Photo: TheWxResearcher, CC0 Free walks & trails in Chicago
Photo: TheWxResearcher, CC0 
Photo: ajay_suresh, CC BY 2.0 Chicago Riverwalk
Free, always
Photo: Victor Grigas, CC BY-SA 4.0 The 606
Free, always
Photo: Andrew Jameson, CC BY-SA 3.0 Pilsen murals
Free, always
Photo: David Hilowitz from San Antonio, USA, CC BY 2.0 Wicker Park murals
Free, always
Photo: Chicago Department of Transportation., Public domain Fulton Market
Free, always
Photo: Loganresident at en.wikipedia, CC BY 2.5