- Getty Tomb Graceland Cemetery, 4011 N Clark St · built 1890 · Louis H. Sullivan · designated March 10, 1971 Uptown Seeking missing report
- Illinois-Indiana State Line Boundary Marker Avenue G, near 103rd St · built 1838 · Office of the United States Surveyor-General · designated September 4, 2002 East Side
- Little Village Arch 3100 W. 26th Street · built 1990 · Adrián Lozano · designated January 26, 2022 South Lawndale
- Paseo Boricua Gateway Flags 2400-West Division Street & 2800 West Division Street · built 1995 · James R. DeStefano, FAIA, RIBA (Principal in Charge); John Adams Dix, AIA (Management Principal); John Edward Windhorst (Project Architect); Rodriguez Associates: Osvaldo “Ozzie” Rodriguez; McClier Company · designated September 21, 2022 West Town
- Rainbow Pylons and the Legacy Walk 3243-3711 North Halsted Street( Odd and Even), · built 1997 · DeStefano+Partners · designated July 24, 2019 Lake View
- Site of Fort Dearborn at the intersection of Michigan Av & Wacker Dr · built 1803-37 · designated September 15, 1971 Loop
- Site of Haymarket Tragedy Desplaines St (650W), betw Randolph & Lake · built 1886 · designated March 25, 1992 Near West Side
- Site of the 1st...Nuclear Chain Reaction East Side of S Ellis Ave between 56th & 57th St · built 1942 · Sculpture "Nuclear Energy" by Henry Moore, 1967 · designated October 27, 1971 Hyde Park
- Site of the John & Mary Jones House SW Corner of W 9th St & Plymouth Ct · designated May 26, 2004 Loop
- Site of the Origin of Illinois & Michigan Canal S Fork of Chicago River at W Levee & W Fuller Sts · built 1838-48 · designated May 9, 1996 Bridgeport
- Site of the Origin of the Chicago Fire of 1871 Dekoven (1050s) & Jefferson (600w) St · built 1871 · Commemorative sculpture "Pillar of Fire" by Egon Weiner, 1961 · designated September 15, 1971 Near West Side
- Site of the Sauganash Hotel/Wigwam SE corner of Lake St & Wacker Dr · built 1831, 1860 · designated November 6, 2002 Loop
- Union Stock Yard Gate Exchange Av (4150S) at Peoria St (900W) · built 1875 · Burnham and Root · designated February 24, 1972 New City