Sustainability within Project Management practice is a new and challenging territory. The current project management practice within the construction industry, particularly highway construction has not yet fully embraced sustainability. Recent literature shows a relation between project success and sustainability. Project success comprises of project success criteria and project success factors. A sustainability success sub-criteria framework of a highway is developed to identify critical success factors for a sustainability oriented highway project during the exploration and planning phase. Three highway projects and four respondents from each case are selected for cross-case methodology. Based on cross-case analysis, critical success factors are identified and applied in an Integrated Project Management model to improve chances of project success during the exploration and planning of a sustainability oriented highway project.