In the United States, the COVID-19 pandemic exacerbated food insecurity and caused global supply chain shortages, highlighting the vulnerability of the conventional globalized food system to large-scale disruptions. In response, actors within alternative food systems mobilized to provide emergency food relief to their communities and generate income for local farmers who lost considerable revenue during the pandemic. I explored how alternative food system actors within Chicago adapted to COVID-19 to support local farmers and provide emergency food relief using organization-generated online content and semi-structured interviews. To compare different strategies taken by food system actors across Chicago, I collected qualitative interviews, social media content, and news articles about four emergency food relief programs initiated in response to the pandemic. Next, I conducted in-depth interviews with organizers behind one of these food relief programs, Market Box, to understand the assets and strategies underpinning the success of this program. Results from this research indicate that emergency food relief programs utilized a variety of approaches to connecting populations with local food during the pandemic. I argue that Market Box gained success by leveraging preexisting relationships with local farmers and food-insecure populations to quickly build a large recipient base. Furthermore, Market Box circumvented traditional barriers to accessing free food resources by providing delivery and waiving ID and proof of income requirements to participate. The results support the expansion of the United States Department of Agriculture’s Supplemental Nutrition Assistance Program Online Purchasing Pilot program to include local farms with online sales platforms to allow users greater freedom in utilizing food assistance. When possible, food relief programs should consider waiving ID requirements and offering delivery to capture a wider proportion of food-insecure populations.