This study examined the journey of families with children seeking shelter to inform future system navigation solutions that will serve this population. Families living in emergency shelter, rapid re-housing, or unsheltered were interviewed (n = 24). Participants created a journey mapping of their path through the homelessness system and described the barriers they encountered. Most participants were women (79%), and the number of children per family ranged from one to five, with an average of 2.5 children. For these 24 participants, the average length of time between the interview and their last permanent housing was 68.5 weeks with one to eight transitions in living situations (e.g., domestic violence shelter, doubled-up) having transpired over that period. The top three barriers to exiting homelessness–transportation issues, finding and keeping employment, and child care needs–co-occurred and appeared to be interrelated. Families faced unique challenges, which included safety concerns, space obstacles, and a need for children’s activities. Examining families’ lived experiences during their homelessness journeys can help policymakers, social service providers, and communities understand the burden that families experiencing homelessness face while attempting to provide for their children and the adverse experiences children may encounter during the journey.