The Christmas Tree Crawl Experience Chicago at the Holidays

Traveling during the holiday season often means braving crowded malls or missing out on authentic local festivities. But if you’re after an experience that combines the magic of Christmas with the charm of Chicago’s downtown, the Christmas Tree Crawl Experience offers a refreshing alternative. This guided tour is designed to not only showcase some of the city’s most beautiful holiday decorations but also to weave in stories and traditions that make this season special.

What really sets this tour apart? First, it’s the knowledgeable guides who bring Chicago’s holiday spirit to life with enthusiasm and insights. Second, the carefully curated stops—ranging from iconic trees to hidden-gem decorations—make sure you see the best without feeling rushed. That said, if you’re seeking a tour with a heavy focus on interior decor or expecting a lengthy walk, you might find it more light than detailed. This tour suits travelers looking for a festive, laid-back outing that combines history, local flavor, and a little sweet indulgence.

Key Points:
– See Chicago’s top holiday trees and secret decorations
– Learn about Christmas traditions from around the world
– Enjoy holiday treats included in the tour price
– Walk about 1.5 miles through downtown Chicago in around 2 hours
– Ideal for those seeking a fun, informative, and festive experience
– Suitable for travelers with moderate physical activity levels

Introduction: Why the Christmas Tree Crawl Stands Out

We don’t often think of Chicago as a holiday wonderland, but this tour proves it can be one of the most charming cities to visit during December. Instead of just passively admiring holiday lights, you’ll explore downtown with a guide who shares stories, history, and a sense of community that makes the season meaningful. We love how this tour combines the visual spectacle—like the twinkling trees—with educational tidbits that deepen your appreciation of Christmas traditions.

Another highlight is the balance of well-known sights and hidden gems. You’ll visit the Christkindlmarkt, a beloved holiday market, and see the historic Marshall Field’s building, now Macy’s, draped in festive decor. Meanwhile, your guide will lead you to off-the-beaten-path displays that most travelers miss. And, because it’s a walk of only about 1.5 miles over two hours, it’s easy to fit into a busy holiday itinerary, while still feeling relaxed and merry.

A potential consideration: this tour is weather-dependent — if it rains or snows heavily, it might be canceled or less enjoyable. Also, while snacks are included, some might find the 2-hour duration a bit short if they prefer more extensive sightseeing. Still, for those looking to soak up Chicago’s seasonal charm without the crowds or expense of larger shows, this experience hits the sweet spot.

This tour is perfect for families, couples, or solo travelers who want a cozy, fun introduction to Chicago’s holiday spirit, with a friendly guide leading the way.

The Itinerary: What’s Included and What’s Not

The tour starts at Peet’s Coffee on North Michigan Avenue, a central spot easy to find and a good warm-up stop. From there, you’ll head out into the heart of downtown, covering roughly 1.5 miles of streets, parks, and plazas decorated for the holidays. The walk is leisurely, and the guide will point out stunning Christmas trees and lighting displays along the route.

The first stop is the Christkindlmarkt, a traditional German-style holiday market, which sets a festive tone with its lights, crafts, and seasonal treats. Here, you’ll get insights into Christmas markets’ history and enjoy some holiday sweets included in the tour. Next, you’ll visit the Marshall Field’s building, famous for its elaborate window displays and historic holiday decor, giving you a glimpse into Chicago’s retail holiday traditions.

Throughout the walk, your guide will share stories and traditions from around the globe, connecting Chicago’s local displays with worldwide customs. This adds a layer of depth that elevates the experience beyond just sightseeing.

While the agenda is flexible, the focus remains on beautiful decorations and engaging stories. The tour concludes at the Christkindlmarket for those who want to linger or explore further on their own.

What’s included?
– A knowledgeable local guide
– Holiday treats to keep spirits bright

What’s not included?
– Gratuities, which are always appreciated but optional

Highlights: What Makes This Tour Special

The true charm of this experience lies in its combination of visual beauty and storytelling. Travelers consistently praise their guides for being fun, friendly, and well-informed, making the tour feel like a holiday gathering with friends.

Many reviewers note that they saw more than they expected — not just the usual big trees but also hidden decorations and interior displays selected for their beauty. One reviewer mentioned, “We saw trees we wouldn’t have thought of,” highlighting how the tour uncovers lesser-known spots.

The inclusion of holiday treats adds a nice touch, giving you a little sugar boost to keep the festive cheer going. The two-hour duration strikes a good balance, providing ample time to enjoy the sights without feeling rushed or exhausted.

The small group size (max 20) ensures everyone has a chance to ask questions and enjoy the personalized attention. And the moderate physical activity level makes it accessible for most travelers, including those who may not want to undertake a strenuous walk.

Detailed Breakdown of the Tour Experience

The Beginning at Peet’s Coffee

Starting point is a well-known, central spot that’s easy to find, so you won’t waste time hunting for the meeting location. From here, the tour kicks off with a warm welcome from your guide, setting a cheerful, friendly tone.

Exploring Downtown Chicago’s Holiday Decorations

As you move along the streets, you’ll be immersed in the glow of thousands of lights, with stops to admire some of the city’s most impressive Christmas trees. Expect to see the iconic trees in public squares, shop windows, and department stores. The tour emphasizes the history behind these displays, helping you appreciate not just the beauty but the tradition they represent.

Christkindlmarkt

Depending on the day, you might browse the market stalls, enjoying the German-inspired holiday atmosphere. Here, you’ll get a taste of Christmas markets’ origins, plus a chance to purchase handcrafted ornaments or local treats.

Marshall Field’s / Macy’s Department Store

This historic retail space is famed for its holiday window displays and decorative interiors. Your guide will share stories about Chicago’s retail history and how the holiday displays have evolved over the years.

Hidden Gems and Off-the-Radar Decorations

What makes this tour stand out are the lesser-known decorations your guide will point out—perhaps a cozy corner with a charming nativity scene or a lesser-visited plaza with a stunning tree. These spots allow for great photo opportunities and give you a sense of discovering Chicago’s seasonal secrets.

Ending at Christkindlmarket

The tour concludes here, where you can continue exploring on your own or enjoy a warm drink. Many travelers appreciate how the tour wraps up in a lively, festive environment.

Authentic Reviews: What Fellow Travelers Say

One reviewer described the experience as “a fun activity on a nice day,” praising the guide’s energy and knowledge. Another shared that Hillary, their guide, was “a wealth of knowledge,” and her friendly attitude made the tour especially enjoyable. Many appreciated how the guides transformed a big group into a close-knit festive community, making the experience feel warm and personal.

Some feedback points to the quality of decoration viewing—one review mentioned only seeing a handful of decorations, but clarifications from the tour operator confirm that you’ll see many interior and exterior displays, including beautiful trees and architecture.

The consensus is clear: this tour offers excellent value for the price—a chance to see a variety of holiday sights with an expert guide for just $35.

Practical Details: What You Should Know Before Booking

The tour costs $35 per person, which is quite reasonable considering the quality of guidance, the sights, and included treats. It’s booked about 35 days in advance on average, so plan ahead if visiting during peak holiday season.

The meeting point at Peet’s Coffee is centrally located on North Michigan Avenue, and the tour ends at Christkindlmarket, making it easy to continue exploring afterward. The two-hour duration is perfect for fitting into a busy day or as a warm-up to a night out.

Weather considerations are important: since the tour doesn’t operate in heavy rain or snow, be prepared for potentially canceled plans if the weather turns bad. The tour provides a mobile ticket, making access straightforward.

Group size is limited to 20 people, ensuring a friendly atmosphere but also requiring early booking for those keen to join.

FAQs

Is this tour suitable for children or families?
Yes, it’s family-friendly and suitable for most ages. The festive atmosphere and stories make it engaging for kids, though parents should be prepared for about 1.5 miles of walking.

How much does the tour cost?
The price is $35 per person, offering good value considering the guided experience, holiday treats, and sightseeing.

What’s included in the price?
A knowledgeable local guide and holiday sweets are included. Gratuities are not included but are customary if you enjoy the tour.

Does the tour operate in bad weather?
No, the tour does not operate during heavy rain or snowy weather. You will be contacted the morning of if the weather cancels the tour, with a full refund offered.

How long is the tour?
Approximately 2 hours, covering about 1.5 miles of walking.

Where does the tour start and end?
It starts at Peet’s Coffee at 410 N Michigan Ave and ends at Christkindlmarket at 50 W Washington St.

Can I cancel if my plans change?
Yes, you can cancel up to 24 hours in advance for a full refund.

The Sum Up: Is It Worth It?

For travelers wanting a relaxed, engaging, and visually stunning holiday experience in Chicago, this tour is a fantastic choice. It offers excellent value—a knowledgeable guide, a mix of famous and hidden decorations, and tasty holiday treats—all in a manageable 2-hour walk. The guides seem to make the experience warm, fun, and informative, which many guests find adds to the holiday cheer.

This tour is especially suited for those who appreciate stories and traditions behind holiday displays, or those looking for a low-stress way to see the city’s festive lights. It’s ideal if you want an authentic, behind-the-scenes look at Chicago’s holiday decor without the crowds of larger events.

It’s perfect for families, couples, or solo travelers who enjoy walking and learning, and for travelers seeking a memorable way to celebrate the season. Just remember to book early in the season, dress warmly, and be prepared for a cheerful, lively walk through Chicago’s holiday heart.