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 such as the Puritans when the Puritan movement was gaining strength. The trend to ignore Middleton as one of the great dramatists of the seventeenth century continued throughout the next two centuries. There were exceptions to this, however. For example, in his 1887 essay on Middleton for The Best Plays of the Old Dramatists, Algernon Charles Swinburne argues that Middleton is a "genius," and calls A Chaste Maid in Cheapside "a play of quite exceptional freedom and audacity, and certainly one of the drollest and liveliest that ever broke the bounds of propriety or shook the sides of merriment.’’

In fact, Middleton's works did not earn a substantial amount of critical attention until this century, and even then his image suffered from the fact that he often collaborated with others. Scholars still debate which of his plays Middleton wrote alone, which ones he wrote in collaboration, and which ones were actually written by others. For the most part, however, modern critics count Middleton as one of the great English dramatists and A Chaste Maid in Cheapside as one of the great English comedies. Many critics cite the play' s deft combination of comedy and tragedy, especially as it serves to highlight humanity's vices. F. R. Mulryne says in his 1979 entry on Middleton for British Writers, "The play's gusto and seriousness, combined, make it one of theater's richest statements on money, sex, and society.’’ Many critics note the realistic qualities of the play; it gives an astonishingly accurate portrayal of what real life was like for London citizens of the time. However, as Martin W. Sampson notes in his 1915 introduction to Masterpieces of the English Drama: Thomas Middleton, Middleton's realism differs from the realistic, or naturalistic, movement that took place at the turn of the twentieth century. Sampson says, "The Elizabethan with utter frankness reveals passions and prejudices, foolish, ignominious, or debasing, but he is free of bitterness and superiority.’’

In fact, the morality of the play—with its many tricks and deceptions—has elicited the most comment from critics. As Dorothy M. Farr notes of the play in her book Thomas Middleton and the Drama of Realism: A Study of Some of the Representative Plays, "We often meet greedy tricksters and false brides in Jacobean drama, but few so cleverly placed in relation to one another as these.’’ Critics offer several explanations of the immoral behavior in the play which has sometimes elicited negative comments from critics. In his book Thomas Middleton's City Comedies, Anthony Covatta sums up the sentiment from these critics. According to Covatta, ‘‘For them the play's world is a very dark one indeed, its characters completely lacking in moral and religious conviction and in normal human love.’’ Covatta is one of the critics who believes that the characters' motivations can be traced to a desire to help their families. Covatta says, ‘‘Characters step outside the boundaries of propriety and morality but do so because the real advantages to be gained outweigh the hypothetical benefits of maintaining sterile order.’’