We study families with children in transitional housing in the city of Chicago, using data from HMIS, 312 call center, and Chicago Public Schools. We identify their service utilization, and pathways into homelessness. We demonstrate doubled-up as a common pathways into homelessness, and how the system could potentially have large impact on families through better targetting. This work was awarded Les Brown for Excellence in Public Policy Work for contributing to a much greater understanding and acceptance of this form of homelessness, which was not previously recognized by the city.