Originally Posted by ashill

Why transfer the Chase points at all? You don't say which cabin you're looking for, but for economy, that round trip will cost you 38,000 Avois plus USD$125 or so in carrier-imposed fees and taxes, on the very limited days and flights when AA has availability. The cash cost starts at USD$514 for basic economy or USD$597 for regular economy for the days I found in Februrary that have AAward availability. $597 is 39,800 Chase points when using the Chase portal (at least for Chase Sapphire Reserve cards) with no cash payment required, and when paying through the Chase portal you get to choose any flight on any day at the going cash price, plus you earn miles (BA, AA, or any other AA partner).

Sometimes, the value of miles is hard to evaluate. With Chase points, it's not hard at all: you should never, ever transfer points away from Chase if you're getting less than 1.5 cents per point on your intended redemption. For economy redemptions or intra-North America, it's pretty rare to beat that value by transferring away. (If you want to redeem for an intercontinental business or first trip, you might do better than 1.5c per point if you value the award at something close to the cash cost of buying that business or first ticket.)