- Allerton Hotel 701 N. Michigan Avenue · built 1922-24 · Murgatroyd & Ogden with Fugard & Knapp · designated April 29, 1998 Near North Side
- Belle Shore Apartment Hotel 1062 W. Bryn Mawr Avenue · built 1928-29 · Nathaniel Koenigsberg & Leon Weisfeld · designated November 6, 2002 Edgewater
- Blackstone Hotel 636 S. Michigan Avenue · built 1910 · Marshall & Fox · designated April 29, 1998 Loop
- Bryn Mawr Apartment Hotel 5550 N. Kenmore Avenue · built 1927-28 · Alexander L. Levy & William J. Klein · designated November 6, 2002 Edgewater
- Essex Inn 800 S. Michigan Avenue · built 1961 · A. Epstein & Sons · designated March 29, 2017 Loop
- Palmer House Hotel 17 E. Monroe Street · built 1925-27 · Holabird & Roche · designated December 13, 2006 Loop
- Shoreland Hotel 5454 South Shore Drive · built 1925-1926 · Meyer Fridstein · designated September 8, 2010 Hyde Park
- Union Park Hotel Viceroy Hotel 1519 West Warren Boulevard · built 1930 · Benjamin Albert Comm · designated June 9, 2010 Near West Side
- Whistle Stop Inn 4200 W. Irving Park Road · built 1889 · designated December 5, 1990 Irving Park