Last week I booked myself an award from Chicago to Buenos Aires in United economy for 30,000 United miles + $5.60. This award was very simple, but it illustrated three interesting concepts:

When will last second award space open up?
United's secret extra award space.
The trick to save $75 on last second United award bookings.

Last Second Award Space
I had been searching award space for months from Chicago to Buenos Aires, and there was never any on the inflexible date I wanted to fly.

On Saturday in Chicago, I gave two presentations–one on the award chart sweet spots and the other a “Live” American Airlines Award Booking.

In this post, I'll recap the “Live” American Airlines Award Booking, including the audio of the award booking phone call.

Next month I want to fly Lufthansa First Class from the United States to Europe, like I did a few years ago, because I love the Lufthansa First Class Terminal in Frankfurt, the luxury of sitting in the nose of a 747-8, and the onboard food and drinks.

But I want to do it smartly. Instead of paying 110,000 United miles one way, I want to pay 40,000 Starpoints.

I get questions all the time like this:
Hi, I have a million American Express Membership Rewards/Chase Ultimate Rewards/Citi ThankYou Points, what is the best transfer partner to go from [here] to [there.]
There are basically two ways to answer the question:

Look at award charts of all the points' transfer partners and then look for award space using the cheapest miles. I used this method to suggest to my friend that he transfer his Membership Rewards to Flying Blue miles to get from Denver to Tel Aviv.

Last week my friend flew 24 hours of Lufthansa First Class and had a 3.5 hour layover in the famous Lufthansa First Class Terminal, which he booked for 125,000 United miles and $58.

For the second time, I used 5,000 ThankYou Points to book a one way Air Serbia flight award flight.

I just booked myself an award from Los Angeles to Santiago, Chile in Business Class for 35,000 Asiana miles + $24. United would have charged 55,000 miles for the same flights!

Why Asiana Miles
Asiana has really cheap awards to Europe and South America and really expensive awards elsewhere.

I have a big Asia trip coming up in January.

In October, I booked what might have been my favorite award ever: a Three One Way award that would allow me to see Pohnpei, Palau, and the Philippines while flying the Island Hopper. Read about it here.

Alas, something came up, so I can't fly it. I decided to just fly directly to Japan instead, but that still left the thorny issue of how to turn my old award into an award to Japan.

United charges $200 to cancel an award and re-credit the miles.

I booked myself an award from Honolulu to Manila with eight take offs and landings and multi-day stops on Pohnpei and Palau for 47,500 United miles by taking advantage of the free stopover on roundtrip United awards and how lenient the definition of "roundtrip" is.

A few weeks ago I shared how you can book United's amazing Island Hopper route with miles and stopover at one of the otherwise-nearly-impossible-to-reach islands along the way.

The Island Hopper.