Paint Southport 2020 was a one-day plein air event on October 10, 2020, featuring Chicago-area artists drawing and painting the fall afternoon scenery along Southport Avenue in Chicago.

Paint Southport 2020 was a one-day plein air timed art event held on October 10, 2020. It featured 12 Chicago-area artists drawing and painting the fall afternoon scenery along Southport Avenue in Chicago, between Grace and Roscoe Streets. The artist entrants selected from an online application administered through the EntryThingy Company, a popular artist online application platform. Paint Southport took place on a sunny fall Saturday afternoon. The combination of beautiful weather, fall foliage, and the Dine Out Southport street closure between Grace and Waveland Streets helped make this first-time plein air competition a memorable and successful event. Participants included students, professional artists, and members of the arts organizations Plein Air Painters of Chicago and the Palette and Chisel Academy of Fine Arts.

The public watched as the artists set-up and painted the neighborhood scenery in a 7-block area in real time, from 1:00–4:00 p.m. Visitors to the area and the Dine Out Southport location were able to watch the artists’ creative process, enjoying the neighborhood scenery and watching how the artists interpret it. At 4:00 p.m., artists put down their brushes, and with the help of event staff, framed their work, and brought it to the original check-in location at the Southport branch of Fifth Third Bank. Their work was judged for four awards: Best of Show; Second Place; Honorable Mention; and a “People’s Choice” award that was voted on during the event by event visitors and Lakeview neighbors. Finished paintings on display at the end of the event were available for sale by the artists directly to the public.

AWARD WINNERS
Best in Show: Luna Prysiazhniuk, View of the Brown Line
Second Place: Christina Body, Music Box Theatre
Honorable Mention: Maggie Hubbard, Mercury Theatre
"People's Choice": Kuhn Hong, Walking by Music Box Theatre