Being from Western South Dakota, it usually takes me about 10 1/2-11 1/2 hours in a car to get back to see the family and friends during holidays. As a freshman in college it wasn't a big deal. Being out of school now, I can't stand it. By the time I complete the trek there or the trek back, I feel exhausted, sore, and sick. Not fun.
The only issue is that flying into Rapid City costs a boatload. So the trip is less than $200 in terms of driving there and back but flying is probably in the low $400s. Thanks to my company not giving raises in forever, it makes the decision still gear more towards driving then living the sweet life of being able to do the flying more often.
Not to mention if I get this arm candy of mine a ring in the next year or so, the expenses shall increase on both sides of the deal. At least when you drive solo you can push it and crank the rock. With a partner on the road, you stop more often (which sometimes is a good thing for your well-being if you push it all the time like I do), eat more, and listen to shittier music.
Tough decision dude. And I drive through Wall Drug every time. Imagine having to drive through eastern south dakota with nothing to offer except a wall-drug sign every 2 seconds.