Expo Chicago 2025

THE HOLE | Booth 339

April 24-27, 2025

The Hole is proud to announce our return to Expo Chicago. This year we present a solo booth by Chicago-born Caitlin Cherry. The centerpiece of the booth (above) is Cherry’s freestanding painting within a metal sculpture “Bruja Cybernetica”. The fair is its final stop after appearing in “The Culture: Hip Hop and Contemporary Art in the 21st Century” at The Baltimore Museum of Art, the Saint Louis Art Museum and Art Gallery of Ontario. The walls of the booth feature new paintings by Cherry: centering femme entertainers and musicians as her muses, Cherry depicts popular radical aesthetics within the global Black diaspora. Our booth installation features foam soundproofing, a nod to the recording studio setting these female musicians inhabit.

Caitlin Cherry (b. 1987 Chicago), a painter of cyber-multitudes, draws on painting, sculpture and installation in her multifaceted practice, coalescing into articulate and alluring representations of Black femininity. Resisting easy placement in the cultural marketplace of hot-takes—these paintings decline respectability politics in favor of a nuanced and unabashedly sexy assessment of online drama, distortion and desire. Cherry’s work features larger-than-life subjects: Black femme figures, drawn from an image culture that thrives on appropriating these women’s likeness while rarely crediting their creativity. These women’s bodies are overlaid with cryptic alphanumeric symbols—kaleidoscopic incursions that refer back to the codes and algorithms that power our media landscape, fueling the algorithmic tools of Black culture’s dissemination and extraction.

HOURS

Thursday, April 24th: VIP Preview: 12–8pm
Friday, April 25th: 11am–7pm
Saturday, April 26th: 11am–7pm
Sunday, April 27th: 11am–6pm

LOCATION

Navy Pier in the Festival Hall, 600 E Grand Ave, Chicago IL 60611

For more information on attending EXPO CHICAGO, click HERE.

Caitlin Cherry, Bruja Cybernetica, 2022, oil on canvas, 57.6 x 102.5 inches, 146.3 x 260.4 cm

Caitlin Cherry, Byford Dolphin, 2025, oil on canvas, 56.5 x 56.5 inches, 143.5 x 143.5 cm

Caitlin Cherry, Plosives and Fricatives, 2025, oil collage on canvas, 57 x 57 inches, 145 x 145 cm

Caitlin Cherry, Baby Barracuda, 2025, oil on canvas, 24 x 18 inches, 61 x 46 cm

Caitlin Cherry, Black Snapper, 2025, oil on canvas, 24 x 18 inches, 61 x 46 cm