Chicago - Definitely spend several days at the Museum of Science & Industry, The Field Museum, Adler Planetarium, and Shedd Aquarium, but don't miss...
These phenomenal works of Frank Lloyd Wright:
The Frank Lloyd Wright Home and Studio
The Robie House
Lobby Renovations of the Rookery Building
The Emil Bach House
These phenomenal works of Louis Sullivan:
The Sullivan Center
The Auditorium Theater (Designed with Dankmar Adler)
The James Charnley House (Designed with contributions from Frank Lloyd Wright)
Chicago - For an outstanding introduction to the rich architectural history of Chicago, take a walking or river cruise tour sponsored by the Chicago Architecture Center. (The CAC also schedules in-depth tours of specific buildings and neighborhoods.)
Chicago - Now a part of the Art Institute of Chicago, The Roger Brown Study Collection is the preserved 1880's storefront home of one the leaders of the Chicago Imagists art movement of the 1960's.
Filled with Brown's own artwork as well as his kaleidoscopic collection of all things amazing. BONUS LINK: a c. 1995 video of Roger Brown leading a tour of his collection, c. 1995.
Chicago - Graceland Cemetery. (Here's the official website.)
Chicago - Of course you'll go to the Art Institute of Chicago. Just don't miss far too little-known genius Ivan Albright's That Which I Should Have Done I Did Not Do (The Door).
Chicago - And ya gotta go here: Intuit: The Center for Intuitive and Outsider Art.
Elmhurst (suburban Chicago) - Relatively unknown, The McCormick House is one of Mies van der Rohe's
three built house designs in the U.S. (Now open to the public as part of the Elmhurst Museum of Art.)
Wilmette (suburban Chicago) - The Baha'i House of Worship
Plano (far suburban Chicago) - The Farnsworth House - by the god of steel and glass architecture, Ludwig Mies van der Rohe.
In my narrow opinion, one of the top 5 works of American architecture.
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