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Chicago Paintings

Chicago Paintings

There is a lot to see and do in the Windy City of Chicago. From iconic sports teams to historic sites in American history, these paintings reflect both the lighter and darker moments of Chicago's history. They will accent your decoration in either the home or the office, all the while showcasing the people and culture of one of the best known cities in the world. Put one in your den to add some color.

1 - 72 of 3,062 chicago paintings for sale

Results: 3,062

Results: 3,062

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

Twilight Serenity II Painting

Doug KreugerArrow Down

$20

Wall Art - Painting - Jordan - The Best There Ever Was by Bobby Zeik

Jordan - The Best There Ever Was Painting

Bobby ZeikArrow Down

Print:

$17

Original:

$200

Wall Art - Painting - Hawks by Elliott Aaron From

Hawks Painting

Elliott Aaron FromArrow Down

$22

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

Chicago Cityscape- Art by Linda Woods Painting

Linda WoodsArrow Down

$22

Wall Art - Painting - Michael Jordan 2 by Paul Meijering

Michael Jordan 2 Painting

Paul MeijeringArrow Down

Print:

$27

Original:

$2,000

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

Chicago Skyline - John Hancock Tower Painting

Jeff PittmanArrow Down

Print:

$27

Original:

$850

Wall Art - Painting - Chicago El and Warehouse by Christopher Arndt

Chicago El and Warehouse Painting

Christopher ArndtArrow Down

$37

Wall Art - Painting - Chicago Skyline Black by Naxart Studio

Chicago Skyline Black Painting

Naxart StudioArrow Down

$22

Wall Art - Painting - Chicago by Naxart Studio

Chicago Painting

Naxart StudioArrow Down

$22

Wall Art - Painting - Simple Speak Chicago by Grace Pullen

Simple Speak Chicago Painting

Grace PullenArrow Down

$29

Wall Art - Painting - Chicago Cloud Gate 78 of 100 by W Michael Meyer

Chicago Cloud Gate 78 of 100 Painting

W Michael MeyerArrow Down

$27

Wall Art - Painting - Autumn Serenity II by Doug Kreuger

Autumn Serenity II Painting

Doug KreugerArrow Down

$20

Wall Art - Painting - Chicago Cloud Gate 77 of 100 by W Michael Meyer

Chicago Cloud Gate 77 of 100 Painting

W Michael MeyerArrow Down

$27

Wall Art - Painting - Chicago Pritzker Pavilion 64 of 100 by W Michael Meyer

Chicago Pritzker Pavilion 64 of 100 Painting

W Michael MeyerArrow Down

$27

Wall Art - Painting - Chicago The Hancock 66 of 100 by W Michael Meyer

Chicago The Hancock 66 of 100 Painting

W Michael MeyerArrow Down

$27

Wall Art - Painting - Chicago Shedd Aquarium 83 of 100 by W Michael Meyer

Chicago Shedd Aquarium 83 of 100 Painting

W Michael MeyerArrow Down

$27

Wall Art - Painting - Chicago Blackhawks logo by Elliott Aaron From

Chicago Blackhawks logo Painting

Elliott Aaron FromArrow Down

$22

Wall Art - Painting - Chicago Dance by Alejandro Flores

Chicago Dance Painting

Alejandro FloresArrow Down

Wall Art - Painting - Victory At Last - Cubs 2016 World Series Champions by Lourry Legarde

Victory At Last - Cubs 2016 World Series Champions Painting

Lourry LegardeArrow Down

$53

Wall Art - Painting - Chicago Cubs by Elliott Aaron From

Chicago Cubs Painting

Elliott Aaron FromArrow Down

$22

Wall Art - Painting - Chicago Theatre- Illinois by Ryan Fox

Chicago Theatre- Illinois Painting

Ryan FoxArrow Down

$37

Wall Art - Painting - Impressions of Chicago by Robert Reeves

Impressions of Chicago Painting

Robert ReevesArrow Down

$37

Wall Art - Painting - Meet Me Under The Marshall Field's Clock by Glenn Galen

Meet Me Under The Marshall Field's Clock Painting

Glenn GalenArrow Down

$37

Wall Art - Painting - Rush Hour 2 - Chicago by Ryan Radke

Rush Hour 2 - Chicago Painting

Ryan RadkeArrow Down

$22

Wall Art - Painting - Chicago Metra Train Downtown by Christopher Arndt

Chicago Metra Train Downtown Painting

Christopher ArndtArrow Down

$37

Wall Art - Painting - Chicago Cubs Wrigley Field by Christopher Arndt

Chicago Cubs Wrigley Field Painting

Christopher ArndtArrow Down

$37

Wall Art - Painting - Michael Jordan by Paul Meijering

Michael Jordan Painting

Paul MeijeringArrow Down

Print:

$27

Original:

$3,500

Wall Art - Painting - Bus Stop - Chicago by Ryan Radke

Bus Stop - Chicago Painting

Ryan RadkeArrow Down

Print:

$22

Original:

$230

Wall Art - Painting - Chicago Blackhawks by Tony Rubino

Chicago Blackhawks Painting

Tony RubinoArrow Down

Print:

$22

Original:

$1,400

Wall Art - Painting - Vintage Negro American League Baseball by David Hinds

Vintage Negro American League Baseball Painting

David HindsArrow Down

$18

Wall Art - Painting - Chicago River Boat Migration by Christopher Arndt

Chicago River Boat Migration Painting

Christopher ArndtArrow Down

$37

Wall Art - Painting - Spring Serenity by Doug Kreuger

Spring Serenity Painting

Doug KreugerArrow Down

$32

Wall Art - Painting - Chicago Franklin Street Bridge by Christopher Arndt

Chicago Franklin Street Bridge Painting

Christopher ArndtArrow Down

$37

Wall Art - Painting - One Way Street - Chicago by Ryan Radke

One Way Street - Chicago Painting

Ryan RadkeArrow Down

Print:

$22

Original:

$260

Wall Art - Painting - Santas On Parade - Chicago State Street by Glenn Galen

Santas On Parade - Chicago State Street Painting

Glenn GalenArrow Down

$32

Wall Art - Painting - Chicago Cubs at Wrigley Field - Chicago, Illinois by Paul Strahm

Chicago Cubs at Wrigley Field - Chicago, Illinois Painting

Paul StrahmArrow Down

$32

Wall Art - Painting - Michael Jordan by Maria Arango

Michael Jordan Painting

Maria ArangoArrow Down

Print:

$24

Original:

$1,500

Wall Art - Painting - Buckingham Fountain Vintage Travel Poster by Studio Grafiikka

Buckingham Fountain Vintage Travel Poster Painting

Studio GrafiikkaArrow Down

$20

Wall Art - Painting - Rush Hour - Chicago by Ryan Radke

Rush Hour - Chicago Painting

Ryan RadkeArrow Down

Print:

$22

Original:

$260

Wall Art - Painting - Frank Lloyd Wright Robie House by Christopher Arndt

Frank Lloyd Wright Robie House Painting

Christopher ArndtArrow Down

$37

Wall Art - Painting - Art Institute in Chicago by Christopher Arndt

Art Institute in Chicago Painting

Christopher ArndtArrow Down

$37

Wall Art - Painting - Downtown Chicago by Ryan Radke

Downtown Chicago Painting

Ryan RadkeArrow Down

Print:

$22

Original:

$440

Wall Art - Painting - Chicago, vacation city, areal view on the beach by Long Shot

Chicago, vacation city, areal view on the beach Painting

Long ShotArrow Down

$17

Wall Art - Painting - Chicago railway, steam trains by Long Shot

Chicago railway, steam trains Painting

Long ShotArrow Down

$17

Wall Art - Painting - Chicago, world's fair, vintage travel poster by Long Shot

Chicago, world's fair, vintage travel poster Painting

Long ShotArrow Down

$17

Wall Art - Painting - Windy City Autumn by Johnathan Harris

Windy City Autumn Painting

Johnathan HarrisArrow Down

Print:

$36

Original:

$2,400

Wall Art - Painting - Martin Luther King Jr. painting by Suzann Sines

Martin Luther King Jr. painting Painting

Suzann SinesArrow Down

Print:

$19

Original:

$210

Wall Art - Painting - Ernie Banks Portrait by Suzann Sines

Ernie Banks Portrait Painting

Suzann SinesArrow Down

Print:

$19

Original:

$140

Wall Art - Painting - Chicago Gotham City Skyline Black and White Panorama by Christopher Arndt

Chicago Gotham City Skyline Black and White Panorama Painting

Christopher ArndtArrow Down

$41

Wall Art - Painting - Oriental Theater - Chicago by Ryan Radke

Oriental Theater - Chicago Painting

Ryan RadkeArrow Down

Print:

$22

Original:

$440

Wall Art - Painting - Hoochie Coochie Man by Paul Lovering

Hoochie Coochie Man Painting

Paul LoveringArrow Down

$22

Wall Art - Painting - Chicago, big city by Long Shot

Chicago, big city Painting

Long ShotArrow Down

$17

Wall Art - Painting - Chicago, world fair, vintage travel poster by Long Shot

Chicago, world fair, vintage travel poster Painting

Long ShotArrow Down

$17

Wall Art - Painting - Christmas - Meet Me Under The Marshall Fields Clock at Christmas by Glenn Galen

Christmas - Meet Me Under The Marshall Fields Clock at Christmas Painting

Glenn GalenArrow Down

$37

Wall Art - Painting - Chicago Theatre Marquee Sign by Christopher Arndt

Chicago Theatre Marquee Sign Painting

Christopher ArndtArrow Down

$37

Wall Art - Painting - Chicago City Skyline by Naxart Studio

Chicago City Skyline Painting

Naxart StudioArrow Down

$22

Wall Art - Painting - Holiday Time at Carsons - State Street Chicago by Glenn Galen

Holiday Time at Carsons - State Street Chicago Painting

Glenn GalenArrow Down

$32

Wall Art - Painting - State Street Snow by Glenn Galen

State Street Snow Painting

Glenn GalenArrow Down

$32

Wall Art - Painting - Chicago Skyline Red by Naxart Studio

Chicago Skyline Red Painting

Naxart StudioArrow Down

$22

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

Retro Travel Poster Chicago Painting

Debbie DeWittArrow Down

$25

Wall Art - Painting - Chicago Skyline Blue by Naxart Studio

Chicago Skyline Blue Painting

Naxart StudioArrow Down

$22

Wall Art - Painting - Al Capone Watercolor by Naxart Studio

Al Capone Watercolor Painting

Naxart StudioArrow Down

$22

Wall Art - Painting - Buddy Guy by Art

Buddy Guy Painting

Art Arrow Down

$20

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

Theatre District - Chicago Painting

Ryan RadkeArrow Down

Print:

$22

Original:

$260

Wall Art - Painting - Busy City - Chicago by Ryan Radke

Busy City - Chicago Painting

Ryan RadkeArrow Down

Print:

$22

Original:

$440

Wall Art - Painting - Chicago Impressions by Ryan Radke

Chicago Impressions Painting

Ryan RadkeArrow Down

Print:

$22

Original:

$260

Wall Art - Painting - Chicago Watercolor Skyline by Naxart Studio

Chicago Watercolor Skyline Painting

Naxart StudioArrow Down

$22

Wall Art - Painting - Josh Gibson by Suzann Sines

Josh Gibson Painting

Suzann SinesArrow Down

$21

Wall Art - Painting - Art Institute in Chicago Lion by Christopher Arndt

Art Institute in Chicago Lion Painting

Christopher ArndtArrow Down

$37

Wall Art - Painting - Wrigley Field by Matt Gaudian

Wrigley Field Painting

Matt GaudianArrow Down

$17

Wall Art - Painting - Martin Luther King Jr Watercolor by Suzann Sines

Martin Luther King Jr Watercolor Painting

Suzann SinesArrow Down

Print:

$19

Original:

$140

Wall Art - Painting - Streets of Chicago by Naxart Studio

Streets of Chicago Painting

Naxart StudioArrow Down

$22

 

1 - 72 of 3,062 chicago paintings for sale

There is a lot to see and do in the Windy City of Chicago. From iconic sports teams to historic sites in American history, these paintings reflect both the lighter and darker moments of Chicago's history. They will accent your decoration in either the home or the office, all the while showcasing the people and culture of one of the best known cities in the world. Put one in your den to add some color.