17th Overall: Chicago's natural first-round selection by virtue of points percentage among the teams eliminated in the opening round of the Stanley Cup Playoffs
46th Overall: Pittsburgh's natural selection in the second round that has been involved in a pair of trades for starting-caliber goalies. Pittsburgh originally traded the pick to Vegas on June 21, 2017 officially in exchange for "Expansion Draft considerations" -- essentially the Penguins sent Vegas this pick to ensure that the Golden Knights took Mark-Andre Fleury in the 2017 Expansion Draft. At the trade deadline in February, Vegas sent the pick, along with Malcolm Subban and prospect Slava Demin, to Chicago in exchange for netminder Robin Lehner. Ironically, now Lehner and Fleury appear to be vying for the starting job in Vegas next year (should Lehner re-sign in the desert), a virtue of both being acquired with this second-round pick.
81st Overall: Calgary's natural third-round selection. Chicago acquired "the higher of Calgary's two third-round picks" at the trade deadline this year in exchange for defenseman Erik Gustafsson. As of now, Calgary only holds this one third-round selection, but that could change. Last summer, Calgary traded James Neal to Edmonton's for Milan Lucic and as a result of an NHL ruling on the conditions of the trade after the shortened season, Edmonton owes Calgary a third-round selection in either this year's draft or in 2021. If Edmonton elects to send their third-round pick in this year's draft (No. 76 overall) to Calgary, that pick would then transfer to the Blackhawks as the higher pick in the round. The Oilers have until the third round starts to decide in which year they want to send the pick.
Round 2, 48th Overall &Round 7, 203rd Overall: The Blackhawks traded their natural second- and seventh-round picks in the 2020 NHL Draft to the Montreal Canadiens, along a third-round pick in 2021, on June 30, 2019 in exchange for forward Andrew Shaw and a seventh-round pick in 2021.