The Christmas Tree Crawl: Chicago’s Holiday Walking Tour
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.
Details
Celebrate the festive season in the heart of Chicago with "The Christmas Tree Crawl: The Magic of Chicago at the Holidays," a private walking tour that brings the city’s holiday spirit to life. Guided by Inside Chicago Walking Tours, this enchanting experience takes you through iconic locations and hidden holiday spots, showcasing dazzling decorations and beloved Christmas traditions. As you stroll through downtown Chicago’s decorated streets, you’ll learn about classic holiday characters and the local customs that make the city’s holiday season so special. The pop-up nature of this tour offers a unique chance to warm up with cozy indoor stops, making it perfect for chilly winter days. Whether you're traveling with friends or family, this walk is a heartwarming way to connect with the city’s vibrant holiday culture, discover charming neighborhoods, and create lasting memories.
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
Hidden Gems
- The charming alley murals decorated with holiday themes
- Cozy, lesser-known local cafes perfect for a festive drink break
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.
Frequently Asked Questions
Photography Tips
Best Times
Best Viewpoints
- Michigan Avenue decorated storefronts
- Magnificent Mile at night with holiday lights
- Daley Plaza Christmas tree area
What to Photograph
Recommended Gear
Warm Coat
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
Staying hydrated is important even in cold weather during your walk.
Smartphone or Camera
Capture the festive lights and memorable moments on the tour.