Junior Growing up in
Langley, British Columbia, Cholowski played
bantam hockey in his hometown until he was selected by the
Prince George Cougars of the
Western Hockey League (WHL) in the 10th round, 200th overall, of the 2013
WHL bantam draft. Following his selection, Cholowski stepped up his game and joined the
Chilliwack Chiefs of the
British Columbia Hockey League (BCHL). During the
2013–14 season, his first with the team, Cholowski only played one game with the Chiefs. In 2014, Cholowski committed to play for the
St. Cloud State Huskies, part of the
National Collegiate Hockey Conference. In the
2014–15 season, through regular season and playoffs, he put up four goals and 30 assists through 67 games. Due to his performance, he was named to the 2016 BCHL Second All-Star Team. The Red Wings used the 20th overall pick they acquired to select Cholowski. His selection made him the highest-drafted St. Cloud State commit, surpassing
Matt Cullen's 35th overall selection in
1996.
College and major junior During the
2016–17 season, his first season with the St. Cloud State Huskies, Cholowski recorded one goal and 11 assists in 36 games. On April 5, 2017, the Detroit Red Wings signed Cholowski to a three-year,
entry-level contract. He played his first professional game with the Griffins on April 15, their last regular season game, in a 5–1 victory over the
Milwaukee Admirals. Cholowski would remain a healthy scratch for the Griffins during their playoff run. Before the
2017–18 season, on September 26, 2017, Cholowski was assigned to the Prince George Cougars of the WHL. On November 21, 2017, Cholowski was named captain of the Cougars. On January 10, 2018, Cholowski was traded to the
Portland Winterhawks, along with Ty Taylor, in exchange for Ilijah Colina, Connor Bowie, and WHL bantam draft picks, including a first-round pick in 2020, a second-round pick in 2018, a second-round pick in 2019, and a third-round pick in 2020. Before being traded, he recorded 13 goals and 26 assists in 39 games for the Cougars, ranking second in the WHL in goals by a defenceman, and sixth in points. Cholowski finished this time with the Winterhawks with one goal and 26 assists in 32 games. That season, he ranked eighth in points among the WHL's top defencemen, tied for sixth in goals and eighth in assists. On April 18, 2018, Cholowski was reassigned to the Grand Rapids Griffins. He played in one playoff game on April 25 against the
Manitoba Moose, registering only one shot on goal.
Professional Detroit Red Wings During the
2018–19 season, after participating in the Detroit Red Wings' training camp, Cholowski made the team's opening night roster. He made his NHL debut for the Red Wings on October 4, 2018, and scored his first career NHL goal in the second period against
Joonas Korpisalo of the
Columbus Blue Jackets. On February 14, 2019, Cholowski was assigned to the Grand Rapids Griffins. Before being assigned to the Griffins, he recorded seven goals and nine assists in 52 games for the Red Wings, ranking third in points among rookie defencemen in the NHL. With the Griffins, Cholowski recorded 12 assists through 25 games. Cholowski was once again named to the Red Wings' opening roster for the
2019–20 season. On December 11, 2019, he was assigned to the Griffins. Before the move, he had collected two goals and six assists for eight points through 21 games, tied for second place among Red Wings defencemen in scoring. In 30 games with the Griffins, Cholowski notched three goals and 10 assists before AHL play was stopped due to the
COVID-19 pandemic. His season with the Red Wings ended with him not collecting any more points than he had before his reassignment, ending with 36 games played and a -26
plus–minus rating. During the shortened
2020–21 season, in January 2021, Cholowski made the Red Wings'
taxi squad, taxi squads being a safety measure put in place by the NHL for that season. On February 1, he, along with fellow taxi squad members
Chase Pearson and
Gustav Lindstrom, was assigned to the Griffins. With the Griffins, Cholowski totaled three goals and seven assists through 13 games. In Detroit, he collected one goal and two assists in 16 games.
Seattle Kraken and Washington Capitals On July 18, 2021, the Red Wings released their protected player list for the
2021 NHL expansion draft, being held for the
Seattle Kraken, on which Cholowski was not featured. On July 21, he was selected by the Kraken in the draft from the Red Wings. On September 7, he signed a one-year, deal with the Kraken. On October 12, Cholowski was named to the Kraken's opening roster for the
2021–22 season. The next day, he was placed on waivers, and the day after that, he was claimed by the
Washington Capitals. During his four months with the Capitals, Cholowski featured in just seven games, registering one assist and three shots on goal. On February 8, 2022, Cholowski was waived by the Capitals, and the next day, he was subsequently re-claimed by the Kraken. He was immediately reassigned by the Kraken to join the Charlotte Checkers, their AHL affiliate. In 31 games with the Checkers, Cholowski tallied three goals and 15 assists before he was recalled by the Kraken on April 25. After the Kraken's season ended, he was sent back to Charlotte, having collected two assists in four games with Seattle. Through six
Calder Cup playoff games, Cholowski notched one assist.
New York Islanders and New Jersey Devils On August 23, 2022, Cholowski, as a
free agent, signed a two-year, entry-level contract with the
New York Islanders. Cholowski played with the Islanders' AHL affiliate, the
Bridgeport Islanders, for the beginning part of the season, until he was called up to New York on January 18, 2023. He played his first game with New York that same day, skating in 13:58 of a 4–1 loss to the
Boston Bruins. After playing two games with New York, he was returned to Bridgeport on January 23. That goal was his only one during the
2022–23 season; he finished with an additional 37 assists through 67 games, his point total leading all Bridgeport defencemen. On October 6, 2023, Cholowski was placed on waivers to be assigned to Bridgeport, and he cleared them the next day to join the team. On June 24, as a
restricted free agent, Cholowski re-signed with the Islanders in a one-year, entry-level deal after having been extended a qualifying offer. Cholowski began the
2024–25 season with the Islanders, totaling three goals and seven assists through 33 games before being placed on waivers on February 20, 2025. He cleared waivers the next day, and scored one goal in six games. On March 7, Cholowski was traded by New York to the
New Jersey Devils in exchange for
Adam Beckman. With the Devils, Cholowski skated in six regular season games and two playoff games, Following the season, on July 1, Cholowski re-signed with the Devils for for one year. ==International play==