Freedom in nations can affect the happiness of citizens both positively and negatively. This study takes stock of the balance of effects. It considers 1) whether there is a positive net-effect at all, 2) which freedom variants contribute most to happiness 3) in what conditions. Freedom is conceived as chance to choose, requiring 'opportunity' to choose, and 'capability' to choose. Opportunity to choose is measured by absence of restrictions in economic, political and personal life. Capability to choose is measured by information and inclination to go one's own way. Happiness is conceived as the overall appreciation of ones life as a whole. Average happiness in nations is measured by responses to questions on the matter in representative surveys. Data on both freedom and happiness is available for 46 nations in the early 1990's. Analysis shows first of all positive correlations between freedom and happiness. Yet closer analysis reveals that freedom and happiness do not always concur.Freedom is positively related to happiness among rich nations, but not among poor nations. Apparently freedom does not pay in poverty. Further, freedom is related to happiness only when 'opportunity' and 'capability' coincide.A notable exception is economic freedom. Opportunity for free trade is positively related to happiness in poor nations, but not in rich nations. Similarly, the relation between economic freedom and happiness is strongest in nations where capability to choose is lowest. The findings show that freedom does not always breed happiness, and suggest that economic freedom deserves priority.