- (Wirt) Dexter Building 630 S. Wabash Avenue · built 1887 · Adler & Sullivan · designated July 31, 1996
- 30 North LaSalle 30 N. LaSalle Street · built 1972-1974 · Thomas E. Stanley II · designated May 20, 2026 Loop
- 300 West Adams Street Office Building 300 W. Adams Street · built 1927 · Jens J. Jensen · designated May 13, 2009 Loop
- 333 North Michigan Building 333 N. Michigan Avenue · built 1928 · Holabird & Roche/Holabird & Root · designated February 7, 1997 Loop
- 35 East Wacker Building Jewelers Building, Pure Oil Building, North American Life Insurance Building 35 E. Wacker Drive · built 1925-27 · Joachim G. Giaver & Frederick P. Dinkelberg, architects; Frederick J. Thielbar & John Reed Fugard, supervising architects · designated February 9, 1994 Loop
- American Book Company Building 320 E. Cermak Road & 2132 S. Calumet Avenue · built 1912 · Nelson Max Dunning · designated July 29, 2009 Near South Side
- Bankers Building 105 W. Adams Street · built 1927 · Burnham Brothers, Inc. · designated November 18, 2025 Loop
- Brooks Building 223 W. Jackson Boulevard · built 1910 · Holabird & Roche · designated January 14, 1997 Loop
- Bush Temple of Music 100 W. Chicago Avenue · built 1901 · J.E.O. Pridmore · designated June 27, 2001 Near North Side
- Carbide and Carbon Building 230 N. Michigan Avenue · built 1929 · Burnham Brothers, Inc. · designated May 9, 1996 Loop
- Carson Pirie Scott & Company Building 1 S. State Street · built 1898-99 · Louis H. Sullivan, 1905-6:D.H. Burnham & Co. · designated November 5, 1970 Loop
- Century Building Twentieth Century Building, Buck & Rayner Building, Home Federal Building 202 South State Street · built 1915-16 · Holabird & Roche, William Sevic · designated April 19, 2025 Loop
- Champlain Building designated October 1, 1992
- Chapin and Gore Building 63 E. Adams · built 1904 · Richard E. Schmidt and Hugh M.G. Garden · designated January 21, 1982 Loop Seeking missing report
- Chicago and North Western Railway Office Building 226 W. Jackson Boulevard · built 1905 · Frost and Granger · designated May 20, 2020 Loop
- Chicago Board of Trade Building 141 W. Jackson Boulevard · built 1930 · Holabird & Root · designated May 4, 1977 Loop
- Chicago Building Chicago Savings Bank Building 7 W. Madison Street · built 1905 · Holabird & Roche · designated March 26, 1996 Loop
- Chicago Daily News Building 2 N. Riverside Plaza / 400 W. Madison Street · built 1928-29 · Holabird & Root · designated July 15, 2026
- Chicago Motor Club Building 68 E. Wacker Place · built 1928 · Holabird & Root · designated May 9, 2012 Loop
- Consumers Building State and Quincy Building 220 South State Street · built 1911-13 · Mundie & Jensen · designated April 19, 2025 Loop
- Continental Center 55 East Jackson Boulevard · built 1961-62 · C.F. Murphy Associates · designated June 27, 2012 Loop
- Daley Center 50 West Washington Street · built 1965 · C.F. Murphy Associates, Sculptor:Pablo Picasso · designated November 6, 2002 Loop
- Delaware Building 36 W. Randolph Street · built 1872-74 · Wheelock & Thomas, 2 story add + atrium 1889 Huber · designated November 23, 1983 Loop
- Farwell Building 664 N. Michigan Avenue · built 1927 · Philip B. Maher · designated March 10, 2004 Near North Side
- Field Building 135 S. LaSalle Street · built 1924-34 · Graham, Anderson, Probst & White · designated February 9, 1994 Loop
- Fine Arts Building 410 S. Michigan Avenue · built 1885 · Solon S. Beman, 1898 addn & remodel · designated June 7, 1978 Loop
- Fisher Building 343 S. Dearborn Street · built 1896 · D.H. Burnham & Co. 1907:side add. Peter Weber · designated June 7, 1978 Loop
- Gage Group 18, 24, and 30 S. Michigan Avenue · built 1899-1900 · Louis H. Sullivan (18), Holabird & Roche (25 & 30) · designated September 11, 1996 Loop
- Halsted-Willow Group Four buildings located at the intersection of North Halsted and West Willow Streets, including 1727-1729 North Halsted, 1733 North Halsted, 1730-1732 North Halsted / 807 West Willow, and 1800 North Halsted · designated August 5, 2021
- Haskell-Barker-Atwater Buildings 18-28 S. Wabash Avenue · built 1875-77 · Wheelock & Thomas and John M. Van Osdel · designated November 13, 1996 Loop
- Heyworth Building 29 E. Madison Street · built 1904 · D.H. Burnham & Co. · designated September 27, 2000 Loop
- Holden Block 1027 W. Madison Street · built 1872 · Stephen Vaughn Shipman · designated May 4, 2011 Near West Side
- IBM Building 330 North Wabash Avenue · built 1969-72 · Ludwig Mies van der Rohe; C. F. Murphy Associates (engineers) · designated February 6, 2008 Near North Side
- Illinois Bell Building Ameritech Building 225 W. Randolph Street · built 1966 · Holabird & Root · designated January 27, 2021 Loop
- Inland Steel Building 30 W. Monroe Street · built 1957 · Skidmore, Owings & Merrill · designated October 7, 1998 Loop
- Jewelers' Building Jewelers Building, Jewelers Building 15-17 S. Wabash Avenue · built 1881-82 · Dankmar Adler with Louis H. Sullivan · designated December 18, 1981 Loop
- Johnson Publishing Company Building 820 S. Michigan Avenue · built 1969-71 · John Warren Moutoussamy · designated November 21, 2017 Loop
- 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 Loop
- Leiter II Building 403 S. State Street · built 1891 · William Le Baron Jenney · designated January 14, 1997 Loop
- 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 Loop
- Ludington Building 1104 S. Wabash Avenue · built 1891 · William Le Baron Jenney · designated June 10, 1996 Loop
- Ludlow Typograph Company Building 2028-2062 N. Clybourn Avenue · built 1913; 1918, 1922, 1928, 1948 (Additions) · Alfred S. Alschuler · designated April 27, 2022 Lincoln Park
- Manhattan Building 431 S. Dearborn Street · built 1891 · William Le Baron Jenney · designated July 7, 1978 Loop
- Marquette Building 140 S. Dearborn Street · built 1895 · Holabird and Roche · designated June 9, 1975 Loop
- Marshall Field and Company Building 111 N. State Street · built 1892 · Daniel H. Burnham & Charles Atwood (1892 original Annex Building); D. H. Burnham & Company (1902 North State Street section, 1906 connecting section, 1907 South State Street section); Graham, Burnham & Co. (1914 North Wabash Avenue addition) · designated November 1, 2005 Loop
- Mather Tower 75 E. Wacker Drive · built 1928 · Herbert Hugh Riddle · designated March 7, 2001 Loop
- McGraw-Hill Building 520 N. Michigan Avenue · built 1928-29 · Thielbar & Fugard · designated February 7, 1997 Near North Side
- Monadnock Block 53 W. Jackson Boulevard · built 1889-91 · North Phase: Burnham & Root; South Phase: Holabird & Roche · designated November 14, 1973 Loop
- Mutual Insurance Building Emerman Building 4750 N. Sheridan Road · built 1921, 1926 · Fugard & Knapp, 1921; B. Leo Steif & Co., 1926-27 · designated March 13, 2013 Uptown
- New York Life Building 37-43 S. LaSalle Street · built 1893-94 · Jenney & Mundie, 1898 addn; Unknown, 1903 addn · designated July 26, 2006 Loop
- Old Colony Building 407 S. Dearborn Street · built 1894 · Holabird & Roche · designated July 7, 1978 Loop
- Old Republic Building Bell Building 307 N. Michigan Avenue · built 1924 · K. M. Vitzthum & Co.; J.J. Burns, Associate · designated December 8, 2010 Loop
- Oliver Building 159 N. Dearborn Street · built 1907 · Holabird & Roche 1920 top addn. · designated May 9, 1984 Loop
- One North LaSalle Building 1 N. LaSalle Street · built 1929-30 · Karl M. Vitzthum & Co. with J.J. Burns · designated April 16, 1996 Loop Seeking missing report
- Page Brothers Building 177-191 N. State Street · built 1872, 1902 · John M. Van Osdel; Hill & Waltersdorf, 1902 facade · designated January 28, 1983 Loop
- Palmolive Building 919 N. Michigan Avenue · built 1927-29 · Holabird & Root · designated February 16, 2000 Near North Side
- Pittsfield Building 55 E. Washington Street · built 1927 · Graham, Anderson, Probst & White · designated November 6, 2002 Loop
- Plymouth Building 417 South Dearborn Street · built 1899; 1945 (Terra-Cotta Exterior Remodeling) · Simeon B.Eisendrath; W. Scott Armstrong · designated December 14, 2016 Loop
- Rector Building 79 W. Monroe Street · built 1905, 1923 · Jarvis Hunt (1905); Holabird & Roche (1923 South Addition) · designated March 12, 2025 Loop
- Reid, Murdoch and Company Building 320 N. Clark Street · built 1914 · George C. Nimmons · designated November 15, 1976 Near North Side
- Reliance Building 32 N. State Street · built 1895 · Burnham & Root, Base; D.H. Burnham & Co. Upper · designated July 11, 1975 Loop
- Riviera Motor Sales Company Building 5948-60 N. Broadway · built 1925-26 · R. Bernard Kurzon · designated June 6, 2012 Edgewater
- Roanoke Building and Tower 11 S. LaSalle Street · built 1915, 1922 · Holabird & Roche; Rebori, Wentworth, Dewey & McCormick · designated December 12, 2007 Loop
- Rookery Building 209 S. LaSalle Street · built 1885-88 · Burnham & Root · designated July 5, 1972 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 North Lawndale
- Spiegel Administration Building 1038 W. 35th Street · built 1936, 1941 · Battey & Kipp (1936), A. Epstein (1941-1942) · designated May 4, 2011 Bridgeport
- Steger Building 28 E. Jackson Boulevard · built 1909-10 · Marshall & Fox · designated June 5, 2013 Loop
- Tribune Tower 435 N. Michigan Avenue · built 1923-25 · Raymond M. Hood and John Mead Howells · designated February 1, 1989 Near North Side
- Trustees System Service Building Century Tower, Century Tower Condominiums, Trustees System Service Bank Building 201 N. Wells Street · built 1929-30 · Thielbar & Fugard; Artists: Eugene & Gwen Lux, Edgar Miller · designated January 14, 2004 Loop
- Veseman Building Vesemen Building 444 N. LaSalle Street · built 1886, 1930 · Unknown; Geo. F. Lovdall, 1930 facade, 3rd fl addn · designated December 12, 2007 Near North Side
- Washington Block 40 N. Wells Street · built 1873-74 · Frederick & Edward Baumann · designated January 14, 1997 Loop
- Wholesale Furniture Exposition Building 1323 S. Michigan Avenue · built 1904 · Hugh M.G. Garden · designated October 8, 2014 Near South Side
- Wrigley Building 400-410 North Michigan Avenue · built 1921 · Graham, Anderson, Probst and White · designated May 9, 2012 Near North Side
- Yondorf Block and Hall 758 W. North Avenue · built 1887 · Frederick Ahlschlager · designated July 25, 2001 Lincoln Park