Visual arts of Chicago refers to paintings, prints, illustrations, textile art, sculpture, ceramics and other visual artworks produced in Chicago or by people with a connection to Chicago. Since World War II, Chicago visual art has had a strong individualistic streak, little influenced by outside fashions. "One of the unique characteristics of Chicago," said Pennsylvania Academy of Fine Arts curator Bob Cozzolino, "is there's always been a very pronounced effort to not be derivative, to not follow the status quo." The Chicago art world has been described as having "a stubborn sense ... of tolerant pluralism." However, Chicago's art scene is "critically neglected." Critic Andrew Patner has said, "Chicago's commitment to figurative painting, dating back to the post-War period, has often put it at odds with New York critics and dealers." It is argued that Chicago art is rarely found in Chicago museums; some of the most remarkable Chicago artworks are found in other cities (such as the brilliantly warped epic drawings of Henry Darger at the American Folk Art Museum in New York City, or Carlos Cortez' collection of early 20th-century Chicago "Wobbly" (Industrial Workers of the World) woodcut prints, now in the Walter P. Reuther Library at Wayne State University in Detroit).

The School of the Art Institute of Chicago was founded in 1879, from the remains of the Chicago Academy of Design, an earlier school founded in 1866 (thus the school predates the museum of the same name). Early students and faculty were conservative and derivative in their tastes, imitating popular European models. Arthur B. Davies, a former SAIC student and one of "the Eight" was considered a disappointment for being a member of a radical group of urban modernists. In 1913, SAIC students held a protest with costumes and bonfires against the Chicago showing of the Armory Show, a collection of the best new modern art; the newspapers described the students' activity as a riot.

Only a year later the African-American realist Archibald J. Motley, graduated from the School of the Art Institute of Chicago; he kept his modern, jazz-influenced paintings secret for some years after.

For many years the Art Institute of Chicago regularly held annual exhibits of local artists, but these ended decades ago. Mary Agnes Yerkes, (1886–1989), was an American Impressionist painter and one such exhibitor at AIC from 1912-1915. Born in Oak Park, she studied at the Chicago Academy of Fine Arts, where she also taught, and then at the currently named School of the Art Institute of Chicago. She is noted for her plein-air painting while camping the American West and its National Parks.

The time period between the World Wars witnessed an outpouring of artistic creativity in Chicago, led by artists of the caliber of Stanislav Szukalski, Todros Geller and Albin Polasek.

The Chicago art scene was not strictly an all-boys club however; Sr. Maria Stanisia was able to overcome the patriarchal attitudes both within early 20th century Chicago and the hierarchy of the Roman Catholic Church to become acclaimed as one of the greatest painters in the field of religious art. Another woman artist Gertrude Abercrombie who like Stanisia attended the School of the Art Institute of Chicago, sold her surrealist paintings in art fairs that took place near the Art Institute of Chicago.

Early evidence of Chicago's unique style came with Ivan Albright, with his "excruciatingly detailed surfaces depicting things in states of decay." Eldzier Cortor documented African-American life for the WPA. Vera Berdich, an influential surrealist printmaker, taught many future Chicago Imagists at the School of the Art Institute of Chicago.

Claes Oldenburg was born in Sweden and only spent a few years in the 1950s in Chicago, but he sold his first works here, 5 pieces at the 57th Street Art Fair for $25.