By Jeremy Lindenfeld

The well-regarded Chicago Detours tour company offers a wide variety of options when it comes to experiencing Chicago. Whether you are interested in learning more about the city’s interior architecture or its rich music scene, Chicago Detours has programs dedicated to that niche curiosity. To get into the holiday/winter spirit, I recently took their Chicago Holiday Tour of Drinks, Daleys and Dead Guys.

Guide

The first and perhaps most important impression I got of the tour experience was meeting my guide. She was immediately very welcoming and enthusiastic about the tour even though she had led it, no doubt, many times before. She was also very vigilant about keeping everyone together in certain locations to make the experience as smooth and efficient as possible. She did a very good job of keeping everybody on the tour consistently engaged with wherever we were and whatever we were learning.

Locations

The locations we visited on the tour were quite interesting. Spots like Miller’s Pub were fun to hang out in for a bit and grab a drink, while iconic buildings like the Palmer House Hotel showcased the true holiday spirit of the city. It was exciting to learn intimate details about these places, like how the Gallios brothers, who bought Miller’s Pub in 1950, did not have enough money to change the restaurant’s sign so they just kept the name. As promised by the name of the tour, we also got to visit some spooky sites. Perhaps the scariest of which was Macy’s, which acted as a morgue during the 1903 Iroquois Theater fire. Some employees and visitors still claim to feel the presence of those who perished there over a hundred years ago.

No matter where or what we were doing, the guide was always teaching us some obscure piece of Chicago holiday trivia, like how the city distributes the Ebenezer Award every year to acknowledge “the most absurd affronts to the Christmas and Hanukah season.”

Unfortunately, steady rain prevented us from doing any outdoor activities like the Christkindlmarket, but I’m sure if given the opportunity, that would have been enjoyable as well. With a lot of amazing things to see in Chicago during the holiday season, this tour moves around quite a bit — and at a steady pace — so if you’re looking for a more relaxing excursion, it may be wise to look at the company’s other options.

Facts

Another exciting aspect of the tour was the constant learning. No matter where or what we were doing, the guide was always teaching us some obscure piece of Chicago holiday trivia, like how the city distributes the Ebenezer Award every year to acknowledge “the most absurd affronts to the Christmas and Hanukah season.” One such unlucky winner of this prize was none other than former Chicago Mayor Richard Daley when, in 2004, he removed The Nativity Story film from the Christmas festival. All this fun info and anecdotes make the tour feel well-researched and more interesting.

X-factor

Some of the cooler aspects of this tour were also some of the most unique. iPads being used for images and videos made the experience seem modern and easily accessible, while being able to order drinks at many spots along the tour made the journey even more casual and enjoyable.

Final thoughts

All in all, the tour was a fun and educational time that I wish I could have experienced on a day with better weather. I’m looking forward to scanning the rest of the options Chicago Detours offers for my next adventure.

More info

Visit ChicagoDetours.com for tour information and reservations.