With a new planning system taking shape, and a new Bill of Rights embodied in a transformative Constitution having been introduced in South Africa in 1994, this article grapples with the dual questions as to whether the new spatial planning system fits within the spirit of the Bill of Rights, and the Bill of Rights assists the new spatial planning system in the realisation of its objectives. As a prequel to the engagement with these questions, a brief overview of the events leading to institution of the Bill of Rights and its contents is provided. This is followed by a brief historical overview of the creation of the South African spatial planning system and a summary of its key features. These features can be reduced to the following basic components: (1) meaningful participation in all aspects of spatial planning; (2) an open, inclusive and just decision-making process where information is readily available; (3) recognition of religion and culture and equal treatment in application and decision-making; (4) an awareness of environmental issues; and (5) the significance of property and housing. The way in which these components are addressed in the Bill of Rights and other parts of the Constitution provides the starting point to determine the extent to which there is a meaningful and mutually beneficial fit between the planning system and the Bill of Rights.