He graduated from New York University and its law school. He learned the real estate business and bought several apartment buildings.
He started Trans Caribbean Airlines with two DC-9s. It was through the airline that in the mid 1960's he eventually purchased the 800-mile rail line, International Railways of Central America, that transported bananas in Central America. Later he purchased a banana plantation. Later Mr. Chalk sold his airline to American Airlines in exchange for shares and became the single largest shareholder.
He purchased the Washington, D.C. transit system in 1955 and in 1959 attempted to purchase New York's transit system.
Mr. Chalk owned the building in Georgetown Washington DC with the famous steps where the part of the film "The Exorcist" was filmed. The building was part of the Washington trolley system which circulated through Washington DC.
Mr. Chalk helped the newley formed Russia draft its first constitution after splitting from the USSR. Mr. Chalk work consisted in analyzing early drafts of the United States constitution and noting the changes from draft to draft for the newley formed Russian republic constitution committee.
Mr. Chalk was a founder of the American-Korean Foundation and as a result the South Korean Government gave him its National Medal of Honor.
Mr. Chalk donated the famous "Chalk Emerald" to the Smithsonian Museum of Natural Science. It is prominently displayed next to the "Hope Diamond" on the museum's Washington Mall building.
Mr. Chalk was chairman of the United Nations finance committee for several years and was a prominent fund raiser for the Democratic Party in the 1960's. He also helped raise money for the United Negro College Fund and served on the Georgetown University Board of Regents.
He died from cancer in a New York hospital at the age of 88.