The Christmas Tree Crawl Experience Chicago at the Holidays

If you’re looking for a way to enjoy Chicago’s holiday spirit without the crowds or the chaos, the Christmas Tree Crawl Experience might just be your ticket. This tour promises a cozy yet lively two hours of wandering through downtown Chicago, taking in some of the city’s most breathtaking Christmas trees, decorated storefronts, and hidden holiday gems. It’s a neat way to get into the festive mood and learn a bit about Christmas traditions — all with the company of a friendly local guide.

What we love about this tour is how it balances fun and information. First, it’s a chance to see both well-known holiday sights like the Christkindlmarkt and some lesser-known, tucked-away decorations that often go unnoticed. Second, the lively storytelling from the guide makes history and tradition accessible and engaging, even for those who aren’t typically holiday buffs.

One thing to consider, though, is the weather — the tour doesn’t operate in rainy conditions, so if rain or snow is forecasted, you might want to plan for an alternative. Also, since the tour moves about 1.5 miles through downtown, it’s best suited for folks with moderate mobility.

This experience seems perfect for visitors wanting a laid-back, festive walk with a local’s perspective. Families, couples, or groups of friends looking for a holiday activity that’s both charming and educational will likely find a lot to enjoy here.

Key Points

• Accessible holiday sights: See Chicago’s top Christmas trees and decorations in a relaxed walking tour.
• Local storytelling: The guide shares holiday stories and traditions from around the world.
• Fun treasure hunt: It’s not just sightseeing — there’s a lively, engaging element to find hidden holiday spots.
• Treats included: Holiday sweets add a tasty touch and keep spirits high.
• Weather considerations: The tour doesn’t run in bad weather, so check the forecast.
• Ideal for moderate walkers: Covers about 1.5 miles over two hours, so some mobility is helpful.

The Tour Itinerary in Detail

Start Point: Peet’s Coffee on Michigan Avenue

The adventure begins at Peet’s Coffee on 410 N Michigan Ave. Here, you’ll meet your guide and get a quick rundown of what’s to come. The meeting point is central, making it easy to find and close to many other holiday sights in downtown Chicago.

Walking Through Chicago’s Holiday Decorations

Over roughly 1.5 miles of walking, you and your group will meander through the city’s holiday display zones. Expect to see some of the city’s most iconic Christmas trees, beautifully decorated storefronts, and festive window displays. Your guide will share insights about the history and traditions behind what you’re seeing, making the experience both visual and educational.

Stop at Christkindlmarkt and Marshall Field’s

Two of the highlights are the Christkindlmarkt in Daley Plaza, a Chicago holiday tradition modeled after the famous German market, and memories of the old Marshall Field’s (now Macy’s) holiday window displays. These stops are perfect photo ops and provide a deeper context for Chicago’s holiday traditions.

Hidden Gems and Local Spots

Beyond the well-known sites, your guide will take you to some lesser-known spots, which often hide impressive holiday decor that might otherwise go unnoticed. This is where the tour really shines — it’s about discovering Chicago’s secret holiday corners.

Learning and Sweets

Throughout the walk, your guide will share stories about Christmas traditions from across the globe, adding some cultural depth to your holiday experience. Plus, the treats included will give you a little boost of holiday cheer to keep your energy up.

End at Christkindlmarket in Daley Plaza

The tour wraps up at the Christkindlmarkt, where you can continue exploring or just soak in the holiday spirit. It’s a fitting end to a cheerful and festive experience.

What Travelers Are Saying

Looking at reviews, it’s clear that this tour hits the right notes for many visitors. Several reviewers praised the guides, mentioning how knowledgeable, friendly, and engaging they are. For instance, one review says, “Hillary is a wealth of knowledge and very friendly,” highlighting how personal and approachable the guides are. Others appreciated how much they learned about Chicago and Christmas traditions, along with the opportunity to see beautiful trees they hadn’t known about.

A notable point from a review by Reese_K is that the guide “knew a lot,” and made the experience more enjoyable with their upbeat attitude. Even in cold weather, travelers like Michael_K found the guide’s passion infectious, making the chilly walk feel warm and lively.

Some reviews, however, had a slight critique about the number of decorations seen, with one mentioning seeing only a few. But the owner responds confidently that the tour includes many interiors and more decorations than the review suggests — so if you’re expecting a Christmas spectacle, you’ll probably be pleasantly surprised.

Most agree that the tour provides good value. At $35 per person, it offers a mix of sights, stories, treats, and a friendly guide — all within about two hours — making it a reasonable expense for a memorable holiday outing.

The Practical Details

Price: $35 per person — considering the guided experience, treats, and the chance to see some of Chicago’s best Christmas sights, this feels like fair value.

Duration: Around 2 hours — enough time to soak in the sights without feeling rushed or exhausted.

Group Size: Max 20 travelers — small enough for a personal touch but lively enough to keep the energy up.

Weather: The tour does not operate in rainy conditions, which is worth noting if your weather forecast looks murky.

Mobility: About 1.5 miles of walking, so moderate fitness is recommended, but the pace is comfortable.

Booking: Usually booked around 35 days in advance, so plan ahead if you have specific dates in mind.

Meeting Point: Peet’s Coffee on Michigan Ave, ending at Christkindlmarket — both central and easy to find.

Who This Tour Suits Best

This Christmas Tree Crawl is ideal for visitors who want a festive, local experience without spending hours in crowded malls or markets. It’s a relaxed walk with a friendly guide, perfect for those interested in holiday traditions, beautiful decor, and some cultural insights.

It’s also a good choice if you enjoy a mix of sightseeing and storytelling, especially if you’re traveling with friends, a partner, or even solo but looking to connect with others. If you’re after a high-energy or fast-paced tour, this might not be the best fit, but for those wanting a cozy, well-rounded glimpse into Chicago’s holiday offerings, it’s quite charming.

Final Thoughts

The Christmas Tree Crawl Experience in Chicago offers a thoughtful mix of holiday sights, stories, and treats, all within a manageable two-hour window. Its small group size, friendly guides, and focus on both well-known and hidden decor make it a memorable way to celebrate the season.

If you’re someone who loves to learn about local traditions while enjoying festive views, you’ll likely find this tour both delightful and worthwhile. The price point feels fair given the personalized experience and included sweets, and the reviews suggest that the guides truly make the experience special.

On the flip side, keep in mind the weather limitations and the walking distance if you have mobility challenges or are visiting during inclement weather. But overall, this tour is a lovely way to learn about Chicago’s holiday spirit, especially if you enjoy stories, beautiful lights, and a touch of local charm.

FAQ

Is this tour suitable for children?
While not explicitly aimed at children, the relaxed pace and festive atmosphere make it generally suitable for families. Just keep in mind the walking distance and weather conditions.

What is included in the price?
You get a guided walk through downtown Chicago’s holiday decor, along with some holiday sweets to enjoy along the way.

Does the tour operate in bad weather?
No, the tour does not operate in rainy weather. If weather conditions are poor, you’ll be contacted in the morning with a cancellation and refund option.

How long does the tour last?
Approximately two hours, covering about 1.5 miles of walking through the city’s Christmas sights.

Where does the tour start and end?
It begins at Peet’s Coffee on Michigan Avenue and ends at the Christkindlmarket in Daley Plaza.

How far in advance should I book?
Most people book around 35 days ahead, so it’s good to plan early for peak holiday times.

Is there a group size limit?
Yes, a maximum of 20 travelers, which helps keep the experience personal and engaging.

If you’re after a cheerful, informative, and beautifully decorated holiday walk in Chicago, this tour seems well worth considering. It’s a cozy way to explore the city’s festive spirit, meet new friends, and enjoy some holiday cheer in the heart of downtown.