Free cancellation

Chicago Christmas Tree Crawl: Holiday Decorations & Traditions

4.9 (44 reviews) · By Inside Chicago Walking Tours

Experience the magic of the holiday season with the Christmas Tree Crawl Experience in Chicago. This fun and educational tour takes you on a festive "treasure hunt" through downtown Chicago, where you'll discover some of the city's most stunning Christmas trees and holiday decorations. Whether you're a local or visiting, this tour offers a unique way to celebrate and learn about holiday traditions.

We'll visit well-known spots like the Christkindlmarkt and the historic Marshall Field’s, along with hidden gems tucked away in the city’s streets. Along the way, you'll hear fascinating stories about the origins of popular Christmas characters—some from Chicago, others from around the world—and explore the history behind various holiday customs.

Join us for a lively 2-hour adventure that combines sightseeing, history, and holiday cheer. Plus, enjoy some special holiday sweets included in the tour. It’s perfect for families, friends, or anyone looking to get into the festive spirit while learning about Christmas traditions worldwide.

Frequently asked questions

How long is the Christmas Tree Crawl Experience?

The tour lasts approximately 2 hours.

What language is the tour conducted in?

The tour is conducted in English.

What is the group size?

Up to 20 participants.

Is the tour suitable for children?

Yes, children aged 6 to 10 can join, along with adults and seniors. Travelers should have at least a moderate level of physical fitness.

What’s included in the tour?

A local guide and some special holiday sweets.

Can I cancel my booking?

Yes. You can cancel for a full refund if you do so at least 24 hours before the scheduled start time.

Free cancellation

For a full refund, cancel at least 24 hours before the scheduled departure time.

Reserve now

Check a date here, then finish booking with our partner. Payment options are confirmed at checkout.

Duration 2 hours

Check availability to see start times.

Live tour guide

English

Key facts

Duration 2 hours
Languages English
Group size Up to 20
Ages Child 6–10; Adult 11–64; Senior 65–99
Accessibility Travelers should have at least a moderate level of physical fitness

What's included

Included

  • Local guide
  • A couple of special holiday sweets

Not included

  • Gratuities

Itinerary

Explore about 1.5 miles of downtown Chicago’s holiday decorations, learning about their history and traditions along the way.

  1. Stop 1

    We will cover approximately 1.5 miles of beautiful holiday decorations and traditions in downtown Chicago, learning about the history behind each sight as we go.

    2 hours

Meeting point & pickup

Meet at the starting point

We meet outside the Peet's Coffee Shop in the Wrigley Building. The address is 400 N. Michigan Avenue. The Peet's Coffee is located in the walk-through plaza between the two parts of the Wrigley Building, just off Michigan Avenue.

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Cancellation & confirmation

Free cancellation

For a full refund, cancel at least 24 hours before the scheduled departure time.

  • 100% refund if cancelled at least 1 day before
  • 0% refund if cancelled within 0–1 day

Instant confirmation

Your booking is confirmed immediately after checkout.

From $35.00 per person

Child Age 6–10
0
Adult Age 11–64
1
Senior Age 65–99
0
  • Free cancellation
  • Secure checkout with our booking partner

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