Drag in the Windy City

Throughout its history, various neighborhoods in Chicago have been bastions of queer activity—from cruising for gay sex to establishments that catered to a queer (and often also criminal)—demographic. The map located on this site focuses on bars and clubs that featured drag performers and/or patrons, both male and female impersonators. Further, locations are indicated across the city that hosted the many drag balls that began in Chicago in 1901.

The Levee District

The location of First Ward Balls created by "Hinky Dink" Kenna and "Bathhouse John" Coughlin in 1896, this area contained hundreds of brothels and gambling establishments. Many historians attribute the beginning of the Chicago crime syndicate to Kenna and Coughlin, who were Aldermen from 1923 to 1938 and 1939 to 1946, respectively. The Levee, now known as the Loop, was densely populated and well known as a Vice District. Before attaining official political power, Kenna and Coughlin used the annual Balls to collect money from the illegal operations in exchange for protecting them from police raids. The First Ward Balls prominently featured female impersonators, but Kenna and Coughlin banned cross-dressers in 1909 to appease the Vice Commission and many historians claim the Balls ended in 1908. The Levve was essentially shut down through continued raids in the 1910, perhaps leading Kenna and Coughlin to puruse a more "legitimate" career path in politics.

Towertown

This neighborhood covered about one mile west of the Water Tower, the only structure that survived the Chicago fire of 1871. Also known as "the Quarter" and "the Village," the main streets included Wabash Avenue and Ohio, Erie, Huron, Superior, Pearson, Chestnut and State Street. Many arists settled in this area after the World's Columbian Exposition ended in 1894. Towertown was considered the “most vital literary and artistic upsurge in the history of the country” as well as a “haven for queer men” (Elledge, 65). The "Bohemian" residents of this neighborhood gathered for "radical meetings," many at the Dill Pickle Club, “what many considered to be the single most important site for both queer and non-queer people in Towertown in 1915” (71). The location also featured "masquerades," another term for cross-dressing. 

Towertown was a queer haven for cruising and social activity, with about 35 "pansy parlors" opening in July, 1929 alone (81). This rise of queer establishments coincided with rising property values and the development of luxury shops on Michigan Avenue, making it difficult for artists and queers alike to continue to live in Towertown. In its prime, the slogan for Towertown was "Gin, din and sin for a fin" (77). By the time the Century of Progress International Exposition was held in Chicago in 1933-1934, Towertown had become essentially a spot for tourists. 

Bronzeville

On the South Side of Chicago, this neighborhood between 31st Street on the north and Pershing Road to the south was a destination for many black citizens during the Great Migration. One of the few areas in the city that allowed for black home ownership, Bronzeville featured many black-owned business and clubs, with South State Street functioning as "the Stroll" with its many shops and music venues. Unlike Towertown, the establishments that featured cross-dressing also generally welcomed black and white patrons; these clubs were referred to as "black and tans" (Elledge, 103). Many female impersonators shared a stage with blues performers like Jelly Roll Morton, Louis Armstrong, Fats Waller, and Cab Calloway (142). Bronzeville generally accepted queer men and women, as long as they were performers, the list including Tony Jackson, and Frankie "Half Pint" Jaxon, who performed as a woman singing falsetto. Jaxon is credited with creating the term "rock and roll," hosted a popular radio show, created the song "I'm So Happy I'm Brown Skin," and was the only performer of color and female impersonator hired for the 1933 Chicago World's Fair (166-167). 

Many female impersonators adapted the names of famous white actresses. For example, "Sepia Gloria Swanson," who performed at the Cabin Inn before beginning her own club, Gloria's, on East 35th Street. Other cabarets, like the Plantation Cafe and Joe's DeLuxe, also hosted drag shows, bringing together heterosexual, queer, black and white patrons. However, queer people of color were not afforded the same freedom of movement that extended to white queer men during the pansy craze. Police raids moved south from Towertown to Bronzeville in the 1940s, ostensibly ostcracizing queer establishements from this neighborhood when they were no longer profitable.