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The paper presents an empirical investigation of telecommuting frequency choices by post-secondary students in Toronto. It uses a dataset collected through a large-scale travel survey conducted on post-secondary students of four major universities in Toronto and it employs multiple alternative econometric modelling techniques for the empirical investigation. Results contribute on two fronts. Firstly, it presents empirical investigations of factors affecting telecommuting frequency choices of post-secondary students that are rare in literature. Secondly, it identifies better a performing econometric modelling technique for modelling telecommuting frequency choices. Empirical investigation clearly reveals that telecommuting for school related activities is prevalent among post-secondary students in Toronto. Around 80 percent of 0.18 million of the post-secondary students of the region, who make roughly 36,000 trips per day, also telecommute at least once a week. Considering that large numbers of students need to spend a long time travelling from home to campus with around 33 percent spending more than two hours a day on travelling, telecommuting has potential to enhance their quality of life. Empirical investigations reveal that car ownership and living farther from the campus have similar positive effects on the choice of higher frequency of telecommuting. Students who use a bicycle for regular travel are least likely to telecommute, compared to those using transit or a private car.