For long now, the urban child has been considered to be more likely than his/her rural counterpart in being able to realize the dream of fully participating in school. This observation has mainly been attributed to what is commonly known as the “urban advantage”. This “urban advantage” is associated with increased access to facilities such as schools in urban areas. Recent work documenting population health in urban and rural areas has however begun to suggest that some sections of the urban population do not benefit from the “urban advantage”. For example, a child in the slums of Nairobi is more likely to suffer from diarrhea than a child in rural Kenya. In addition, a child from the richest household in the slums is more likely to suffer from diarrhea than a child from the poorest family in rural Kenya. This paper explores patterns of school enrollment comparing urban slum, urban non-slum and rural children. The paper uses data from the KenyaDemographicandHealthSurvey (KDHS) for 1993, 1998 and 2003. A contrast with school enrollment in Nairobi slums is done using the KDHS-type Nairobi Cross Sectional Slum Survey for 2000. Data from focus group discussions collected in the slums of Nairobi provide the context for discussion. The results suggest that school enrollment is higher in urban non-slum than in urban slum areas, and is higher in slums than in rural areas at younger ages. However, this is only true up to age 9 for females and 11 for males, from which school enrollment for slum children declines and the rate of decline is faster than among their rural counterparts. The corresponding ages at which the enrollment among the rural children begins to visibly decline are 13 years for males and 14 years for females. Factors contributing to these results point to the poor quality of primary schools in slums, limited access to secondary school for slum children, increased vulnerability to coercion into sexual activity and other ills that hinder school participation, disabling environment at home and increased child labor.