Instead of trying to fly from Dickinson ND, can you get to the airport in Fargo? Or any other slightly larger airports in the region? For summer travel, you don't need to worry about blizzards causing severe driving conditions, although it would essentially be a full day's drive to MSP.

For award tickets with DL miles, domestic connecting flights can drive up the price in miles, so it's better to avoid them if you reasonably can do so. DL almost surely doesn't make these domestic connecting flights available to AS since they're not available for low DL miles.

If you can get to MSP, you can avoid domestic connections and try for MSP-AMS-MXP ro MSP-CDG-MXP (or maybe intraEU flights to/from Linate instead of Malpensa).

You can also consider purchasing the domestic connecting flights but (1) you need to allow lots of time for connections on separate tickets, including possibly not being able to check luggage through, as officially you're not interlined or protected with separate tickets and (2) this route is likely to be expensive and infrequent.