Cholowski signed an entry-level contract with the Wings after spending one season in college at St. Cloud State.
He spent the first part of last season with the Prince George Cougars of the Western Hockey League, recording 13 goals and 26 assists in 37 games.
On Jan. 10, the Cougars then traded Cholowski to the Portland Winterhawks, where he had one goal and 26 assists in 32 games.
"My season was good in the WHL," Cholowski said. "I thought I put up some good numbers, went to Grand Rapids and got to play a game, which was fun, got a little bit of experience there. It was a playoff game, so that helped a lot. Carry that over into next season."
When he got to the Winterhawks, they often played the Tri-City Americans, the team captained by Michael Rasmussen, the Wings' 2017 first-round pick, ninth overall.
"He's a heck of a player," Rasmussen said of Cholowski. "I didn't see him too much in PG but then he moved to Portland, I saw him all the time. Cholo's really solid D-man, good skater, moves the puck well. Definitely have a player there, too."
In the WHL playoffs, Cholowski had five goals and two assists in 12 games before Portland was eliminated.
Cholowski then joined the AHL's Grand Rapids Griffins and played in one playoff game with them.
"I thought it was good," Cholowski said. "I would have liked to have been more assertive with the puck and skated a little more but it was my first game. That's always tough but generally I think it was good."
Cholowski ran the power play in the WHL and knows that skill will be needed at the next level.
In training camp with the Wings last fall, Cholowski had an opportunity to watch the veterans run the power play during the preseason.
"I talked to a couple of them," Cholowski said. "Mike Green, I've always liked the way he played, skates very well, runs a power play well. Watching him and a few of the other guys really helped me."
The Wings have told Cholowski that he needs to be more assertive with the puck and not worry so much about making mistakes.
"Quicker decisions, more aggressive, always wanting the puck on my stick and being able to be the guy that's going to make a play to create a chance or break the puck out," Cholowski elaborated.
It's still a little early to see if Cholowski can beat out Filip Hronek for a spot or if perhaps they both could make the team.
"I'll have a better idea once exhibition games come around," Cholowski said.
"Right now I think it's trending pretty well."