Paint Southport 2021 was a one-day plein air conpetition on August 21, 2021, featuring Chicago-area artists drawing and painting the summer scenery along Southport Avenue in Chicago.

Twelve Chicago-area artists were selected from the online entry to draw and paint the afternoon scenery along Southport Avenue in Chicago.

The public watched as the artists set-up to paint or draw the neighborhood scenery in an 8-block area (Southport Avenue from Byron to Roscoe) in real time, from 1:00-4:00 p.m. Together, artists and spectators were happily immersed in the creative process, enjoying the unique features of the Southport neighborhood, and watching how the artists interpret it. Visitors to the event happened upon artists working away in front of cafés, under the Music Box marquee, and under the busy El tracks, capturing the colorful and vibrant activities and goings-on, much as artists did 100 years ago in Paris. The steamy weather did not deter the artists’ creativity. A few passers-by decided to buy a work of art, while others were inspired to create!

Artists staked out their favorite spots, pre-sketched before the starting horn, and then live painting began in earnest with the starting horn at 1:00 p.m. At 4:00 p.m. sharp, all artists put down their brushes, framed their work, and carried it to the parking lot at 5/3 Bank at Addison and Southport, to be judged for four awards: Best of Show; Second Place; Honorable Mention; and a “People's Choice” award, voted on by over 65 event visitors using a handy online QR code. Artwork was reviewed by the judge both during its creation and in final form. Finished paintings on display at the end of the event's were available for sale directly to the public by the artists.

Paint Southport 2021 was presented by Spectra Fine Art, and sponsored by the Lakeview Roscoe Village Chamber of Commerce, with support from Chicago's Special Service Area 27 (SSA#27)

CLICK HERE to see last the Paint Southport 2020 winners,
and photos from the inaugural event.