Bailey agreed to a professional tryout with the Senators on Thursday.
Bailey had eight goals and 25 points in 64 games with the Islanders last season. The Islanders dealt him to Chicago in June, and the Blackhawks subsequently bought out the final season of his six-year, $30 million contract. Although Bailey has fallen hard from his height of 71 points in 2017-18, the 33-year-old might still be a solid bottom-six forward this year.