- 63rd Street Bathing Pavilion South Lake Shore Dr and 63rd St · built 1919 · South Park Commission Architects · designated December 8, 2004 Sports and recreation Woodlawn
- Adolf Schmidt House 6331- 33 N. Sheridan Road · built 1916-1917 · George W. Maher · designated June 13, 2013 Houses Edgewater
- Allan Miller House 7121 S. Paxton Avenue · built 1915 · John S. Van Bergen · designated December 1, 1993 Houses South Shore
- American Book Company Building 320 E. Cermak Road & 2132 S. Calumet Avenue · built 1912 · Nelson Max Dunning · designated July 29, 2009 Offices and commercial buildings Near South Side
- American System-Built Houses, 10410 S. Hoyne Ave. 10410 S. Hoyne Avenue · built 1917 · Frank Lloyd Wright · designated July 13, 1994 Houses Beverly
- American System-Built Houses, 10541 S. Hoyne Ave. 10541 S. Hoyne Avenue · built 1917 · Frank Lloyd Wright · designated July 13, 1994 Houses Beverly
- Apollo's 2000 2875 W. Cermak Road · built 1917 · Alexander L. Levy · designated April 17, 2024 Theaters and entertainment South Lawndale
- Biograph Theater 2433-43 N. Lincoln Avenue · built 1914 · Samuel N. Crowen · designated March 28, 2001 Theaters and entertainment Lincoln Park
- Blackstone Hotel 636 S. Michigan Avenue · built 1910 · Marshall & Fox · designated April 29, 1998 Hotels Loop
- Brooks Building 223 W. Jackson Boulevard · built 1910 · Holabird & Roche · designated January 14, 1997 Offices and commercial buildings Loop
- Calumet National Bank Bldg (Former) 9117 S. Commercial Avenue · built 1910 · John A. Domicksen · designated July 9, 2008 Banks South Chicago
- Carl Schurz High School 3601 N. Milwaukee Avenue · built 1910 · Dwight H. Perkins · designated December 7, 1979 Schools and education Irving Park
- 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 Offices and commercial buildings Loop
- Chess Records Office and Studio 2120 S. Michigan Avenue · built 1911 · Horatio Wilson · designated May 16, 1990 Studios and workshops Near South Side
- Chicago & Illinois Western Railway Bridge Collateral Channel Water Lot D, 33rd, E of Kedzie · built 1914 · Theodor Rall · designated December 12, 2007 Bridges South Lawndale
- Consumers Building State and Quincy Building 220 South State Street · built 1911-13 · Mundie & Jensen · designated April 19, 2025 Offices and commercial buildings Loop
- Continental and Commercial National Bank Building 208 South LaSalle Street · built 1914 · D. H Burnham & Co.; Graham Anderson Probst & White · designated December 12, 2007 Banks Loop
- Cook County Hospital Administration Building 1835 West Harrison Street · built 1912-14 · Paul Gerhardt, Sr. · designated January 23, 2019 Hospitals and health care Near West Side
- Eighth Church of Christ, Scientist 4359 S. Michigan Avenue · built 1911 · Leon E. Stanhope · designated June 9, 1993 Places of worship Grand Boulevard
- Emil Bach House 7415 N. Sheridan Road · built 1915 · Frank Lloyd Wright · designated September 28, 1977 Houses Rogers Park
- Engine Company 78 1052 W. Waveland Avenue · built 1915 · Charles W. Kallal · designated October 1, 2003 Firehouses Lake View
- Harris Trust & Savings Bank 111 West Monroe Street · built 1911, 1960 · Shepley, Rutan & Coolidge; Skidmore,Owings · designated June 18, 2025 Banks Loop
- Kenna Apartments 2214 E. 69th Street · built 1916 · Barry Byrne · designated September 12, 1990 Apartment buildings South Shore
- Lake Shore & Michigan Southern Rwy Bridges (pair) Calumet River, N of 98th St & E of Chicago Skyway · built 1912-1915 · Waddell & Harrington; Dravo Contracting Co. (substructure) · designated December 12, 2007 Bridges East Side
- Lakeview Avenue Row House District 2700-2710 N. Lakeview Avenue · built 1915-17 · designated November 16, 2016 Residential districts
- Lion House - Lincoln Park Zoo Kovler Lion House, Pepper Family Wildlife Center 2001 N. Clark Street · built 1912 · Perkins, Fellows & Hamilton · designated November 30, 2005 Parks and landscapes Lincoln Park
- Ludlow Typograph Company Building 2028-2062 N. Clybourn Avenue · built 1913; 1918, 1922, 1928, 1948 (Additions) · Alfred S. Alschuler · designated April 27, 2022 Offices and commercial buildings Lincoln Park
- Medinah Temple 600 N. Wabash Avenue · built 1912 · Huehl & Schmid · designated June 27, 2001 Clubs and social halls Near North Side
- Mid-City Trust & Savings Bank Buildings (Former) 2 S. Halsted Street · built 1911-12 · Horatio R. Wilson (Original Bldg) · designated April 24, 2012 Banks Near West Side
- Morning Star Baptist Church of Chicago 3993 S. Drive Martin Luther King, Jr. Drive · built 19121-1968 · Harry Bergen Wheelock (1912); Walter Thomas Bailey (1937-39); Hunter, Konn & Duster and Associates (1963-68) · designated June 18, 2025 Places of worship Grand Boulevard
- Mt. Pisgah Missionary Baptist Church Complex 4600-4628 S. Drive Martin Luther King Jr. Drive · built 1912 · Alfred Samuel Alschuler · designated April 24, 2020 Places of worship Grand Boulevard
- Municipal Tuberculosis Sanitarium Complex Chicago Municipal Tuberculosis Sanitarium, Chicago Municipal Tuberculosis Sanitarium District 5801 N. Pullaski Road · built 1911-1915 · Otis & Clark, Ossian C Simonds, Jarvis Hunt · designated March 13, 2019 Hospitals and health care North Park
- Navy Pier (Headhouse and East End Building) Grand Av and Streeter Dr at Lake Michigan · built 1916 · Charles Summer Frost · designated November 14, 1977 Parks and landscapes Near North Side
- Oppenheimer-Goldblatt Bros. Dept. Store Building Oppenheimer-Goldblatt Bros. Department Store Bldg 4700 S. Ashland Avenue · built 1915, 29, 33 · Alfred S. Alschuler · designated May 8, 2013 Stores and markets New City
- Pennsylvania Railroad Bridge S Branch Chgo River, 19th St, SE of Lumber St · built 1914 · Waddell & Harrington (Consulting Engineers), Kansas City, OH; J.C. Bland (Supervising Engineer), Pennsylvania Lines · designated December 12, 2007 Bridges Armour Square
- Perkins, Fellows & Hamilton Office and Studio 814 N. Michigan Avenue · built 1917 · Perkins, Fellows & Hamilton · designated December 1, 1993 Studios and workshops Near North Side Seeking missing report
- Portage Park Theatre Building 4042-4060 N. Milwaukee Ave.; 4905-4915 W. Cuyler Avenue · built 1919-20 · Lindley P. Rowe, in association with Fridstein & Co · designated May 8, 2013 Theaters and entertainment Portage Park
- Pulaski Park Fieldhouse 1419 W. Blackhawk Street · built 1912-14 · William Carbys Zimmerman · designated July 29, 2003 Parks and landscapes West Town
- R.R. Donnelley & Sons Co. Calumet Plant 350 E. Cermak Road · built 1912-25 · Howard Van Doren Shaw · designated March 31, 2004 Factories and warehouses Near South Side
- Reid, Murdoch and Company Building 320 N. Clark Street · built 1914 · George C. Nimmons · designated November 15, 1976 Offices and commercial buildings Near North Side
- Roanoke Building and Tower 11 S. LaSalle Street · built 1915, 1922 · Holabird & Roche; Rebori, Wentworth, Dewey & McCormick · designated December 12, 2007 Offices and commercial buildings Loop
- Robert Lindblom Technical High School Robert Lindblom Technical High Schoool building, Lindblom Technical High School, Lindblom College Prep High School, Robert E. Lindblom Math & Science Academy High School (LMSA) 6130 S. Wolcott Avenue · built 1917-1919 · Arthur F. Hussander · designated June 9, 2010 Schools and education West Englewood
- Shedd Park Fieldhouse 3660 W. 23rd Street · built 1916-17 · William Drummond · designated February 11, 2004 Parks and landscapes South Lawndale
- St Charles Air Line Bridge S B Chgo River, N of 16th St & E of Lumber St · built 1917-1919; relocated in 1930 · Strauss Bascule & Concrete Bridge Co. · designated December 12, 2007 Bridges Near West Side
- St. Adalbert Church Building (Former) 1638 W. 17th Street · built 1914 · Henry J. Schlacks · designated June 18, 2025 Places of worship Lower West Side
- St. Paul Christian Methodist Episcopal (C.M.E.) Church Emanuel Society of the United Evangelical Church 4644 S. Dearborn Street · built 1917-1925 · Ecklund, Fugard & Knapp · designated May 20, 2026 Places of worship Grand Boulevard
- 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
- Swedish American State Bank Bldg (Former) 5400 N. Clark Street · built 1913 · Ottenheimer, Stern & Reichert · designated July 9, 2008 Banks Edgewater
- The Warehouse 206 S. Jefferson Street · built 1910,-1977 · Vernon W. Behel · designated June 21, 2023 Stores and markets Near West Side
- Three Arts Club 1300 N. Dearborn Street · built 1914 · Holabird and Roche · designated June 10, 1981 Clubs and social halls Near North Side
- Union Station 210 S. Canal Street · built 1913-25 · Graham, Anderson, Probst & White · designated May 1, 2002 Railroad and transit stations Near West Side
- Vassar Swiss Underwear Company Bldg 2543 - 2545 W. Diversey Avenue · built 1913-24 · Unknown; Lawrence Hallberg & Co., 1923-24 addn · designated July 30, 2008 Factories and warehouses Logan Square
- Village Theatre 1546-1550 N. Clark Street · built 1915-16 · Adolph Woerner · designated May 13, 2009 Theaters and entertainment Near North Side
- Wrigley Field 1060 W. Addison Street · built 1914 · Zachary T. & Charles G. Davis · designated February 11, 2004 Sports and recreation Lake View