Holabird grew up in Rottstown, Pennsylvania, and in 1903 enrolled in the Military Academy at West Point. After graduating there in 1907, he served as Second Lieutenant in the U.S. Corps of Engineers. In 1909 he resigned his commission and went to Paris to study architecture at the Ecole des Beaux-Arts and the Atelier Redon. On returning to Chicago in 1913, he entered his father's architectural firm, Holabird & Roche, but during World War I he returned to active duty and served as a Colonel in the Field Artillery of the U.S. Army. During that conflict, he was awarded the Distinguished Service Medal and the Croix de Guerre.
At the end of the war, Holabird returned to his father's firm and quickly assumed a leading position in the office. After the death of both his father of his partner Martin Roche, the younger Holabird went into partnership with his colleague John W. Root, establishing the firm of Holabird & Root. In the following year, Holabird worked on a number of major commissions in Chicago including the Chicago Temple, the Palmer House Hotel, the Chicago Daily News Building, the Palmolive Building, and the Chicago Board of Trade Building.
He was a fellow of the American Institute of Architects, a trustee of the Art Institute of Chicago, a member of the Chicago Plan Commission, and served on the committee of architects for the Century of Progress Exposition in Chicago, an event for which his firm designed the Chrysler Building in 1933.
He died on his fifty-ninth birthday.
