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Chicago Holiday Tour of Drinks, Daleys and Dead Guys

Stay mostly indoors and hear both forgotten and famous 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, this mostly indoors tour mostly walks through interior spaces to fully enjoy the spirit of the holidays in downtown Chicago. Tours are selling out so we advise you to book now! 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. The duration of the walking tour will be 2.5 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 often sell 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!

Some elements of this tour may not be appropriate for children (eg: drinks, dead guys). We recommend this tour for ages 16 and up.

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 hours


.5 Miles


$36, with optional drink package

  • Days & Times

  • Friday

    1:15pm & 5:00pm

    See highlighted dates in calendar below


    1:15pm & 5:00pm

    See highlighted dates in calendar below


    1:15pm & 5:00pm

    See highlighted dates in calendar below


  • Classic and cozy Miller’s Pub
  • Decked out decorations in a historic hotel
  • Whimsical window displays
  • The famous Walnut Room Christmas Tree
  • A secret view over bustling State Street
  • Festive Christkindlmarket at 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

  • 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 for two drinks and server gratuities. Drinks include a holiday cocktail and a glass of wine or beer.
  • Tour guide gratuity or giving program donation.

Tour Location

This walking tour begins inside Sugar Bliss Patisserie at 122 S Wabash Ave
We end inside Block 37, 108 N. State St. across from Christkindlmarket.

Book Now


Call: 312.350.1131
E-Mail: [email protected]