Reb Finkel grew up as a "typical American Jewish boy" who enjoyed playing basketball and baseball. He was known as Nathan in school and Natie to his friends. He was one of the first students of the Central Park Hebrew Day School (later renamed Arie Crown Day School) and received after-school tutoring in Torah studies from Rabbi Yehoshua Levinson. In 1957, at the age of 14, he accompanied his parents on a trip to Israel to visit the holy sites and his father's family. His great-uncle, Rabbi Eliezer Yehuda Finkel ("Reb Leizer Yudel"), the Mir rosh yeshiva, recognized his ability to think clearly and have patience for studying, and asked his parents to let him stay and study in his yeshiva. Finkel remained at the Mir for eight months, studying with top-notch "chavrutas" (study partners) to develop his skills. He returned to Chicago to take his secondary education at the co-ed, Modern Orthodox Ida Crown Jewish Academy, where he was president of the student council and a starting centerfielder for the baseball team. At the age of 17, Finkel returned to Jerusalem to learn at the Mir under the guidance of his great-uncle. He learned diligently for the next six years. With one of his "chavrutas", Rabbi Zundel Kroizer, he completed the entire Talmud each year.