- 333 North Michigan Building 333 N. Michigan Avenue · built 1928 · Holabird & Roche/Holabird & Root · designated February 7, 1997 Offices and commercial buildings Loop
- Brooks Building 223 W. Jackson Boulevard · built 1910 · Holabird & Roche · designated January 14, 1997 Offices and commercial buildings Loop
- Chicago Historical Society Building (Former) 632 N. Dearborn Street · built 1892 · Henry Ives Cobb · designated February 26, 1997 Museums and cultural institutions Near North Side
- Crown Hall S. R. Crown Hall 3360 S. State Street · built 1950-56 · Ludwig Mies van der Rohe · designated October 1, 1997 Schools and education Douglas
- Lake-Franklin Group 227-35 W. Lake Street & 173-91 N. Franklin Street · built 1872-75 · Burling & Adler, Geo. Edbrooke. 1896 Addn:Adler · designated February 26, 1997 Offices and commercial buildings Loop
- Leiter II Building 403 S. State Street · built 1891 · William Le Baron Jenney · designated January 14, 1997 Offices and commercial buildings Loop
- McGraw-Hill Building 520 N. Michigan Avenue · built 1928-29 · Thielbar & Fugard · designated February 7, 1997 Offices and commercial buildings Near North Side
- Tree Studios, Annexes and Courtyard 601-23 N. State Street / 4-10 E. Ohio Street / 3-7 E. Ontario Street · built 1894 · Parfitt Brothers, with Bauer & Hill · designated February 26, 1997 Studios and workshops Near North Side
- Washington Block 40 N. Wells Street · built 1873-74 · Frederick & Edward Baumann · designated January 14, 1997 Offices and commercial buildings Loop