A Holiday Tour of Drinks, Daleys and Dead Guys


36 USD

On this special holiday walking tour, we'll see some classic holiday sights, and get the off-the-beaten path stories of Christmas' past over a couple drinks.

Duration: 3 hours
    Available in
  • English


  • Sip on local brew while gazing at the Macy’s Holiday Tree
  • Understand the artistry of department store window displays
  • Interact with the new Wabash Lights public art installation
  • Hear the story of the “Christmas Tree Tragedy”
  • Learn of the gimmicks of holiday seasons past
  • Drink a “Tom and Jerry” cocktail at the historic Miller’s Pub


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 downtown Chicago to fully enjoy the spirit of the holidays. While we can’t predict the weather, you won’t get too cold! We’ll venture into a few warm 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 Christmas and Hanukkah. Hear 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 will run beginning November 16 at 1:15pm on Fridays and Saturdays, 5pm on Saturdays and other special dates.

What’s included & not included

  • Expert tour guide commentary
  • Shared iPads with historic photos
  • Candy gift
  • Printed Pedway map
  • Drinks: Guests bring $24 cash to cover two drinks and server gratuities. Drinks include a holiday cocktail and a glass of wine or local beer. Tour guide gratuity or giving program donation.

Meeting point

Tour starts at Falafel Islands/Rawabi Grill at 24 E. Adams St. and ends at Block 37 108 N. State St. (across Daley Plaza, Christkindlmarket).

From 36 USD per person

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Tour operated by: Chicago Detours