If you're looking for both affordable and investment art by well-known artists, Printworks is the place to go. They've been in Chicago for almost 30 years.
The gallery sells limited editions by many prominent artists: Leon Golub, Philip Pearlstein, Richard Hunt, Audrey Niffenegger, and more. They also have a collection of artworks available for $300 or less. The Tony Fitzpatrick prints shown here fall within the more expensive category, but we've rounded up some affordable picks below...

Top: Tony Fitzpatrick, O and H

Left: Audrey Niffeneger, Siamese Death, Edition of 200, 10 x 6 inches, $150
Right: Daniel Leary, Stump, Edition of 30, 7.5 x 5.5 inches, $150

Harvey Daniels, Static, Edition of 30, 7.5 x 10.75 inches, $200

Left: Bruce Thayer, Good Guy, Edition of 4, 22 x 15 inches, $275
Right: Ray Martin, Dress Code, Edition of 12, 20 x 15 inches, $250

Jim Koss, Ghost Play, Ink and Watercolor, 6.5 x 7.5 inches, $300
The small River North gallery carries both limited editions and originals. Their focus is prints and drawings, and they also have an extensive catalog of art books for sale. To view more affordable art from Printworks online, click here. To see their roster of artists, click here.
Tony Fitzpatrick = cool.
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Boy, I really love that Harvey Daniels print, and his others on the "Affordable" webpage. They have a great mid-C flair and color and would be perfect in my office. They are just expensive enough to cause serious internal tsuris about whether I should splurge for one or not. Thanks for posting this, though. It's a wonderful resource for not-run-of-the-mill decoration.
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SOMEWHAT UNRELATED BUT INTERESTING UPDATE IN CHICAGO ART SCENE --- there is a new non-denominational, Christian church at the corner of Avers and Irving Park Road called Tapestry. Mark Johnson is the pastor and he has very innovative ideas on how to draw his community together. He offers GALLERY ART SHOWINGS now and then. Sorry, I don't have the phone number, but I'm sure you can find it at superpages.com or some such place.
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