There is currently a nice transfer for AMEX->southwest:

If you go directly 1.5k AMEX MR = 1 Southwest RR credit
Free Southwest flight = 16 RR credits so you need 24k AMEX MR for 1 free Southwest flight

However, if you have a few weeks time and don’t mind a phone call or two that you’d need to make – there’s a better way:

5k AMEX MR -> 5k Continental OnePass
5k Continental OnePass -> 5k Amtrak GuestRewards (5k is the transfer interval CO allows)
5k Amtrak GuestRewards -> 25k Choice (hotels) Points
25k Choice Points -> 10 Southwest RR credits

If we used 25k AMEX MR – you’d get 50 Southwest RR credits! That’s 3 free flight tickets!

Caveats:
- You can only transfer out 25k Amtrak Guest Rewards/calendar year
- Transfers might take a while
- Transfer ratios might devalue over time

You can make it even better by transferring 25,000 AMEX points prior to year-end, and then again after January 1. Why? Because another cool feature of the Southwest Rapid Rewards program is that if you earn 100 Rapid Rewards credits over any 12-month period, you are given a companion pass that is good for a year. The companion pass allows you to name a specific individual who is allowed to fly with you on any Southwest flight for a year, even if your ticket is an award ticket. So essentially you get 6 free flights plus the companion pass that can become the same as 6 more free flights.

With two little ones on the way, we probably won’t be traveling much in the coming year, but hopefully someone else out there can use this.