Chicago: Holiday walking tour with Christmas trees & sweets

Summary

Wander Chicago’s festive streets in search of holiday magic

You’ll follow a local guide through downtown Chicago on a festive day trip searching for famous Christmas trees and hidden holiday displays. Taste special seasonal sweets along the way and hear quirky stories behind Chicago’s traditions. Expect laughter, new facts about familiar sights, and moments of unexpected warmth you’ll remember long after your walk ends.

What’s the experience like?

I lost a glove before we’d even left the first stop — classic me. Our guide, Sam, just grinned and told me not to worry, “It’s Chicago, you’ll warm up fast.” We started right in the middle of downtown, where the air smelled like roasted nuts from a nearby vendor and car horns mixed with some distant choir music. I didn’t expect to feel this much like a kid again, craning my neck to spot ornaments way up on those massive trees.

We zigzagged through the city for about a mile and a half — it didn’t feel that long though, probably because Sam kept tossing out little stories about Chicago’s own Christmas legends (I had no idea Rudolph had a local connection). At Christkindlmarkt, the crowd was thick but friendly; someone handed us tiny gingerbread cookies as we squeezed past. The old Marshall Field’s windows were next — honestly, I could’ve stood there for an hour just watching kids press their faces to the glass. There was something about the way the lights reflected off the wet pavement that made everything feel softer.

I tried pronouncing “Glühwein” at one point — Li laughed and corrected me gently (I still got it wrong). The sweets they gave us weren’t fancy but tasted like December should: cinnamon, sugar, maybe nostalgia? My toes were cold by then but I barely noticed. Sometimes we’d pause so Sam could explain why certain decorations looked the way they did — apparently some are inspired by Polish traditions brought over generations ago. It made me look at all those shiny baubles differently.

I keep thinking about that moment outside the big tree when everyone just went quiet for a second — no phones out, just looking up together. Not sure why that stuck with me. Maybe it was seeing strangers share something small and bright in the middle of winter. Anyway, if you’re in Chicago around Christmas and want more than just photos, this day trip through downtown is worth it for the stories alone.

Step-by-step itinerary

Day 1 — Holiday Decorations Walk in Chicago

• Walk 1.5 miles of holiday decorations

Top questions

How long is the Chicago holiday walking tour?

The tour covers about 1.5 miles through downtown Chicago.

Is there food included on this Christmas tree crawl?

Yes, you’ll get to try a couple of special holiday sweets during the tour.

Does this tour operate in bad weather?

No, it does not run in rainy weather; you’ll be contacted the morning of if there’s a cancellation.

Do I need to be physically fit for this walking tour?

You should have at least a moderate level of physical fitness since you’ll be walking 1.5 miles.

Are there any famous stops on this holiday decorations tour?

Yes, you’ll visit places like Christkindlmarkt and see the old Marshall Field’s windows among other decorated spots.

What’s included

Your experience includes guidance from a local expert who leads you through downtown Chicago’s best holiday displays and traditions; plus you’ll enjoy special seasonal sweets along your walk before finishing back in central Chicago.