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On this special holiday tour, we’ll see 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 walk (in mostly heated indoor spaces) to fully enjoy the spirit of the holidays in downtown Chicago. While we can’t predict the weather, we can promise you won’t get too cold! We’ll venture into a few cozy locales and talk history over couple drinks. Non-drinkers are more than welcome, too, as this is more than a drinking tour.

We have some inside stories on our holiday lights tour! Hear about how Mayor Richard J. Daley saved the Christmas Parade, and then how his son, Richard M., was almost awarded a stocking of coal for his affront to the holidays. Your 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 walking tour is not your typical holiday lights tour of Chicago!

The holiday tour has some classic experiences, too. We’ll go into the former Marshall Field’s Department Store, where Chicago holiday traditions have a rich and long history. You’ll 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 and discover forgotten stories and make new memories. We'll even gaze from a cozy place at the holiday and not holiday lights on State Street, and consider the nostalgia of old Chicago. We end across the street from the Christkindlmarket, where you can choose to explore on your own and perhaps get a steaming serving of German mulled wine!

Holiday Tour Highlights

  • Sip on local brew while gazing at the Macy’s Holiday Tree
  • Understand the artistry of department store window displays
  • See the new Muddy Waters mural and discover 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
  • Drink a “Tom and Jerry” cocktail at the historic Miller’s Pub


Holiday Tour Sights
Historic Miller’s Pub
Palmer House Hotel
State Street and its Holiday Lights
Macy’s Department Store
The Chicago Christmas Tree in Millennium Park
Chicago Theatre and its Famous Marquee
Christkindlmarkt in Daley Plaza

Please be aware that these locations have crowds during this holiday season. We will have to navigate crowds and there may be a wait to get our drinks. Because it is difficult to predict the traffic flows, the duration of the walking tour will be between 2.5 and 3 hours.

Bundle up!
We’ll be inside half the time, and the other half we’ll be in warm, cozy places having drinks.


Ticket Price
Ticket price includes tour guide commentary, candy gift, and printed Pedway map. 

Guests bring $24 cash to cover two drinks and server gratuities: 1. a holiday cocktail 2. A glass of wine or local beer. Non-drinkers don't need to bring cash. 

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USD 36.00
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