This study compared the prevalence and predictors of gambling behaviors between Filipino Americans who live in San Francisco (S.F.) or Honolulu. Data from the 1998–1999 Filipino American Community Epidemiological Survey were used to answer two research questions: (1) What are the prevalence and types of gambling behaviors among Filipino Americans and (2) What are the protective/risk factors of heavy gambling for Filipino Americans in S.F. and Honolulu? Overall, S.F. Filipino Americans had a higher level of participation in gambling, and the odds of gambling increased among older age groups, males, those who were US-born, and those with more health problems. Multinomial logistic regression analyses revealed that factors associated with infrequent and regular gambling participation were different between the S.F. group (older, male, higher education) and Honolulu group (male, US-born, more health concerns). Differential gambling environments, i.e., wide open gambling in S.F. and the restrictive gambling in Honolulu, may contribute to gambling participation and predictors of risk gambling Filipino Americans living in Honolulu and S.F. Policy makers and health professionals need to be aware of these differences to serve this population more effectively.