- Armitage-Halsted District Various addresses · built various · designated February 5, 2003 Commercial districts Lincoln Park
- Assumption School 319 W. Erie Street · built 1899 · Frederick R. Foltz · designated July 9, 2003 Schools and education Near North Side
- Chicago Harbor Lighthouse S End of the North Breakwater,N side of Harbor Ent · built 1893 · designated April 9, 2003 Infrastructure and utilities
- Elks National Memorial Headquarters Building 2750 N. Lakeview Avenue · built 1924-26 · Egerton Swartwout · designated October 1, 2003 Monuments and sculpture Lincoln Park
- Engine Company 104, Truck 3 (Former) 1401 S. Michigan Avenue · built 1905 · Charles F. Hermann · designated October 1, 2003 Firehouses Near South Side
- Engine Company 129, Truck 50 8120 S. Ashland Avenue · built 1928-29 · Argyle E. Robinson · designated October 1, 2003 Firehouses Auburn Gresham
- Engine Company 27 (Former) 1244 N. Wells Street · built 1874 · 1874; 1907 (add.) Board of Public Works · designated October 1, 2003 Firehouses Near North Side
- Engine Company 35, Truck 28 (Former) 1625 N. Damen Avenue · built 1894, 1904 · Board of Public Works, add: W. C. Zimmerman · designated October 1, 2003 Firehouses West Town
- Engine Company 45, Truck 15 4600 S. Cottage Grove Avenue · built 1928 · Argyle E. Robinson · designated October 1, 2003 Firehouses Grand Boulevard
- Engine Company 5, Truck 2 324 S. Desplaines Avenue · built 1928 · Alfred S. Alschulter · designated October 1, 2003 Firehouses Near West Side
- Engine Company 59, Truck 47 5714 N. Ridge Avenue · built 1928 · Argyle E. Robinson · designated October 1, 2003 Firehouses Edgewater
- Engine Company 61 5349 S. Wabash Avenue · built 1927-28 · Charles W. Kallal · designated October 1, 2003 Firehouses Washington Park
- Engine Company 65, Truck 52 3000 W. 42nd Street · built 1929 · Paul Gerhardt, Jr. · designated October 1, 2003 Firehouses Archer Heights
- Engine Company 78 1052 W. Waveland Avenue · built 1915 · Charles W. Kallal · designated October 1, 2003 Firehouses Lake View
- Engine Company 84, Truck 51 6204 S. Green Street · built 1929 · Paul Gerhardt, Jr. · designated October 1, 2003 Firehouses Englewood
- Engine Company 86 (Former) 2414 W. Cuyler Avenue · built 1899 · Board of Public Works · designated October 1, 2003 Firehouses North Center
- Jewelers Row District Various addresses · built various · designated July 9, 2003 Commercial districts Loop
- Old Dearborn Bank Building Lake-State Bank Building 203 N. Wabash Avenue · built 1928 · C.W. & George L. Rapp · designated June 4, 2003 Banks Loop
- Pate-Comiskey House 5131 S. Michigan Avenue · built 1901 · George Maher · designated October 1, 2003 Houses Washington Park
- Pulaski Park Fieldhouse 1419 W. Blackhawk Street · built 1912-14 · William Carbys Zimmerman · designated July 29, 2003 Parks and landscapes West Town
- S. Pond Refectory/Men's & Ladies Comfort Station 2019 N. Stockton Drive · built 1908 & 1888 · Perkins & Hamilton (refectory, 1908); Joseph Lyman Silsbee (comfort station, 1888) · designated February 5, 2003 Parks and landscapes Lincoln Park
- Statue of the Republic Jackson Park at Hayes & Richards Drs · built 1918 · Daniel Chester French, sculptor; Henry Bacon, architect · designated June 4, 2003 Monuments and sculpture Woodlawn
- Wendell Phillips High School 244 E. Pershing Road · built 1904 · William Bryce Mundie · designated May 7, 2003 Schools and education Douglas
- West Town State Bank Building 2400 W. Madison Street · built 1929-30 · Mundie & Jensen · designated October 1, 2003 Banks Near West Side
- Wood-Maxey-Boyd House 2801 S. Prarie Avenue · built 1885 · John C. Cochrane · designated October 1, 2003 Houses Douglas
- Yale Apartments 6565 S. Yale Avenue · built 1892-93 · John T. Long · designated April 9, 2003 Apartment buildings Englewood