Chicago Christmas Tree Crawl

Highlights

Description

Chicago sparkles in winter, and the Christmas Tree Crawl captures its holiday magic in motion. Led by expert local guides, this two-hour walking tour takes you through 1.5 miles of festive streets and glittering architecture. Follow your guide through downtown Chicago’s most spectacular holiday scenes — from the iconic Christkindlmarkt in Daley Plaza to the former Marshall Field’s building, adorned with its legendary windows and a towering Christmas tree. Along the way, step inside ornate lobbies and hidden atriums to find secret trees that even locals overlook. Hear the stories behind global Christmas traditions, meet the city’s own contributions to holiday folklore, and learn how Chicago helped shape seasonal celebrations across America. This tour blends history, architecture, and nostalgia with twinkling lights and warm laughter. Perfect for families, friends, or visitors, it’s a joyful, educational, and photo-worthy way to experience the city at its most magical time of year.

Itinerary

2:45 PM Check-In → Arrive at Peet’s Coffee in the Wrigley Building, 400 N. Michigan Ave. 3:00 PM Tour Begins → Meet your guide and start the festive walking tour. 3:15 PM Stop 1 → Visit historic lobbies featuring Chicago’s hidden indoor Christmas trees. 3:45 PM Stop 2 → Explore Christkindlmarkt and learn about Old World holiday traditions. 4:15 PM Stop 3 → Visit the Marshall Field’s windows and iconic tree. 5:00 PM Conclude → End near Daley Plaza with time for evening photos.

Price & Availability

Adults $30 | Seniors/Children $25 | Under 4 free. Refunds or reschedules available for weather.

Food & Drink

No food included; refreshments available for purchase near Christkindlmarkt.

Instructions

Arrive 15 minutes early; tours depart on time; rain or shine unless weather severe.

Restrictions

Not wheelchair accessible on all routes; some stairs and crowded areas.

Transportation

Street and garage parking available near Wrigley Building.