Chicago’s art fairs and festivals range from events such as EXPO Chicago, which draws celebrity artists, contemporary art collectors, and galleries around the world to Navy Pier, to festivals in the neighborhoods, such as the Ravenswood ArtWalk, that allow the public to view artwork in local artists’ studios. A variety of events fall in between these two extremes, including celebrations of student work, such as Columbia College’s Manifest Festival and Chicago Park District events such as the Festival of Arts.
And then there are visual art festivals such as the 57th Street Art Fair and Old Town Art Fair - the city's oldest art fairs. Each of these draws tens of thousands of art lovers to Chicago neighborhoods to enjoy the work of artists from around the United States who have been selected by a jury of artists, gallerists, and museum workers. What all these varied events have in common is that the art fairs are focused on personal exchange between the artists and the public that has come to purchase their work.

Chicago has long been a city friendly to artists, with strong fine and commercial art education programs, intelligent and independently-minded art collectors, and a variety of industries that support working artists, including advertising, design, and publishing. By the late 1940s and early 1950s, when art fairs started to be organized in the city, the GI Bill and the city’s strong Works Progress Administration’s Federal Art Project had drawn young artists to the Institute of Design and the School of the Art Institute of Chicago.
However, there were few galleries in Chicago showing contemporary work by local artists, and these student artists had few places to show their work, a problem that intensified when student work was banned from the Art Institute of Chicago’s annual juried exhibition of work by artists in Chicago and Vicinity in 1948. Art fairs provided artists with an opportunity to show their work and to explain their contemporary style and working methods to the public without mediation by galleries or museums. This public was eager to purchase artworks to decorate their homes in new housing developments such as Lake Meadows in Bronzeville or Sandburg Village in Old Town. 

As these events became commercially successful, art fairs spread to new neighborhoods and took on new purposes. Margaret Burroughs, a Chicago artist and co-founder of the DuSable Black History Museum and Education Center, went on to establish art fairs that would highlight the work of local African American artists and encourage the development of local collections of African American art. Some art fairs developed as business organizations with the intention to draw crowds to their neighborhoods. Others developed as venues to highlight work created by students in gang-alternative programs, participants in Chicago Park District arts programs, or incarcerated people. 

During the 1970s, art fairs became so prolific and profitable for artists that annual guides were published to help artists place their work; these contained audience counts and information on the price to exhibit in art fairs. Soon after, companies such as Highland Park’s Amdur Productions were founded to take on the organization and promotion of art fairs, leading to a shift away from many of the volunteer-led neighborhood events of the mid-20th century. Today, art fairs remain a highlight of summer in Chicago, providing new and evolving spaces for artists and the public to meet.