Preparing for the future is a major developmental task during adolescence and early adulthood. However, youth experiencing homelessness face additional challenges relating to economic instability, housing insecurity, and a lack of social support. Semi-structured interviews were conducted with 38 youth, from Ottawa and Toronto, who were experiencing homelessness and participating in a randomized controlled trial of Housing First for Youth (HF4Y). This qualitative study explores youths’ visions for the future, including their goals, aspirations, plans, and barriers to achieving them. Overall, findings demonstrated that youth had positive visions of the future and strove to reach developmentally appropriate goals and responsibilities. Compared to youth receiving HF4Y, the future expectations of those receiving treatment as usual (TAU) were characterized by uncertainty and lacked clear direction. Additionally, they emphasized self-reliance and autonomy, while HF4Y prioritized forming relationships and reconnection. Findings highlight the importance of stable housing intervention, and social, community, and financial support in planning for the future and transitioning out of homelessness. Implications for intervention, directions for future research, and limitations are provided.