MileValue is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers. Terms apply to American Express benefits and offers. Enrollment may be required for select American Express benefits and offers. Visit to learn more.

Note: Some of the offers mentioned below may have changed or are no longer be available. You can view current offers here.

I’m going to spend most of the rest of the year in Buenos Aires, but I want to spend Christmas with my family in Hawaii. I recently put on hold an award that will allow me to do that. I am going to fly Business Class in a flat bed from Argentina back to Honolulu for 50,000 American Airlines miles and $87.

For a limited time, the Citi® / AAdvantage® Executive World Elite™ MasterCard® offers 75,000 bonus American Airlines miles after spending $7,500 in the first three months.


In the end, the award searching was very easy in this case, but I hope this Anatomy of an Award will illuminate:

  • how to book awards around the peak Christmas travel season
  • how far in advance you should start searching for awards
  • how American Airlines free holds work
  • how I choose between different Business and First Class products

The History

How far in advance should you search for award space?

It’s one of the most common questions I get. The answer: whenever you know your travel goal, start searching for award space. That way if there is space now, you can book it. If there isn’t, you can keep searching and hope space opens up. You can also estimate the chances that award space will open up by tracking it over time.

It has been my plan to go to Honolulu for Christmas for at least five months. Following my own advice, I’ve occasionally been searching for award space from Buenos Aires to Honolulu during mid- or late-December for the last five months. Finding award space right before Christmas is very difficult because airlines only release award seats when they expect to have unsold seats, and they don’t expect to have many unsold seats around Christmas.

So I have been realistic with my searches, mostly hoping to find award space some time between December 14 and 18 because that is the week before the last weekend before Christmas, when I imagine Christmas travel will really pick up.

Screen Shot 2015-09-28 at 2.43.07 AM

I had found the occasional award using Copa and United flights to get to Hawaii, but Copa Business Class is just a recliner seat, and that sounds terrible for such a long day of traveling. I could book that award space with 60,000 United miles.

I had also found awards to Los Angeles in AeroMexico Business Class with the longest flight on a flat bed, but I couldn’t find Delta award space from Los Angeles to Honolulu. I could have booked just to Los Angeles in AeroMexico Business Class for 62,500 Delta miles, but I kept searching.

I hadn’t found anything good on LAN or American Airlines that I could book with American Airlines miles, until Saturday.

The Search

On Saturday, I lucked out and found American Airlines award space. American Airlines has the cheapest awards between Southern South America and Hawaii:

  • 20,000 or 30,000 miles in economy one way depending on the time of year
  • 50,000 miles in Business Class one way
  • 62,500 miles in First Class one way

I always start with a simple search. Maybe I’ll get lucky and find award space immediately without having to search segment-by-segment. On Saturday, I went to and typed in my search:

Screen Shot 2015-09-26 at 6.42.22 PMEconomy space is rare in December, with only one day with Saver award space.

Screen Shot 2015-09-26 at 6.43.17 PM

Business Class award space also only had one day available, much closer to Christmas, in the December 14 to 18 window I was targeting.

First Class had the most award space with five days at the Saver level in December, with one in the week I was targeting.Screen Shot 2015-09-26 at 6.43.32 PM

I compared the Business Class and First Class awards that were closest to Christmas. The Business Class award costs 50,000 miles, features a travel time of 27.5 hours, and has two stops. One major drawback is that the 6.5 hour flight from Phoenix to Honolulu is in economy because First Class award space isn’t available on that flight. (You are entitled to fly First Class domestically on international Business Class awards. If that space doesn’t exist at the Saver level, you can book Saver economy space, but you don’t get a discount.)

Screen Shot 2015-09-26 at 6.43.53 PM

American Airlines Business Class used to be an angled-flat laughingstock. New planes and retrofits are slowly converting the fleet to fully flat. I clicked “View Available Seats” for the flight from Buenos Aires to New York to see whether the seats would be fully flat or angled.

Screen Shot 2015-09-28 at 2.18.55 AM

The seat map shows a plane that has been retrofitted with flat beds in Business Class. You can confirm that by comparing it to seat maps on Seat Guru until you find the one that matches and then reading Seat Guru’s description of Business Class on that plane. The triangles indicate seats that face backwards. Here is a trip report with photos of the Business Class cabin on this American Airlines 777. It looks very nice.

Next I looked at the First Class award. It is 12,500 miles more, 1.5 hours more travel time, and also features economy on the last segment.

Screen Shot 2015-09-26 at 6.44.00 PM

I flew this exact First Class product a in 2013 to Buenos Aires (trip report), and I can see why it is being phased out. It’s not up to First Class standards. It’s just a decent flat bed Business Class product in my opinion.

I figured that the Business Class itinerary is better because:

  1. I’ll save 12,500 miles.
  2. I’ll get 1.5 hours extra in a flat bed. I usually prefer longer flights to maximize sleep when I have a bed conducive to sleeping.
  3. I’ll take off from Buenos Aires 1.5 hours later, which is better for my sleep schedule.
  4. I’ll travel 1.5 hours less, which is good because even 27.5 hours is possibly my longest itinerary ever.
  5. I think the Business Class and First Class products on these two awards will be of very similar quality, and I haven’t flown the new Business Class, so novelty gives it the edge.

I selected the Business Class itinerary, and it priced out at 50,000 American Airlines miles + $87. That is all government taxes; American Airlines only collects fuel surcharges on British Airways and Iberia award flights.
Screen Shot 2015-09-26 at 6.44.23 PM I selected seats on each flight, input my personal information, and clicked through to the purchase screen.Screen Shot 2015-09-26 at 6.44.30 PM But I don’t currently have 50,000 miles in my American Airlines account, so I was only given the option to hold the award. (Why don’t I have 50k? I have 120,000 miles tied up in an award I want to cancel, but I am waiting for a schedule change to get the $150 cancellation fee waived, and I just booked a 90,000 mile award to fly Etihad First Class on its A380 from India to the United States.)Screen Shot 2015-09-26 at 6.47.17 PM If you do have enough miles in your account, you can still get a free award hold. You’ll see these options at the time of payment; select AAdvantage Hold.

Screen Shot 2015-09-26 at 6.53.12 PM

Award holds last five days and expire at midnight in the city of departure.

Screen Shot 2015-09-26 at 6.47.40 PM

If you do nothing, the hold cancels itself. If you want to book, you have to log back into your account and book.

I am only about 7,000 miles short of the 50,000 needed to ticket this award, so I transferred some SPG Starpoints to my American Airlines account. That process usually only takes a few days. If it doesn’t look like my transfer will post in time, then I will cancel that 120,000 mile award I mentioned above.

Loose End

I really would like to get that Phoenix to Honolulu leg into First Class, since it would be zero extra miles if Saver award space opens up.

I have a couple options. First, American Airlines has been known to open up award space if you call and ask on the pretense that you found an award that is almost perfect and is just missing the award space you want on one leg. When my American Airlines account has 50,000 miles in it, I will call and ask for an agent to open up First Class award space from Phoenix to Honolulu and then ticket the whole award.

If that doesn’t work, I have set an alert on the award space. If it opens up, I’ll change the award. This will be free until 21 days before departure and $75 within 21 days.

American Airlines sometimes opens up award space in the last month or week before departure. I notice this quite a bit on its Hawaii routes in particular. To estimate the chances that award space will open up in First Class on the Phoenix to Honolulu flight closer to departure, I searched award space for the next month:
Screen Shot 2015-09-26 at 6.50.20 PMThere is Saver award space on four days in the next week and a half. I’m guessing there’s about a 40% chance that the award space opens up for me.

If it does, I’ll know because I set a free alert with the Wandr Me tools. I also set an alert for JFK to Honolulu in case a different route to Hawaii opens up with award space in First Class on the same day, maybe via Los Angeles or Dallas.

Screen Shot 2015-09-27 at 8.48.37 PM

Bottom Line

Search early and often on every airline that can get you where you want to go. Compare your award options to determine the best value for you. In this case, I prefer a new Business Class product to an old First Class product.

Put your award on hold when possible to secure the award space while you get the necessary miles.

If the award isn’t perfect, like maybe it has one leg in economy, book anyway and set an alert in case better award space opens up.

If you don’t want to deal with your own award bookings, hire the MileValue Award Booking Service.

Earn 60,000 bonus points after you spend $4,000 on purchases in the first 3 months from account opening.

Just getting started in the world of points and miles? The Chase Sapphire Preferred is the best card for you to start with.

With a bonus of 75,000 points after $4,000 spend in the first 3 months, 5x points on travel booked through the Chase Travel Portal and 3x points on restaurants, streaming services, and online groceries (excluding Target, Walmart, and wholesale clubs), this card truly cannot be beat for getting started!

Editorial Disclaimer: The editorial content is not provided or commissioned by the credit card issuers. Opinions expressed here are the author’s alone, not those of the credit card issuers, and have not been reviewed, approved or otherwise endorsed by the credit card issuers.

The comments section below is not provided or commissioned by the bank advertiser. Responses have not been reviewed, approved, or otherwise endorsed by the bank advertiser. It is not the bank advertiser’s responsibility to ensure all questions are answered.