This research, which uses an intersectional feminist methodological approach, explores the relationships and intersections among women, public urban space, and bicycling, and the gendered processes through which the use of space is claimed, negotiated, and constrained. It builds on the existing scholarship on the gendered nature of public space, and uniquely uses bicycling as the site of inquiry. Drawing primarily from interviews with women cyclists in Chicago, this article explores how gender and other social identities are constructed, challenged, and constituted through an interaction with public space, urban processes and structures, and societal expectations and attitudes. It brings to the forefront and centers these narratives and empirically contextualizes them by linking the scholarship on the gendered (and raced, classed, and sexualized) nature of public space with the scholarship on women’s participation rates and barriers to bicycling. This research examines, through the everyday lived experiences of bicyclists and their multiple subject positions and privileges, how the gendered nature of public space affects the participation and experiences of women cyclists; how public space is negotiated and constrained; and how gender can be both (re)produced and challenged in and through urban space via women bicyclists’ actions. In particular, the research findings explore how women bicyclists must demand and negotiate public space; how their movement and activities are constrained in public space; how gender roles and social reproduction issues intersect with bicycling; and how social, quasi-advocacy group bicycle rides are used as a strategy, with mixed results, to address barriers to women bicyclists’ mobility.