The idea of Nylander joining the Blackhawks is quite interesting. With the Blackhawks not expected to be competitive next year, the team is likely to revolve around Connor Bedard. Giving Bedard all of the resources at his disposal will be pivotal in his developments so acquiring an established star could go a long way.
Bedard is currently expected to play alongside Taylor Hall and Lukas Reichel. While they're good players, both Hall is past his prime and Reichel is still quite young. Bringing in Nylander could really boost Bedard's performance even more than his current potential linemates.
If the Blackhawks want Nylander, they would probably need to offer future assets in return. Key players like Seth Jones and Taylor Hall have expensive contracts, and Connor Bedard is probably off-limits.
However, the Blackhawks have two first-round picks in the next couple of drafts. They could give Toronto their 2025 1st round pick, which the Leafs might be interested in using. Adding a top prospect like Kevin Korchinski, Frank Nazar, or even Bedard's projected linemate, Lukas Reichel, to the deal could also make it appealing. Another option could be keeping 50% of a contract, like Nick Foligno's or Corey Perry's, to help the Leafs in their quest for the championship.
Even though this would mean the Leafs trading away a top player for future prospects, if Nylander seems unwilling to re-sign, Chicago could become the leading contender to get him.