Chicago’s Seasonal Stroll Walking Tour

  • 2 Hours3:30pm Daily
  • Ages from 1+
  • Level: An easy stroll
  • Length: 1.25 mile
Ages Pricing
Adult (12+) $29.99
Youth (4-11) $25.99
Infant (0-3) $9.99

Holiday Stroll Through Chicago

Stroll your way through the holiday season on this walking tour of Chicago’s downtown festive holiday attractions! The guided 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’s Included

  • Informative walking tour of Chicago’s holiday festivities downtown.

What to Bring

  • Please bring an ID.
  • Please bring a bottle of water.
  • Wear comfortable clothing/shoes.

Important Info

  • Please arrive 15 minutes before scheduled tour time!
  • Tours run snow, rain, or shine!

Departure Locations

  • Petterino’s Restaurant, 150 N Dearborn St, Chicago, IL 60601
  • You will meet your guide inside the restaurant. We fully encourage you to arrive earlier than the suggested 15 minutes if you would like to grab a cocktail, or a quick bite or a hot cup of to-go coffee that you can enjoy on the tour, as they have excellent food and beverages.

Locations Visited Include:

  • Traditional German Christmas Market
  • Millennium Park Christmas Tree
  • Chicago Theatre
  • Michigan Avenue Lights and Shopping District
  • Marshall Fields Holiday Window Displays
  • Christkindlmarket

What to Expect

The adventure begins at the Chriskindlemarket, Chicago’s outdoor german holiday fair. Get their early, before the tour to explore on your own and feel free to buy something at the numerous shops. Then your guide will lead you down the Holiday-filled lights of State street in route to Millennium Park. At this stop you’ll catch a peek of some of our favorite (and most-heavily Instagrammed) works of public art such as Cloud Gate, the Pritzker Pavilion, and the Crown Fountain. You’ll learn about Chicago’s long history of Christmas tree distribution and see the annual city Christmas tree, donned with thousands of twinkling lights. Ample photo opportunities guaranteed! The ice skating rink is located right below the Chicago ‘Bean’.

After the excitement of Millennium Park, we’ll head back over to State Street for a glimpse of the Christmas window displays at the flagship Marshall Field’s department store (now a Macy’s). These narrative dioramas have been drawing crowds since their debut in the 1940s, and get more creative and elaborate every year. Then we’ll be on our way to the Chicago Theatre on our way to the Chicago Riverwalk. We’ll end the tour on the lit up Magnificent Mile, underneath the Wrigley building and it’s adorning Christmas tree.

The tour will conclude at Chicago’s legendary Magnificent Mile of Michigan Avenue, the epicenter of holiday shopping in the Midwest.

This tour is sure to get you in the Holiday spirit!



Extra Information

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 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.

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