Photo: Ken Lund from Reno, Nevada, USA, CC BY-SA 2.0 Free landmarks in Chicago
Photo: Ken Lund from Reno, Nevada, USA, CC BY-SA 2.0 
Photo: ajay_suresh, CC BY 2.0 Chicago Cultural Center
Free, always
Photo: Hbodine, CC BY-SA 4.0 Navy Pier
Free outside, paid inside
Photo: H. Michael Miley from Schaumburg, USA, CC BY-SA 2.0 Buckingham Fountain
Free at certain times
Photo: Bernt Rostad, CC BY 2.0 Chicago Water Tower
Free, always
Photo: J. Crocker, Public domain Chicago Picasso
Free, always
Photo: John Picken, Public domain Flamingo
Free, always
Photo: Marlene Calderon, CC BY-SA 3.0 The Rookery
Free, alwaysMarquette Building
Free, always
Photo: Teemu08, CC BY-SA 3.0 Robie House
Free outside, paid inside
Photo: Sea Cow, CC BY-SA 4.0 Wrigley Field
Free outside, paid inside
Photo: Jeramey Jannene, CC BY 2.0 Union Station Great Hall
Free, always
Photo: Ken Lund from Reno, Nevada, USA, CC BY-SA 2.0 Tribune Tower
Free outside, paid inside
Photo: Diego Delso, CC BY-SA 3.0 Marina City
Free outside, paid inside
Photo: Joe Ravi (Shutterstock iStock Dreamstime), CC BY-SA 3.0 Chicago Board of Trade Building
Free outside, paid inside
Photo: Boven, CC0 Pullman National Historical Park
Free, always
Photo: daryl_mitchell from Saskatoon, Saskatchewan, Canada, CC BY-SA 2.0