Adverse effects of anthropogenic climate change spanning environmental, public health, and socio-political domains have motivated institutions around the globe to commit to a decarbonized future. Entities have consequently set climate goals to formally engage with and take responsibility for pursuing a more sustainable way of life. In Chicago, some pursuits involve reducing carbon emissions produced by residential buildings, which make up around twenty-seven percent of the city’s annual greenhouse gas (GHG) emissions (City of Chicago, 2022). This paper examines how the decarbonization of residential heating using electric heat pumps powered by low-carbon energy presents many opportunities and serious challenges for Chicago. The city of Chicago relies overwhelmingly (up to 97% in some areas) on carbon-emitting natural gas to heat homes with furnaces and boilers (U.S. Census Bureau, 2021). The combination of Chicago’s extensive natural gas infrastructure and the expensive nature of electrification could leave less financially equipped groups in the area struggling to keep pace with broader electrification efforts. This paper reveals the need for long-term, comprehensive, and proactive planning to navigate the equitable decarbonization of residential heating in Chicago. Proposed plans such as Chicago’s 2022 Climate Action Plan are crucial to achieving a greener city. However, these plans often lack discussion of what the goals they lay out imply, the potential repercussions of poorly executed transition, and the steps that should be taken early on to avoid future hardship. To examine these potential consequences, this analysis explores decarbonization processes in Chicago. Through an assessment of the potential effects of a heat pump rollout, various community stakeholders such as electricity providers, legislative bodies, and technical workforces, and energy-related legislation, this paper argues that the transformative character of electrification necessitates that decisions made in Chicago today must both anticipate and inform a long-term decarbonized future.