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Public transit in the U.S. has an unsettled future. The onset of the COVID-19 pandemic saw a dramatic decline in transit ridership, with agency operations, and user perceptions of safety changing significantly. However, one new factor beyond the control of agencies is playing an outsized role in transit ridership: the shifting employment patterns in the hybrid work era. Indeed, a lasting and widespread adoption of telework has emerged as a key determinant of individual transit behaviors. This study investigates the impact of teleworking on public transit ridership changes across the different transit services in the Chicago area during the pandemic, employing a random forest machine learning approach applied to large-scale survey data (n = 5637). The use of ensemble machine learning enables a data-driven investigation that is tailored for each of the three main transit service operators in Chicago (Chicago Transit Authority, Metra, and Pace). The analysis reveals that the number of teleworking days per week is a highly significant predictor of lapsed ridership. As a result, commuter-centric transit modes—such as Metra—saw the greatest declines in ridership during the pandemic. The study's findings highlight the need for transit agencies to adapt to the enduring trend of teleworking, considering its implications for future ridership and transportation equity. Policy recommendations include promoting non-commute transit use and addressing the needs of demographic groups less likely to telework. The study contributes to the understanding of how telework trends influence public transit usage and offers insights for transit agencies navigating the post-pandemic world.