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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. If purchased this artwork will be available to ship after September 1, 2025. Contact...

Category

21st Century and Contemporary Contemporary Landscape Paintings

Materials

Canvas, Acrylic

"Industrial Cityscape, Chicago" WPA Modernism Mid-Century Cityscape 20th Century
"Industrial Cityscape, Chicago" WPA Modernism Mid-Century Cityscape 20th Century

"Industrial Cityscape, Chicago" WPA Modernism Mid-Century Cityscape 20th Century

By Aaron Bohrod

Located in New York, NY

BIO Known for a range of work in watercolor and gouache that included realist figures in cityscapes, landscapes, surrealism, and trompe l'oeil painting, Aaron Bohrod spent his early ...

Category

1930s American Modern Landscape Paintings

Materials

Oil, Board

Chicago River Wrigley Clock Tower Cityscape Urban Painting by Michael Budden
Chicago River Wrigley Clock Tower Cityscape Urban Painting by Michael Budden

Chicago River Wrigley Clock Tower Cityscape Urban Painting by Michael Budden

By Michael Budden

Located in Chesterfield, NJ

Along the Chicago River, Wrigley Clock Tower oil/panel 8 x 10 unframed, 14.5 x 16.5 framed signed LL Along the Chicago River, Wrigley Clock Tower is an oil painting on canvas panel...

Category

21st Century and Contemporary Realist Landscape Paintings

Materials

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

One of a kind Mixed Medium on Canvas Artwork: Original abstract mixed media work on canvas, which combines new media - digital original hand painting, printed on canvas, then hand ...

Category

2010s Contemporary Landscape Paintings

Materials

Canvas, Varnish, Archival Ink, Acrylic, Mixed Media

LaSalle Street - Cityscape of Chicago from the River- Albert Vidal
LaSalle Street - Cityscape of Chicago from the River- Albert Vidal

LaSalle Street - Cityscape of Chicago from the River- Albert Vidal

By Albert Vidal Moreno

Located in Chicago, IL

Albert Vidal paints a view of the Historical Landmark Reid Murdoch Building and world famous Marina Towers sitting at the edge of the Chicago River. Using vibrant colors and an abstr...

Category

21st Century and Contemporary Contemporary Landscape Paintings

Materials

Canvas, Acrylic

'Lakeshore Drive, Chicago', Modernist Cityscape, Woman Artist, Crocker Museum
'Lakeshore Drive, Chicago', Modernist Cityscape, Woman Artist, Crocker Museum

'Lakeshore Drive, Chicago', Modernist Cityscape, Woman Artist, Crocker Museum

By Muriel Backman

Located in Santa Cruz, CA

A mid-century, Modernist view of Chicago, seen in the evening with the lights of numerous buildings reflected in the still waters of Lake Michigan. Signed lower right "M. Backman" f...

Category

1960s Landscape Drawings and Watercolors

Materials

Watercolor, Handmade Paper

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’s Southside. Willis honed his technical abilities in the Chicago Public Schools, where...

Category

1980s Contemporary Landscape Drawings and Watercolors

Materials

Cardboard, Ballpoint Pen, Felt Pen

Wendell Hall Oil Painting On Canvas Signed Chicago Cityscape Child Portrait Art
Wendell Hall Oil Painting On Canvas Signed Chicago Cityscape Child Portrait Art

Wendell Hall Oil Painting On Canvas Signed Chicago Cityscape Child Portrait Art

Located in Bloomington, MN

Wendell Hall Authentic & Large Original Oil Painting on Canvas, Professionally Custom Framed and listed with the Submit Best Offer option Accepting Offers Now: Accepting Offers Now:...

Category

20th Century Expressionist Figurative Paintings

Materials

Canvas, Oil

Wendell Hall Large Original Oil Painting On Canvas Signed Chicago Cityscape Art
Wendell Hall Large Original Oil Painting On Canvas Signed Chicago Cityscape Art

Wendell Hall Large Original Oil Painting On Canvas Signed Chicago Cityscape Art

Located in Bloomington, MN

Wendell Hall Authentic & Large Original Oil Painting on Canvas, Professionally Custom Framed and listed with the Submit Best Offer option Accepting Offers Now: Accepting Offers Now:...

Category

20th Century Expressionist Figurative Paintings

Materials

Canvas, Oil

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 with buildings and bridges over the Chicago river.

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 on an overcast day. The painting has the perspective from one end of the street wi...

Category

Mid-20th Century American Mid-Century Modern Paintings

Materials

Paint

Blueberry Night - Cityscape of Chicago Skyline - Albert Vidal
Blueberry Night - Cityscape of Chicago Skyline - Albert Vidal

Blueberry Night - Cityscape of Chicago Skyline - Albert Vidal

By Albert Vidal Moreno

Located in Chicago, IL

**This artwork is on exhibition and if purchased will be available to ship after June 15, 2025 Albert Vidal paints a direct view of one of the most notable points in the Chicago sky...

Category

21st Century and Contemporary Contemporary Landscape Paintings

Materials

Canvas, Acrylic

May Chic - Cityscape of Chicago's Streeterville Area and Lake Michigan
May Chic - Cityscape of Chicago's Streeterville Area and Lake Michigan

May Chic - Cityscape of Chicago's Streeterville Area and Lake Michigan

By Albert Vidal Moreno

Located in Chicago, IL

Albert Vidal's abstract landscape painting is a bird's eye view of the Chicago Skyline, more specifically, the Streeterville Neighborhood and Lake Michigan. The buildings are cast i...

Category

21st Century and Contemporary Contemporary Landscape Paintings

Materials

Linen, Oil

Bridge vs. Willis - Cityscape of Chicago River & Willis Tower - Albert Vidal
Bridge vs. Willis - Cityscape of Chicago River & Willis Tower - Albert Vidal

Bridge vs. Willis - Cityscape of Chicago River & Willis Tower - Albert Vidal

By Albert Vidal Moreno

Located in Chicago, IL

Albert Vidal paints a direct view of one of the most notable points in the Chicago skyline. Using vibrant colors and an abstract view of city architecture, Vidal depicts a bridge ris...

Category

21st Century and Contemporary Contemporary Landscape Paintings

Materials

Canvas, Acrylic

Cityscape - Stylized Birds Eye View of Chicago, Original Work on Paper, Framed
Cityscape - Stylized Birds Eye View of Chicago, Original Work on Paper, Framed

Cityscape - Stylized Birds Eye View of Chicago, Original Work on Paper, Framed

By Patrick Vale

Located in Chicago, IL

Patrick Vale Cityscape acrylic and ink on paper 24h x 38w in 60.96h x 96.52w cm Framed: 28.50h x 42.50w x 2.25d in 72.39h x 107.95w x 5.71d cm PKV020 See What I See Why are Chicago...

Category

2010s Modern Landscape Drawings and Watercolors

Materials

Ink, Acrylic, Archival Paper

Cityscape Lithograph Chicago Modernist
Cityscape Lithograph Chicago Modernist

Cityscape Lithograph Chicago Modernist

By Richard Florsheim

Located in Surfside, FL

Genre: Other Subject: Landscape Medium: lithograph Surface: Canvas Country: United States Dimensions with Frame: 12.75 X 15.75 The artist Richard Florsheim depicts a Seascape using ...

Category

20th Century Modern Landscape Paintings

Materials

Lithograph

"Chicago Rain" (2023) - Original Oil Painting, Impressionist Cityscape
"Chicago Rain" (2023) - Original Oil Painting, Impressionist Cityscape

"Chicago Rain" (2023) - Original Oil Painting, Impressionist Cityscape

By Jacob Dhein

Located in Denver, CO

Jacob Dhein's "Chicago Rain" a 2023 original oil on panel, stands at 17.7 x 23.6 inches. This piece highlights Dhein's ability to capture reflection, diffusion, and a beautiful impre...

Category

2010s American Impressionist Figurative Paintings

Materials

Oil, Panel

Vienna Image, Large Abstract Cityscape Oil Painting Chicago Jewish Modernist
Vienna Image, Large Abstract Cityscape Oil Painting Chicago Jewish Modernist

Vienna Image, Large Abstract Cityscape Oil Painting Chicago Jewish Modernist

By Fred Rappaport

Located in Surfside, FL

Rappaport (1912-1989), Jewish Modernist painter and woodcut artist. Fred Rappaport was born in Vienna, Austria in 1912. He graduated from the Wien Akadamie der Bildenden Kunste and w...

Category

1970s Expressionist Landscape Paintings

Materials

Oil, Board

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.

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

Words that describe this painting: Chicago, cityscape, city, impressionism, Wrigley Building, Chicago River, river, architecture, bridge, buildings, Illinois, water, downtown, archit...

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

Yangzi is an alumnus of DePaul University in Chicago.Words that describe this painting: Chicago, rain, cityscape, urban, street, road, cars, city, night, evening, dusk, Illinois, sto...

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

Yangzi is an alumnus of DePaul University in Chicago.Words that describe this painting: Chicago, city, cityscape, urban, evening, reflection, night, outdoor, downtown, buildings, sma...

Category

21st Century and Contemporary Abstract Impressionist Interior Paintings

Materials

Oil

French  school Provence Village - Rare Oil painting Signed
French  school Provence Village - Rare Oil painting Signed

French school Provence Village - Rare Oil painting Signed

Located in Zofingen, AG

He started to use thick painting for the representation of landscape or cityscape (see Chicago paintings) Condition : Good condition - No cracks, no discoloration, no missing par...

Category

1920s Impressionist Landscape 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

Gouache on paper portrait by listed Chicago artist Franklin Van Court. Known for his modernist paintings of Chicago cityscapes, Van Court studied at the Art Institute of Chicago and ...

Category

Vintage 1950s American Drawings

Materials

Gouache, Paper

People Also Browsed

Paul K. Smith New Mexico Adobe Church Oil Southwestern Modernist Painting
Paul K. Smith New Mexico Adobe Church Oil Southwestern Modernist Painting

Paul K. Smith New Mexico Adobe Church Oil Southwestern Modernist Painting

By Paul Kauvar Smith

Located in Denver, CO

A highly collectible mid-century modern oil painting by Paul Kauvar Smith, this New Mexico Adobe Church captures one of the most iconic and enduring subjects in Southwestern American...

Category

1940s American Modern 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

WWI American Scene Ashcan Modern 20th Century Historical Realism Industrial WPA Gerrit Beneker (1882-1934) "Constant Driving Will Win the War" 30 x 40 inches Oil on canvas Signed an...

Category

1910s Figurative Paintings

Materials

Canvas, Oil

WPA Era, Industrial Scene Steel Mill by Chicago Modern Artist, Harold Haydon
WPA Era, Industrial Scene Steel Mill by Chicago Modern Artist, Harold Haydon

WPA Era, Industrial Scene Steel Mill by Chicago Modern Artist, Harold Haydon

By Harold Haydon

Located in Chicago, IL

A dynamic 1930s, WPA era industrial scene watercolor of a steel mill and factory workers by notable Chicago Modern artist, Harold Haydon. A wonderful example of early Twentieth Cent...

Category

1930s American Modern Landscape Drawings and Watercolors

Materials

Watercolor, Paper

Fishing Boats in Gloucester Harbor by Emile A. Gruppe
Fishing Boats in Gloucester Harbor by Emile A. Gruppe

Fishing Boats in Gloucester Harbor by Emile A. Gruppe

Located in Rockport, MA

The early (pre-war) Gloucester Harbor scene by Emile A. Gruppe is richly atmospheric and captures the working waterfront in the golden glow of early evening. Gruppe’s mastery of coas...

Category

20th Century American Impressionist Landscape Paintings

Materials

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

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

Neighbors

Norman BarrNeighbors, 1939

$3,250

H 22 in W 26 in D 1 in

Neighbors

By Norman Barr

Located in Los Angeles, CA

Neighbors, 1939, oil on canvas, signed and dated lower right, 22 x 26 inches Norman Barr was an American Scene painter and muralist known for his poignant depictions of working-clas...

Category

1930s American Modern Figurative Paintings

Materials

Canvas, Oil

NYC Subway Mid 20th Century American Scene Social Realism WPA Modern 1930s
NYC Subway Mid 20th Century American Scene Social Realism WPA Modern 1930s

NYC Subway Mid 20th Century American Scene Social Realism WPA Modern 1930s

By Daniel Ralph Celentano

Located in New York, NY

NYC Subway Riders Mid 20th Century American Scene Social Realism WPA Modern 1930s Daniel Celentano (1902 - 1980) Subway Scene, 1930s 8 x 9 inches Ink and wash on paper Singed lower ...

Category

1930s American Realist Figurative Drawings and Watercolors

Materials

Paper, Ink, Gouache

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

"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

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

"Golden Girls" Aaron Bohrod, Pun Humor, Magic Realism, Television Show
"Golden Girls" Aaron Bohrod, Pun Humor, Magic Realism, Television Show

"Golden Girls" Aaron Bohrod, Pun Humor, Magic Realism, Television Show

By Aaron Bohrod

Located in New York, NY

Aaron Bohrod Golden Girls, 1987 Signed lower right Oil on gesso panel 9 x 12 inches Aaron Bohrod's work has not been limited to one style or medium. Initially recognized as a region...

Category

1980s Realist Animal Paintings

Materials

Oil, Board

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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.