Cities are complex settlements that can create economic and cultural wealth while generating serious environmental degradation with life threatening outcomes. Researchers consider urban planning, underpinned by collaborative governance an important tool in ameliorating urban challenges thus enhancing liveability in ecological wellbeing and human health. This study aimed to examine urban planning and its approaches that enhance these fundamental features and to assess their application in three cases studies in Nairobi City. Qualitative research method formed the study design. Document reviews, face-to-face interviews, participant observation and multiple case studies comprised research instruments. The unit of analysis was the purposively selected geographic areas of Karura Forest, Uhuru Park and Lavington Estate with results displayed in descriptive form. The study findings showed limping urban planning, alienation of public open spaces and one case of collaboration that advanced liveability. It recommended transformation of urban planning, repossession of especially non-substitutable critical capital and collaborative governance.