Walk the Loop under holiday lights and discover the architecture, animated windows and Christkindlmarkt that define Chicago’s downtown at Christmastime. This small-group 90–120 minute tour pairs history with seasonal flavors and local stories.
More ways to explore the area's outdoor wonders
A cold breath of Lake Michigan wind meets the glow of animated store windows as you gather beneath the Great Tree at Michigan Ave and Washington St. The Loop hums with holiday traffic and incandescent decorations; your small group peels off into alleyways and grand lobbies where history and commerce trade space in equal measure.
Difficulty
moderate
Duration
1.5–2 hours
Fitness Level
Moderate—able to walk 1.5 miles and manage short staircases at a steady pace.
Wildlife
History
The Loop’s current streetscape rose from the ashes of the Great Fire of 1871 and became a testing ground for the Chicago School of architecture and the modern department store era.
Conservation
Keep the Loop clean by using bins and supporting small vendors; minimize solitary littering and use reusable mugs at market stalls when possible.
Reserve your spot on the Chicago Christmas Loop Tour today and enjoy a trusted, highly rated experience designed to help you make the most of your adventure.
Dress in layers
Chicago winters are cold and windy; insulating layers plus a windproof outer shell keep you comfortable during outdoor stops.
Wear grippy shoes
Expect 1.5 miles of walking and some stairs—waterproof footwear with good traction helps on slushy sidewalks.
Bring transit fare or a pass
Public transit is the easiest way to reach the Loop and avoids parking hassles; have your fare ready for arrival and departure.
Time your tour for lights
If you want the full window and tree illumination, book a late-afternoon or early-evening slot when displays are lit.
Warm insulated jacket
Keeps you comfortable during outdoor portions and while waiting at viewpoints.
winter
Waterproof walking shoes
Provides traction and keeps feet dry on slush-covered sidewalks.
winter
Transit card or app on phone
Makes arrival and departure faster and avoids parking delays.
Small daypack
Carries water, camera, extra layers, and any purchases from the market.