The foreign-born population continues to grow in Canada and in 2011 they represented 20.6% of the population (Statistics Canada, 2013). In particular, Manitoba is seeing an influx of immigrants from the Philippines and with them they bring their children who must seek ways of making Canada their new home. When immigrants move they go through the process of acculturation to renegotiate their new identities in their new society. There are four acculturation orientations that one can follow: integration, assimilation, separation or marginalization. Of the four, integration has been the most successful orientation for immigrants because they can maintain facets of their native culture, while adding facets of the host society’s culture. This multiple-case study examined the resettlement experiences of four Filipino youth and set out to understand the personal and contextual factors that helped them integrate. In the end, the personal factors that helped with their identity renegotiation and subsequent integration were their age at migration, gender, social capital, and their attitudes towards learning. The contextual factors that helped were educational policies, perceived community attitudes towards immigrants, and their country of origin.