Adventure Collective
The Christmas Tree Crawl: Chicago’s Holiday Walking Tour - Chicago

The Christmas Tree Crawl: Chicago’s Holiday Walking Tour

Chicagoeasy

Difficulty

easy

Duration

2–3 hours

Fitness Level

Suitable for most fitness levels; requires comfortable walking ability over city sidewalks.

Overview

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.

Walking Tour
Chicago, Illinois

The Christmas Tree Crawl: The Magic of Chicago at the Holidays

Let's see all the best decorations before they're gone!

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Adventure Photos

The Christmas Tree Crawl: The Magic of Chicago at the Holidays photo 1

About This Adventure

Discover and enjoy some of the city's best holiday decorations & traditions!

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!

Duration

2 Hours 1.5 miles on foot

Highlights of the Tour

  • See some beautiful buildings' interiors, as we do on all of our regular tours;
  • Find and photograph some of the most beautiful Christmas trees a big city like Chicago can offer;
  • Get a fun, up-close experience of the most famous and authentic Christkindlmarkt in the USA;
  • Participate in both "Old World" holiday traditions and newer ones;
  • Learn about the history of well-known Christmas characters and symbols;
  • Much more!

Tour Details

  • Runs rain or shine, though we will cancel with notice if the weather seems particularly unpleasant.
  • Meeting Location: 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.

Adventure Tips

Dress in Warm Layers

Chicago winters can be chilly and windy, so wearing layers will help you stay comfortable throughout the tour.

Wear Comfortable Footwear

Expect to walk several city blocks on varied surfaces, so sturdy, comfortable shoes are a must.

Bring a Camera or Smartphone

There are plenty of festive photo opportunities along the route – don’t miss capturing the city’s holiday lights and decorations.

Book in Advance

This popular seasonal tour fills up quickly, so secure your spot early to avoid disappointment.

Local Insights

Wildlife

  • Urban squirrels commonly seen scampering in city parks
  • Various songbirds that frequent Chicago’s green spaces

History

Chicago has a longstanding tradition of lavish holiday celebrations, with downtown decorations dating back over a century.

Conservation

Local walking tours encourage sustainable tourism by promoting pedestrian exploration, reducing reliance on motorized transportation.

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Adventure Hotspots in Chicago

Frequently Asked Questions

Recommended Gear

Warm Coat

Essential

Keeps you comfortable during chilly outdoor portions of the tour.

winter specific

Waterproof Boots

Useful if snow or wet conditions are present to keep your feet dry.

winter specific

Reusable Water Bottle

Essential

Staying hydrated is important even in cold weather during your walk.

Smartphone or Camera

Essential

Capture the festive lights and memorable moments on the tour.