Architecture of Mysterious Chicago Walking Tours

View from the hidden deck in the Tribune Tower, which Adam visited in Jan, 2017.

Chicago was the birthplace of the skyscraper – and some still consider it “the skyscraper capitol of the world!” Built right into the gorgeous architecture, one can find hints about the city’s history – the different ways we’ve envisioned city living at different times, the ways we’ve used new technologies, and the ways we’ve adapted to a changing world. But sometimes there’s no physical trace of the most unbelievable things that have happened in and around these buildings. Only the stories remain…

Adam of Mysterious Chicago has spent years running architecture tours, including hundreds of river tours. The Architecture of Mysterious Chicago covers works by some of history’s leading architects, such as Daniel Burnham, Louis Sullivan, Ludwig Mies Van der Rohe, William Le Baron Jenney, and more. But unlike other architecture tours, the Architecture of Mysterious Chicago tour also weaves in some of the great tales of unsolved mysteries, crimes, disasters, and more that took place in and around the buildings over the years. An incredible way to discover the city! Which of these buildings was Al Capone really in? How about HH Holmes?

Tours typically meet around the south end of Millennium Park, and cover about a mile to a mile and a half over 75-90 minutes. A great choice for school groups!

Want a tour at a date/time not listed? If you have at least 3 people, we can add one at a custom date and time (schedule permitting). Walking tour tickets are just 20/person – special rates available for groups! Email with dates and requests to make arrangements! For private groups over 25, additional guides may be used, particularly for school groups.


Even in his time before working as a river tour guide, Adam noticed that a lot of architectural tours included stories that didn’t happen to be true! A couple of the more common myths have been covered in Mysterious Chicago articles:

Was Al Capone in the Dome of the Jeweler’s Building? 

Why Did Old Man Insull Build an Opera House? 

Why Is Chicago “The Windy City?”