Whittaker Chambers was born in Philadelphia, Pennsylvania, and spent his infancy in Brooklyn. His family moved to Lynbrook, Long Island, New York, in 1904, where he grew up and attended school. His parents were Jay Chambers and Laha (Whittaker). Chambers described his childhood as troubled because of his parents separation and caring for their mentally ill grandmother. Chambers' brother committed suicide shortly after withdrawing from his first year of college. Chambers would cite his brother's troubled life and eventual suicide as one of many reasons that he was drawn to communism as a young man.
After graduating from South Side High School in neighboring Rockville Centre in 1919, Chambers worked at a variety of jobs before attending Williams College in 1920. He later enrolled as a day student at Columbia University. At Columbia his fellow students included Meyer Schapiro, Louis Zukofsky, Clifton Fadiman, John Gassner, Lionel Trilling (who later fictionalized him as a main character in his novel The Middle of the Journey), and Guy Endore. In the intellectual environment of Columbia he gained friends and respect. His professors and fellow students found him a talented writer and believed he might become a major poet or novelist.
Early in his sophomore year, Chambers wrote a play called A Play for Puppets for Columbia's literary magazine The Morningside, which he edited. The work was deemed blasphemous by many students and administrators, and the controversy spread to New York City newspapers. Later, the play would be used against Chambers while testifying against Alger Hiss. Disheartened over the controversy, Chambers left Columbia in 1925. From Columbia, Chambers also knew Isaiah Oggins, who went into the Soviet underground a few years earlier; Chambers' wife, Esther Shemitz Chambers, knew Oggins' wife, Nerma Berman Oggins, from the Rand School of Social Science, the ILGWU, and The World Tomorrow.