Collaboration is often promoted as an effective strategy for conservation and natural resource management. Collaboration and communication can be particularly important—but challenging—in cities where there are many diverse stakeholders. However, there is little information about the factors that increase social interactions in urban stewardship networks. We used social network analysis to examine the extent of collaboration and patterns in the flow of information, ideas, and funding among stakeholders in an industrial urban ecosystem. Organizations associated with a regional conservation alliance (Chicago Wilderness) had more connections than other organizations. Geographic proximity, of both office locations and shared field sites, also increased interactions. All interaction types were correlated with each other, suggesting that one form of interaction may lead to additional connections. Despite spanning a large geographic area and incorporating many diverse organizations, the network we evaluated appeared to be remarkably well connected and shows great promise for successful conservation outcomes. Our approach can be used to identify strengths and weaknesses in other collaborative stewardship efforts and uncover key actions that may improve conservation in urban areas.