Most cities around the world have never stopped working to re-urbanize and revitalize strategic areas of their downtown core. Over the past decades, previous urban development has caused environmental issues such as fragmentation and
pollution.This study qualitatively examines how elements and guidelines of green infrastructure and connectivity may be combined to enhance sustainable urban development within three urban green infrastructure systems: urban open space (community & habitat), transportation (mobility) and stormwater management (water). Data collected through a literature review and case examples are analyzed using an inductive approach and synthesized into design guidelines that contribute to creating sustainable urban connectivity. The elements and system guidelines of green infrastructure are demonstrated by the site concept design of the Union Station District in Toronto, Ontario, providing an opportunity to assess and critically review their applicability, and explore potential design solutions for the district.