In A Chaste Maid in Cheapside, almost every character is either wed or seeking marriage. The main conflict centers on the planned marriage between Sir Walter and Moll Yellowhammer. Sir Walter consents to marry Moll in return for arranging a marriage between Tim Yellowhammer and his so-called "niece." This initial setup introduces the first layer of deceit. While Moll is genuinely a chaste maid, as the title implies, Sir Walter’s "niece" is, in truth, a prostitute, far from the Welsh gentlewoman she pretends to be. While journeying into Cheapside with this woman, Sir Walter instructs her in her deception, saying, "Here you must pass for a pure virgin." Sir Walter also misleads the Allwits by concealing his marriage plans, knowing they would try to stop it to preserve his financial support as an unmarried man. When Davy informs Allwit of Sir Walter's plan to marry Moll, Allwit hastily departs, exclaiming, "I have no time to stay, nor scarce to speak, / I'll stop those wheels, or all the work will break." By this, he means the effort he and his wife have invested in benefiting from Sir Walter.

Though Sir Walter intends to marry Moll, she is genuinely in love with Touchwood Junior and wishes to marry him instead. Their attempts to marry are continually thwarted. Initially, Touchwood Junior tricks Moll's father, a goldsmith, into crafting the ring he intends to use in their marriage. Boldly, he tells Yellowhammer that the ring is for eloping with a man's daughter. However, Yellowhammer, unaware he is the father in question, criticizes such oblivious parents, saying, "And parents blinded so, but they're served right / That have two eyes, and wear so dull a sight." Yellowhammer interrupts Moll and Touchwood Junior's wedding just in time to stop the parson from completing the ceremony. From that point on, the Yellowhammers confine Moll until her wedding to Sir Walter. Yellowhammer declares, "In the meantime, I will lock up this baggage, / As carefully as my gold." Despite their efforts, Moll escapes once more with help but is forcibly brought back by her mother. Pretending to be gravely ill, Moll "dies."

Moll's parents are so focused on arranging Tim's marriage to a Welsh gentlewoman that they miss the funeral where Moll and Touchwood Junior rise from their coffins and get married. The parson announces, "Hands join now, but hearts for ever, / Which no parent's mood shall sever." Surprisingly, the Yellowhammers remain calm and supportive of the union, especially after they learn that Sir Walter is imprisoned for debt and Tim has unknowingly married Sir Walter's prostitute. Yellowhammer laments, "My poor boy Tim is cast away this morning, / Even before breakfast: married a whore." Tim is also upset until his mother reminds him of his previous words, saying, "You told me once, by logic you would prove / A whore an honest woman, prove her so Tim." Accepting the challenge, Tim begins his reasoning, but his new wife quickly counters, asserting, "Sir if your logic cannot prove me honest, / There's a thing called marriage, and that makes me honest." In the end, both marriages conclude happily.

Alongside its emphasis on marriage, the play is rife with references to sexual themes, particularly affairs outside of marriage. Several male characters, as well as a few female characters, partake in these extramarital liaisons. During the seventeenth century, when a man had an affair with another man's wife, it was said that he had cuckolded the husband. This concept of cuckoldry, often depicted with horns on the husband's head, served as a comedic element in plays of this nature. In this play, both Mr....

Sir Kix is unaware of being cuckolded, yet he inadvertently alludes to it at times. In one particular instance, Touchwood Senior, known for his exceptional fertility and intending to impregnate the childless Lady Kix, plans to attribute her pregnancy to a sham fertility potion he sells to her husband. He asks Sir Oliver if he remembers their arrangement. Sir Oliver replies, "Or else I had a bad head," a comment that might suggest memory issues. However, others might interpret it as a nod to the metaphorical cuckold's horns that Sir Oliver is about to gain.
Besides the themes of marriage and sex, the characters are heavily focused on finances. Sir Walter anticipates acquiring a dowry of two thousand pounds by marrying Moll. Despite appearing financially secure, it is revealed by the play's conclusion that he has faced difficulties paying his debts. Yellowhammer points out that Sir Walter "lies i'th' knight's ward now." The knight's ward was a specific area in debtor's prison reserved for knights. Yellowhammer also notes, "His creditors are so greedy." Initially, it appears Sir Walter is interested in Moll mainly for her virginity, but it soon becomes evident that he also needs the dowry to settle his debts, many of which likely arise from supporting the Allwits. Through his ongoing affair with Mrs. Allwit, Sir Walter funds the upbringing of their children and all the Allwits' living expenses, significantly draining his resources. Ultimately, the Allwits leverage the property and possessions provided by Sir Walter to elevate their social status. Allwit comments, "We are richly furnished wife, with household stuff." Mrs. Allwit suggests they "let out lodgings then, / And take a house in the Strand." Essentially, they plan to rent out their current home in Cheapside and use the income to buy a more prestigious residence in London's Strand area.

Touchwood Senior and his wife also face financial concerns due to his extraordinary fertility, which results in more children than they can financially support. However, after convincing Sir Kix that his fertility water—and not an affair between Touchwood Senior and Lady Kix—led to her pregnancy, Sir Kix offers to provide for any children Touchwood Senior might have. Kix assures him, "Be not afraid to go to your business roundly, / Get children, and I'll keep them." From this moment, Touchwood Senior and his family no longer have financial worries.