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Chicago Seasonal Stroll Walking Tour of Holiday Attractions

Chicago Seasonal Stroll Walking Tour of Holiday Attractions

Overview

There’s nothing more magical than downtown Chicago during the holiday season. 2-hour guided walking tour through the Chicago Loop, Millennium Park and the Magnificent Mile. This tour is brought to you, internationally recognized tour company headquartered right here in Chicago. Our entertaining guides will get your holiday spirit primed with plenty of fun facts, general knowledge, and the best of Chicago holiday decor. Did you know Rudolph the red-nosed reindeer was a story created in Chicago? You’ll see the fabulous Christmas window displays at the original Marshall Field’s department store, Chicago's city Christmas tree, the ice skating rink at Millennium Park, and the legendary Christkindlmarket, a traditional German Christmas Market. This tour is a walking tour only. No food/drinks on this particular tour.

City: Chicago

Sun 01 Jun

Other dates

You can choose the date already on the booking website

Starting at $44.99

Make a reservation

Sun 01 Jun

Starting at $44.99

Make a reservation

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What's Included

Holiday attractions

Local tour guide

Additional Info

Service animals allowed
Public transportation options are available nearby
Infants and small children can ride in a pram or stroller
All areas and surfaces are wheelchair accessible
Suitable for all physical fitness levels
Transportation options are wheelchair accessible
Wheelchair accessible
All of our walking tours at the present moment do allow for ADA compliant and wheelchair accessible.
Operates in all weather conditions, please dress appropriately
TripAdvisor rated Bobby’s Bike Hike its highest-level Traveler’s Choice Award each year since 2002.
Minimum numbers apply. There is a possibility of cancellation after confirmation if there are not enough guests to meet requirements. In the event of this occurring, you will be offered an alternative or full refund.

What To Expect

Christkindlemarket

Visit Chicago's open-air German Christmas market.

Palmer House Hilton Historic Lobby

Stroll down State Street where the lights, decorations and window displays dazzle. While inside the historic building, your guide shows you the magnificent interior architecture of this grand old hotel, where many famous guests have stayed since it opened in 1875.

Cloud Gate

Iconic Chicago attraction

Macy's on State Street

Enjoy the Holiday decor

The Chicago Theatre

We will stop in front of the Chicago Theatre to take pictures and explain the history of the building.

Millennium Park

We will give a tour of Millennium Park, with a focus on the City Christmas Tree and Ice Skating Rink.

Michigan Avenue Bridge

Walk down Chicago's Magnificent Mile Shopping and Light district

Daley Bicentennial Plaza

Enjoy Christkindlmarkt in Chicago

Jay Pritzker Pavilion

Gorgeous open air amphitheater

Show 6 more stops

Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Traveler Photos

Reviews (4)

Donnette_G

Dec 2024

This seasonal waking tour was great and informative very nice at Christmas time. I enjoyed the walk with Fran our tour guide. She was amazing and gave us a fun experience.

Q2337DWstevej

Dec 2024

Amazing stroll around the city! Fran was awesome and shared her knowledge about Chicago with us!! Took lots of photos and truly enjoyed the stroll! Highly recommend this Bobby’s Bike hike seasonal stroll. Steve and Penny

Marlis_B

Dec 2022

Josie was a great guide! She was so fun and full of interesting facts about Chicago. It was a cold and rainy night and even thought the weather wasn't great, the tour was so fun!! We appreciated her and her enthusiasm!