He was born in Wamego, Kansas.
His automobile career began when the American Locomotive Company (ALCO) decided to diversify into the automobile business. Chrysler was the plant manager. ALCO had some racing success but less in the way of sales success. Chrysler saw the way things were going and took a job at the Buick Motor Company in 1911, two years before ALCO quit the automobile business. He resigned his job as president of Buick in 1919 and became a director of Willys-Overland and Maxwell Motor Company in 1921, which became the Chrysler Corporation in 1925. He commissioned the Chrysler Building in New York City, which was at the time of its completion the world's tallest building.
His autobiography was titled The Life of an American Workman.
He is buried at Sleepy Hollow Cemetery.