Architecture of Mysterious Chicago Walking Tours

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


An architectural tour… but with more murders! 

From the art deco flash of the Board of Trade building to the beaux arts splendor of The Rookery, few cities boast such a broad range of stunning architecture as Chicago. But there’s more to the story than just the architects and ornamentation: there’s a hidden observation deck locked away in the Board of Trade, “White City Devil” HH Holmes was a known face in the Rookery, and an early airship crashed into the building that stood between them in 1919!
In the incredible Architecture of Mysterious Chicago tour, author and historian Adam Selzer combines an architectural tour – featuring a broad range of the city’s architectural history from post-fire Cast Iron buildings to modernist masterpieces- with an unbelievable historical tour, including tales of “Hell’s Half Acre,” the early gangland criminals who stalked State Street, strange murders, unsolved mysteries, and more. The 75-90 minute tour is endlessly fascinating, ridiculously informative, and totally entertaining. Featuring both famous city highlights and little nooks that even most locals never find, it’s a great way for visitors to discover the city, or for locals to explore further with stories you won’t hear on any other tour. You won’t just learn what to look for in architecture, you’ll hear which gangster jumped out of which building, which used to contain gambling dens, and which were once bombed by The Black Hand – all based on deep research, not just urban legends!
Selzer is the author of more than 20 published books, including Mysterious Chicago, HH Holmes: The True History of the White City Devil, Chronicles of Old Chicago, Speaking Ill of the Dead: Jerks from Chicago History, and Ghosts of Chicago. He’s also been a tour guide for more than a decade, running nearly 300 tours per year since 2005, including riverboat architecture tours, cemetery tours, ghost tours, gangster tours, and more. He appears regularly on the History, Travel and Discovery Channels, including such shows as Mysteries at the Museum (five episodes), American Ripper (four episodes), Monumental Mysteries, Hotel Secrets and Legends, Haunted History, and more. He is a field agent for Atlas Obscura, and runs both the Mysterious Chicago and Astonishing Chicago tour companies.
ARCHITECTURE OF MYSTERIOUS CHICAGO begins and ends in the historic Pickwick Place courtyard (22. E Jackson, near the corner of Jackson and State Street, in between the salad place and the bibambop bowl place). The total walk is roughly 1 mile. The starting location is convenient to LOTS of public transportation; Pickwick Place is within two blocks of the Jackson red or blue line stops, the Libary/Van Buren brown line, or the Adams/Wabash stop on the brown, pink, green, orange or purple lines). The #29 State bus stops at Jackson, as well.

See the sidebar for dates – 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?”