The Blackhawks and IceHogs have been in this situation before.
One brother in the organization and hoping for the other, a rising college star, to sign a contract before his draft rights expire.
They swung and missed back in 2014 with Kevin Hayes, but are hoping for greater things from the Sikura siblings.
Icehogs forward Tyler Sikura would be bouncing off the boards to hear that his brother Dylan is coming to Rockford.
"We've talked about it, but it's not something that's 100 percent," said Tyler. "It would be cool to one day play together. I think we'd compliment each other's games really well. I skate and train with him in the summer and it's so fun to be out on the ice with him."
Tyler is having the best year of his pro career with 15 goals and seven assists in Rockford. Meanwhile, younger brother Dylan is leading Northeastern with one of the best seasons by any college skater with 15 goals and 30 assists.
The younger sibling is in his senior season with the Huskies, however, Chicago's 2014 sixth round draft pick only has until August to sign a contract with the Hawks or become a free-agent. That decision may take some time.
"We haven't been thinking about that too much," said Dylan. "Obviously I have a few months left in school and I have a lot to look forward to here. I'm just trying to stay in the present and not look too far into the future."
Either way, the future seems bright for the Hobey Baker finalist who has guided the Huskies to their first Beanpot trophy in three decades. While there are still more chances for success in college, Dylan says he would really enjoy playing with Tyler.
"I think the last time I played with him was maybe in high school when I was in grade nine and he was in grade 12 and we played junior varsity together, but other than that we just skate together in the summer," said Dylan. "Not a lot of brothers can say they got a chance to play with each other at the pro level so that would be awesome."
The Sikuras have skated similar paths to the pros with both forwards playing in the Ontario Junior Hockey League before moving on to Dartmouth and Northeastern.
While Tyler continues his career year in Rockford, he hopes that Dylan can have a successful start with the Blackhawks.
"I'm hoping that Chicago is able to make a run and stay in the playoffs," said Tyler. "That would be my preference for him and for the organization, but if something were to happen where it worked out then that would be a fantastic opportunity and something I would never forget."