Chester Loomis attended Cornell University from 1868 to 1871. He studied with Harry Ives Thompson in West Haven, Connecticut before travelling to Eruope in 1875 to continue his artistic education. In Paris he attended the Acad‚mie Julian, while also entering the atelier of Leon Bonnat for two years. In 1883 Loomis married Sara S. Dana. Loomis remained in France for eleven years, during which time he traveled to Italy. He was part of the circle of American artists in Paris, which also included Henry Siddons Mowbray, Charles Sprague Pearce and Frederick Arthur Bridgman.
After his return in 1885, Loomis spent time on his brother's ranch in Texas. He built a house and studio in Englewood, New Jersey in 1890. He became a member of the Society of American Artists in 1888.