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

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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 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.

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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 Sugar Bliss Patisserie and ends at Block 37 108 N. State St. (across Daley Plaza, Christkindlmarket). (Sugar Bliss Patisserie, 122 S. Wabash, Chicago, IL 60603)

This operator has 10 reviews for other tours


Wonderful tour!
We had a wonderful time on our walking tour. It was enlightening and entertaining and we would gladly do it again. Thanks!
Loop Interior Tour...FANTASTIC!
Having never been on any type of tour in Chicago before, we weren't sure what to expect. Wow! We were we blown away by all of the fascinating things we discovered while on our Interior Loop tour yesterday. Elizabeth was a FANTASTIC guide! Chicago architecture and history rolled up into a fun/informative walk. Loved it! Can't wait to try some of the other tours that they offer!

Best Architecure Tour, absolutely the best
I went on a architecture tour with this group I consider myself an architecture enthusiast and I still learned so much. The tour was very professional and had aspects to suit anyone. The company had spent years going through archives and books to find information that even google cannot find for you. Plus we got to go into a church inside a 22 story skyscraper, the Chase bank headquarters, and even the Chicago pedway. The pedway is pretty much a series of tunnels under the city that goes for over 5 miles, plus the tunnel goes under buildings and is one of the coolest parts of the tour. The tour guide who's name is Alex Bean was funny and enthusiastic. I will never forget the eternal flame that was surrounded by pigeons who where using it to warm up. Mr Bean also told us that once a pigeon on fire flew over him when he was teaching a tour. All in all I highly reccomend this tour that helps you appreciate Chicago more than the average tourist.

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36 USD
  • Full refund if you cancel up to 72 hours before the tour
  • No booking fees
  • Pay by credit card or PayPal

Tour operated by: Chicago Detours