Stroll the City’s Brightest Holiday Landmarks
Experience Chicago’s holiday cheer on a guided two-hour walking tour through its most iconic festive sites. From the Magnificent Mile lights to Christkindlmarket and Millennium Park, every step captures the spirit of the season.
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$30 USD
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All Ages
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2 hours
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Illinois, United States
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Chicago
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- Millennium Park Christmas Tree
- Christkindlmarket Stroll
- Magnificent Mile Lights
- Chicago Theatre Visit
- State Street Holiday Windows
- Iconic “The Bean” Stop
- Family-Friendly Tour
- Festive Local Guide
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- Two-hour guided holiday walking tour through downtown Chicago.
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- Wear warm, comfortable shoes and winter layers.
Chicago Seasonal Stroll Holiday Walking Tour Features
Holiday Walking Adventure
Enjoy a guided stroll through Chicago’s downtown holiday highlights, from festive lights to historic decorations.
Festive City Landmarks
Visit Millennium Park’s Christmas tree, Cloud Gate, the Chicago Theatre, and State Street’s famous holiday windows.
Chicago Seasonal Stroll Holiday Walking Tour Details
- Highlights
- Description
- Itinerary
- Price & Availability
- Food & Drink
- Instructions
- Restrictions
- Transportation
Highlights
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Millennium Park Christmas Tree
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Christkindlmarket Stroll
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Magnificent Mile Lights
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Chicago Theatre Visit
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State Street Holiday Windows
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Iconic “The Bean” Stop
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Family-Friendly Tour
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Festive Local Guide
Description
Take a merry walk through Chicago’s most festive sites with Bobby’s Seasonal Stroll Holiday Walking Tour. This two-hour experience captures the city’s holiday magic with visits to Millennium Park, the Christkindlmarket, the Chicago Theatre, and the Magnificent Mile. Guests will see the city aglow with thousands of lights and hear stories of Chicago’s Christmas traditions from a friendly local guide. Designed for all ages, this tour offers a perfect mix of culture, sightseeing, and holiday cheer—ideal for families, friends, or solo travelers looking to celebrate the season in style.
Itinerary
- 3:15 PM – Check in at Petterino’s Restaurant, 150 N Dearborn St
- 3:30 PM – Depart for guided holiday stroll
- 3:45 PM – Visit Christkindlmarket and Millennium Park
- 4:30 PM – View State Street holiday windows and Chicago Theatre
- 5:15 PM – Finish at Magnificent Mile Christmas lights
Price & Availability
$29.99 adults, $25.99 youth, $9.99 infants. Runs daily from late November through Dec 24.
Food & Drink
Food and beverages available for purchase at Christkindlmarket.
Instructions
Arrive 15 minutes early for check-in at Petterino’s.
Restrictions
Operates in all weather; bring gloves and hot drink.
Transportation
Guests meet at Petterino’s Restaurant, 150 N Dearborn St.
Frequently Asked Questions
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Contact Us
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Christmas Holiday Tours
Fort Collins, CO 80526 -
Meeting locations vary for each tour: You will be sent a meeting location after you book
