Playfulness intertwined with city-related themes, such as participatory planning and civic media are becoming more popular. In the last ten years, game designers have taken up the theme of play in relation to the urban environment. In this paper, we present a conceptual mapping of “urban play,” through the analysis of eight examples of urban games. Better conceptual tools are necessary to discuss and reflect on how games draw on, or deal with, urban issues. While urban games are diverse in medium, intent, and experience, across the spectrum analyzed in this paper, they hold the potential for various player experiences emerging through play that may be useful to designers. These are: a sense of agency and impact; feelings of relatedness and empathy; an awareness and understanding of complexity, perspective-taking and scenario-building, and either planning or taking action. The conceptual mapping offers scholars and practitioners a more nuanced vocabulary for designing games and playful interventions that might be used to tackle societal issues that either require or could benefit from genuine public involvement as engaged citizens.