Chiles was probably the son of Walter Chiles (also Childs or Childes) and was born in Bristol, England, where his father was a textile merchant. His mother’s name is uncertain. Baptized in the church of Saint Mary Redcliffe, in Bristol, on March 20, 1609, Chiles entered the textile trade there, married a woman named Elizabeth, whose maiden name may have been Sanders, and had at least two sons.
Chiles made his first recorded trip to Virginia in the service of the merchants William Harris and Nicholas Jolly aboard the Blessing, probably in 1636. By 1638 Chiles had fitted out his own ship and returned to the colony with his wife and sons. During the next few years he patented about 1,000 acres of land in Charles City County and regularly traveled between Virginia and England transporting merchandise and immigrants. In hope of expanding his business, Chiles joined three other men in June 1641 in petitioning the General Assembly for permission to “undertake the discovery of a new river or unknowne land bearing west southerly from Appomattake river.” The assembly granted them a license in January 1642 and renewed it in 1643, but the Anglo-Powhatan War of 1644–1646 temporarily halted exploration and closed trading opportunities in the west. They did not attempt to obtain another license.
Chiles was elected a burgess from Charles City County for the assembly that met on January 12, 1642, and signed a declaration against a revival of the. He represented the county again in 1643 and took part in the last meetings of the General Assembly as a unicameral body and the first sessions of the House of Burgesses as a separate branch of the assembly. About that time the county court unsuccessfully recommended him to the governor for appointment as sheriff of Charles City County. Chiles then moved to James City County, which he represented in the assemblies that began on November 20, 1645; October 5, 1646; and October 10, 1649. It is possible that his absence from some of the intervening legislative sessions was a consequence of trips to England.
On March 23, 1650, Chiles purchased fromthe brick house in where governors had resided for more than a decade. Owning one of the largest and finest dwellings in the colony and acquiring a new title of lieutenant colonel, Chiles had clearly become a man of importance, and the governor appointed him to the Council. Because most of the Council’s records for the period are lost, almost nothing is known about his tenure. The only surviving documents recording his attendance at Council meetings are dated May 21 and September 20, 1651. Chiles did not remain a councillor after Virginia in March 1652, perhaps because he was not in Virginia at that time.
Chiles was still engaged in trade. He owned his own ships and may have carried messages between the governor and the Crown and, after the future king Charles II fled England for the Netherlands, between the government in Virginia and the court in exile. Late in January 1652 Chiles sailed for Rotterdam in his ship the Fame of Virginia. Five months later he returned and anchored off the Eastern Shore. As the ship was departing for Jamestown on June 13, a local militia captain detained it for violating Parliament’s Navigation Act, which forbade unauthorized trade with the Netherlands. Chiles informed the county court that the terms of Virginia’s surrender to Parliament exempted Virginians from that interdiction of trade, but faced with a new charge that Dutch merchants were the real owners of the ship, he remained fearful that his property might still be lost. Eastern Shore taxpayers worried that because a county militia officer had attempted to confiscate the ship, they might have to pay Chiles for the Fame of Virginia. The following summer Chiles embraced an opportunity to preserve his investment by agreeing to exchange one vessel for another. For £400 he acquired another ship that had been seized for violating the law, the larger Leopoldus of Dunkirk, and its valuable cargo.
The resulting legal complications and their political and commercial ramifications required the General Assembly to intervene. When the assembly met on July 5, 1653, Chiles was a burgess from James City County and also a candidate for Speaker. Governor Richard Bennett, anxious not to add another complication to an already difficult situation, advised the burgesses not to choose Chiles. The burgesses, jealous of the right to elect their own officers without executive interference, elected Chiles Speaker of the House anyway and so notified the governor. The next day Chiles resigned, citing the impropriety of presiding over the House of Burgesses while it settled the question of who owned the Fame of Virginia. Preconcerted or not, these acts of political theater enabled the House of Burgesses to preserve the right to elect the Speaker, Chiles received the honor of being elected, and by resigning he made it possible for the governor and other members of the assembly to resolve the controversies and seal the deal that gave him the Leopoldus of Dunkirk. The episode was important in preserving the independence of the House of Burgesses as a powerful parliamentary body during a time of political uncertainty, and it led to a peaceful solution of most of the problems.
Walter Chiles’s name drops from documents relating to public affairs with the conclusion of the assembly session about a week later, and it is probable that he died not long thereafter. Dutch documents place a “Walter Chiels, merchant, living in the Virginias” in Amsterdam in August 1654 and indicate that he intended to sail for New Netherland the following month. The wording of an order of the Charles City County Court on December 17, 1655, indicates that Chiles might have still been alive then, but on November 5 of that year, when a deed he had executed in 1652 was recorded in James City County, a witness authenticated the document, suggesting that Chiles might have been dead by that date. The widow of his namesake son stated on November 20, 1673, that Walter Chiles had died in or about 1653.