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A work made of oil on canvas.

The Old Temple, 1787/88

Hubert Robert

A loose perspective sketch, as through viewed from street level, of an L-shaped high-rise building emphasizing vertical columns.

Highrise Buildings Sketch, Chicago, Illinois, Perspective Sketches, c. 1946–1948

Ludwig Mies van der Rohe

A drawing of a red trapezoidal radio with a silver handle and face consisting of speakers, a round dial, and two buttons.

Fada Radio Design, Red Radio, Presentation Drawing, 1946

Henry Peter Glass

A work made of painted wood.

Auditorium Building: Column Capital and Portion of a Frieze, 1887–89

Adler & Sullivan, Architects

A work made of charcoal and ink wash on linen.

Flatiron Building, New York, New York, Perspective, 1902

Jules Guérin

A work made of graphite on tracing paper.

Gene and Nancy Bavinger House, Studio Floor Plan Section, Norman, Oklahoma, Working Drawing, 1950–1951

Bruce Goff

A work made of graphite pencil on tracing paper mounted on board.

Farmers and Merchants Union Bank, Columbus, Wisconsin, Elevation, 1919

Louis H. Sullivan

A rough sketch in green ink of a building interior drawn in one-point perspective. Arrows and text throughout the image annotate the scene.

Art Institute of Chicago Addition, Concept Sketch Perspective, 2001

Renzo Piano

A work made of graphite and watercolor on paper.

View of the Proposed Civic Center Plaza and Buildings, The 1909 Plan of Chicago, 1908

Daniel Hudson Burnham

A work made of graphite on linen.

860-880 North Lake Shore Drive, Chicago, Illinois, Plan, 11/22/1949

Ludwig Mies van der Rohe

A work made of marble.

Capital with Man Fighting Lion (A) and Riding Griffin (B), c. 1180

Lombard

Drawing of a street view of a light-beige Art Deco–style skyscraper surrounded by a dark-blue sky.

Cornell Towers, Chicago, Illinois, Perspective Rendering, c. 1925

Maurice L. Bein

A work made of black chalk and graphite on cream laid paper.

Sheet of Sketches: Architectural and Erotic Drawings, n.d.

Pierre Antoine Mongin

A drawing of a soaring, ethereal white skyscraper situated by water and surrounded by short buildings. In the sky are birds and a blimp.

Century of Progress Exposition Tower of Water and Light, Chicago, Illinois, Final Design, 1930

Ralph Thomas Walker

A gray-scale drawing from street level of a building with a prominent central dome framed by lower vertical wings with diagonal ends.

Adler Planetarium and Astronomy Museum Addition: Design Drawings, West Elevation, c. 1995 (building completed 1999)

Lohan Associates

A work made of terra-cotta.

Spandrel Panel from the Western Methodist Book Exchange, Chicago, Illinois, c. 1899

Harry Bergen Wheelock

A work made of graphite on linen.

860-880 North Lake Shore Drive, Chicago, Illinois, Elevations, 11/22/1949

Ludwig Mies van der Rohe

7 South Dearborn Street, Chicago, Illinois, Perspective View

7 South Dearborn Street, Chicago, Illinois, Perspective View, 1999

Adrian D. Smith

A color drawing of a spiral-shaped, stone-clad house with a suspended bridge projecting from it on the left, trees in the background.

Gene and Nancy Bavinger House: North Elevation Showing Suspension Bridge over Ravine, 1950/51

Bruce Goff

A sketch made up of scribbles in black ink centered on the page with a line of notes, difficult to decipher, and a signature in the bottom-right corner.

Frederick R. Weisman Art Museum, Minneapolis, Minnesota, Concept Sketch, 1990

Frank O. Gehry

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