Purpose: This study examines the career and educational search competencies (CESC), a capability which may be necessary for a successful transition from high school to work or postsecondary education, of students from Shanghai and Hong Kong. Design/Approach/Methods: The data for this study was taken from the Main Study of PISA 2012 in Shanghai and Hong Kong. Regression analysis was used to examine the relative impact of different forms of career and educational exploratory activities on students' CESC. Findings: Results showed a consistent pattern of socio-economic inequality in student's self-reported CESC in the two Chinese cities, which was largely mediated by the family capital or resources. Besides, career and educational exploratory activities initiated by schools, enterprises or the students themselves were found to have significant positive associations with CESC regardless of socioeconomic status. Originality/Value: The paper provides empirical evidence for enhancing students' career search capacity through engaging in career exploration in the face of structural barriers. In light of this, the roles of schools, business sectors, and governments in students' capacity building are discussed.