On 21 April 2018, Chekhovich was signed by the San Jose Sharks in the last round of the 2017 NHL Entry Draft to a three-year, entry-level contract.
[2] With the 2020–21 North American season set to be delayed by the COVID-19 pandemic, Chekhovich was loaned by the Sharks to remain in his native Russia, on a season-long agreement with Torpedo Nizhny Novgorod of the Kontinental Hockey League (KHL).
He made his NHL debut on 30 April 2021, in a 0–3 loss to the Colorado Avalanche and finished the season with four appearances with the Sharks, registering one assist.
[5] Unclaimed and as a free agent, Chekhovich returned to Torpedo on a one-year contract on the opening day of the 2021–22 season on 1 September 2021.
[6] On 23 May 2022, Chekhovich left Torpedo as he was traded to fellow KHL club, Lokomotiv Yaroslavl, in exchange for prospects and financial compensation.