Cholowski's parents, Natalie and John, his older brother, Fred, aunt, uncle and several friends will be among 10-15 people cheering him on.
Last year, in Cholowski's rookie season, he was a healthy scratch in Vancouver as the Wings lost, 3-2, on Jan. 20.
Although his friends and family were disappointed, Cholowski displayed maturity beyond his years in the way he handled that situation and getting sent down to the AHL's Grand Rapids Griffins a few weeks later.
"Big wake-up call, eye-opener, however you want to call it," Cholowski said last Friday of that game. "It was tough but I think it only made me better and stronger. I came back this year with a good attitude and a positive mindset."
Wings coach Jeff Blashill said that Cholowski is a better player than he was at the end of last season.
"I think that's a real tribute to him and the fact that he put tons of work in during the summer and he's stronger," Blashill said after Monday's practice. "And he's listened to things that he has to be better at. One of the biggest challenges to getting better is if you're not willing to understand that you have to get better. I think when guys realize that, they tend to grow at a much bigger rate.
"I think he understands the areas of the game defensively and kind of management of the game, knowing when to try and make a play and when to punt, is a huge part of managing your game. That comes with maturity lots of times. I think his game management and his defensive game still needs to improve but it is improving. It wasn't as good last game as he had been in the previous four but he's gonna get another chance (tonight) to go out and be real good."
Cholowski said everything he went through last season has helped his development.
"Having the experience of last year, playing in the NHL and AHL has helped me a lot," Cholowski said. "I feel a little older and a little more experienced this year.
"I'm just more calm, more relaxed, better in the D-zone, I'm winning more of my battles now. They can rely on me to put me on the ice in more situations now."
With his left-handed shot, Cholowski is the quarterback on the Wings' top power play with Dylan Larkin, Anthony Mantha, Tyler Bertuzzi and Taro Hirose.
"It's pretty cool, it's exciting, it's obviously a lot of talent with those four guys," Cholowski said. "To be on that is pretty exciting for me, and I just try to get them the puck when they need it and then contribute whatever way I can."
Mantha has both of Detroit's power-play goals this season among his six overall, which will make him a marked man with the man-advantage.
"They'll be watching video for sure," Cholowski said. "They'll be pushing up on him hard. I'm not sure if they will tonight or what we expect tonight. We'll read off of it when we get there and if he's open I'm going to get him the puck whenever I can."
In practice and during the morning skate, Cholowski has been paired with Alex Biega, who will be making his Detroit debut against his former team.