When the shelter-in-place order went into effect for Illinois, the My CHI. My Future. initiative surveyed organizations that serve Chicago youth to better understand community needs and engagement strategies employed across the city. While COVID-19 has interrupted how organizations, city agencies, and communities serve their youth, providers are finding creative ways to connect. This report highlights various strategies for engaging youth while physical spaces are closed and identifies concerns that providers have right now related to their organizations and the youth and families they serve.