- (Wirt) Dexter Building 630 S. Wabash Avenue · built 1887 · Adler & Sullivan · designated July 31, 1996 Offices and commercial buildings
- 860-880 Lake Shore Drive 860-880 N. Lake Shore Drive · built 1949-51 · Ludwig Mies van der Rohe · designated June 10, 1996 Apartment buildings Near North Side
- Carbide and Carbon Building 230 N. Michigan Avenue · built 1929 · Burnham Brothers, Inc. · designated May 9, 1996 Offices and commercial buildings Loop
- Chicago Building Chicago Savings Bank Building 7 W. Madison Street · built 1905 · Holabird & Roche · designated March 26, 1996 Offices and commercial buildings Loop
- DuPont-Whitehouse House 3558 S. Artesian Avenue · built 1876 · Oscar Cobb & Co. · designated April 16, 1996 Houses Mckinley Park
- Essanay Studios 1333-35 W. Argle Street · built 1908; additions through 1915 · Various Architects · designated March 26, 1996 Studios and workshops Uptown
- Fisher Studio Houses 1209 N. State Parkway · built 1936 · Andrew Rebori & Edgar Miller · designated July 31, 1996 Studios and workshops Near North Side
- Gage Group 18, 24, and 30 S. Michigan Avenue · built 1899-1900 · Louis H. Sullivan (18), Holabird & Roche (25 & 30) · designated September 11, 1996 Offices and commercial buildings Loop
- Haskell-Barker-Atwater Buildings 18-28 S. Wabash Avenue · built 1875-77 · Wheelock & Thomas and John M. Van Osdel · designated November 13, 1996 Offices and commercial buildings Loop
- Hawthorne Place District Various addresses · built various · designated March 26, 1996 Residential districts Lake View
- Hotel St. Benedict Flats 40-52 E. Chicago Avenue · built 1882-83 · James J. Egan · designated March 26, 1996 Apartment buildings Near North Side
- Humboldt Park Boathouse Pavilion 1301 N. Humboldt Boulevard · built 1907 · Richard E. Schmidt, Garden & Martin w/ Jens Jensen · designated November 13, 1996 Parks and landscapes West Town
- John Raber House 5760 S. Lafayette Avenue · built 1870 · Major Alterations, 1894; Thomas Wing · designated April 16, 1996 Houses Washington Park
- Kaufmann Store and Flats 2312-14 N. Lincoln Avenue (S Half:1883;North Half:1887) · built 1883 · Adler & Sullivan · designated April 16, 1996 Apartment buildings Lincoln Park
- London Guarantee Building Stone Container Building, London Guaranty & Accident Building, Crain Communications Building 360 N. Michigan Avenue · built 1922-23 · Alfred S. Alschuler · designated April 16, 1996 Offices and commercial buildings Loop
- Ludington Building 1104 S. Wabash Avenue · built 1891 · William Le Baron Jenney · designated June 10, 1996 Offices and commercial buildings Loop
- One North LaSalle Building 1 N. LaSalle Street · built 1929-30 · Karl M. Vitzthum & Co. with J.J. Burns · designated April 16, 1996 Offices and commercial buildings Loop Seeking missing report
- Peoples Gas-South Chicago Neighborhood Store 8935 S. Commercial Avenue · built 1925 · Hermann V. von Holst & George Grant Elmslie · designated April 16, 1996 Stores and markets South Chicago
- Printing House Row District Various addresses · built various · designated May 9, 1996 Commercial districts 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 Sites and commemorative markers Bridgeport
- Soldiers' Home 739 E. 35th Street · built 1864-1923 · William W. Boyington, 1866 section · designated April 16, 1996 Hospitals and health care Oakland
- Stephen Foster House and Stable 12147 S. Harvard Avenue · built 1900 · Frank Lloyd Wright · designated May 9, 1996 Houses West Pullman