The pursuit of high quality schools for their children is one of the key factors motivating the departure of middle-class families from urban neighborhoods. While there is much debate about what constitutes a “quality” school, the dominant national focus on standardized test scores and similar metrics suggests that families with the financial means to do so are likely to seek out schools, typically in the suburbs, that are reputed to rank highly on such indicators. This paper examines how middle-class parents who have made a different decision – i.e., to stay in the city and educate their children in urban public schools – evaluate the options that are available to them. Based on in-depth interviews with a sample of parents in Boston, the paper explores the relative importance of a range of criteria that respondents took into account as they considered various neighborhood elementary schools. In many cases, the schools that were deemed most desirable were not necessarily the highest performing. As the findings reveal, these parents, nearly all of whom are highly educated, place less of an emphasis on traditional measures of academic quality and rigor, in part, because they are confident that their own cultural capital enables them to supplement or compensate for any weaknesses in their chosen public school. This belief appears to have its limits, however; as parents look ahead to the prospect of sending their children to one of Boston’s public high schools, the academic excellence of a school takes on increased importance.