Frank Lloyd Wright tour (Oak Park)
Architectural Foundation River tour (see the "corncobs")
Museum of Science and Industry
Robie House
Willis (Sears) Tower
Hancock Building (view from lounge at top)
"Movie Houses" ("Home Alone," "Planes, Trains, and Automobiles," etc.)
Cultural Center (old public library, with Tiffany glass dome)
Indoor pool at Intercontinental Hotel on Michigan
Blues Brothers sites
Lake Point Tower
Rookery Building
Seventeenth Church Of Christ, Scientist
Chicago Water Tower
Merchandise Mart
Old Post Office

Many more.