The COVID-19 pandemic has significantly influenced all modes of transportation. However, it is still unclear how the pandemic affected the demand for ridesourcing services and whether these effects varied between small towns and large cities. We analyzed over 220 million ride requests in the City of Chicago (population: 2.7 million), Illinois, and 52 thousand in the Town of Innisfil (population: 37 thousand), Ontario, to investigate the impact of the COVID-19 pandemic on the ridesourcing demand in the two locations. Overall, the pandemic resulted in fewer trips in areas with higher proportions of seniors and more trips to parks and green spaces. Ridesourcing demand was adversely affected by the stringency index and COVID-19-related variables, and positively affected by vaccination rates. However, compared to Innisfil, ridesourcing services in Chicago experienced higher reductions in demand, were more affected by the number of hospitalizations and deaths, were less impacted by vaccination rates, and had lower recovery rates.