Previous quantitative research on family homelessness has addressed a question of why some households become homeless. However, why some homeless families return the shelter to repeat their homelessness has not been explored well. This study aims at providing a comprehensive insight into the dynamics of homeless families by identifying the physical, social, and economic characteristics of a homeless family affecting the likelihood of their decision to stay, exit, and return the shelter. The relationships of factors with shelter exit and return were examined using Kaplan-Meier estimates of survival times and Cox Proportional Hazard regression analysis. This study employs a sample of 2348 historical records for 1462 homeless families registered to the Homeless Management Information System (HMIS) database between January 1, 2015 and December 31, 2017. The results indicate that structural factors such as subsidized housing program enrollment during a homeless episode and prior income play a significant role in reducing the risks of shelter exit and return rather than physical characteristics of a homeless family. Additionally, results show that variations in prior residence and exit destination of homeless families serve as factors determining the length of their shelter stay and the likelihood to return to the shelter. Integration of both shelter exit and return analysis results make policymakers and urban planners think about developing policies for coordination of housing and economic stability to address family homelessness.