In the book Sister Carrie by Theodore Dreiser, the character of Carrie Meeber visits a series of cities as she develops from a frightened and inexperienced girl into a successful career woman. The two locations that have the most significant impact on Carrie’s personal development are those of Chicago – where Carrie begins her journey – to that of New York – where Carrie accomplishes her dreams of becoming a successful actress. This paper examines the contrast created by Dreiser in terms of his presentation of both Chicago and New York and how these two cities impacted Carrie’s development into a professional and accomplished woman.