By the time Middleton wrote the play in the early 1610s, most of his comedies had been performed in front of private audiences. However, A Chaste Maid in Cheapside was written and performed for a popular audience. Charles Barber says in his critical introduction to the University of California Press version of the play, "This may help to explain the richness and exuberance of the play compared with its predecessors, and the fuller and more sympathetic handling of the romantic lovers."

In his own time, Middleton was a popular playwright with audiences, but was not held in as high esteem critically as was William Shakespeare, Ben Jonson, and other major playwrights of the Elizabethan and Jacobean time periods. Despite this fact, A Chaste Maid in Cheapside would certainly have been seen as a daring play in its time since it harshly satirized religious hypocrisy among groups...