Architecture of Mysterious Chicago - Atlas Obscura

Chicago, Illinois

Architecture of Mysterious Chicago

Author Adam Selzer highlights the histories and unsolved mysteries of the city's landmarks.

From the Art Deco flash of the Board of Trade building to the Beaux Arts splendor of The Rookery, the broad range of stunning architecture across Chicago is second to none. But there’s much more to the story than just the architects and ornamentation of these downtown skyline staples. 

Join Atlas Obscura for an insightful evening of architecture and alternative history with author and historian Adam Selzer as he shares the stories behind some of Chicago's most notable buildings. This architecture tour shares the tales of the city’s post-fire Cast Iron buildings and modernist masterpieces: the early gangland criminals who stalked State Street, strange murders, unsolved mysteries, and more. You'll hear about the hidden observation deck locked away in the Board of Trade, the stories of “White City Devil” H.H. Holmes as a known face in the Rookery, and an early airship that crashed into a building in 1919.
The tour is endlessly fascinating, ridiculously informative, and totally entertaining. 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.

Adam Selzer is the author of Mysterious ChicagoH.H. Holmes: The True History of the White City Devil, and several other books. In addition to writing, he hosts the Cemetery Mixtape podcast and has been a tour guide in Chicago and New York for more than a decade.


  • The tour begins and ends in the historic Pickwick Place courtyard, on Jackson Boulevard between State Street and Wabash Avenue, across from the Barnes and Noble.
  • This tour runs rain or shine.
  • ADA Access limited by the quality of Chicago’s sidewalks.
  • The starting location is convenient to public transportation; Pickwick Place is within two blocks of the Jackson Red or Blue line stops, the Library/Van Buren Brown Line, or the Adams/Wabash stop on the Brown, Pink, Green, Orange, or Purple lines). The #29 State bus also stops at Jackson Boulevard nearby.
  • Plenty of parking lots are nearby, but street parking and free parking are very hard to find in the Loop. 


Stay connected! Subscribe to the Atlas Obscura Society Chicago newsletter and join our Facebook Group for a first glimpse at upcoming events.

Advance ticket sales only. All ticket sales are final. No refunds or exchanges.