Flight Booking and Frequent Flyer Mile Tips

Let me start off with this – unfortunately, there aren’t any major tricks to booking airfare.  I’ve read this book – Decoding Airfare.  And while it was an informative book, it hasn’t been too useful for my type of travel; and I guess the same would apply to most reading this.

That said, there are some tips to help you get the best airfare possible.

I use the ITA Matrix Search to find airfares.  This is what all other aggregator sites use, so you will definitely find as good of a price anywhere on ITA Matrix.  Plus it has a ton of search options.

ITA Matrix does not sell any tickets, so my recommendation is just to go buy the ticket directly from the airline selling the ticket you want.

I would also recommend before buying a ticket – unless it is already at a price you are very happy with – that you keep checking ticket  prices every day.  And by every day, I mean every day.  Airfare prices are weird; I can’t explain them.  But, they are constantly changing.  So keep checking, and don’t be scared to wait until your flight is not that far away.

Occasionally there will be deals between certain city pairs.  AirfareWatchdog is the best site to use to keep up with those.

I do have one good tip when it comes to booking tickets.  Citi issues the Thank You Prestige Card that comes with a companion ticket (per user) and a 15% discount on airfare.  This companion ticket is actually useable – and very beneficial – compared to many credit card companion tickets.  I saved $800 on flights to Chicago and San Francisco last year using my Thank You Premier companion ticket…and that is real savings that I would have paid otherwise – not a “look at my $20,000 first class ticket” type savings.  Though I like those as well.

The problem is that the Thank You Premier no longer comes with the companion ticket/15% discount, and the Thank You Prestige carries a $400 annual fee.

Yep, $400.  And I’m about to recommend you get it if you are a couple and fly together several times a year.

First, you get $400 worth of points the first year, so that offsets the first year fee.  Every subsequent year, you’ll probably get some kind of retention offer – or you can just keep alternating cancelling and signing up again between spouses.

Second, you get $200 of air related expenses reimbursed a year (e.g. baggage fees, economy plus seats, on board drinks, etc.).  So if you can make use of that $200 reimbursement, the annual fee is only $200 a year.  You can easily save far in excess of that on companion tickets…Especially to places like the Caribbean.

It also comes with things like some free hotel nights, free rounds of golf, and some lounge access.  But the selling point here is the companion ticket (two assuming you add your companion as an authorized user).

The companion ticket catch – it has to be the cheapest (or near cheapest) flight on the route.  But, I have yet to fail to purchase the exact ticket I wanted by checking ITA Matrix every day for a couple weeks.  Southwest Airlines flights are the only ones that can be more difficult to get.

I’ll also add that US Airways and Delta credit cards also come with airline specific companion passes that can be valuable in certain circumstances.

Airline Perks

Holding an airline branded credit card will get you a lot of perks these days.  With Citi/American Airlines, you get priority boarding, a free checked bag per passenger, and a 10% mileage refund.

With US Airways, you get priority boarding, first class check in, and some lounge passes.

United gets you some lounge passes, priority boarding, and a free checked bag.

Any/all of these can be useful for the free checked bags and priority boarding.

Frequent Flyer Mile Award Tickets

You’ve all heard it before – “it’s impossible to actually use airline miles.”  I’m not going to disagree much.  It can be very difficult and frustrating…but not impossible.

Before I get too far, I’ll point out that there are people who book award tickets for a fee.  They are literally pros at it and better than you or I could ever be.  Using them will save you hours upon hours of research; plus they will be able to find more/better seats anyway.  The downside is that you have to pay.  Still, it can definitely be worthwhile if your result is a $6000 business ticket to Asia that you got for free (miles).


The same bloggers I mentioned previously are the ones I’d recommend for this.  Ben at One Mile at Time and Gary at View from the Wing.  And no, I’m not getting anything by recommending them.  They don’t even have any idea that I’m recommending them.  I just know they are good at what they do, and I think their fees are reasonable ($250-$300 for a couple).

Assuming those of you still reading want to torture yourself with award bookings, let’s move on.

First, learn about airline alliances.  There are three major aliiances (with their major American carrier in parentheses) – One World (American Airlines), Star Alliance (United), and Skyteam (Delta).

Why do you need to know about airline alliances?  Because you can redeem award tickets on any airline alliance partner (or other airline partner).  This guy gives a pretty good overview of airline alliances: Link.

I’m assuming you can find the award chart of every airline you have miles with.  If not, go back up a couple paragraphs and hire one of those guys to book your ticket….Alright, I’ll give you a hint – Google _____[airline you want] award chart.

Another thing to be aware of is that some airlines charge fuel surcharges on award tickets (also called YQ).  Some airlines only do it for specific carriers (e.g. AA does not typically charge fuel surcharges on award tickets, but they will if you’re flying on British Airways, usually)…You’ll discover things like this as you go.

Back to booking…You need to know how to search for award tickets on the whole alliance.  United has a very good site for Star Alliance; ANA does as well.  My favorite sites for OneWorld awards are Qantas and British Airways.  Some sites may require you to sign up for their frequent flyer programs to search.  I won’t even pretend to be an expert on Delta, as I largely avoid them.

Gary at View from the Wing recently wrote an excellent piece on finding award tickets – see it here.  I’m not going to rehash a lot of what he said, but I’ll hit a couple things.

This is a big one – search segment by segment.  Do not search New Orleans to Chiang Mai Thailand.  Search San Francisco (or Los Angeles or New York, etc.) to Bangkok (or some intermediate cities if you have a better idea of alliances/hubs/routes).  You can find New Orleans to wherever later.

Going in to this knowing which routes typically have award availability is a huge advantage.  Here is a pretty good list to get started – though this is always changing.

A big tip is that you will have greater success if you are flexible in your dates.


Timing is a topic that you’ll hear many things on.  Some people will say that you need to book the ticket 331 days out at midnight, or you are flat out of luck.  Others will say that close in is the way to go.  Both can be right; it depends on the airline.

I’ve had great success with Qantas/Cathay Pacific at 331 days out via American Airlines miles.  Qantas actually loads their award space about a year out, so you can see ahead of time what is available and jump on it immediately when AA allows award booking (331 days out).  I was on the phone at midnight making sure I gobbled up two Qantas first class tickets (which are very hard to book) at midnight.


On the other hand, just because that is the earliest (or whatever date we’re talking about) you can book tickets, it doesn’t mean airlines will actually open tickets that day.  Some will, some won’t…There are rarely any patterns when it comes to airline tickets.

If you’re way ahead of the game, search far out for other dates on the flight you are looking to take to get an idea of how the airline typically handles things, and you will be ready when your time comes up.

Many airlines do open award tickets close in to the flight date (within two weeks).  Unfortunately, most of us need significantly more notice than that.

My recommendation to that is to search within two weeks of the current date to get an idea of what opens up.  Then book a “backup plan” should nothing open up (either more connections/a worse product/economy/etc.) and be ready to hop on any flights that open up for your date of travel.  You should be ready for this because you know what typically opens up (and you can see how many tickets of that class are still for sale on particular flights, but that’s getting more complicated).  Just be aware of seasonal differences – high/low season.

This way, you have a definite plan should nothing open up; but you can also take advantage of the close in award seat openings.  You will have to pay a change fee on most airlines (like $75 a person), but it is usually worth it.

So I know I didn’t say all that much…That’s because it is a complicated subject.  Hopefully, I gave you enough to get you started.  If it’s too much…bite the bullet and pay an award booking service.  You’ll be happy that you did when you’re flying in business class for miles.

Further Reading

Milevalue seems to have a really thorough overview on booking award tickets.  I didn’t read all the articles, but skimming over them he seems to cover some good stuff.  See the link.

View from the Wing General Advice.

Learn about routing rules, stopovers, open jaws, etc.  You can do some cool things on a single award ticket.  Google is your friend to find reading material.

ETA (March 2014): View from the Wing advice on timing of purchasing flights.

2 thoughts on “Flight Booking and Frequent Flyer Mile Tips

  1. Pingback: Updated Points/Miles Strategy | JustinAndAlyce

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