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Chicago’s Seasonal Stroll Walking Tour

Holiday Stroll Through Chicago

Stroll your way through the holiday season on this walking tour of Chicago’s downtown festive attractions! This holiday stroll begins at the end of November and runs through Christmas Eve. Bobby’s Seasonal Stroll is a great way to experience all that Chicago has to offer during the winter holidays in a single afternoon guided walking tour! See the holiday lights of the Magnificent Mile, the Millennium Park ice skating rink and Christmas tree, enjoy Christkindlmarket, Chicago theatre and more! This two-hour Chicago holiday stroll is perfect for families, friends, holiday parties, and anyone looking to celebrate the season in an exciting new way.

What To Expect

Cloud Gate, known affectionately as “The Bean” debuted in Millennium Park in 2006. Designed by famed Indian artist, Anish Kapoor, this giant, stainless steel masterpiece has become one of the most famous symbols of Chicago arts and culture.

The Chicago municipal Christmas tree has been a Windy City tradition since 1913. The tree is locally grown and decorated with thousands of lights, lit for the first time in an annual lighting ceremony.

The Marshall Field’s Christmas Windows have been cheering up the sidewalks of State Street since the 1940s. These playful, holiday-themed displays draw crowds from all over the midwest with their elaborate theming and animatronics.

The Loop is Chicago’s bustling business district, named for its location within the rectangular convergence of multiple “El” train tracks.

The Magnificent Mile lights are a twinkling sensation in the downtown shopping district. The illumination kicks off with an annual festival and parade, with thousands of lights lining Michigan Avenue and beyond.

The Chicago Theatre was added to the National Register of Historic Places June 6, 1979, and was listed as a Chicago Landmark January 28, 1983. The distinctive Chicago Theatre marquee, “an unofficial emblem of the city”, appears frequently in film, television, artwork, and photography.

  • Traditional German Christmas Market
  • Millennium Park Christmas Tree
  • Chicago Theatre
  • Michigan Avenue Lights and Shopping District
  • Marshall Fields Holiday Window Displays
  • Christkindlemarket
Petterino’s Restaurant, 150 N Dearborn St, Chicago, IL 60601
Arrive early before the tour to enjoy a late lunch or cocktail at the bar, or get some hot coffee to go. (not included in tour price)

410 N. Michigan Avenue,
Chicago, IL 60611

wrigley building of chicago on guided walking tour
chicago holiday market stalls
marshall field and company in chicagochicago sign

What Our Customers Are Saying“We did the Seasonal Stroll walking tour and our guide was extremely knowledgeable and friendly. We learned a lot about the history of Chicago and some fun holiday-specific history. It was a great way to enjoy the holidays. And very affordable!”

– Sarah P.  Atlanta, Georgia

Chicago’s Seasonal Stroll – Walking Tour

Duration: 2 hours
Length: 1.25 mile
Level: An easy stroll
Schedule: 3:30pm Daily
Age: 1+

(Discounted Online Rates Shown)

Price: Fri-Sun Mon-Thurs
Adults $29.99 $29.99
Youth (Ages: 4-11) $25.99 $25.99
Infants (Ages: 0-3) $9.99 $9.99

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Private Tour
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