Discover many of Chicago’s best-known landmarks’and see the city dressed up in its festive best’on this holiday walking tour of the Windy City. Meet your guide in the afternoon, be sure to come bundled, and set off with a small group. In between admiring sights like Millennium Park, the Chicago Theater, and more, you’ll also visit the city’s Christkindlmarket, see Christmas window displays, and more.

This small-group tour makes for a personalized way to explore
Discover Chicago’s top tourist attractions as you go
Admire Christmas markets, window displays, ice rinks, and more
Soak up the city’s special festive atmosphere

What To Expect

Christkindlemarket

Visit Chicago’s open-air German Christmas market.
5 minutes • Admission Ticket Included

Chicago Christmas Tree

Visit Chicago’s City Christmas Tree in Millennium Park
5 minutes • Admission Ticket Free

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.
15 minutes • Admission Ticket Free

Cloud Gate

Iconic Chicago attraction
5 minutes • Admission Ticket Free

Macy’s on State Street

Enjoy the Holiday decor
10 minutes • Admission Ticket Free

The Chicago Theatre

We will stop in front of the Chicago Theatre to take pictures and explain the history of the building.
5 minutes • Admission Ticket Not Included

Millennium Park

We will give a tour of Millennium Park, with a focus on the City Christmas Tree and Ice Skating Rink.
30 minutes • Admission Ticket Free

Michigan Avenue Bridge

Walk down Chicago’s Magnificent Mile Shopping and Light district
15 minutes • Admission Ticket Free

Daley Bicentennial Plaza

Enjoy Christkindlmarkt in Chicago
20 minutes • Admission Ticket Free

Jay Pritzker Pavilion

Gorgeous open air amphitheater
5 minutes • Admission Ticket Free

Highlight

Confirmation will be received at time of booking
Service animals allowed
Near public transportation
Stroller accessible
Surfaces are wheelchair accessible
Most travelers can participate
Transportation is 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.
This tour/activity will have a maximum of 15 travelers

Include

Holiday attractions
Local tour guide

Exclude

$6 per person (or more) suggested guide gratuity. (via Cash, Venmo and PayPal)
Hotel pickup and drop-off
This is purely a walking tour, no food or drink offered on this tour