Join our fun "Christmas Tree Crawl" and let company owner, Hillary, show you some of the city's best holiday decorations!

Christmas waves a magic wand over the world, and behold, everything is softer and more beautiful.
— Norman Vincent Peale

About This Tour Route...

Let Inside Chicago Walking Tours take you on an enchanting stroll through the heart of the city at its prettiest time — during the winter holiday season.

On this engaging tour, company owner and celebrated Chicago tour guide Hillary will lead you on a sort of "Christmas treasure hunt" through downtown Chicago in search of the most stunning and impressive Christmas trees and other holiday decorations — and she knows where they are!  She calls this tour a "pop-up tour" because she's decided to add it to the schedule for a very limited time, and purely because she wants to show off the city's beauty at this time of year — it's like a private tour offered at a public tour price!  

Come enjoy the beautiful seasonal decorations and lively atmosphere while learning about beloved Christmas traditions.  We'll pop into several buildings to see Christmas trees indoors, where we can warm up for seeing the impressive outdoor trees.  You won't find a boat, a bus, or even a segway where we're going.  Come and take a holiday stroll with us — it's a fun stress-buster and perfect time to set aside for hanging out with family and friends!


On this LIMITED-TIME SEASONAL tour, you will:

  • See some beautiful buildings' interiors, as we do on all of our regular tours;

  • Find and photograph some of the most beautiful Christmas trees a big city like Chicago can offer;

  • Get a fun, up-close experience of the most famous and authentic Christkindlmarkt in the USA;

  • Participate in an "Old World" holiday tradition shared by your Polish-American tour guide;

  • Much, much more!



  • Saturdays from November 16th through December 23rd

  • 2pm - 4pm (starts near the Wrigley Building — exact starting location given with ticket purchase)

  • Tours cover approximately 1.5 miles on foot, and last 2 hours.

  • Ticket prices (NOTE: Discounts like Groupon, Living Social, etc., do NOT apply to this seasonal route):

    • $30 General Admission (ages 11 to 65);

    • $25 Children (ages 6-11) & Seniors (over 65);

    • Free for kids 5 and under!

  • Tours do NOT run in case of rain — we will contact you the morning of the tour if we decide to cancel, and refund your tickets.

  • This tour is also bookable as a PRIVATE tour a fun way to get out and about with family & friends in town for the holidays! Contact Hillary here to inquire about dates and rates!