Cheesman was born in England, likely about 1598, but the date and place of his birth and the names of his parents are not known. Contemporaries spelled his surname in a variety of ways, the most common being Cheesman and Chisman. Families with those names resided in the county of Kent and elsewhere near London, and it is likely that he was a member of one of them. He may have been the John Cheesman who married Anne Willett in the parish of Saint Saviour’s, Southwark, in Surrey, on June 24, 1616. He became a merchant and probably established connections with other merchants before he traveled to Virginia in 1621 aboard the Flyinge Hart. He settled initially at Kiccoughtan (later Elizabeth City County), where he and two brothers resided. When Cheesman patented 200 acres of land near there in September 1624, he was identified as a gentleman and not long afterward as a lieutenant, classifications that suggest he arrived in Virginia with his social rank already established.
Cheesman married a second time, possibly in Virginia during the 1620s. The maiden name of his second wife, Margaret, is not recorded. They had at least one son. Through his marriage and the marriages of his brothers, Cheesman became related to other Virginia families that were prominent during the second quarter of the century, notably the Mason and Matthews families. He engaged in commerce between Virginia and England during the 1620s and moved to Charles River County (after 1643 York County) soon after that part of the colony was opened to settlement in 1630. Cheesman acquired more than 1,000 acres of land and lived on a 600-acre tract on what became known as Chisman Creek. He may have used his connections to other merchants to acquire the workers of African origin or descent who labored on his plantation alongside the white.
Cheesman was one of the first commissioners, or justices, of the peace for Charles River County and was a captain in the militia by 1637 and a lieutenant colonel by April 1652. He also served as aviewer in the county on January 6, 1640, and a tobacco collector in November 1648. Cheesman represented York County in the General Assembly that met on March 2, 1643, when for the first time burgesses and Council members met separately, and thus had the distinction of being a member of the first House of Burgesses. Incomplete records do not disclose whether that was his only service in the assembly before April 30, 1652, when the two houses elected him to the governor’s Council after the colony surrendered to Parliament following the conclusion of the . It is possible that Cheesman received the appointment because of his support of Parliament, his standing in York County, his mercantile connections, or some combination of the three. The scant surviving records do not reveal how long he served on the Council.
Cheesman returned to England, possibly after learning of the restoration of King Charles II in May 1660. He and his wife resided across the Thames River from London, in the parish of Saint Mary Magdalen, Bermondsey, in the county of Surrey. In August 1661 Cheesman executed a power of attorney authorizing Lawrence Smith, of York County, to lease his land in that county to his younger brother, Edmund Cheesman. In December 1663 Cheesman wrote a new will, leaving his English properties and his York County land to his wife and his land in Gloucester County to his young granddaughter, with a proviso that if she died without heirs, the land would descend to his nephews, one of whom, Edmund Cheesman, was a participant in(1676–1677). Cheesman died on an unrecorded date before May 2, 1665, when his will was proved in the Prerogative Court of Canterbury. Thirteen years later his widow authorized a relative in Virginia to manage the York County property she had inherited from her husband. She died before July 21, 1680.