Private Group Downtown Chicago Holiday Walking Detour

From USD $60.00
  • Duration: 120 Minutes (approx.)
  • Location: Chicago, IL
  • Product code: PG-HOLIDAYTOUR

On this private holiday tour for 2-15 guests, your guests will experience classic Chicago holiday traditions and hear their forgotten histories. You won't get too cold on this walking tour as we’ll venture into a few warm locales and stay inside more than half the time. 

Chicago Detours award-winning tour guides will lead this experience with their expertise and engaging stories. You'll see the top holiday highlights, and hear some inside stories on this holiday lights tour! Hear of Rudolph the Red Nosed Reindeer’s birth in Chicago, or about how Mayor Richard J. Daley saved the Christmas Parade. We’ll even have an overview of the development of consumerism for Christmas. This walking tour is not your typical holiday lights tour of Chicago!

Holiday Tour Highlights

  • Drink a “Tom and Jerry” holiday cocktail at the historic Miller’s Pub
  • Understand the artistry of department store window displays
  • See the Great Tree of the historic Walnut Room at Macy's
  • Hear the story of the “Christmas Tree Tragedy”
  • Discover the Chicago roots of little white holiday lights
  • Conclude at the Christkindlmarket in Daley Plaza

Holiday Tour Sites

  • Historic Miller’s Pub
  • Palmer House Hotel
  • Holiday lights on State Street
  • Macy’s Department Store
  • The Chicago Christmas Tree in Millennium Park
  • Chicago Theatre and its Famous Marquee
  • The Chicago Pedway System

Private Tour Rate and Details

$60 covers tour design, professional tour guide commentary, printed Pedway map gift, postcard souvenir and exclusivity to just your guests.  

$14 per person includes a Tom and Jerry cocktail - we can invoice and charge you in advance, or you can just cover the bill for your group at the tour. No substitutions other than water. 

Must show proof of vaccination to participate. Masks must be worn indoors at all times, unless drinking. Masks are optional outside. 

Small Groups (8 or less): The minimum charge is based on 9 guests. If you have fewer guests and want a private tour, then just select quantity of 9 when booking. If you have 8 or less guests and are open to joining others, then consider a public tour

Optional Swag

Badass Women Journal or Chicago Detours Skyline Tote Bag are optional gifts that you can select to purchase at check-out. 


Tour starts inside Sugar Bliss Cakes, 122 S. Wabash. 

Ends inside Block 37, just across from the Christkindlmarket.

Tour Dates

Please view available dates in the calendar for most Mondays-Thursdays 4pm-6pm for corporate groups, and Saturdays at 2:15pm. Dates are selling out. 

Call us for other times. 

Cancellation Policy

100% refundable up to 7 days before. 

Individual guest cancellations are 100% refundable up to 48 hours before. 

Are You Curious?

Chicago Detours has been bringing curious people to tour Chicago architecture, history and culture since 2010. Learn more here

Call us at 312.350.1131.