John Chesterfield was born around 1818 in England. He married Eliza Tippet, and they had at least ten children: Richard, born on February 25, 1842; John, born around 1843; William, born around 1845; Eliza, born around 1846; Charles, born around 1850; George, born around 1852; Mary, born around 1855; James, born around 1856; Samuel, born around 1858; and Richard, born around 1862.
They immigrated to America around 1847 and settled in Mineral Point, Wisconsin. Chesterfield worked as a miner, and by 1850, he owned $75 of real estate. They moved to Willow Springs, Wisconsin, in the 1850s, and he worked as a farmer there. By 1860, he owned $800 of real estate and $400 of personal property. They returned to Mineral Point in the 1860s, and by 1870, he owned $5,600 of real estate and $5,000 of personal property. His wife on April 7, 1898, and he passed away of pneumonia in Lincoln, Nebraska, on January 31, 1903.