Chicago Skyline Paintings

These Chicago skyline paintings capture the iconic beauty of the city. From its towering skyscrapers to its wide-open lakefront, these paintings will take you on a journey through one of America's most beloved cities. With vibrant colors and striking details, each painting brings the energy of The Windy City straight into your home or office. Whether you're a native Chicagoan or just visiting for the first time, these paintings will evoke lasting memories of this great metropolis!

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1 - 72 of 1,074 chicago skyline paintings for sale

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Results: 1,074

Twilight Serenity II Painting

$20

Chicago Cityscape- Art by Linda Woods Painting

$22

Chicago Skyline - John Hancock Tower Painting

Print:

$27

Original:

$850

Chicago Skyline Black Painting

$22

Autumn Serenity II Painting

$20

Chicago Illinois Skyline Painting

$20

Impressions of Chicago Painting

$37

Chicago Flag Watercolor Painting

$16

Chicago Skyline #1 Painting

$20

Chicago City Skyline #6 Painting

$20

Chicago Flag Painting

$17

Chicago Illinois Skyline #4 Painting

$20

Chicago North Skyline Park Painting

$37

Chicago Illinois Skyline #4 Painting

$20

Chicago City Skyline #1 Painting

$20

Chicago City Skyline #3 Painting

$20

Chicago Skyline Painting

$20

Chicago Illinois Skyline #2 Painting

$20

Chicago Illinois Skyline Painting

$20

Sunset Evening Skyscrapers Chicago Rails Chicago Urban Sunset Railroad Tracks Leading Through a Cityscape Painting

$22

Chicago Illinois Skyline #1 Painting

$20

Chicago Ilinois Skyline Painting

$20

Hey Chicago Vintage Painting

$17

Urban Renewal II Painting

$58

Chicago Skyline Painting

$20

Chicago Illinois #1 Painting

$20

Chicago Illinois Painting

$20

Chicago Illinois Skyline #3 Painting

$20

Los Angeles Skyline Painting

Print:

$79

Original:

$3,000

Chicago Skyline Painting

$37

Spring Serenity Painting

$32

Chicago Skyline I Painting

$22

Hey Chicago Crop Sp Painting

$17

Chicago City Skyline Painting

$22

Windy City Autumn Painting

Print:

$36

Original:

$2,400

Wrigley Field Chicago Skyline Painting

$37

Chicago Skyline Red Painting

$22

Retro Travel Poster Chicago Painting

$25

Chicago Skyline Blue Painting

$22

Theatre District - Chicago Painting

Print:

$22

Original:

$260

Chicago Watercolor Skyline Painting

$22

City In Green Painting

Print:

$58

Original:

$300

Chicago Cityscape Abstract Watercolor Painting Painting

$14

Chicago Skyline Painting

$17

Golden Skyline II Painting

$58

Chicago Air Balloon Painting

$22

Chicago Skyline Yellow Painting

$22

Golden Skyline III Painting

$58

Chicago Skyline II Painting

$22

Chicago Lincoln Sunset Tower Evening Willis Park Cityscape Sunset with Water Reflection and Moon Painting

$22

Tower Skyscrapers Willis Chicago Sunrise Morning Red City Skyline Abstract Urban Art Painting Painting

$22

Centers Chicago Skyscrapers Business Evening Night Cityscape with Frozen River and Lights Painting

$22

Tower Willis Chicago Chicago Modern Cityscape A View From Above Painting

$22

Sunset Skyscrapers Chicago Chicago Evening Tower Willis Cityscape Sunset with Dramatic Clouds - Urban Landscape Art Painting

$22

Chicago Skyline Sunset Vibrant Urban Landscape Willis Skyscrapers Evening Chicago Sunset Tower Painting

$22

Chicago Skyline Sunset Vibrant Cityscape Skyscrapers Sunset Tower Willis Evening Chicago Painting

$22

Chicago River Skyline Sunset Cities Buildings Chicago American Chicago Illinois River Modern Painting

$22

Vibrant Chicago Skyline Sunset North Michigan Sears Chicago 875 Tower Center Avenue Tower Willis Aon Painting

$22

Chicago Illinois Skyline Painting

$22

Chicago Illinois Skyline Chicago Skyline Watercolor - Urban Architecture Painting

$22

Chicago Illinois Skyline Stunning Watercolor Cityscape at Sunset Painting

$22

Chicago Illinois Skyline Watercolor Cityscape with Reflection - Urban Architecture Art Painting

$22

Chicago Illinois Skyline Vibrant Cityscape Art Painting

$22

Chicago Illinois Skyline Chicago Skyline Watercolor Art Painting

$22

Watercolor painting of skycrapers of downtown Chicago as viewed #2 Painting

Print:

$37

Original:

$350

Watercolor painting of skycrapers of downtown Chicago as viewed Painting

Print:

$37

Original:

$350

Vibrant Cityscape Sunset Reflection Chicago Cityscape Buildings Evening Chicago Skyscrapers Modern Painting

$22

Vibrant Cityscape with Sunset and Skyscrapers Sunset Evening Skyscrapers Chicago Tower Willis Painting

$22

Vibrant Cityscape Sunset with Skyscrapers and River Reflection Evening Sunset Skyscrapers Willis Chicago Tower Painting

$22

Vibrant Cityscape with Sunset and River Reflection American Illinois Buildings Chicago Modern Cities Painting

$22

Urban Renewal I Painting

$58

Wrigley Building Painting

$32

1 - 72 of 1,074 chicago skyline paintings for sale

12 3 4 5

These Chicago skyline paintings capture the iconic beauty of the city. From its towering skyscrapers to its wide-open lakefront, these paintings will take you on a journey through one of America's most beloved cities. With vibrant colors and striking details, each painting brings the energy of The Windy City straight into your home or office. Whether you're a native Chicagoan or just visiting for the first time, these paintings will evoke lasting memories of this great metropolis!