Restoration of forests, prairies, and other ecosystems is important for many reasons. Forest Service scientists and research partners examined how oak woodlands in the Chicago Wilderness region were restored. (Chicago Wilderness is an alliance of organizations that share a goal of sustaining and enhancing biodiversity throughout the broad Chicago metro region). The research team’s analysis of the rules, norms, and strategies found in practice highlighted a set of philosophical, yet practical, principles to guide the practice of ecological restoration. Avoiding harm, listening to the land, practicing follow-up actions, and taking a qualitative approach to actions and outcomes characterize these organizations’ restoration approaches. Importantly, all organizations are also guided by basic principles of social collaboration, both internally and externally. Because all organizations, regardless of management style, expressed these principles, they can be seen as a regional system of collective action that is beneficial for the larger good. In the metropolitan region of Chicago Wilderness, this shared understanding represents a strength of the alliance and can be a model for other conservation efforts.