Cities are restoring rivers to recapture the social, ecological, and economic benefits of rehabilitated rivers. But, traditional urban planning and flood management tools may not address the complex relationships between humans, the built environment, and natural elements in the social-ecological systems of which rivers are an important part. They also may not acknowledge and address the factors that led to channelization. The field of regenerative design and development—an eco-centric approach that aims to dismantle the underlying processes and viewpoints behind the most pressing environmental problems—offers tools to plan more effective and inclusive river restoration projects. To explore these issues and the potential of regenerative design and development, we reviewed 15 urban river restoration plans, followed by a comparative case study of the Los Angeles River, CA and the Kinnickinnic River, WI. We conducted a content analysis of plans and popular press articles, and interviewed key actors. Results indicate many participants exhibit regenerative thinking and participate in regenerative processes, but they are unable to fully implement regenerative projects due to several constraints at institutional, social, economic, physical levels. Study recommendations emphasize rooting restoration in the unique aspects of place, reframing projects as part of nested social-ecological systems, working from potential, addressing broader socioeconomic challenges, and leveraging strategic nodes. Changes to planning education and practice are needed to empower planners to think and act regeneratively.