I've been collecting miles and points for about 2 years, and have accumulated a fair amount.
But when it comes to using the miles, I fall short. I own a successful business that only functions when I am there...so my schedule is very tight, and vacation time extremely valuable.
Even though I am flexible on destinations, I am not flexible on times.
Because all of my travel has to be Th PM-Sun or Mon if I take an extra day, long connections are difficult to fit into my plans, and award space is scarce.

I find myself buying revenue tickets time and time again, because the award tix don't fit my schedule (NYC-MCO trip last weekend, NYC-UVF on Thanksgiving were both bought for cash).

I've been trying to get away to Rio or Buenos Aires for a weekend, but non-stop premium cabin award space does not exist for any weekend in the next 12 months. So, I am considering redeeming at AAnytime or Standard levels. The redemptions are pricey - 200K/250K for business, for a $4K revenue ticket. However, I figure if I get most of my Chase UR pts at 5 pts per dollar, it may be worth it.

So, my question is, if I have to shell out lots of miles, how do I at least make as much from my high-level redemption as I can?
I understand the free-one ways, are there any other ways to make redeeming awards at these ridiculous levels more palatable?

Thanks!

Award space to these destinations often appears at the last minute, if you are really up to being that flexible. Remember that holders of US passports need visas for Brazil and need to pay a reciprocity fee online ahead of time for Argentina.

While I like AA, if you have Chase UR points I would transfer them to UA. UA just has far more award inventory available.

You'll probably do better redeeming on partner airlines, most of whom are not covered by the AA website search. In particular, I don't think LAN or TAM are offered on the AA site.

See this thread's introduction: http://www.flyertalk.com/forum/ameri...er-awards.html

Just be careful that you get a price quote before booking, as some partners incur hefty fuel surcharges.

Using your numbers, 250,000 points for a $4K long haul business is not bad.
It is 1.6cpm, if you are getting your UR at 5X, or even 2X, I will say it is decent redemption.

Wait, I"m confused. AAnytime miles are not a transfer partner of Ultimate Rewards points. Maybe you are trying to use Avios? That might explain the poor redemption value for such a long flight.

Well what points/programs do you have?

MDtR beat me to it, but call up and go through the OW partner airlines - same with *A partners. Between both OW and *A you should be able to find something to fit your timeframe.

My other question is, how far are you willing to fly in that short a frame? I'd hate to fly over 8 hours to a destination with that timing.

High value redemptions are usually problematic when you have the words "weekend" or 'Thanksgiving" in your request. Not so bad if you can schedule last-minute, or have access to expanded award inventory as an elite member. YMMV.

If your time is truly valuable you might be better off just buying the tickets you want, or just paying the higher "Anytime" rates. There's no easy fix for this. The whole point of awards is to give away inventory that would have gone unused.

Only BA & IB.