Hey folks,
I'm not trying to sell anything. Also, I don't recommend this strategy to young kids that can't handle credit card debt, and I wouldn't even recommend this to myself 10 years ago. However, this strategy has allowed and will continue to allow me to make at least one trip a year essentially free. These are trips I would never take, but since they are essentially free...why not?
I can only speak from experience, so here it goes.
First, I got the Delta Gold card and achieved the bonus by spending their requirements. This gave me about 35000 Delta Skymiles (which I think has gone to 50k recently). Next, I got the Starwood Hotel credit card. This gave me about 30000 Starwood points. These can transfer 1:1 with Delta, plus they gave me a bonus for transferring. I bought 2000 Delta points for $70 to get my total to 72000, enough for 4 roundtrip tickets from Dallas to San Francisco ($44 total in taxes).
Next I heard about the Chase Sapphire Preferred card which gives you 2:1 for dining and a bonus of 50,000 points if you meet the spending requirements. I also got the Hyatt card to get two free nights. Anyway, my hotel and airline will be essentially free for the week.
I then kicked it up a notch with the Chase Sapphire Reserve. Don't get a ahead of yourself with this one. I still can't believe I was okay with a $450 annual fee. It sounds ludicrous, but again it's getting me to take trips I would never take.
I have adopted the philosophy of The Points Guy. If you're bored, have decent credit, and want to get out of dodge for a bit, check him out at http://thepointsguy.com/. It's been one heckuva ride so far. Enjoy :)