It’s hour 10 of a 14-hour flight to Tokyo, and as I sit in my business class suite, this seems like the perfect time to share everything I know about winning the miles game. Because nothing feels sweeter than traveling swank and knowing you did it with miles.

My biz class mini-suite on JAL (Japan Airlines).

I’m traveling from NYC to Hanoi, Vietnam on JAL (Japan Airlines). It’s a 23hour trip in total. The cost in real money for this round-trip? $8,000 USD. My cost? 140,000 miles and $75 in taxes. And I booked it three days ago.

So here we go. First I’m going to take you through winning the miles-redemption game. Then we’re going to talk winning the miles-hoarding game.

Miles Redemption

Do Your Homework

Before you ever make a call to your airline’s mileage awards desk, you need to do your homework. Take my trip to Hanoi. I started with a visit to Kayak, to see what the flight options from NYC to Hanoi looked like. I like Kayak for all their filters. I eliminated the 2+ stop trips and focused on 1-stop trips (there are no nonstops). Then I filtered by my airline’s alliance (American is Oneworld), so I could narrow in on only the trips I could access with my miles.

This is a key point that I think many people miss: your miles awards are not limited to trips with your airline only. They are your gateway to all the partner airlines in your airline’s alliance.

So for me, I learned that NYC-Hanoi on Oneworld had quite a few options: Cathay Pacfiic via Hong Kong, JAL via Tokyo, and Qatar via Doha. At this point, I like to filter by “Duration” so I can see what, in a perfect world, would be the shortest trips to my destination.

Then I start printing out pages and getting out my nerd highlighter to start making initial picks. I’m looking at duration, but also the connection city for each airline. Not only because you may have a long enough layover for a day trip, but if on the off-chance you get stuck due to flight delays, where would you most like to get stuck?

Cross Check on SeatGuru

Next, I head over to my beloved SeatGuru, to see what my top trip choices look like in terms of seat quality. If I’m spending 100K or more miles on a seat, and sitting in it for 23 hours, you better believe I’m going to ensure it’s the swankest I can get my freelanceafarian hands on.

For my Hanoi trip, my top three players, Cathay Pacific, JAL, and Qatar were all looking ridiculously good. All truly flat seats (not the tricky "lie-flat angled" seats of some American Airlines and other airlines’ business class).

I’ve flown Cathay biz several times and know that the seats are awesome as are the food and service. The JAL seat specs, food reviews, and photos all looked great too. Same with Qatar.

Okay, so I knew there were no bad options here, but in order of priority, I went in thinking Cathay, then JAL, then Qatar.

Think Positive

You will win this game. There is always a way.

Now dial your airline’s mileage desk. Conjure up your nicest, most jovial self. These phone agents deal with some pretty nasty people. Be one of the nice ones, and you’ll be surprised how well things can go. I like to start by introducing the trip idea in a personal way, by sharing why I’m going (it’s my grandmother’s birthday, or I’m meeting an old friend). Whatever your story is, it’ll help make you a person and not a number that they want to rush off the phone. Ask if they’ve ever been to your destination, or if they have any expert advice on your flights, like which partner airline has the best service or the best seats (can’t hurt to get a second opinion).

Then let them do an initial search of your ideal dates and times. Now of course, there’s always the chance that you’ll get a lucky strike: the exact trip you want, for the lowest number of miles in business class, on exactly the dates you need. If so, then obviously, book it.

If not, now is when you get into the nitty gritty. Pull out your notes.

Ask to be sure the agent checked all the partner flight options. Volunteer that if the shortest itineraries aren’t available, you’d be okay with a longer layover. Give him or her the exact flight times from your notes, “What about the 1:25 from JFK with the longer connection in Hong Kong, and then taking flight 114 at 7:15?”

If that doesn’t turn up the answer, get practical: volunteer to fly business for the long leg and coach for the shorter leg. “What if we do business NYC-Hong Kong, and coach to Hanoi?” This has worked for me many, many times. And, when you book this way, you can keep checking to see if the short leg opens up in business class, since you’re redeeming a business class award. Even in transit at the airport, if a business class seat opens up, you’re entitled to move up. Just check at a service desk. If not, c’est la vie. As long as the longest leg was biz, you’re still ahead of the game.

If that doesn’t yield anything, get flexible: can you shift your dates one or two days?

If not, get geographically flexible: what if you get close to, but not all the way to, your destination? Let’s take Hanoi: on the way out, I could get Cathay for NYC – Hong Kong biz, then HK – Hanoi coach, on my desired date. Fine. On the way home, though, there was nothing from Hanoi, not biz nor coach. So I asked if there was availability from Hong Kong – NY, and there was; as the agent checked, I went to kayak to see how cheaply I could get buy HK-Hanoi (under $300USD rt). So fine, I asked the agent to hold the round-trip NYC – Hong Kong. Most airlines (maybe all) let you hold an award itinerary at least 24hours, if not several days.

(Of course, if you don’t live near a major gateway airport, you could also reverse this approach and buy your own ticket from home to whatever airport has availability for the major part of your trip.)

Then I went to sleep. Tomorrow was a new day. The game was not over.

See What Changes Overnight

The next day, late at night, when phone traffic is lightest, I called again. Just to see what might have opened up overnight. And, what a different agent might turn up. And what do you know? This new agent turned up one seat available for… a roundtrip all the way from NYC to Hanoi, on JAL. Bingo! All biz class, and a nice tight layover in Tokyo. She had to check with her supervisor about some zones question, and I don’t know if that’s the reason the first agent hadn’t offered this itin, or if it simply hadn’t been available the day before.

Whatever. I had just won the miles game. An $8,000 roundtrip for 140,000 miles and $76 in taxes. The Tiger Woods fist-pump is nothing compared to the freelanceafarian jumpy-jump, when I win like this.

I should note that I’m Platinum status on American Airlines, so that’s why I didn’t pay any last-minute redemption fees, which can be over $100. It also helps to have status when you’re on the phone with the agents, who are usually inclined to go the extra mile for you. But even in the days before I had status, I would use all the tips outlined above to win the miles game.

You can too.

In my next post, I’ll review how to become a champion miles hoarder, like me.

It came to my attention recently that a well-traveled friend of mine had never heard of SeatGuru. Quel horreur!

While I, of course, remain your primary guru, the SeatGuru is definitely one you need to add to your repertoire.

Because when it comes to traveling, we all know that beyond the airline, the seat itself can make or break your experience. Legroom lounger or toilet attendant? You make the call.

Even in business or first class, there are huge differences in seat quality. Even within one airline, in the same class, on different plane types.

Simply put: SeatGuru helps you pick the best seat on every flight you take. And if really use it like a pro, it will actually influence which flight you buy.

The SeatGuru website has come a long way since its underground-nerd-forum days of yore. (Yore!) Now you simply search your airline and then select your flight number or aircraft (which is found in the details of any flight you’ve bought or are considering). You’ll get great maps of seat layout (how many coach, biz, first class seats) and details on seat quality. Seat quality is the biggie here.

Let’s say you’re ready to cash in your hard-earned and well-hoarded miles for a swank seat in business to the other side of the planet. You want to make sure you’re getting the best quality seat possible.

What do I mean by seat quality? THIS:

American Airlines' deceptively named "flatbed" Biz Class seat.

American Airlines' Biz Class "lie-flat" seat.

Same airline, both business class. Hard to know the difference at first. Well, one is the “fully-lie-flat” seat. The other is the deceptively named “flatbed” seat, which yes, is a flatbed, but TILTED at a 10 degree angle, which means you get to slide down your bed all night. Blood clot, anyone?

Let’s take it to coach, where seat quality may not differ much from plane to plane on the same airline (except for TV availability, which still does vary greatly in the U.S.), but hell yes differs from spot to spot. SeatGuru will have the seats color-coded, so that at a quick glance you can get a sense of good or bad. Roll over with your cursor to read specific comments and pros/cons on a seat.

For every aircraft, you’ll also find info about TV availability, charger ports, wifi, and more for all classes of service. Many will have user-contributed photos to help you out, including pics of seats, meals, overnight kits, and more.

As a last note, I want to return for a moment to the mileage cash-in moment. Let’s say you’re planning a really long vacation flight, like a 10+ hour journey. Remember that your miles don’t necessarily have to be used on the airline you earned them on. Your airline has partner airlines, some of whom may have waaaaay nicer seats than your regular carrier. Make a little visit to SeatGuru's comparison section before you make the call, to check which partner airline has the best-quality seat for your miles. Then, of course, it’ll be a game of award availability, and you may or may not win. But at least you’ll make your final choice like a pro.

You're welcome.