Christmas Tree Crawl Chicago: Holiday Decorations Tour

Hunt for Chicago's best Christmas trees and learn the stories behind holiday traditions worldwide.

The Christmas Tree Crawl is a guided walking tour through downtown Chicago that takes you on a treasure hunt for the city's most impressive holiday decorations, including the Christkindlmarkt and hidden gems beyond the famous stops. A local guide leads the 1.5-mile route, sharing the origins of Christmas characters and traditions from around the world, and includes holiday sweets along the way. The tour runs 2 hours and operates only in dry weather. Children are welcome from age 6.

Step-by-step itinerary

Holiday decorations tour in Chicago

• Walk 1.5 miles downtown
• Visit Christkindlmarkt
• See old Marshall Field’s decorations
• Explore lesser-known holiday stops
• Learn history of Christmas traditions
• Discover origins of Christmas characters

The experience

The tour starts in downtown Chicago and covers about 1.5 miles on foot, moving between well-known holiday displays and lesser-known spots that hold some of the best decorations the city has to offer. You'll pass through the Christkindlmarkt and the old Marshall Field's building, but the real draw is finding the trees and displays most visitors miss: the ones a local guide actually knows about. Along the way, you learn where some of the world's most famous Christmas characters came from, some rooted in Chicago itself, and the history behind holiday traditions practiced across different cultures.

A couple of special holiday sweets are included, timed into the walk so you're not carrying treats the whole way. The guide speaks English and keeps the pace steady enough that families with children from age 6 can manage it comfortably, though you should have at least a moderate level of fitness for the distance and the Chicago winter conditions. The tour does not run if rain is forecast. The operator contacts you the morning of the tour with a cancellation and refund if weather doesn't cooperate.

What’s included

• Local guide leading the route in English.
• holiday sweets included along the way.

Before you book

Days and timesEvery day except Tuesday and WednesdayDepartures at 15:00 and 16:00

Book up to1h before

AgesAdult (11 to 64 years) · Senior (65 and older) · Child (6 to 10 years) · Under 6: can't be booked

GroupUp to 20

Live guideEnglish

Meeting point and pickupNo hotel pickup: you go to the meeting point. Ends at a different place from where it starts.

Cancellation and refundsFree cancellation up to 24 h before the start. After that, no refund.

Prices and times updated today

Good to know

Moderate physical effortPets welcomePublic transport nearby

Operated by Inside Chicago Walking Tours

Is this one for you?At 2 hours, this tour fits into a morning or afternoon without consuming your whole day, leaving time to explore other Chicago holiday attractions or neighborhoods on your own. The walking distance and pace suit families with children from 6 up, though you'll want moderate fitness for the full 1.5 miles in winter conditions.

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Top questions

Can children come?

Yes. Ticket types: Child (6 to 10 years). Children under 6 can't be included in the booking.

How far do you walk on the Christmas Tree Crawl?

The tour covers about 1.5 miles through downtown Chicago, moving between holiday displays and decorations on foot. The pace is steady and suited to families with children from age 6 onward, though you should be comfortable walking for the full 2 hours.

What are the stops on this Christmas tour in Chicago?

The Christmas Tree Crawl includes the Christkindlmarkt and the old Marshall Field's building, plus several lesser-known downtown stops known for standout holiday decorations. The guide chooses the route to show you trees and displays most visitors don't find on their own.

Does the tour run if it rains?

The Christmas Tree Crawl does not operate in rainy weather. The operator contacts you the morning of your tour with cancellation and refund information if conditions don't cooperate.

What do you learn about on this holiday tour?

The guide shares the origins of world-famous Christmas characters (some from Chicago, some from elsewhere), and explains the history behind holiday traditions practiced around the world. You learn the stories behind the decorations you're seeing as you walk.