Blackhawks send:
Mike Hoffman, $3.7m (2018-19)
Brandon Dubinsky, $3.7m (2017-18)
Round 5
Oilers send:
Joe Pavelski, $7.9m (2017-18)
Pavelski is no longer what he used to be but still prefer him to Hoffman, so adding Dubinksy/late pick to make it happen. Plus, he will likely be cheaper to resign if I go that route.