- Arlington and Roslyn Place District Arlington & Roslyn Various addresses · built various · designated November 15, 1989 Residential districts Lincoln Park
- Jackson Park Highlands District Various addresses · built various · designated October 25, 1989 Residential districts South Shore
- Metropolitan Missionary Baptist Church 2151 W. Washington Boulevard · built 1901 · Hugh M.G. Garden · designated February 16, 1989 Places of worship Near West Side
- Seven Houses on Lake Shore Drive District Various addresses · built various · designated June 28, 1989 Residential districts Near North Side
- Thalia Hall 1215-25 W. 18th Street · built 1892 · Faber & Pagels · designated October 25, 1989 Theaters and entertainment Lower West Side
- Tribune Tower 435 N. Michigan Avenue · built 1923-25 · Raymond M. Hood and John Mead Howells · designated February 1, 1989 Offices and commercial buildings Near North Side