The Christmas Tree Crawl Experience Chicago at the Holidays
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September 2026
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Who is going?
Adults
Age 13 and over
Children
Age 12 and under
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Free cancellation up to 24 hours before. Same price on Viator, Outty earns a commission.
Traveler rating
4.9/5
Based on 44 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is The Christmas Tree Crawl Experience Chicago at the Holidays worth booking?
The Christmas Tree Crawl Experience Chicago at the Holidays is a 2-hour experience in Chicago, United States, from $35 per person. It scores 75 out of 100 on the Outty Ranking, which we label “Strongly Recommended”, based on a 4.9/5 rating across 44 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 75 / 100
- Rating
- 4.9/5 (44)
- Duration
- 2 hours
- From
- $35 per person
On this nostalgic and educational tour, we will lead you on a "Christmas treasure hunt" through downtown Chicago in search of the most stunning and impressive Christmas trees and other holiday decorations — and we know w
What you get
About this experience
On this nostalgic and educational tour, we will lead you on a "Christmas treasure hunt" through downtown Chicago in search of the most stunning and impressive Christmas trees and other holiday decorations — and we know where they are! This tour includes not only visits to well-known stops like the Christkindlmarkt and the old Marshall Field’s, but also to little-known stops that contain some of the best holiday decorations downtown. You’ll learn about the origins of some world-famous Christmas characters — some of them from Chicago, some not — as well as the history behind Christmas traditions practiced by people around the world.
What's included
Included
- Local guide
- Snacks
Not included
- Gratuities
What you'll see and do
Chicago
We will be covering about 1.5 miles worth of beautiful holiday decorations and traditions in downtown Chicago, learning about the history of everything we see along the way!
120 minutes here
Where it starts and ends
Meeting point
Chicago
We meet outside the Peet's Coffee Shop in the Wrigley Building. Nearest address is 400 N. Michigan Avenue. The Peet's Coffee Shop is located in the walk-through plaza BETWEEN the two parts of the Wrigley Building, just off of Michigan Avenue.
Hotel pickup
No pickup: everyone meets at the start point.
Ends at
We end a few blocks from the Christkindlmarket so that you can choose if you'd like to go back or not.
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Languages
- en
- Ticket
- Mobile Only
- Runs on
- Tue, Wed, Fri, Sat
- Group size
- Up to 15 travelers per booking
- Operated by
- Inside Chicago Walking Tours
Know before you go
- Travelers should have at least a moderate level of physical fitness
- Does NOT operate in case of bad (rainy) weather -- we will contact you THE MORNING OF THE TOUR with cancellation and refund in that case.
Photos
What travelers are saying
Outty’s summary of the themes that recur across 44 traveler reviews. Written by us, not quoted from reviewers.
The guide
7 mentionsTravelers single out the guide as the reason the experience works.
Knowledge and storytelling
5 mentionsReviewers describe the commentary as informative rather than scripted.
Value for money
2 mentionsTravelers feel they got more than they paid for.
Good for families
2 mentionsReviewers traveling with kids report it landed well with their group.
Pace and timing
2 mentionsSeveral reviewers found the schedule tight or the day long.
Traveler reviews
44 verified traveler reviews for The Christmas Tree Crawl Experience Chicago at the Holidays. Ratings and reviews provided by Viator and Tripadvisor.
Amazing time
We booked The Christmas Tree Crawl Experience in Chicago through TripAdvisor on December 13, and we had amazing time. The tour was enjoyable regardless of the cold and windy weather indicative of the season, thanks to the excellent knowledge of our guide, Hillary, who combined insight into architecture and history with her outstanding knowledge of Christmas traditions to create a memorable tour experience. We are planning to return next year.
via Tripadvisor
A totally delightful, festive tour
My sister and I spent a few days in Chicago right before Christmas, and we did this tour on a lark… And it was absolutely delightful. It’s an inside and outside walking tour of downtown, highlighting all kinds of Christmas decorations. Hilary (who also happens to own the company) was a fantastic guide – knowledgeable, fun, super warm, and full of historical and architectural information along with the festive Christmas stuff. Completely, utterly delightful.
via Tripadvisor
A Festive Delight
My sister and I did this while in Chicago for a few days. It was so fun and charming and festive. Hilary (who actually owns the tour company) could not have been more knowledgeable - and she’s a freaking delight. The tour ends at the Palmer House, which is a gorgeous, historic hotel (super festive at Christmas). Fantastic guide, fantastic tour!
via Viator
Such a disappointment
This tour was a total disappointment. Our guide took a call as soon as we were about to start. Walked away from the entire group and was on his phone for 15 minutes. We were all just standing there in the cold waiting. He then told us he had to make some “changes” to the tour. He started walking extremely fast and was way in front of us all. By the time we got to the first stop two people already left the tour. The first stop, we could not even go in to see the tree. At the second indoor stop 5 people decided they wanted to quit the tour so he had to spend another 10 minutes trying to give them a refund, while we all just stood inside this office building. Third stop he gave us very frozen Frango mints in the dirty underground train station. Kept showing us Christmas pictures from a ratty notebook. We ended up exiting the tour at Macy’s. This was a poorly run tour with only 1 Christmas tree being seen. The guide seemed very overwhelmed and unprepared.
Response from the operator: Georgette, I am truly sorry that the first part of this tour was full of unexpected obstacles that your guide had to try to resolve on the fly, and that it ruined the experience for you. It is not at all representative of this tour nor this company, and I would like to clarify for you (and for future customers) what happened with this tour. Scott gets many excellent reviews, and is an excellent guide -- but even the best guides would get overwhelmed by the many unexpected customer issues at the start of this tour. One large group mistakenly booked thinking it was a trolley tour, so they left. Another large group hadn't alerted us to needing handicap accessibility for one of their guests (though it is clearly marked that this particular tour route is not handicap accessible), and so they eventually left, and Scott was stuck fielding their insistence on a refund while other guests waited and got irritable. Scott was on his phone at the start of the tour trying to help many late guests locate the starting point (and it's the late guests that made the tour start late). Then, for the first couple stops, he was texting *with me* trying to work out how he could discretely adjust the tour route to accommodate a wheelchair user when the tour route is generally not handicap accessible (for future guests, please let us know if you'll have a wheelchair or stroller so that we can make proper accommodations). That's why he was on his phone so much. In addition to all this, he had angry guests bullying him, saying "looks like you're having personal issues -- we want another guide" (or calling his binder "a ratty notebook"). I am sincerely sorry that you didn't get the experience all of our other tour groups get, but I want to clarify that you did see two of the scheduled Christmas trees (out of the 5-6 we show): to be clear, there was no tree to be seen in the first place we usually enter that your guide skipped due to needing impromptu handicap accessibility, and there's nothing to see inside that building anyway -- we simply enter this building to take the Pedway into the first actual Christmas tree stop, which you saw. You must have decided to leave just before I met your group in Macy's to apologize to the group for the start-of-tour issues that were out of our control. I would have been happy to speak with you individually about how we could make it up to you. You decided to leave the tour at Macy's -- and if you didn't see the Walnut Room tree where I met the group, then you must have left as soon as the group got to Macy's through the Pedway (the "dirty underground train station," as you called it, which we use to keep guests warm), so you didn't see the 3rd tree. I do understand why you decided to leave, but unfortunately you didn't get to experience the entire second half of the tour, which took place without any further issues, and which saw the rest of the trees and decorations as usual.
via Tripadvisor
Well-run tour that our kid enjoyed! Comfortable pace that shows so much!
Highly recommended! We brought our 4 year old along expecting to abandon after 30 minutes or so, but the boy loved the full 2 hours. Perfect mix of indoor/outdoor with a bathroom break. Scott was fantastic as guide. I’ve been to Chicago this time of year a dozen times, and learned/saw MANY new things - wish I had done this way sooner! There were 20 total in the group (5 in our family), and everyone was so nice! I would do this again!!!
via Tripadvisor
Good to know
- Duration
- 2 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Tue, Wed, Fri, Sat
- Hotel pickup
- No pickup, meet at start point
- Booked in 30 days
- 15
- Verdict
- Strongly Recommended
Why this scores 75
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
The Christmas Tree Crawl Experience Chicago at the Holidays: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Chicago.
How much does The Christmas Tree Crawl Experience Chicago at the Holidays cost?
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Prices start at $35 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Chicago usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.
How long does The Christmas Tree Crawl Experience Chicago at the Holidays take?
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Plan for about 2 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in Chicago is not rushed.
Is The Christmas Tree Crawl Experience Chicago at the Holidays worth it?
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It holds an Outty Ranking of 75 out of 100, which we label "Strongly Recommended". That score blends traveler sentiment (4.9/5 across 44 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in Chicago, and how flexible the cancellation terms are.
Can I cancel or reschedule The Christmas Tree Crawl Experience Chicago at the Holidays?
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Yes. Cancel free up to 24 hours before the start time for a full refund. Inside that window the booking is non-refundable, and no-shows are not refunded.
Is The Christmas Tree Crawl Experience Chicago at the Holidays suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 2-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book The Christmas Tree Crawl Experience Chicago at the Holidays?
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Around 15 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in Chicago can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.
What should I bring or wear?
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Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in Chicago and add a light layer if any part of the 2-hour experience runs outdoors or after sunset.
Where does The Christmas Tree Crawl Experience Chicago at the Holidays start and how do I get there?
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The exact meeting point and directions are on your voucher once you book, and they sit in central Chicago within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.
What are the best things to do in Chicago?
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Chicago's signature experience is still the architecture boat cruise, and the difference between the docent-led originals and the party-boat imitators is the single biggest quality gap in the city. Beyond the river: gangster history walks, Art Institute access, deep-dish and hot-dog crawls, and skydeck timed entry. Outty Ranking leans on guide credentials and how consistently the promised route runs. On Outty we rank every Chicago experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include Original Chicago Architecture Interiors Tour: Dazzling Interiors, Chicago Murder Mystery Tour, Chicago Favorites Ultimate Food and Walking Tour. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.
When is the best time to visit Chicago?
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May to October. Winter cruises stop running when the river ices. Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.
How many days do you need in Chicago?
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Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.
Do I book through Outty or through the operator?
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Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.
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