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Chicago Cityscape Paintings

Midtown - Cityscape of Chicago Skyline, Original Painting
Midtown - Cityscape of Chicago Skyline, Original Painting

Midtown - Cityscape of Chicago Skyline, Original Painting

By Albert Vidal Moreno

Located in Chicago, IL

***This artwork is currently on exhibit at the Instituto Cervantes, Chicago until September 2025

Category

21st Century and Contemporary Contemporary Landscape Paintings

Materials

Canvas, Acrylic

Chicago Cityscape Mixed Media Painting on Canvas 38 x 56"
Chicago Cityscape Mixed Media Painting on Canvas 38 x 56"

Chicago Cityscape Mixed Media Painting on Canvas 38 x 56"

By Irena Orlov

Located in Los Angeles, CA

combines new media - digital original hand painting, printed on canvas, then hand painted with acrylic, 3D

Category

2010s Contemporary Landscape Paintings

Materials

Canvas, Varnish, Archival Ink, Acrylic, Mixed Media

Recent Sales

Chicago Cityscapes
Chicago Cityscapes

Wesley WillisChicago Cityscapes, 1984

Unavailable

H 22.25 in W 26.38 in D 1.13 in

Chicago Cityscapes

By Wesley Willis

Located in Chicago, IL

Wesley Willis (1963-2003) was a self-trained artist and native Chicagoan, growing up on Chicago

Category

1980s Contemporary Landscape Drawings and Watercolors

Materials

Cardboard, Ballpoint Pen, Felt Pen

Chicago Cityscape Mixed-Media Collage Signed Original Painting
Chicago Cityscape Mixed-Media Collage Signed Original Painting

Chicago Cityscape Mixed-Media Collage Signed Original Painting

Located in Dallas, TX

This picturesque mixed-media painting is titled Chicago and depicts the Downtown view of the city

Category

2010s American Modern Contemporary Art

Materials

Canvas, Paint, Paper

Midcentury Abstract Chicago Cityscape Signed Oil Painting by Lee Reynolds
Midcentury Abstract Chicago Cityscape Signed Oil Painting by Lee Reynolds

Midcentury Abstract Chicago Cityscape Signed Oil Painting by Lee Reynolds

By Lee Reynolds

Located in London, England

A large midcentury signed oil painting by Lee Reynolds (Vanguard Studios) of a Chicago street scene

Category

Mid-20th Century American Mid-Century Modern Paintings

Materials

Paint

Cityscape Lithograph Chicago Modernist
Cityscape Lithograph Chicago Modernist

Cityscape Lithograph Chicago Modernist

By Richard Florsheim

Located in Surfside, FL

. Richard Aberle Florsheim was born 1916, in Chicago, Illinois. He attended the Chicago Latin School (1923

Category

20th Century Modern Landscape Paintings

Materials

Lithograph

Abstract Cityscape Painting on Board by Chicago Artist William McBride, Jr.
Abstract Cityscape Painting on Board by Chicago Artist William McBride, Jr.

Abstract Cityscape Painting on Board by Chicago Artist William McBride, Jr.

Located in Chicago, IL

Abstract cityscape painting on board by Chicago artist, William McBride, Jr. McBride was born

Category

Vintage 1950s American Mid-Century Modern Paintings

Materials

Wood, Paint

Chicago from the River, Midday, Oil Painting
Chicago from the River, Midday, Oil Painting

Chicago from the River, Midday, Oil Painting

By Suren Nersisyan

Located in San Francisco, CA

describe this painting: Chicago, cityscape, city, impressionism, Wrigley Building, Chicago River, river

Category

21st Century and Contemporary Abstract Impressionist Interior Paintings

Materials

Oil

South Michigan Ave, Oil Painting
South Michigan Ave, Oil Painting

South Michigan Ave, Oil Painting

By Yangzi Xu

Located in San Francisco, CA

>Words that describe this painting: Chicago, rain, cityscape, urban, street, road, cars, city, night

Category

21st Century and Contemporary Abstract Expressionist Interior Paintings

Materials

Oil

Evening on Wacker Drive, Oil Painting
Evening on Wacker Drive, Oil Painting

Evening on Wacker Drive, Oil Painting

By Yangzi Xu

Located in San Francisco, CA

University in Chicago.Words that describe this painting: Chicago, city, cityscape, urban, evening

Category

21st Century and Contemporary Abstract Impressionist Interior Paintings

Materials

Oil

Franklin Van Court Framed Gouache On Paper
Franklin Van Court Framed Gouache On Paper

Franklin Van Court Framed Gouache On Paper

Sold

H 20 in W 17.25 in D 1 in

Franklin Van Court Framed Gouache On Paper

By Franklin Van Court

Located in Chicago, IL

paintings of Chicago cityscapes, Van Court studied at the Art Institute of Chicago and the National Academy

Category

Vintage 1950s American Drawings

Materials

Gouache, Paper

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WWI American Scene Ashcan Modern 20th Century Historical Realism Industrial WPA
WWI American Scene Ashcan Modern 20th Century Historical Realism Industrial WPA

WWI American Scene Ashcan Modern 20th Century Historical Realism Industrial WPA

By Gerrit Beneker

Located in New York, NY

WWI American Scene Ashcan Modern 20th Century Historical Realism Industrial WPA "Constant Driving Will Win the War," 30 x 40 inches. Oil on canvas. Signed and dated 1918 lower right...

Category

1910s Figurative Paintings

Materials

Canvas, Oil

"Five Josephs, " Important Art Deco Painting w/ Male Nudes, Provincetown, 1930s
"Five Josephs, " Important Art Deco Painting w/ Male Nudes, Provincetown, 1930s

"Five Josephs, " Important Art Deco Painting w/ Male Nudes, Provincetown, 1930s

By William L'Engle

Located in Philadelphia, PA

An extraordinary example of Art Deco painting with allegorical meaning -- like so many murals painted in the 1920s and 1930s -- this large work by William L'Engle depicts five nude m...

Category

Vintage 1930s American Art Deco Paintings

Materials

Paint

"Workers" Russian Constructivist 1920s Modern Social Realism Cubism Figurative
"Workers" Russian Constructivist 1920s Modern Social Realism Cubism Figurative

"Workers" Russian Constructivist 1920s Modern Social Realism Cubism Figurative

Located in New York, NY

"Workers" Russian Constructivist 1920s Modern Social Realism Cubism Figurative VLADIMIR VASIL’EVICH LEBEDEV (1891-1967) "Workers" Gouache on paper Monogramed lower right 15 1/8 x 10...

Category

1920s Constructivist Figurative Paintings

Materials

Paper, Gouache

"Times Square" Mid 20th Century 1937 Modernism Broadway Drawing NYC Cityscape
"Times Square" Mid 20th Century 1937 Modernism Broadway Drawing NYC Cityscape

"Times Square" Mid 20th Century 1937 Modernism Broadway Drawing NYC Cityscape

Located in New York, NY

"Times Square" Mid 20th Century 1937 Modernism Broadway Drawing NYC Cityscape Philip Goodwin (20th Century) "Times Square," 23 ½ x 17 ¼ inches. Gouache on paper. Signed and dated ’3...

Category

1930s American Modern Landscape Drawings and Watercolors

Materials

Paper, Gouache

Man Working Mid 20th Century American Scene Social Realism Industrial WPA Modern
Man Working Mid 20th Century American Scene Social Realism Industrial WPA Modern

Man Working Mid 20th Century American Scene Social Realism Industrial WPA Modern

By Jo Cain

Located in New York, NY

Man Working Mid 20th Century American Scene Social Realism Industrial WPA Modern Jo Cain (1904 - 2003) Telephone Pole Worker 38 1/4 x 18 1/2 inches Oil on paper c. 1930s Signed lowe...

Category

1930s American Realist Figurative Drawings and Watercolors

Materials

Paper, Gouache

WPA 1940s Framed Figurative Village Landscape with Figures, Houses & Mountains
WPA 1940s Framed Figurative Village Landscape with Figures, Houses & Mountains

WPA 1940s Framed Figurative Village Landscape with Figures, Houses & Mountains

By Charles Ragland Bunnell

Located in Denver, CO

This evocative watercolor on paper painting, titled The Way War First Comes (1940), was created by noted American artist Charles Ragland Bunnell (1897-1968) during the Depression era...

Category

1940s American Modern Figurative Drawings and Watercolors

Materials

Watercolor

Boys Swimming Industrial Landscape WPA Mid 20th Century Social Realism Modernism
Boys Swimming Industrial Landscape WPA Mid 20th Century Social Realism Modernism

Boys Swimming Industrial Landscape WPA Mid 20th Century Social Realism Modernism

By Henry Ernst Schnakenberg

Located in New York, NY

Boys Swimming Industrial Landscape WPA Mid 20th Century Social Realism Modernism Henry Schnakenberg (1982 - 1970) Boys Swimming Industrial Landscape 11 1/2 x 15 1/2 sight Oil on Can...

Category

1940s American Modern Figurative Paintings

Materials

Canvas, Oil

Lawrence Beall Smith, Solitude
Lawrence Beall Smith, Solitude

Lawrence Beall Smith, Solitude

By Lawrence Beall Smith

Located in New York, NY

Lawrence Beall Smith draws four men in a park, each with his back to a giant, strong tree. The year is 1938 and the country is coming out of the Depression but World War II is alread...

Category

Mid-20th Century Ashcan School Landscape Prints

Materials

Lithograph

"Manhattan Bridge" NYC American Scene Modernism Watercolor WPA Urban Realism
"Manhattan Bridge" NYC American Scene Modernism Watercolor WPA Urban Realism

"Manhattan Bridge" NYC American Scene Modernism Watercolor WPA Urban Realism

By Reginald Marsh

Located in New York, NY

Reginald Marsh "Manhattan Bridge" NYC American Scene Modernism Watercolor WPA Urban Realism, 20 x 14 inches. Watercolor and pencil on paper, 1938. Signed lower right. Housed in a stu...

Category

1930s American Modern Landscape Drawings and Watercolors

Materials

Paper, Watercolor, Pencil

House Beautiful Cover Proposal. American Scene Social Realism Industrial WPA
House Beautiful Cover Proposal. American Scene Social Realism Industrial WPA

House Beautiful Cover Proposal. American Scene Social Realism Industrial WPA

By Antonio Petruccelli

Located in New York, NY

House Beautiful Cover Proposal. American Scene Social Realism Industrial WPA Antonio Petruccelli (1907 – 1994) Mixing Mortar 12 1/2 X 14 3/4 inches (sight) Framed 19 1/2 X 21 3/4 in...

Category

1930s American Modern Figurative Paintings

Materials

Gouache, Board

"Drama Teacher" 1938 WPA Mid 20th Century American Theatre Surrealism Modernism
"Drama Teacher" 1938 WPA Mid 20th Century American Theatre Surrealism Modernism

"Drama Teacher" 1938 WPA Mid 20th Century American Theatre Surrealism Modernism

By Leon Bibel

Located in New York, NY

"Drama Teacher" 1938 WPA Mid 20th Century American Theatre Surrealism Modernism. 30 x 24 inches. Oil on Canvas. Signed land dated ’38 lower left. The photograph in the listing depic...

Category

1930s American Modern Figurative Paintings

Materials

Canvas, Oil

"Factory on the River" Modernist and Precisionist WPA Industrial New York Scene
"Factory on the River" Modernist and Precisionist WPA Industrial New York Scene

"Factory on the River" Modernist and Precisionist WPA Industrial New York Scene

By William Sharp

Located in New York, NY

William Sharp (1900 - 1961) Factory on the River Oil on canvas 17 1/2 x 23 1/4 inches Initialed lower right: WS Provenance: Estate of the artist Private Collection, New York Swann A...

Category

Mid-20th Century American Realist Landscape Paintings

Materials

Canvas, Paint, Oil

Storm Over Victor, Colorado – 1940s WPA Era Oil Painting of Mountain Town
Storm Over Victor, Colorado – 1940s WPA Era Oil Painting of Mountain Town

Storm Over Victor, Colorado – 1940s WPA Era Oil Painting of Mountain Town

Located in Denver, CO

Oil on board painting by George Vander Sluis (1915-1984) titled Storm Over Victor (Colorado Mountain Town) from 1946. WPA Era Mountain Landscape with houses, trees, and clouds. Prese...

Category

1940s American Modern Landscape Paintings

Materials

Oil

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Chicago Cityscape Paintings For Sale on 1stDibs

On 1stDibs, there are several options of chicago cityscape paintings available for sale. Finding the ideal Contemporary, Expressionist or Modern examples of these works for your living room, whether you’re looking for small- or large-size pieces, is no easy task — start by shopping our selection today. These items have long been popular, with older editions for sale from the 20th Century and newer versions made as recently as the 21st Century. Adding a colorful piece of art to a room that is mostly decorated in warm neutral tones can yield a welcome change — see the chicago cityscape paintings on 1stDibs that include elements of gray, black, brown and more. These artworks have been a part of the life’s work for many artists, but the versions made by Muriel Backman, Aaron Bohrod, Richard Florsheim, Irena Orlov and Michael Budden are consistently popular. Frequently made by artists working in paint, oil paint and fabric, all of these available pieces are unique and have attracted attention over the years.

How Much are Chicago Cityscape Paintings?

Chicago cityscape paintings can differ in price owing to various characteristics — the average selling price for items in our inventory is $2,750, while the lowest priced sells for $500 and the highest can go for as much as $16,000.

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