Guiteau was born in Freeport, Illinois, the fourth of six children of Luther Wilson Guiteau and Jane Howe. He moved with his family to Ulao, Wisconsin in 1850 and lived there until 1855, when his mother died. Soon after, Guiteau and his father moved back to Freeport.
Guiteau was routinely beaten by his father as a child and left home at an early age. He inherited $1000 from his grandfather (worth about $100,000 in year-2005 dollars) as a young man and went to Ann Arbor, Michigan, in order to attend the University of Michigan. Due to inadequate academic preparation, he failed the entrance examinations. After some time trying to do remedial work in Latin and algebra at Ann Arbor High School, during which time he received numerous letters from his father haranguing him so to do, he quit and joined the controversial religious sect known as the Oneida Community, in Oneida, New York, to which Guiteau's father already had close affiliations. Despite the "free love" aspects of that sect, he was generally rejected during his five years there, and he was nicknamed "Charles Gitout". He left the community twice. The first time he went to Hoboken, New Jersey, and attempted to start a newspaper based on Oneida religion, to be called "The Daily Theocrat". This failed and he returned to Oneida, only to leave again and file lawsuits against the community's founder, John Humphrey Noyes. Guiteau's father, embarrassed, wrote letters in support of Noyes, and Noyes maintained that he did not hold any ill-will towards Guiteau, saying "I consider him insane".
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