The notion of urban/city schools in developing countries in Africa, such as Malawi, is different from that of developed countries, such as America. For instance, while city schools are considered poor schools by American standards, urban schools in Malawi are regarded as high-status schools by Malawian standards. In the context of developing countries, such as Malawi, urban schooling is considered a privilege or an opportunity by both parents and children. However, there are some challenges that urban schools face that render their opportune status questionable. It is therefore the purpose of this chapter to discuss the opportunities a child attending urban schools has in Malawi and the challenges urban schools face in providing education to the urban population and the socially disadvantaged. In order to contextualize urban schooling in Malawi, the chapter begins with a brief discussion of the geographical characteristics of Malawi, its socio-economic and political contexts, and the education system. This discussion is followed by a brief description of cultural capital and education as a guiding theoretical framework for the chapter. Thereafter, the opportunities of attending urban schools in Malawi are presented, followed by discussion of the challenges. These are illustrated using the city of Blantyre as a case-study. In some instances, comparative references to rural schools are made in order to clearly explain issues of urban schooling in Malawi. The chapter concludes with recommendations to improve urban schooling in Malawi. It is important to note that the urban schools discussed in this chapter are those that are public.