- Alfred Caldwell Lily Pool North end of Lincoln Park Zoo at Fullerton Parkway · built 1936-38 · Landscape Architect: Alfred Caldwell · designated November 6, 2002 Parks and landscapes Lincoln Park
- Belle Shore Apartment Hotel 1062 W. Bryn Mawr Avenue · built 1928-29 · Nathaniel Koenigsberg & Leon Weisfeld · designated November 6, 2002 Hotels Edgewater
- Bryn Mawr Apartment Hotel 5550 N. Kenmore Avenue · built 1927-28 · Alexander L. Levy & William J. Klein · designated November 6, 2002 Hotels Edgewater
- Congress Theater 2117-39 N. Milwaukee Avenue / 2117-39 N. Rockwell Street · built 1925-26 · Fridstein & Co. · designated July 10, 2002 Theaters and entertainment Logan Square
- Daley Center 50 West Washington Street · built 1965 · C.F. Murphy Associates, Sculptor:Pablo Picasso · designated November 6, 2002 Offices and commercial buildings Loop
- Historic Michigan Boulevard District Various addresses · built various · designated February 27, 2002 Commercial districts Loop
- Illinois-Indiana State Line Boundary Marker Avenue G, near 103rd St · built 1838 · Office of the United States Surveyor-General · designated September 4, 2002 Sites and commemorative markers East Side
- Pittsfield Building 55 E. Washington Street · built 1927 · Graham, Anderson, Probst & White · designated November 6, 2002 Offices and commercial buildings Loop
- Sears, Roebuck and Company Administration Building 3333 W. Arthington Street · built 1905-14 · Nimmons & Fellows and George C. Nimmons & Co. · designated September 4, 2002 Offices and commercial buildings North Lawndale
- Site of the Sauganash Hotel/Wigwam SE corner of Lake St & Wacker Dr · built 1831, 1860 · designated November 6, 2002 Sites and commemorative markers Loop
- Ukrainian Village District Various addresses · built various · designated December 4, 2002 Residential districts
- Union Station 210 S. Canal Street · built 1913-25 · Graham, Anderson, Probst & White · designated May 1, 2002 Railroad and transit stations Near West Side
- Washington Square District Extension Various addresses · built various · designated July 10, 2002 Residential districts Near North Side