Chicago Holiday Tour of Drinks, Daleys and Dead Guys

Stay mostly indoors while hearing forgotten holiday tales

On this Chicago 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. We’ll venture into a few cozy locales and talk history over a couple drinks. Non-drinkers are more than welcome, too, as this is more than a bar tour.


We have some inside stories on our Chicago 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 Chicago tour 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!

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 also consider nostalgia for old Chicago with a view at the holiday- and not-so-holiday-lights on State Street. The holiday tour ends across the street from the Christkindlmarket, where you can choose to explore on your own and perhaps get a hot 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, 2018.

Please be aware that these locations have crowds during this holiday season, so we’ll have to navigate crowds and there may be waits 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.


Who wants to listen to a volunteer tour docent reading from notecards? 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, both downtown and in Chicago neighborhoods!

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 have been selling out of this very popular holiday tour. If the tour date and time you want is sold-out, please consider our other public tours, such as the Historic Chicago Walking Bar Tour or the 1893 World’s Fair Tour with Bars!

With groups of 9 or more, consider booking this holiday tour as a private group tour, great for families or corporate team building events for the holidays.


2.5-3 Hours


.5 Miles


$36 + drink money
  • Days & Times
  • Monday
  • Tuesday
  • Wednesday
  • Thursday
  • Friday
  • Saturday
    1:15pm & 5pm
  • Sunday


  • 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

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

Tour Includes

  • Expert tour guide commentary
  • Shared use of iPads with historic photos
  • Candy gift
  • Printed Pedway map

Reservation Does Not Include:

  • Drinks: Guests bring $25 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.

Tour Reviews

This was an AMAZING historical tour. Our tour guide Elizabeth was wonderful! She was so fun and knowledgeable. We learned so much that we didn’t know about this great city! We can’t wait to do another tour on our next visit.

Tour Meeting Spot

  • Tour starts inside Falafel Island/Rawabi Grill, at 24 E. Adams St.
  • Tour ends inside Block 37, 108 N. State St. (across from Daley Plaza, Christkindlmarket).
  • Bundle up! We’ll be outdoors for 5 to 10 minutes at a time, and spend the majority of the walking tour in warm, cozy places having drinks.
  • Due to limited availability and high demand, if you have not arrived by the tour start time, your spot may be given to a guest “flying standby.” Check-in begins 15 minutes before tour start time. Look for the guide with the name tag and clipboard.

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