Holiday Walking Tour and Seasonal Sights in Chicago
Difficulty
easy
Duration
2 hours
Fitness Level
Suitable for all fitness levels; requires moderate walking stamina
Overview
Discover Chicago’s festive heart with a two-hour holiday walking tour featuring dazzling lights, Christkindlmarket, and the iconic holiday tree.
Chicago's Seasonal Stroll Walking Tour
Starting at $29.99 | 2 Hours | See how Chicago celebrates the holidays!
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Adventure Photos
About This Adventure
Experience the magic of the holiday season on Bobby’s Seasonal Stroll, a delightful two-hour walking tour through downtown Chicago. Discover the dazzling lights of the Magnificent Mile, immerse yourself in the festive atmosphere of Christkindlmarket, and get up close to the iconic holiday tree. Perfect for families and friends!
Rates
Prices starting at $29.99
Duration
2 Hours
About
Stroll your way through the holiday season on this downtown walking tour! This holiday-themed tour begins at the end of November and runs through Christmas Eve. Bobby’s Seasonal Stroll is a great way to experience all that Chicago has to offer during the winter holidays in a single afternoon stroll! See the lights of the Magnificent Mile, experience the German-inspired festivities of Christkindlmarket, and walk right up to Chicago's holiday tree! This two-hour Chicago holiday tour is perfect for families, friends, holiday parties, and anyone looking to celebrate all that the season has to offer. This is a walking tour only.
Adventure Tips
Dress in layers for Chicago winter
The city can be cold and windy, so wearing thermal layers helps keep you comfortable during the stroll.
Wear comfortable walking shoes
Expect about two hours on your feet along city sidewalks; sturdy shoes improve comfort.
Bring a reusable cup
Many market vendors serve hot drinks—bring a cup to reduce waste and stay warm.
Arrive early to avoid crowds
Tour mornings or weekdays have fewer visitors, making for a more relaxed experience.
Local Insights
Wildlife
- Urban squirrels
- City pigeons
History
Chicago’s Magnificent Mile has been a premier shopping destination since the early 20th century and hosts annual holiday celebrations since the 1950s.
Conservation
Local vendors at Christkindlmarket emphasize reusable materials and sustainable packaging to reduce holiday waste.
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Adventure Hotspots in Chicago
Frequently Asked Questions
Recommended Gear
Warm jacket
Keeps you comfortable in chilly Chicago temperatures during the walk.
winter specific
Comfortable walking shoes
Necessary for navigating city sidewalks throughout the tour.
winter specific
Hat and gloves
Protects extremities from cold wind and enhances overall warmth.
winter specific
Portable phone charger
Ensures your phone stays powered for photos and navigation.