Chicago Christmas

Explore festive Christmas tours in Chicago including river cruises, holiday walks, and private city tours. Celebrate the holidays with unique Chicago experiences.

No tours match these filters.

Chicago Seasonal Stroll Walking Tour of Holiday Attractions

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 Chic

★ 5.0 (5)

From $44.99 USD

Chicago-Style Holiday Hike: Festive Food and Walking Tour

There’s nothing more magical than downtown Chicago during the holidays. Bobby’s Bike Hike & Food Tours—internationally recognized for quality—presents the Holid

★ 4.9 (81)

From $84.99 USD

Christmas Eve Plated Dinner Cruise on Lake Michigan

Celebrate the magic of the season on the water with a Christmas Eve Premier Dinner Cruise in Washington DC. You and your guests will enjoy a holiday 3-course, p

From $198.18 USD

Historical and Architectural Chicago Fireboat River & Lake Cruise

Travel on a piece of history, learning Chicago fire history as well as Architecture! We travel on Lake Michigan and through the Chicago River seeing the sights.

★ 4.9 (488)

From $47.00 USD

Private Christmas Walking Tour in Chicago with Christkindlmarket

This private Christmas walking tour in Chicago captures seasonal traditions within a historic urban setting. You will begin along Michigan Avenue, where archite

★ 5.0 (1)

From $1,029.00 USD

Private Holiday City Tour

Enjoy the city of Chicago during a magical time! This private experience takes you around Chicago in a private luxury vehicle with your own personal guide! Enjo

★ 5.0 (3)

From $499.00 USD

The Christmas Tree Crawl Experience Chicago at the Holidays

On this nostalgic and educational tour, we will lead you on a "Christmas treasure hunt" through downtown Chicago in search of the most stunning and impressive C

★ 4.9 (44)

From $35.00 USD