There has been a long-standing debate about whether urban living is more or less sustainable than suburban living, and quality of life (QoL) is one of several key measures of the social sustainability of residential living. However, to our knowledge, no study to date has examined life satisfaction among residents of downtown high-rise living compared to residents living in suburban low-rise housing. Further, very few studies have utilized building or neighborhood-scale data sets to evaluate residents' life satisfaction, and even fewer have controlled for both individual and household-level variables such as gender, age, household size, annual income, and length of residence, to evaluate residents' life satisfaction across different living scenarios. Therefore, the goal of this study was to investigate residents' satisfaction with their place of residence as well as overall life in general via surveys of individuals living in existing high-rise residential buildings in downtown Chicago, IL, and in existing low-rise residential buildings in suburban Oak Park, IL. Over 1500 individuals were contacted directly, resulting in over 500 responses. The number of fully completed responses for this study was 177, including 94 from residents of four downtown high-rise buildings and 83 from residents in suburban low-rise homes. Residents living in downtown high-rise buildings had significantly higher life satisfaction scores than residents living in suburban low-rise homes when controlling for demographic differences; however, the differences were small, as housing type explained less than 5% of the observed variance in life satisfaction outcomes. The research also evaluated five life satisfaction domains including travel, accessibility, social interaction, safety, and overall residential environment (ORE). In all cases, residents of the downtown high-rises reported higher satisfaction levels, although the scores on all these five satisfaction domains reported from both urban scenarios were very high. Moreover, all five satisfaction domains were highly associated with each other, and accessibility and safety were found as the strongest predictors of ORE for individuals.