The Christmas Tree Crawl Experience Chicago at the Holidays

Experience Chicago’s holiday magic with The Christmas Tree Crawl Experience. For just $35 per person, you’ll spend about two hours wandering through downtown Chicago, discovering both iconic and lesser-known Christmas trees and holiday displays. Your guide, Hillary (or Heath, based on reviews), will lead you through about 1.5 miles of decorated streets, sharing stories behind the lights and traditions across the globe. Along the way, you’ll stop at the Christkindlmarkt and the historic Marshall Fields building, ending in Daley Plaza’s festive Christkindlmarket.

What we love most about this tour is the chance to see a variety of stunning Christmas trees—from famous city landmarks to hidden gems tucked away in Chicago’s vibrant downtown. Plus, the inclusion of holiday treats makes the experience feel extra special, giving you a taste of local Christmas cheer. The lively storytelling from guides who are knowledgeable and engaging keeps the atmosphere warm and fun.

A consideration worth noting is the weather dependency — since the tour doesn’t operate in rainy conditions, you’ll want to plan for clear, cold days. But if you’re prepared for the chill, this tour offers a lively, cheerful way to get into the holiday spirit. It’s perfect for those who enjoy walking, local history, and a bit of holiday trivia, especially if you love discovering new corners of a city during its most festive season.

This experience suits families, couples, and solo travelers alike—especially those who want an authentic local perspective on Chicago’s holiday traditions without the crowds of large holiday events. If you appreciate guides who are both friendly and knowledgeable, and want a balanced mix of sightseeing and storytelling, this tour will likely become a holiday highlight.

Key Points

• Famous and hidden Christmas trees showcased in downtown Chicago
• Engaging stories and traditions shared by passionate guides
• Two hours of walking covering about 1.5 miles of festive sights
• Holiday sweets included to boost your holiday cheer
• Ideal for those who enjoy walking, history, and seasonal decor
• Weather can impact the tour; it does not operate in rain

A Detailed Look at the Christmas Tree Crawl Experience Chicago at the Holidays

What to Expect and Why It’s Special

This two-hour tour is designed to bring holiday cheer directly to your senses, offering an easygoing yet lively stroll through Chicago’s most decorated streets. Starting at Peet’s Coffee on North Michigan Avenue, the tour is accessible, with a moderate pace that allows plenty of time to enjoy the sights and listen to stories. It’s about 1.5 miles of walking, which is manageable for most people with a reasonable level of fitness, and the group size is capped at 20 to keep things intimate and engaging.

What really makes this tour stand out is the mix of well-known attractions and lesser-seen treasures. For example, you’ll visit the Christkindlmarkt, a beloved Chicago holiday tradition, and see the beautifully decorated Marshall Fields (now Macy’s) building, which is full of historic charm. But what’s truly delightful are the hidden-gem spots—quiet corners and shop windows dressed up with impressive holiday displays that many travelers might miss on their own.

Tour Highlights and Itinerary

Stop 1: Downtown Chicago
The tour begins with a focus on the most iconic Christmas trees in the city. Guides share stories about the history behind these decorations, making the experience educational as well as festive. You’ll walk past some of the city’s most elaborate displays, taking in the sparkle and glow of holiday lights, all while learning about Chicago’s holiday traditions.

Stops include:
– The Christkindlmarkt at Daley Plaza, known for its charming German-style holiday market
– The historic Marshall Fields store (now Macy’s) windows, famous for their elaborate holiday displays
– Smaller, lesser-known spots with impressive decorations that often go unnoticed by casual passersby

Throughout the walk, your guide will tell stories about Christmas customs around the world, adding a global flavor to your local experience. This storytelling aspect is highly praised, with reviewers noting guides like Hillary and Heath as being “fun, knowledgeable, and charming.”

Holiday Treats
A sweet surprise awaits midway through the tour—holiday treats included to keep spirits high and stomachs satisfied. These small bites help to create a cozy, festive atmosphere, perfect for bonding with your fellow travelers.

Authenticity and Value

The price point of $35 per person is quite reasonable considering the depth of experience—seeing the city’s holiday decor while learning about the history and culture behind it. Visitors often mention that the tour offers more than just pretty lights; it’s about understanding the traditions and stories that make Chicago’s holiday season unique. One reviewer calls it “well worth it,” highlighting the knowledgeable guides and the fun, relaxed vibe.

The Guides and Their Impact

From the reviews, it’s clear that guides like Hillary and Heath elevate this experience. Multiple reviewers mention how guides keep the group engaged, share insightful stories, and foster a friendly, welcoming atmosphere. For example, Jill praises Hillary as “a wealth of knowledge,” while John notes, “she magically transformed us into a group that watched out for each other.” This personal touch makes the tour feel less like a scripted walk and more like a friendly exploration with local experts.

Practical Details and Considerations

Timing & Meeting Point
The tour starts promptly at 3:00 pm at Peet’s Coffee on Michigan Avenue. Ending at Daley Plaza’s Christkindlmarket makes it easy to continue exploring or grab a warm drink afterward. Because the tour is weather-dependent—cancelled in rain—you’ll want to check the forecast and dress warmly, with sturdy shoes suitable for walking.

Group Size & Pacing
With a maximum of 20 travelers, the tour maintains an intimate feel, allowing plenty of interaction with your guide and fellow travelers. The pace is moderate, suitable for most fitness levels, but keep in mind the walk covers about 1.5 miles over two hours.

Weather and Cancellation Policy
If the weather is poor, the tour will be canceled, with full refunds available if you cancel more than 24 hours in advance. This flexibility helps travelers plan but also underscores the importance of good weather for maximum enjoyment.

Final Thoughts: Who Will Love This Tour?

If you’re someone who appreciates authentic local experiences with a festive twist, this tour hits the spot. It’s ideal for travelers who love walking tours, are interested in Christmas traditions, and want an insider’s view of Chicago’s holiday decor. Families, couples, and solo visitors who enjoy stories and beautiful sights will find plenty to love here.

While it’s not a comprehensive city tour, its focus on holiday decorations and traditions offers a joyful, memorable way to experience Chicago’s festive spirit. It’s especially perfect if you want a less crowded, more personal way to enjoy the city’s holiday sights without the hassle of large crowds or expensive tickets.

FAQ

Is this tour suitable for children?
Most likely yes, especially if children enjoy walking and holiday sights. The tour is about 1.5 miles long, which is manageable for kids, and the festive treats and stories can keep them engaged.

How long does the tour last?
Approximately two hours, covering about 1.5 miles of downtown Chicago.

Where does the tour start and end?
Starts at Peet’s Coffee, 410 N Michigan Ave, and ends at the Christkindlmarket in Daley Plaza, 50 W Washington St.

What is included in the price?
A knowledgeable local guide and holiday treats are included. No additional admission fees apply.

Can I cancel the tour if the weather is bad?
Yes, the tour does not operate during bad weather. You will be contacted the morning of your scheduled tour to confirm cancellation and receive a full refund if applicable.

How many people are typically on the tour?
Maximum group size is 20 travelers, which helps keep the experience intimate and engaging.

Is this tour suitable for people with limited mobility?
The moderate pace and 1.5-mile walk make it suitable for most, but very limited mobility might pose challenges.

Do I need to bring anything?
Dress warmly, especially if there’s a chill in the air. Comfortable shoes for walking are recommended.

What is the best time to take this tour?
Starting at 3:00 pm makes for beautiful evening lights and allows you to enjoy the festive atmosphere as it darkens.

Will I see inside any buildings?
The tour focuses on outdoor displays and well-known decorated sites like the Marshall Fields windows, but it does not specify interior visits.

To sum it up, the Christmas Tree Crawl Experience in Chicago offers a warm, lively way to see the city’s holiday decorations while learning about traditions from around the world. Guides bring knowledge and charm, making it feel like exploring with a friendly local friend. It’s a fantastic choice for anyone wanting to combine sightseeing, local history, and festive fun—without breaking the bank or dealing with huge crowds. Perfect for those who love the holiday season and want to see Chicago at its most cheerful.