The company's founding artistic director Barbara Gaines formed the theater in 1986, when it began performances on the roof of the Red Lion Pub in the city's Lincoln Park neighborhood.

In 1999, the company received permission to build its permanent home: a two-venue facility at Navy Pier.

The move was accompanied by a public relations blitz, which even involved Mayor Richard M. Daley naming April 23, 1997, as Shakespeare Repertory Day.

The company began a large-scale capital campaign to finance the move, and opened its 1999-2000 season in its new, state-of-the-art facility.

The 510-seat Courtyard Theater, which is the primary production venue for CST, features state-of-the-art technology and acoustics together with a versatile thrust stage and deep proscenium, that create a flexible performance space.