Chicago Seasonal Stroll: Holiday Attractions Walking Tour
2 Ratings

Experience the enchantment of Chicago city center during the festive season with a 2-hour guided stroll through the Chicago Loop, Millennium Park, and the Magnificent Mile. Presented by a recognized global touring company based in Chicago, our knowledgeable guides will kindle your festive cheer with a trove of interesting trivia, general insights, and the finest of the city’s Christmas decorations. Fun fact: did you know the tale of Rudolph the red-nosed reindeer originated in Chicago? You’ll be treated to the spectacular Christmas-themed window exhibits at the iconic Marshall Field’s department store, the municipal Christmas tree of Chicago, the ice skating rink at Millennium Park, and the fabled Christkindlmarket, an authentic German Christmas Market. Please note, this tour is a walking tour only, no refreshments will be provided.

Duration: 2 hours
Cancellation: 1 day learn more
What's Included
  • Holiday attractions
  • Local tour guide
What's Not Included
  • $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
  • Christkindlemarket - Visit Chicago’s open-air German Christmas market.
  • Chicago Christmas Tree - Visit Chicago’s City Christmas Tree in Millennium Park
  • 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
Additional Information
  • 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.
North Dearborn Street
Departure Point: Petterino's Directions: You will meet your guide inside of Petterino's restaurant. Please feel free to arrive early to grab a bite or cocktail at the restaurant before your tour, or a cup of to-go coffee to take along with you.
Cancellation Policy

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

(2 Ratings)
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1 star
Dec 12, 2022
A cold, rainy walking tour of Chicago! - 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!
Review provided by Viator
Nov 8, 2021
Great time on the Seasonal Stroll walking tour - We really enjoyed this walking tour of the Chicago holiday attractions. The sites were beautiful and the guide was very entertaining. Easy pace for just about anyone. Would recommend.
Review provided by Tripadvisor