Chylak was born in Olyphant, Pennsylvania. His parents, Nestor Sr. and Nellie, were of Ukrainian descent; Chylak was the first of their five children. He attended the University of Scranton, where he studied engineering.\n', '

During World War II, he served in the U.S. Army in Europe. He suffered shrapnel injuries in Battle of the Bulge, which blinded him for several days and hospitalized him for eight weeks. He earned both the Silver Star and Purple Heart during his service. After the war, he began umpiring amateur baseball in 1946, and returned briefly to college.\n', '

After a year in amateur baseball, Chylak moved into the minor leagues as a Pennsylvania-Ontario-New York League umpire. He spent several more minor league seasons in the Canadian–American League, the New England League, and the Eastern League. He debuted in the major leagues in 1954.\n', '

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