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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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"Men in Barracks" WPA Mid 20th Century American Scene Realism Gay Modernism WWII
"Men in Barracks" WPA Mid 20th Century American Scene Realism Gay Modernism WWII

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Located in New York, NY

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Category

1940s American Realist Figurative Drawings and Watercolors

Materials

Paper, Watercolor

New York City Theater Painting Michael Budden Phantom of the Opera Study
New York City Theater Painting Michael Budden Phantom of the Opera Study

New York City Theater Painting Michael Budden Phantom of the Opera Study

By Michael Budden

Located in Chesterfield, NJ

Mystical Phantom oil/panel 8x6 unframed, 13.38 x 11.25 framed signed LR Mystical Phantom is an oil painting study on canvas panel by award winning contemporary artist Michael Budden...

Category

21st Century and Contemporary Realist Landscape Paintings

Materials

Oil

New York City Street Painting Paul Bachem News Stand
New York City Street Painting Paul Bachem News Stand

Michael BuddenNew York City Street Painting Paul Bachem News Stand, 2014

$900Sale Price|25% Off

H 17.38 in W 20.5 in D 1 in

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By Michael Budden

Located in Chesterfield, NJ

A beautiful painting of NYC by contemporary artist Paul Bachem oil on canvas on panel 11 x 14 unframed, 17.38 x 20.5 framed signed LR BIOGRAPHY Paul Bachem studied with Harold R. S...

Category

21st Century and Contemporary Impressionist Landscape Paintings

Materials

Oil

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

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Category

1910s Figurative Paintings

Materials

Canvas, Oil

"Loading the Wagon", Important Regional Scene Ptg, Thomas Hart Benton Colleague
"Loading the Wagon", Important Regional Scene Ptg, Thomas Hart Benton Colleague

"Loading the Wagon", Important Regional Scene Ptg, Thomas Hart Benton Colleague

Located in Philadelphia, PA

This classic example of American Scene painting, depicting a group of four laborers loading the harvest onto a wagon amidst the fields, has the energy and dynamic of Thomas Hart Bent...

Category

Vintage 1930s American Art Deco Paintings

Materials

Paint

Charles Ragland Bunnell WPA 1940s Figurative Village Landscape Mountains
Charles Ragland Bunnell WPA 1940s Figurative Village Landscape Mountains

Charles Ragland Bunnell WPA 1940s Figurative Village Landscape Mountains

By Charles Ragland Bunnell

Located in Denver, CO

A compelling 1940s WPA-era modernist watercolor by Charles Ragland Bunnell depicting a figurative village landscape set against mountainous terrain, where clustered houses, small hum...

Category

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Materials

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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

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Category

1930s American Realist Figurative Drawings and Watercolors

Materials

Paper, Gouache

"War Brides, Wash Sq NYC" American Scene WWII Modernism WPA Mid-Century Oil
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"War Brides, Wash Sq NYC" American Scene WWII Modernism WPA Mid-Century Oil

By Georgina Klitgaard

Located in New York, NY

"War Brides, Wash Sq NYC" American Scene WWII Modernism WPA Mid-Century Oil. 30 x 40 inches. Oil on canvas, c. 1942. Signed lower right. Titled on the stretcher. Housed in a sensatio...

Category

1940s American Modern Landscape Paintings

Materials

Canvas, Oil

Leonard Pytlak, (Industrial Landscape, New York City)
Leonard Pytlak, (Industrial Landscape, New York City)

Leonard Pytlak, (Industrial Landscape, New York City)

By Leonard Pytlak

Located in New York, NY

This lithograph is signed and number in pencil. It is numbered 18/18 indicating there were 18 impressions of this subject printed.

Category

1930s Ashcan School Landscape Prints

Materials

Lithograph

"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

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Category

1930s American Modern Landscape Drawings and Watercolors

Materials

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Lawrence Beall Smith, Solitude
Lawrence Beall Smith, Solitude

Lawrence Beall Smith, Solitude

By Lawrence Beall Smith

Located in New York, NY

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Category

Mid-20th Century Ashcan School Landscape Prints

Materials

Lithograph

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

Jefferson Market Library (Courthouse)
Jefferson Market Library (Courthouse)

Jefferson Market Library (Courthouse)

Located in Los Angeles, CA

This painting is part of our exhibition America Coast to Coast: Artists of the 1930s Jefferson Market Library (Courthouse), c. 1930s, oil on canvas, 30 x 24 inches, signed lower ri...

Category

1930s American Modern Landscape Paintings

Materials

Oil

"Colonial Sand and Stone Company, New York, " Industrial WPA Scene, Precisionist
"Colonial Sand and Stone Company, New York, " Industrial WPA Scene, Precisionist

"Colonial Sand and Stone Company, New York, " Industrial WPA Scene, Precisionist

By William Sharp

Located in New York, NY

William Sharp (1900 - 1961) Factory on the River Oil on canvas 20 1/2 x 28 1/2 inches Initialed lower left: WS Provenance: Estate of the artist Private Collection, New York Swann Au...

Category

Mid-20th Century American Realist Landscape Paintings

Materials

Canvas, Paint, Oil

Antique American Oil Painting, "At The Auction" by Cecil Bell
Antique American Oil Painting, "At The Auction" by Cecil Bell

Antique American Oil Painting, "At The Auction" by Cecil Bell

Located in Buffalo, NY

Antique American modernist interior painting by Cecil Crosley ("Spike") Bell (1906 - 1970). Oil on canvas, circa 1935. Signed. Displayed in a period giltwood frame. Image, 30"L ...

Category

Early 20th Century Modern Figurative Paintings

Materials

Canvas, 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.