This paper investigates the socioeconomic contexts navigated by low-income children enrolled in the Chicago School Readiness Project (CSRP), as they made the transition from preschool to elementary school. The authors focus on the following two questions. First, do families' exposure to poverty-related risks (i.e., low income, maternal education, and employment engagement) change for the better or for the worse, from the fall of preschool to the fall of kindergarten? Second, they examine the share of CSRP-enrolled preschoolers who subsequently attended kindergarten in low-performing elementary schools. They ask whether children's chances of entry into a lower-performing school differ as a function of (a) their current or past exposure to poverty-related risks, (b) having attended a program randomly assigned to treatment versus control group during the intervention year of CSRP, and (c) having attended a Head Start program that was assessed to be lower-quality at pre-treatment baseline. Overall 602 children and 94 teachers participated in CSRP. Children on average were 4 years old and about half were boys. In this study the authors find that even in the period prior to the economic recession (2004-2006), families with young children in Chicago were facing high levels of poverty-related risk. On average, the CSRP-enrolled children had high rates of attending low-performing schools in the transition from Head Start to kindergarten. Their preliminary evidence shows that the CSRP intervention may set children on more positive educational trajectory since children in the treatment group were less likely to attend low-performing schools compared to their peers in the control group. To sustain the benefits of the CSRP intervention as well as those of Head Start, more help should be provided to these disadvantaged children throughout their subsequent school years. (Contains 3 tables.)