Travel Rewards Programs

There was a thread a while back I found regarding travel reward credit cards, but what I wanted to talk about was the different rewards programs for the airlines and hotels.

Been in a dilemma recently, where I got a new job and I'm traveling a ton. They let us keep all of our rewards points. So the dilemma is, that my company prefers Hilton hotels, and for flights, it seems Delta flies more to where I need to go than Southwest. This is leaving out of Seattle.

Now my Chase Sapphire UR points can transfer to Marriott, but not Hilton, so that sucks. And it can transfer to Virgin Atlantic, which is a travel partner to Delta, but have to book flights over the phone I guess? That's annoying.

Should I go against the grain and start to book Marriott's for business to gain the membership levels? Is the Diamond or Platinum levels that different on either one? Of course I can always transfer points to Marriott, and just stay for free without any membership level.

As for Delta vs Southwest, I hear good about both. I like Delta's international locations, but I doubt I'd ever use them anytime soon, and their medallion levels seem near impossible to get. Southwest is gonna be cheaper, and I can transfer directly from my Chase card for points there. I've booked round trips from SEA to PHX for 8k points total. Won't get near that on Delta, although I've seen SEA to Vegas for around 12k points.

I was pretty set on just using Hilton's, as the membership level would be nice on my business travel, and not as cool when traveling personally with family, but I still can't decide between Delta and Southwest.

That's the issue, is that I don't think I'm going to be flying enough in the year to hit it, so then I'm stuck with well, who has the best ways to spend points, because I'll still rack up quite a few points on either one. I suppose if I'm just going for points, then choose Southwest since I can easily transfer points from my Chase card to add to whatever work travel has me doing as well.