First off, at that kind of distance and time, a road trip will NOT be cheaper than shipping. No way no how. Gas, time, food, contingencies, lodging, wear & tear, all add up. This is also not the time of year to impulsively leave on a carefree jaunt across the upper midwest - weather is everything in terms of risk.
That said, if you'd rather have an adventure and a story to go along with the money spent, road trips are always whatever fun you make of them. If you're a road veteran then you know what's up. If you've never done this sort of thing, do some planning. Invite the wife or a buddy along and make the pin pickup a mere "side part" of something larger. I've done it a few times those were always better than the times I went myself.
As for whether a Mousin' is worth the trip, well... only you can answer that. But I think everyone on pinside has that "one title" they would (or did) do something dumb for. Few years back I drove a dying minivan 16 hours round trip to get a Torpedo Alley. Still have fond memories of the trip and the game was definitely worth it. ( Fair disclosure, I had family and therefore a place to crash near the pickup site so that definitely helped )