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Chicago Skyline Paintings

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!

1 - 72 of 948 chicago skyline paintings for sale

Results: 948

Results: 948

Chicago skyline Collections Chicago skyline Artists
Wall Art - Painting - Twilight Serenity II by Doug Kreuger

Twilight Serenity II Painting

Doug KreugerArrow Down

$20

$16

Wall Art - Painting - Chicago Cityscape- Art by Linda Woods by Linda Woods

Chicago Cityscape- Art by Linda Woods Painting

Linda WoodsArrow Down

$22

$18

Wall Art - Painting - Chicago Skyline - John Hancock Tower by Jeff Pittman

Chicago Skyline - John Hancock Tower Painting

Jeff PittmanArrow Down

Print:

$27

$22

Original:

$850

Wall Art - Painting - Chicago Skyline Black by Naxart Studio

Chicago Skyline Black Painting

Naxart StudioArrow Down

$22

$18

Wall Art - Painting - Autumn Serenity II by Doug Kreuger

Autumn Serenity II Painting

Doug KreugerArrow Down

$20

$16

Wall Art - Painting - Chicago Flag Watercolor by Mike Maher

Chicago Flag Watercolor Painting

Mike MaherArrow Down

$16

$13

Wall Art - Painting - Impressions of Chicago by Robert Reeves

Impressions of Chicago Painting

Robert ReevesArrow Down

$37

$30

Wall Art - Painting - Chicago Illinois Skyline by Bri Buckley

Chicago Illinois Skyline Painting

Bri BuckleyArrow Down

$20

$16

Wall Art - Painting - Chicago Flag by Mike Maher

Chicago Flag Painting

Mike MaherArrow Down

$17

$14

Wall Art - Painting - Chicago City Skyline #6 by Bri Buckley

Chicago City Skyline #6 Painting

Bri BuckleyArrow Down

$20

$16

Wall Art - Painting - Chicago Skyline #1 by Bri Buckley

Chicago Skyline #1 Painting

Bri BuckleyArrow Down

$20

$16

Wall Art - Painting - Chicago Illinois Skyline #4 by Bri Buckley

Chicago Illinois Skyline #4 Painting

Bri BuckleyArrow Down

$20

$16

Wall Art - Painting - Spring Serenity by Doug Kreuger

Spring Serenity Painting

Doug KreugerArrow Down

$32

$26

Wall Art - Painting - Chicago Illinois Skyline #4 by Bri Buckley

Chicago Illinois Skyline #4 Painting

Bri BuckleyArrow Down

$20

$16

Wall Art - Painting - Chicago City Skyline #1 by Bri Buckley

Chicago City Skyline #1 Painting

Bri BuckleyArrow Down

$20

$16

Wall Art - Painting - Chicago Illinois Skyline by Bri Buckley

Chicago Illinois Skyline Painting

Bri BuckleyArrow Down

$20

$16

Wall Art - Painting - Urban Renewal II by Shadia Derbyshire

Urban Renewal II Painting

Shadia DerbyshireArrow Down

$37

$30

Wall Art - Painting - Chicago Skyline by Bri Buckley

Chicago Skyline Painting

Bri BuckleyArrow Down

$20

$16

Wall Art - Painting - Hey Chicago Vintage by Michael Mullan

Hey Chicago Vintage Painting

Michael MullanArrow Down

$18

$14

Wall Art - Painting - Chicago City Skyline #3 by Bri Buckley

Chicago City Skyline #3 Painting

Bri BuckleyArrow Down

$20

$16

Wall Art - Painting - Chicago Illinois Skyline #2 by Bri Buckley

Chicago Illinois Skyline #2 Painting

Bri BuckleyArrow Down

$20

$16

Wall Art - Painting - Chicago Illinois Skyline #1 by Bri Buckley

Chicago Illinois Skyline #1 Painting

Bri BuckleyArrow Down

$20

$16

Wall Art - Painting - Chicago Ilinois Skyline by Bri Buckley

Chicago Ilinois Skyline Painting

Bri BuckleyArrow Down

$20

$16

Wall Art - Painting - Windy City Autumn by Johnathan Harris

Windy City Autumn Painting

Johnathan HarrisArrow Down

Print:

$36

$29

Original:

$2,400

Wall Art - Painting - Chicago Skyline by Bri Buckley

Chicago Skyline Painting

Bri BuckleyArrow Down

$20

$16

Wall Art - Painting - Chicago Illinois #1 by Bri Buckley

Chicago Illinois #1 Painting

Bri BuckleyArrow Down

$20

$16

Wall Art - Painting - Chicago Illinois by Bri Buckley

Chicago Illinois Painting

Bri BuckleyArrow Down

$20

$16

Wall Art - Painting - Chicago Illinois Skyline #3 by Bri Buckley

Chicago Illinois Skyline #3 Painting

Bri BuckleyArrow Down

$20

$16

Wall Art - Painting - Chicago Skyline II by Sparx Studio

Chicago Skyline II Painting

Sparx StudioArrow Down

$14

$11

Wall Art - Painting - Chicago Skyline I by Dan Meneely

Chicago Skyline I Painting

Dan MeneelyArrow Down

$22

$18

Wall Art - Painting - Chicago City Skyline by Naxart Studio

Chicago City Skyline Painting

Naxart StudioArrow Down

$22

$18

Wall Art - Painting - Chicago Skyline Red by Naxart Studio

Chicago Skyline Red Painting

Naxart StudioArrow Down

$22

$18

Wall Art - Painting - Retro Travel Poster Chicago by Debbie DeWitt

Retro Travel Poster Chicago Painting

Debbie DeWittArrow Down

$25

$20

Wall Art - Painting - Chicago Skyline Blue by Naxart Studio

Chicago Skyline Blue Painting

Naxart StudioArrow Down

$22

$18

Wall Art - Painting - Theatre District - Chicago by Ryan Radke

Theatre District - Chicago Painting

Ryan RadkeArrow Down

Print:

$22

$18

Original:

$260

Wall Art - Painting - Chicago Watercolor Skyline by Naxart Studio

Chicago Watercolor Skyline Painting

Naxart StudioArrow Down

$22

$18

Wall Art - Painting - Hey Chicago Crop Sp by Michael Mullan

Hey Chicago Crop Sp Painting

Michael MullanArrow Down

$18

$14

Wall Art - Painting - City In Green by Shadia Derbyshire

City In Green Painting

Shadia DerbyshireArrow Down

Print:

$37

$30

Original:

$300

Wall Art - Painting - Chicago Cityscape Abstract Watercolor Painting by Mounir Khalfouf

Chicago Cityscape Abstract Watercolor Painting Painting

Mounir KhalfoufArrow Down

$14

$11

Wall Art - Painting - Chicago Skyline by Avery Tillmon

Chicago Skyline Painting

Avery TillmonArrow Down

$18

$14

Wall Art - Painting - Golden Skyline II by Shadia Derbyshire

Golden Skyline II Painting

Shadia DerbyshireArrow Down

$37

$30

Wall Art - Painting - Chicago Air Balloon by Naxart Studio

Chicago Air Balloon Painting

Naxart StudioArrow Down

$22

$18

Wall Art - Painting - Chicago Skyline Yellow by Naxart Studio

Chicago Skyline Yellow Painting

Naxart StudioArrow Down

$22

$18

Wall Art - Painting - Golden Skyline III by Shadia Derbyshire

Golden Skyline III Painting

Shadia DerbyshireArrow Down

$37

$30

Wall Art - Painting - Chicago Skyline I by Sparx Studio

Chicago Skyline I Painting

Sparx StudioArrow Down

$14

$11

Wall Art - Painting - Chicago by Richard Wallich

Chicago Painting

Richard WallichArrow Down

$14

$11

Wall Art - Painting - Chicago Skyline IIi by Sparx Studio

Chicago Skyline IIi Painting

Sparx StudioArrow Down

$14

$11

Wall Art - Painting - Chicago Skyline II by Dan Meneely

Chicago Skyline II Painting

Dan MeneelyArrow Down

$22

$18

Wall Art - Painting - Urban Renewal I by Shadia Derbyshire

Urban Renewal I Painting

Shadia DerbyshireArrow Down

$37

$30

Wall Art - Painting - Wrigley Building by Paul Strahm

Wrigley Building Painting

Paul StrahmArrow Down

$32

$26

Wall Art - Painting - Chicago Skyline by Elise Palmigiani

Chicago Skyline Painting

Elise PalmigianiArrow Down

$22

$18

Wall Art - Painting - Los Angeles Skyline by Corporate Art Task Force

Los Angeles Skyline Painting

Corporate Art Task ForceArrow Down

Print:

$79

$63

Original:

$3,000

Wall Art - Painting - Autumn Serenity by Doug Kreuger

Autumn Serenity Painting

Doug KreugerArrow Down

$20

$16

Wall Art - Painting - Cityscape Green by Paul Brent

Cityscape Green Painting

Paul BrentArrow Down

$27

$22

Wall Art - Painting - Chicago Skyline Silhouette by Tom Shropshire

Chicago Skyline Silhouette Painting

Tom ShropshireArrow Down

$32

$26

Wall Art - Painting - Cityscape Orange by Paul Brent

Cityscape Orange Painting

Paul BrentArrow Down

$27

$22

Wall Art - Painting - Cityscape Blue by Paul Brent

Cityscape Blue Painting

Paul BrentArrow Down

$27

$22

Wall Art - Painting - Cityscape Red by Paul Brent

Cityscape Red Painting

Paul BrentArrow Down

$27

$22

Wall Art - Painting - Taking a moment, The Buckingham Fountain, Chicago by Paul Strahm

Taking a moment, The Buckingham Fountain, Chicago Painting

Paul StrahmArrow Down

$32

$26

Wall Art - Painting - premium Chicago Skyline by N Akkash

premium Chicago Skyline Painting

N AkkashArrow Down

$17

$14

Wall Art - Painting - premium Chicago Downtown at Night by N Akkash

premium Chicago Downtown at Night Painting

N AkkashArrow Down

$17

$14

Wall Art - Painting - premium Chicago Downtown at Night #1 by N Akkash

premium Chicago Downtown at Night #1 Painting

N AkkashArrow Down

$17

$14

Wall Art - Painting - 'Hancock Skyline Panoramic building Chicago Business Sky Travel by N Akkash

'Hancock Skyline Panoramic building Chicago Business Sky Travel Painting

N AkkashArrow Down

$17

$14

Wall Art - Painting - Chicago by Illinois Central Rail Vintage Travel Poster by Vintage Travel Poster

Chicago by Illinois Central Rail Vintage Travel Poster Painting

Vintage Travel PosterArrow Down

$15

$12

Wall Art - Painting - Chicago Vintage Greyhound Travel Poster by Vintage Travel Poster

Chicago Vintage Greyhound Travel Poster Painting

Vintage Travel PosterArrow Down

$15

$12

Wall Art - Painting - Chicago by Mike Rabe

Chicago Painting

Mike RabeArrow Down

$22

$18

Wall Art - Painting - Ghost City by Shadia Derbyshire

Ghost City Painting

Shadia DerbyshireArrow Down

$37

$30

Wall Art - Painting - Boston City Collage 3 by Corporate Art Task Force

Boston City Collage 3 Painting

Corporate Art Task ForceArrow Down

Print:

$79

$63

Original:

$2,000

Wall Art - Painting - Twilight Serenity by Doug Kreuger

Twilight Serenity Painting

Doug KreugerArrow Down

$36

$29

Wall Art - Painting - Chicago at Night by Jeffrey Kolker

Chicago at Night Painting

Jeffrey KolkerArrow Down

$27

$22

Wall Art - Painting - Chicago Harbor Light by Max Good

Chicago Harbor Light Painting

Max GoodArrow Down

Print:

$21

$17

Original:

$450

Wall Art - Painting - Chicago Skyline Abstract #2 by Bekim M

Chicago Skyline Abstract #2 Painting

Bekim MArrow Down

$22

$18

 

1 - 72 of 948 chicago skyline paintings for sale

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!