Urban farming and community gardening are gaining popularity as strategies to address food insecurity and inequities in city life. Urban agriculture has been proposed as a way to enhance a city’s resilience. This concept is not new, as Ludwig Hilberseimer and Alfred Caldwell demonstrated in the 1940s when they envisioned a more resilient city for the industrialized world utilizing a decentralized, linear development model within a productive living landscape. In asserting that “small farms could solve mass poverty, mass unemployment and inflation– our great national disasters,” Caldwell presented a vision of small-scale farming as an act of resistance and empowerment for individuals, with the goal of initiating large-scale social and environmental transformation. This study takes Caldwell’s assertion as a starting point to investigate what we can learn from existing examples of urban agriculture in order to enhance urban resilience. The research examines three distinct approaches to urban farming currently implemented in Chicago, aiming to extrapolate their scalability and impact on broader societal and environmental change. The selected cases represent a range of farming practices and organizational types, encompassing conventional raised bed farming, aquaponics, hydroponics, and permaculture. Organizational diversity is reflected in the inclusion of a large non-profit organization, a local community group, and a private entrepreneur. Each case is analyzed based on a) The specific approach to farming technologies and practices, b) The corresponding development and implementation process leading to fruition, c) Evaluation of its transformative effects on individuals and its broader societal and environmental impact, d) Identification of perceived opportunities or barriers to growth and long-term success. The study identifies numerous opportunities for scaling up and emphasizes the varied objectives in urban agriculture. To support the growth of urban agriculture within resilient cities, a comprehensive multi-faceted, multi-scalar framework is necessary.