The 35-year-old can become an unrestricted free agent Oct. 9.
"I'm always an optimist, so yeah, I would say in every situation, I'm always looking on the bright side," Blackhawks general manager Stan Bowman said Wednesday, "but until something happens, until something comes to completion, I don't know. I can't really comment.
"We still have time on our side here, and that's what we're working through. We're realistic that [Crawford signing with another team is] a possibility, but that's not what we're focused on. I think we're looking at [re-signing Crawford] and optimistic to do something like that."
A few days before his first meeting with Bowman, Crawford, a two-time Stanley Cup winner with the Blackhawks (2013, 2015), said he wanted to stay in Chicago and playing time was more important than money.
"I think we still have a lot of great pieces on this team and to win another Cup in Chicago would be unbelievable," Crawford said Aug. 25. "That's the main thing, to win a championship, to play, to be the main guy and play a lot. Salary, that can be discussed. That's something that is not as important at this time. We'll see how those discussions go."
Crawford started nine games this postseason and was 4-5 with a 3.31 goals-against average and .907 save percentage. The Blackhawks, the No. 12 seed entering the best-of-5 Stanley Cup Qualifiers, defeated the No. 5 Edmonton Oilers in four games. As the No. 8 seed, they lost the best-of-7 Western Conference First Round in five games to the No. 1-seeded Vegas Golden Knights.
Crawford is 260-162-53 with a 2.45 GAA, a .918 save percentage and 26 shutouts in 488 games (474 starts) through 13 NHL seasons, all with Chicago. He missed 80 games the previous two seasons because of concussions. Crawford was 16-20-3 with a 2.77 GAA, a .917 save percentage and one shutout in 40 games (39 starts) before the season was paused March 12 due to concerns surrounding the coronavirus and missed all but the final day of training camp in July after he tested positive for COVID-19.
Crawford is the main pending unrestricted free agent for the Blackhawks. Potential restricted free agents include forward Dominik Kubalik, a finalist for the Calder Trophy as NHL rookie of the year after scoring 30 goals, centers Dylan Strome and Drake Caggiula, defenseman Slater Koekkoek, and goalie Malcolm Subban.
Bowman said he'd like more clarity on Chicago's unrestricted and restricted free agents before Oct. 9.
"The sooner you can do things, it gives you the ability to plan out the next season better, but that's what we're doing now anyway," Bowman said. "Our job is to be planning on several different fronts. We never assume one thing will happen. We always look at options. We have a lot of contingent plans in place. It's going to have to resolve itself in the coming week or two.
"Sometimes things take time, and as much as you'd like to do them on your own timeline, it doesn't work that way. There are two sides to every negotiation. There have been respectful conversations with agents, no animosity. Sometimes there's just work to be done."