This systematic literature review synthesizes the major physical and socio-physical determinants on space choice behaviors in open (i.e., non-defined uses) versus enclosed (i.e., specific uses defined) spaces. The purpose is to better understand the trade-offs between open and enclosed spaces and how opposing and complimentary design elements influence behavior and occupancy choices. Using the lens of space choice behaviors, we hypothesize that similar design challenges exists at both scales, and that analogous insights can be applied to both urban planning and building design. We analyze the focus areas, research drivers, locations, and methods applied in the reviewed studies, and find overlapping similarities within research at both scales, particularly in the methods applied. The drivers for research into buildings tend to be more about optimizing space allocation, whereas lifestyles and well-being are more common in urban studies. We synthesize the content of the literature and find that challenges of successful public and common spaces in cities and buildings are similar in terms of trade-offs, barriers, and impacts on user activities. The implementation of diverse open spaces create more flexibility and adaptability to changing trends, attract different interest groups, and ultimately provide more synergistic benefits to the use of buildings and cities.