easy
2–3 hours
Suitable for most fitness levels; requires comfortable walking ability over city sidewalks.
Discover Chicago’s festive magic on a charming holiday walking tour. Explore sparkling decorations, cozy stops, and traditions that make the city shine at Christmas.
Let's see all the best decorations before they're gone!
Let Inside Chicago Walking Tours take you on an enchanting stroll through the heart of the city at its prettiest time — during the winter holiday season.
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.
Filled with history, culture, and beautiful sights, this tour is a celebration of Chicago’s festive holiday spirit. We'll pop into several buildings — just like we do on all of our tours! — specifically to see impressive Christmas trees indoors, and to warm up for seeing the outdoor trees. We call this tour a "pop-up tour" because it’s offered for a very limited time, and purely because we want to show off the city's beauty at this time of year. You won't find a boat, a bus, or even a segway where we're going. Come and take a holiday stroll with us — it's a fun stress-buster and perfect time to set aside for hanging out with family and friends!
2 Hours 1.5 miles on foot
Chicago winters can be chilly and windy, so wearing layers will help you stay comfortable throughout the tour.
Expect to walk several city blocks on varied surfaces, so sturdy, comfortable shoes are a must.
There are plenty of festive photo opportunities along the route – don’t miss capturing the city’s holiday lights and decorations.
This popular seasonal tour fills up quickly, so secure your spot early to avoid disappointment.
Chicago has a longstanding tradition of lavish holiday celebrations, with downtown decorations dating back over a century.
Local walking tours encourage sustainable tourism by promoting pedestrian exploration, reducing reliance on motorized transportation.
Keeps you comfortable during chilly outdoor portions of the tour.
winter specific
Useful if snow or wet conditions are present to keep your feet dry.
winter specific
Staying hydrated is important even in cold weather during your walk.
Capture the festive lights and memorable moments on the tour.