Green spaces, particularly urban parks, provide essential environmental, aesthetic, and recreational benefits to human health, well-being, and happiness. However, traditional forms of investigating people’s perceptions of urban parks, such as questionnaires and interviews, are often time- and resource-intensive and do not always yield results that are transferable across sites. In this study, spatially explicit geolocational information (Sina Weibo check-in data) was utilized to analyze expressions of happiness and well-being in urban parks in Shanghai, China. The results showed significant differences in reported happiness inside and outside urban parks in Shanghai over a 6-month period. Accessibility, naturalness factors, and the frequency of park visits were positively associated with happiness. There existed both commonalities and disparities in the results between residents and non-residents. These findings can provide decision makers and urban planners with a comprehensive and timely overview of urban park use so they can accurately identify park needs and improvements.