Christmas Eve Lake Michigan Gourmet Dinner Cruise

Chicago: Christmas Eve Lake Michigan Gourmet Dinner Cruise - Getting to Navy Pier and finding the right boat (Odyssey Lake Michigan)

5.Christmas Eve Lake Michigan Gourmet Dinner Cruise

★★★★★★★★★★4.8 · 12 reviews · from $193

Spend Christmas Eve on Lake Michigan with a 3-course plated dinner, DJ music, and skyline views from Navy Pier aboard Odyssey.

“Improved- food is hot not cold… soda was very flat and syruppy Not sat near the door -everyone kept opening and shutting the door - it was cold. I wore my puffer jacket for the meal Many songs were in Spanish”

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Chicago Seasonal Stroll Walking Tour of Holiday Attractions

Chicago Seasonal Stroll Walking Tour of Holiday Attractions - Christkindlemarket VIP entry: less line anxiety, more holiday time

6.Chicago Seasonal Stroll Walking Tour of Holiday Attractions

★★★★★★★★★★5.0 · 5 reviews · 2 hours (approx.) · from $44

A 2-hour small-group holiday walk in downtown Chicago with VIP Christkindlmarket entry, top lights, and iconic landmarks.

“Josie was a great guide! She was so fun and full of interesting facts about Chicago. It was a cold and rainy night and even thought the weather wasn't great, the tour was so fun!! We appreciated her and her enthusiasm!”

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Private Holiday City Tour

Private Holiday City Tour - Downtown Loop holiday icons: Christkindl Market, Macy’s Walnut Room, and The Bean

7.Private Holiday City Tour

★★★★★★★★★★5.0 · 3 reviews · 3 hours (approx.) · from $499

A private 3-hour Chicago holiday highlights tour with pickup, a licensed guide, and a warm ride through the best light spots.

“Matt and Vick were AMAZING!! The diversity, knowledge, and understanding was one of a kind and know I couldn't find it anywhere else. It was chilly out today but the vehicle was warm and comfortable. The uniqueness of Chicago which makes this city so monumental and the truth inside the bean! We are so happy we took those tour and blessed Matt and Vick were our tour guides and driver!”

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