A Holiday Tour of Drinks, Daleys and Dead Guys

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Arts & DIY

Event Overview

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 also consider nostalgia or old Chicago with a view at the holiday- and not-so-holiday-lights on State Street. The holiday tours ends 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!

We do walk outside for 5-10 minutes at a time, so please – bundle up!

The holiday tour will run at various times on selected dates from November through December. Please check availability for schedule.

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 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 Meeting Spot:

  • Tour starts inside Sugar Bliss Patisserie at 122 S Wabash Ave.

  • Tour ends inside Block 37, 108 N. State St. (across from Daley Plaza, Christkindlmarket).

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

Sights and Stories:

  • 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

What to Bring

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.

Minimum age

All ages welcome

What's Provided

Chicago Holiday Tour Includes:-Expert tour guide commentary-Shared use of iPads with historic photos-Candy gift-Printed Pedway map

Cancellation Policy

There are currently no upcoming dates scheduled for this Dabble. Log in to an account message the host or add to your bucket list to be automatically notified when new dates are posted.


Our Philosophy
We believe that the primary role of a tour guide is to educate, so we create an interactive group dynamic and share educational tools and new perspectives for you to connect with the architecture of Chicago.

We are committed to responsible travel, so our tour company uses green practices and immerse you in a truly local experience.

We know that history is best told with a creative approach, so we use different media, like historic quotes, old photographs, and documentary film clips, to stimulate your imagination and present various perspectives.

We believe that a city like Chicago is more than “highlights,” so we share forgotten stories about both famous city landmarks and lesser-known attractions.

We understand that business is about building community, so our tour company likes to connect with tour operators, conventions, destination management companies, non-profits, community groups, senior groups, universities, cultural organizations, and Chicago businesses.

We treat all our tour guests like a new friend, because we believe in the importance of hospitality, and we love when tour guests have chosen to tour Chicago with a small business.


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    Michele M.
    Reviewed on 12/17/18

    What a fun tour! I liked learning the history of things that have been hiding in plain sight for me, a lifelong Chicago girl. Amanda was friendly and personable and knowledgeable.

    What a fun tour! I liked learning the history of things that have been hiding in plain sight for me, a lifelong Chicago girl. Amanda was friendly and personable and knowledgeable.

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