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This study explores a relationship among parental cosmopolitan orientation, intergenerational aspirations and children’s upward mobility expectations in an East Asian context. Using the PISA 2022, I analyze key pathways (family’s SES → parental cosmopolitan orientation/ intergenerational aspirations → children’s expectations of upward mobility) in South Korea and Hong Kong. Results of this study show that intergenerational aspirations play a mediating role in the relationship between family SES and youths’ expectation of upward mobility in both countries, but national differences are discovered as well. Family SES is indirectly medicated by two mediators in South Korea, but the cosmopolitan orientation of Hong Kong parents does not make a difference in children's prospects of upward mobility.