On 11 March 2020, the World Health Organization made the assessment that a new disease (COVID-19) caused by a novel coronavirus (SARS-CoV-2) could be characterized as a pandemic. From that point, a chain reaction of events and difficult decisions requiring action was launched. National governments all over the world announced partial or total quarantine lockdowns in an effort to control the virus’ spreading in order to save as many lives as possible. The effects of the pandemic were multifaceted and transport was not excluded. The current paper examines data regarding the level of usage (provided by the administrator) of bike-sharing systems in three case studies/medium-sized Greek cities (Igoumenitsa, Chania, and Rhodes) and through a statistical analysis identifies if there is a correlation between the implemented measures and the modal choice of the residents. The main results and conclusions of this analysis reveal that the level of usage of these specific bike-sharing systems was significantly increased during the lockdown period compared to the situation before the lockdown and the pandemic in general.