Ah, the age old question. Road trips are amazing. You hop in your car, load up your buddies, and have a blast driving to Vegas. If you haven't seen your friends in a while, as is usually the case with trips like this, you can catch up on old times and have some fun. Provided the drive isn't too long, you can have a lot of fun.
On the other hand, flying is also fun. You can knock back a few on the plane. Book your tickets early and you can sit near all your buddies. You'll get there in a blink of an eye, and before you know it you'll be sitting at your favorite table making at pass at that cute cocktail waitress.
Of course, both methods have their drawbacks. If you're driving, the trip back is not nearly as fun as the trip there. You're usually tired, a little lighter in the wallet, and you've got nothing to look forward to except going home and facing the wife, kids and boss. It's legendary that the drive back is something that is considered the worst part of the trip.
Flying has it's own drawbacks, especially lately. There's more and more intrusive searches, and you can bring less things on board. Don't expect to carry on a bottle of your favorite scotch. And since airlines are cutting corners wherever they can, don't expect to pay less than ten or fifteen bucks a pop. Not only that, but unless you live a significant distance from the city that never sleeps, your door to door time won't be any less.
So, which should you do? One way people usually decide is based on the rally point. If you've meeting buddies from all over the world, then flying in is best. On the other hand, if you live near each other anywhere near the West Coast, then driving is likely your best bet.
Your lead time is also going to play a part. If you're making a last minute decision, then you might end up driving. It can be difficult to secure any kind of flight reservations at the last minute that aren't going to cost you an arm and a leg. But you never know. If you call around and check some prices, you'll likely find some good deals every once in a while. The bottom line is that you've got to choose based on your situation. In that case, have fun!