About This Tour
There’s nothing more magical than Christmas in Chicago, & this 2hr guided Chicago Walking Tour takes you straight into the heart of it. Journey through the Chicago Loop, Millennium Park, & the Magnificent Mile with an internationally recognized tour company proudly headquartered right here in Chicago. Our entertaining guides will spark your holiday spirit with fun facts, cultural insights, & the very best seasonal décor—like the surprising fact that Rudolph the Red-Nosed Reindeer was created in Chicago! Along the way, you’ll marvel at the iconic Christmas window displays of the original Marshall Field’s store, admire Chicago’s official Christmas tree, Mag Mile lights, and take in the festive Millennium Park ice skating rink. You’ll even enjoy VIP access—no waiting in line—to the legendary Christkindlmarket, the city’s beloved German holiday market. If you’re searching for Things to do in Chicago during the holidays, this experience is a perfect fit. Note: This is a walking tour only.
What's Included
What's Not Included
Photo Gallery
See the Water Tower at Christmas on your Chicago Walking Tour, where its historic stone glow and festive décor bring timeless charm to the Chicago Holidays and Christmas season.
See Cloud Gate on your Chicago Walking Tour, where its bright reflections and snowy shine amplify the Chicago Holidays and Christmas magic in every photo.
Explore Millennium Park on your Chicago Walking Tour, where festive décor and winter energy bring the Chicago Holidays and Christmas season to life.
Popular time slots can fill up fast.
TopTours Insights
Chicago Seasonal Stroll Walking Tour of Holiday Attractions
This 2-hour walking tour explores Chicago's seasonal holiday attractions, taking you through festive decorations and lights during a leisurely stroll. It's ideal for those seeking a low-key way to experience the city's winter charm, especially couples or solo travelers who enjoy a relaxed pace.
Calculating tour characteristics...
Additional Information
Meeting Point
Departure Point: Petterino's (This is the start of your Chicago Seasonal Walking Tour) Directions: You will meet your guide inside of Petterino's restaurant. Please feel free to arrive early to grab a bite or coffee at the restaurant before your tour. Then you'll start your walking tour in Chicago.
Special Instructions
Please arrive 15 minutes before your scheduled Chicago Walking tour time $6per person (or more) suggested guide gratuity. (via Cash, Venmo and PayPal) Wear comfortable clothing/shoes Please use the Restroom before your arrival to your seasonal walking tour in Chicago. Bring water. Tours run rain or shine or snow Ho Ho Ho....Merry Christmas and Happy Holidays!
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
✓ Free cancellation due to bad weather
Tour Operator
Bobby's Bike, Hike & Food Tours - Chicago
Official supplier for this experience. Bookings are completed through our partner with verified operators.
Verified partner
Trusted local operator
Guest Ratings
Total review count and overall rating based on Viator and Tripadvisor reviews
Based on 5 verified reviews
Average rating
Guest Reviews Preview
See what other travelers are saying about this experience.
Frequently Asked Questions
Common questions about Chicago Seasonal Stroll Walking Tour of Holiday Attractions in Chicago
Who operates this experience?
This experience is operated by Bobby's Bike, Hike & Food Tours - Chicago, a local sightseeing provider.
What's included?
This tour includes Walk beneath millions of glittering lights as the Magnificent Mile glows for the season., Skip the Lines—enjoy festive, VIP front-of-line access to Christkindlmarket’s holiday magic., and Stroll through Millennium Park as it sparkles with lights and joyful holiday energy.. Additional amenities and services are included. All inclusions are provided by the tour operator.
How long is this tour?
The experience lasts approximately 2 hours, giving you time to fully enjoy your chosen activity.
Can I cancel this tour?
Yes, you can cancel up to 24 hours before the scheduled departure time for a full refund. If weather conditions are unsafe, the tour may be canceled by the operator. In such cases, you'll be offered a refund or reschedule.
What should I bring?
We recommend bringing comfortable walking shoes, a camera, and weather-appropriate clothing. All necessary equipment is provided.
Will I receive instant confirmation?
Yes, you'll receive instant confirmation when you book.
What to expect on this tour?
This sightseeing experience lasts approximately 2 hours and includes all necessary equipment and guidance. You'll have access to Walk beneath millions of glittering lights as the Magnificent Mile glows for the season. and more.
Ready to book?
- See live times & pricing before you pay
- Instant confirmation when you complete checkout
- Cancellation rules shown before you pay
Private and Luxury in Chicago
Curated picks and more tours in this category for this destination.
Ready to Go?
Book Chicago Seasonal Stroll Walking Tour of Holiday Attractions
Secure your spot with flexible cancellation options and verified customer support on our booking partner.
Trusted partner • Instant confirmation
