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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 4,812 chicago paintings for sale

Results: 4,812

Results: 4,812

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

Jordan - The Best There Ever Was Painting

Bobby ZeikArrow Down

Print:

$17

$14

Original:

$200

Wall Art - Painting - Twilight Serenity II by Doug Kreuger

Twilight Serenity II Painting

Doug KreugerArrow Down

$20

$16

Wall Art - Painting - Hawks by Elliott Aaron From

Hawks Painting

Elliott Aaron FromArrow Down

$22

$18

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 - Michael Jordan 2 by Paul Meijering

Michael Jordan 2 Painting

Paul MeijeringArrow Down

Print:

$27

$22

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

$22

Original:

$850

Wall Art - Painting - Chicago Skyline Black by Naxart Studio

Chicago Skyline Black Painting

Naxart StudioArrow Down

$22

$18

Wall Art - Painting - Chicago by Naxart Studio

Chicago Painting

Naxart StudioArrow Down

$22

$18

Wall Art - Painting - Simple Speak Chicago by Grace Pullen

Simple Speak Chicago Painting

Grace PullenArrow Down

$29

$23

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

$22

Wall Art - Painting - Autumn Serenity II by Doug Kreuger

Autumn Serenity II Painting

Doug KreugerArrow Down

$20

$16

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

$22

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

$22

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

$22

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

$22

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

Chicago Blackhawks logo Painting

Elliott Aaron FromArrow Down

$22

$18

Wall Art - Painting - Chicago Dance by Alejandro Flores

Chicago Dance Painting

Alejandro FloresArrow Down

Wall Art - Painting - Chicago Flag Watercolor by Mike Maher

Chicago Flag Watercolor Painting

Mike MaherArrow Down

$16

$13

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

$52

$42

Wall Art - Painting - Chicago Cubs by Elliott Aaron From

Chicago Cubs Painting

Elliott Aaron FromArrow Down

$22

$18

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

Chicago Theatre- Illinois Painting

Ryan FoxArrow Down

$37

$30

Wall Art - Painting - Impressions of Chicago by Robert Reeves

Impressions of Chicago Painting

Robert ReevesArrow Down

$37

$30

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

Rush Hour 2 - Chicago Painting

Ryan RadkeArrow Down

$22

$18

Wall Art - Painting - Chicago Illinois Skyline by Bri Buckley

Chicago Illinois Skyline Painting

Bri BuckleyArrow Down

$20

$16

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

$30

Wall Art - Painting - Chicago Flag by Mike Maher

Chicago Flag Painting

Mike MaherArrow Down

$17

$14

Wall Art - Painting - Michael Jordan by Paul Meijering

Michael Jordan Painting

Paul MeijeringArrow Down

Print:

$27

$22

Original:

$3,500

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

Chicago City Skyline #6 Painting

Bri BuckleyArrow Down

$20

$16

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

Bus Stop - Chicago Painting

Ryan RadkeArrow Down

Print:

$22

$18

Original:

$230

Wall Art - Painting - Colorful Saxophone by Sharon Cummings by Sharon Cummings

Colorful Saxophone by Sharon Cummings Painting

Sharon CummingsArrow Down

$26

$21

Wall Art - Painting - Chicago Blackhawks by Tony Rubino

Chicago Blackhawks Painting

Tony RubinoArrow Down

Print:

$22

$18

Original:

$1,400

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

Chicago Illinois Skyline #4 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 3 by Richard Wallich

Chicago 3 Painting

Richard WallichArrow Down

$14

$11

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

Vintage Negro American League Baseball Painting

David HindsArrow Down

$18

$15

Wall Art - Painting - Spring Serenity  by Doug Kreuger

Spring Serenity Painting

Doug KreugerArrow Down

$32

$26

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

One Way Street - Chicago Painting

Ryan RadkeArrow Down

Print:

$22

$18

Original:

$260

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

Chicago Illinois Skyline #4 Painting

Bri BuckleyArrow Down

$20

$16

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

Santas On Parade - Chicago State Street Painting

Glenn GalenArrow Down

$32

$26

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

Buckingham Fountain Vintage Travel Poster Painting

Studio GrafiikkaArrow 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 Flag by Ryan Fowler

Chicago Flag Painting

Ryan FowlerArrow Down

$18

$14

Wall Art - Painting - Michael Jordan by Maria Arango

Michael Jordan Painting

Maria ArangoArrow Down

Print:

$24

$19

Original:

$1,500

Wall Art - Painting - Chicago Hand Made by Art Of The Cigar

Chicago Hand Made Painting

Art Of The CigarArrow Down

$14

$11

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

$26

Wall Art - Painting - Chicago Illinois Skyline by Bri Buckley

Chicago Illinois Skyline Painting

Bri BuckleyArrow Down

$20

$16

Wall Art - Painting - Chicago Skyline by Bri Buckley

Chicago Skyline Painting

Bri BuckleyArrow Down

$20

$16

Wall Art - Painting - Wabash and Washington, Chicago by Paul Strahm

Wabash and Washington, Chicago Painting

Paul StrahmArrow Down

$32

$26

Wall Art - Painting - Hey Chicago Vintage by Michael Mullan

Hey Chicago Vintage Painting

Michael MullanArrow Down

$18

$14

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

Rush Hour - Chicago Painting

Ryan RadkeArrow Down

Print:

$22

$18

Original:

$260

Wall Art - Painting - Chicago's Navy Pier - Chicago, Illinois by Paul Strahm

Chicago's Navy Pier - Chicago, Illinois Painting

Paul StrahmArrow Down

$32

$26

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

Chicago City Skyline #3 Painting

Bri BuckleyArrow Down

$20

$16

Wall Art - Painting - dugout by Norman Rockwell

"dugout" Painting

Norman RockwellArrow Down

$27

$22

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

$14

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 - Chicago 4 by Richard Wallich

Chicago 4 Painting

Richard WallichArrow Down

$14

$11

Wall Art - Painting - Downtown Chicago by Ryan Radke

Downtown Chicago Painting

Ryan RadkeArrow Down

Print:

$22

$18

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

$14

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

Chicago railway, steam trains Painting

Long ShotArrow Down

$17

$14

Wall Art - Painting - Chicago, The Loop by Stanton Manolakas

Chicago, The Loop Painting

Stanton ManolakasArrow Down

$14

$11

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 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 by Bri Buckley

Chicago Skyline Painting

Bri BuckleyArrow Down

$20

$16

Wall Art - Painting - Ernie Banks Portrait by Suzann Sines

Ernie Banks Portrait Painting

Suzann SinesArrow Down

Print:

$19

$15

Original:

$140

Wall Art - Painting - Mike by Richard Wallich

Mike Painting

Richard WallichArrow Down

$14

$11

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

Oriental Theater - Chicago Painting

Ryan RadkeArrow Down

Print:

$22

$18

Original:

$440

Wall Art - Painting - Hoochie Coochie Man by Paul Lovering

Hoochie Coochie Man Painting

Paul LoveringArrow Down

$22

$18

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

Chicago, big city Painting

Long ShotArrow Down

$17

$14

 

1 - 72 of 4,812 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.