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Private Group Holiday Tour of Drinks, Daleys and Dead Guys

Discover the ups and downs of Chicago's holiday heritage on this private mostly-indoor tour.

On this private group holiday tour, we’ll experience some classic Chicago holiday traditions and hear off-the-beaten path stories that you expect from Chicago Detours. Instead of whizzing by Christmas lights from a bus, we’ll visit mostly-heated indoor spaces by foot to fully enjoy the warm spirit of the holidays in downtown Chicago. We’ll venture into a couple cozy locales and talk history over a couple drinks. Non-drinkers are more than welcome, too.


We have some inside stories on our private group Chicago holiday lights tour! Hear about how Mayor Richard J. Daley saved the Christmas Parade, and then how his son, Richard M., was criticized for his affront to the holidays. Your private guide will share the story of Rudolph the Red-Nosed Reindeer’s birth in Chicago. We’ll even have an overview of the development of consumerism for Christmas. This historic walking tour is not your typical holiday lights tour of Chicago!

Your private group will also experience some Chicago classics on this holiday tour. We’ll go into the former Marshall Field’s Department Store, where Chicago holiday traditions have a rich and long history. You and your private group will have your choice of a beer from the local Revolution Brewery or a glass of wine. While enjoying those drinks, you’ll gaze at the giant holiday tree in the historic Walnut Room, discover forgotten stories and make new memories. We’ll also go to some secret corners of the building and experience the view of holiday lights on State Street. The holiday tour ends across the street from the Christkindlmarket, where your private group can then choose to explore on your own and perhaps get some brats or or German mulled wine!

(Please note: Christkindlmarket closes on 12/24, so if you book a tour between 12/26-12/30 then you’ll see the closed-up stalls that remain and learn a little about its history!) Route stops, timing and pricing subject to change for bookings made before November 15, 2019.

Please be aware that these locations have crowds during this holiday season, so we’ll have to navigate crowds. There may be waits to get our drinks. Because it is difficult to predict the traffic flows, the duration of the private walking tour will be between 2.5 and 3 hours.


Who wants to listen to a volunteer tour docent rambling a bunch of memorized dates and names? Not us! Our expert Chicago tour guides are highly trained, smart, fun and passionate about Chicago architecture and history.

In business since 2010, we are proud to be a top-rated Chicago tour company with five-stars on Yelp and TripAdvisor. Many of our Chicago architecture walking tours integrate historic bars, food, and music history. We hope you’ll join us to explore stories and places locals don’t even know!

While we can’t predict the weather, we can promise you won’t get too cold! We do walk outside for 5-10 minutes at a time, so please do bundle up.

We do sell out of this very popular holiday tour and dates for private group tours are limited. If the tour date and time you want is sold-out, please consider our other private tours, such as the Historic Chicago Walking Bar Tour or the 1893 World’s Fair Tour with Bars!


2.5-3 Hours


.5 Miles


  • 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
  • Christkindlmarkt in Daley Plaza

Stories & Ideas

  • Drink a “Tom and Jerry” cocktail at the historic Miller’s Pub
  • Understand the artistry of department store window displays
  • Sip a local beer or glass of wine while gazing at the Macy’s Holiday Tree
  • See the Muddy Waters mural and discover the Chicago blues connections to Xmas
  • Hear the story of the “Christmas Tree Tragedy”
  • Learn of the cute gimmicks of holiday seasons past and a history of consumerism

Tour Includes

Tour Location

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Call: 312.350.1131
E-Mail: [email protected]