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Discover Chicago’s festive holiday spirit on the Christmas Tree Crawl Experience, a 2-hour walking tour showcasing stunning trees, local stories, and holiday treats.
The Christmas Tree Crawl Experience Chicago at the Holidays offers a charming way to celebrate the season in downtown Chicago for just $35 per person. With an approximate duration of 2 hours, this tour is perfect for those interested in seeing some of the city’s most impressive Christmas trees and decorations, all while learning about holiday traditions from around the world. The tour departs from Peet’s Coffee at 410 N Michigan Ave and ends at the Christkindlmarkt in Daley Plaza, making it easy to explore more festive attractions afterward.
What makes this experience stand out is its blend of sightseeing, storytelling, and holiday treats. The guides are praised for their knowledge and charm, transforming a simple walk into a lively and educational Christmas adventure. While the tour covers about 1.5 miles of downtown Chicago’s holiday decor, it’s suitable for those with a moderate physical fitness level. Note that the tour does not operate in rainy weather, and bookings are typically made around 35 days in advance, indicating its popularity during the holiday season.


This walking tour begins at Peet’s Coffee, located at 410 N Michigan Ave. The starting time is set for 3:00 pm, making it ideal for those looking to enjoy late afternoon holiday sights. After about two hours of exploring, the route ends at Christkindlmarket Chicago, situated at 50 W Washington St in Daley Plaza. The convenient ending allows visitors to stay and browse the market’s holiday vendors or continue their Chicago Christmas experience.
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The tour covers about 1.5 miles of Chicago’s downtown area, showcasing a mixture of famous and lesser-known Christmas trees and decorations. Attendees get a chance to see trees decorated in grand style and discover hidden holiday decor spots that many visitors might overlook. The guide shares stories and details about the history behind the decorations, adding depth to the visual feast.
Throughout the walk, travelers are treated to holiday sweets, designed to keep spirits high amidst the winter chill. The pace is lively but manageable for those with moderate physical fitness, and the focus is on enjoying the sights while learning the stories that make Chicago’s holiday decorations special.

Visitors will see Chicago’s most famous Christmas trees and decorations, with some stops including the Christkindlmarkt in Daley Plaza. The market is renowned for its festive stalls and authentic holiday atmosphere, making the tour’s conclusion a natural spot to linger. The tour also includes visits to historic sites like the old Marshall Fields building, now Macy’s, with its impressive holiday window displays.
The experience is designed to be engaging and fun, with the local guides sharing Christmas stories and traditions from across the globe. The guides’ enthusiasm and knowledge are frequently praised, making the walk lively and informative.

A recurring theme in reviews is the expertise and charm of the guides, particularly Hillary and Heath. Hillary is described as wealthy in knowledge and friendly, able to transform a large group into a cohesive, watchful community. Heath is praised for his passion for Chicago and his ability to make the experience enjoyable despite cold weather. Their storytelling enriches the walk, making the holiday decorations more meaningful.
Included in the tour are special holiday sweets, which add a tasty and warming touch to the experience. These treats help keep guests cheerful and energized as they take in the scenery. The overall atmosphere is lively, with the holiday spirit amplified by the decorations, stories, and community vibe.
The tour operates with a mobile ticket system, making it easy to show your reservation on your phone. It starts at 3:00 pm, with bookings typically made about 35 days in advance due to high demand. The maximum group size is 20 travelers, ensuring a comfortable, intimate experience.
Cancellation is free up to 24 hours before the scheduled start, providing flexibility for weather-related concerns or schedule changes. If the weather turns bad, the tour may be canceled with a full refund, and the organizers will contact booked guests the morning of the tour.

This tour is ideal for families, couples, or groups who want to enjoy Chicago’s holiday sights in a relaxed, guided setting. It suits those interested in Christmas traditions, holiday decor, and local stories. The moderate walking pace makes it accessible for most visitors, though those with mobility issues should consider their comfort level.
While the tour is an excellent way to experience Christmas in Chicago, it’s important to note that bad weather may lead to cancellations. Guests should plan to dress warmly, especially in winter months.
The Christmas Tree Crawl Experience offers a delightful, budget-friendly way to explore downtown Chicago’s holiday decorations. The expert guides, engaging stories, and inclusion of holiday treats create a warm, festive atmosphere that captures the spirit of the season. The route’s focus on both famous and hidden holiday decor ensures a well-rounded experience for anyone looking to enjoy Chicago’s Christmas charm.
This tour is best suited for those wanting a guided, informative experience with a good dose of holiday cheer. It’s especially appealing to visitors who appreciate local history, festive decorations, and social storytelling. With positive reviews highlighting the guides’ charisma and knowledge, this tour is a solid choice for a memorable holiday outing.
“The tour guide rocked he was fun and knew a lot. He was also up beat and made the whole experience better!”
Is this tour suitable for children?
Yes, the tour’s moderate physical activity and family-friendly atmosphere make it suitable for children, especially if they enjoy holiday decorations and stories.
How long does the tour last?
The tour lasts approximately 2 hours, covering about 1.5 miles of walking through downtown Chicago.
What is included in the ticket price?
The ticket includes the guiding services and holiday sweets to enjoy along the route.
Where does the tour start and end?
It begins at Peet’s Coffee (410 N Michigan Ave) and ends at Christkindlmarket in Daley Plaza (50 W Washington St).
What should I wear for the tour?
Dress warmly, as the tour takes place outdoors in winter, and be prepared for potential cold weather.
Can I cancel if the weather is bad?
Yes, free cancellation is available if you cancel more than 24 hours in advance. The tour may be canceled in bad weather, with a full refund.
How many people are in each group?
A maximum of 20 travelers join each tour, ensuring a comfortable experience.
Is this experience accessible for all?
The tour is designed for those with moderate physical fitness and involves some walking, but no specific accessibility information is provided.
Are tickets available in advance?
Yes, booking is recommended, with tours typically booked about 35 days in advance due to demand.
What makes this tour different from other Chicago holiday activities?
Its focus on both famous and hidden holiday decorations, combined with storytelling and holiday sweets, offers a unique blend of sightseeing and cultural insight in a manageable format.