A Full Review of Chicago’s 2025 Christmas Tree Crawl Experience

You know, there’s just something absolutely different about Chicago when the holidays roll around. I mean, the city puts on its finest winter coat, a bit dusted with snow, and everything seems to sparkle just a little brighter. It’s almost a feeling you can’t quite put into words, right? Honestly, I’ve tried for years to plan the perfect day downtown, trying to see all the famous Christmas trees, but at the end of the day, it’s often a bit of a chaotic rush. So, this year I thought, let’s actually try something new, like an organized tour. That’s where ‘The Christmas Tree Crawl Experience’ came in, pretty much promising a curated look at the city’s best holiday displays. I was a little skeptical, to be honest. I mean, could a tour really capture that special Chicago holiday feeling, or would it feel, you know, kind of plastic? This is basically my full-on breakdown of the 2025 experience, a really honest look at what you get, what you see, and if it’s genuinely the right way for you to soak in the holiday spirit in the city.

What Exactly is the Christmas Tree Crawl? Unpacking the Experience

So, you might be asking yourself what this ‘Crawl’ thing actually is, which is a fair question, really. Basically, it’s a guided walking tour, more or less, that shepherds you through the downtown Loop to see the most celebrated and honestly magnificent Christmas trees Chicago has to offer. The ticket apparently included a guide, a pre-set route, and, as a matter of fact, a cup of pretty decent hot chocolate to keep your hands warm. The whole thing typically lasts about two and a half hours, which at first seemed a little short, but you’d be surprised at how much ground you cover. Anyway, the idea is that you get all the sights without any of the planning headaches. You just, you know, show up and follow along. We think this could be a great fit for newcomers to Chicago’s holiday scene. The group itself was a mix of people, you know, like families, some couples on a date night, and even a few solo folks just soaking in the lights. Frankly, it felt less like a stiff, formal tour and more like a big group of people taking a festive stroll together, which was a very welcome surprise. The whole atmosphere tends to be quite light and full of happy energy from the get-go.

The Main Attractions: A Stop-by-Stop Glimpse

Obviously, the real substance of the tour is the trees themselves. I mean, that is what everyone signs up for, right? The route was actually very well thought out, starting with the biggest and most famous displays and then taking us to some slightly more hidden gems. You sort of get a full spectrum of Chicago’s holiday decorating traditions. The pacing felt just about right, not too fast, and definitely not too slow. As I was saying, it gave us plenty of time at each spot to take photos and really just stand there and appreciate the view for a minute. Seriously, it’s one thing to see these places on Instagram, but it’s a completely different thing to be standing right there, in that moment, with the cold air on your face and the warm glow of thousands of lights in front of you.

Stop 1: The Iconic Millennium Park Tree

Alright, so our first stop was, of course, the big one: the official City of Chicago Christmas Tree in Millennium Park. And wow, it absolutely lives up to the hype. It’s almost overwhelmingly large when you’re standing near its base, literally a giant reaching for the sky. The guide shared a little story about how the city picks the tree each year, which was a kind of nice touch. The whole area was just alive, you know, with the sound of skaters on the rink nearby and the city lights reflecting off the surface of ‘The Bean’. I mean, we spent a good 20 minutes here, and it was the perfect way to kick things off. It just sort of sets the bar for what a real city Christmas feels like. There are so many things to see that you might explore other parts of Millennium Park after the tour, too. Honestly, the number of lights on that one tree alone is probably more than my whole neighborhood has combined.

Stop 2: A Traditional Feel at Daley Plaza

Next, we took a short walk over to Daley Plaza, which, by the way, has a completely different feel. I mean, this is where the Christkindlmarket is set up, so the air is just thick with the smell of cinnamon-roasted nuts and spiced wine. It’s pretty much an attack on the senses in the best way possible. The tree here feels a bit more old-world and classic, similarly to what you might see in a European town square. It stands right next to the Picasso sculpture, creating a really unique contrast of old and new, which is sort of a very Chicago thing to do. The guide gave us some time to wander through the market stalls a little bit, which was honestly a smart move. It’s almost impossible to walk through there and not want to look around. As a matter of fact, some people in our group even managed to buy a souvenir ornament or two, and you might find the best stalls for unique gifts if you look closely. It was just a little more quaint and cozy than the grand spectacle at Millennium Park.

Stop 3: The Walnut Room’s Grand Tree at Macy’s

Okay, so this next stop was arguably my personal favorite. We actually went inside the Macy’s on State Street to see the legendary Great Tree in the Walnut Room. This is just such a classic Chicago tradition, and seeing it as part of the tour felt really special. Unlike the outdoor trees, this one is inside a beautiful, historic dining room, and it practically touches the ceiling. You know, it’s decorated from top to bottom with a specific theme each year. The guide told us about the history of the tree, how it’s been a centerpiece for over a hundred years. Frankly, you can feel that history in the room. You’re sort of standing there, looking up at this 45-foot tree, and you can just imagine generations of families doing the exact same thing. It’s a very heartwarming stop on the tour, and for those interested, learning about its history makes the view even better. It was just a little moment of quiet wonder in the middle of a busy department store, which was a nice change of pace.

Stop 4: A Modern Spectacle at the Art Institute

Finally, our last major stop was outside the Art Institute of Chicago. Now, they don’t have a giant tree in the same way, but instead, they have those absolutely iconic wreaths placed on the two huge bronze lions that guard the entrance. Seriously, seeing those stern lions looking so festive is just quintessentially Chicago. It always makes me smile. It’s a slightly more understated display, yet it’s one of the most photographed holiday scenes in the whole city. Our guide pointed out some of the architectural details of the building itself, which I had honestly never noticed before. This stop felt like a really smart way to end the tour, more or less. It was a little bit elegant, a little bit artistic, and a really powerful image to leave us with. You leave with a sense that holiday decorations can be both grand and, you know, sort of gracefully simple too. Exploring the museum afterward is another great option, with a lot of people checking out the special seasonal displays inside.

The Tour Guide and Logistics: Is It Worth the Price?

Okay, let’s talk about the nitty-gritty stuff, right? A tour can have the best route in the world, but the guide can honestly make or break the experience. Luckily, our guide was pretty great. He was obviously a local who had a genuine fondness for the city and its holiday traditions. He wasn’t just reading from a script; he was telling stories, cracking jokes, and actually answering questions from the group. You know, at one point, he told a personal story about bringing his own kids to see the trees, which was a really humanizing touch. In terms of logistics, the pacing was managed very well. We never felt like we were being herded or rushed along, which can sometimes happen on these kinds of tours. The group size was about 15 people, which felt just right—not too big, not too small. So, was it worth the roughly $75 price tag? To be honest, I think so. When you factor in the guide’s expertise, the convenience of not having to plan a thing, and the cup of hot chocolate that was actually pretty good, it feels like a fair value. You’re paying for a seamless and frankly stress-free holiday outing, and it might be right for you if a guided holiday experience is right for you.

Pro Tips for Making the Most of Your Christmas Tree Crawl

So, if you decide to go on the Christmas Tree Crawl, there are definitely a few things you can do to make your experience even better. I mean, I picked up on a few things along the way that I wish I’d thought of beforehand. You are, at the end of the day, walking around outside in Chicago in the winter, so being prepared is pretty much the most important thing you can do. It’s the difference between a magical night and a very, very chilly one. These are just some practical pieces of advice that I think would really help anyone planning to take this particular tour. You can always read more tips for staying warm and happy during a Chicago winter adventure.

• Dress Like an Onion: Seriously, wear layers. And then add one more layer. The wind coming off the lake is no joke, and while you do pop inside Macy’s for a bit, most of the tour is outdoors. So, you definitely want a hat, gloves, a scarf, and maybe even some thermal underwear if you tend to get cold easily.
• Comfortable Footwear is a Must: You will be on your feet for over two hours. Anyway, this is not the time for fashionable boots with no support. I mean, wear your most comfortable, warmest, and preferably water-resistant shoes. Your feet will thank you, you know.
• Book Your Spot Early: As I was saying, these tours are actually quite popular and often sell out, especially on weekends closer to Christmas. So, if you know your dates, book it well in advance to avoid any disappointment.
• Juice Up Your Phone: Okay, this is an obvious one, but your phone is your camera. You will be taking a ton of photos. It’s almost guaranteed. Make sure your phone is fully charged before you go, and maybe even bring a small portable power bank, just in case.
• Engage with Your Guide: Honestly, ask questions. Our guide had so many little-known facts and fun stories that weren’t part of the main script. If you’re curious about a building or a tradition, just ask. That interaction can make the whole experience feel a lot more personal.

My Honest Thoughts: Who Is This Experience For (and Who Should Skip It)?

At the end of the day, is the Christmas Tree Crawl for everyone? Frankly, no. But for the right person, it’s a really fantastic experience. So, who would absolutely love this? Well, I think first-time visitors to Chicago during the holidays would get a huge amount of value from it. It’s sort of a perfect introduction to the city’s festive side. I also think it’s great for people who feel overwhelmed by planning or just want to show up and have a good time without any stress. You know, couples looking for a simple, romantic holiday date night would probably really enjoy it, too. On the other hand, who might want to sit this one out? Well, seasoned Chicago locals who have their own holiday traditions probably don’t need a guided tour to see these spots. And, to be honest, if you’re on a super tight budget, the ticket price might be a bit steep, as you can technically see all these trees for free on your own. Families with very young children might also find it a bit challenging, just because of the cold and the amount of walking. It really all depends on your style and what you’re hoping to find on your ideal festive Chicago night out.