How to book your first award flight using airline miles

Jan 17, 2021

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While most of us aren’t traveling right now, it’s important to look ahead and plan for when we can get back out on the road. Whether you want to stay connected to faraway friends and family, visit exotic locations, explore your country’s national parks or achieve thousands of other bucket-list trips, TPG wants to help make your travel goals a reality. More specifically, if you are new to the world of points and miles — or still just considering it — we want to guide you through that all-important first award booking with airline miles.

It all starts with a dream

Walt Disney may have started his empire with a cartoon mouse but your future of traveling on miles and points starts with a dream: a travel dream. Dream big or dream small, just decide where you want miles and points to take you. You can have a long list of travel dreams but start your points-and-miles journey with one specific trip in mind. The rest of getting started will be much easier if you know where you want to go.

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(Photo courtesy of Brian Baril Photography/ Getty Images)
(Photo courtesy of Brian Baril Photography/Getty Images)

Read the beginner’s guide

TPG has a fantastic tool created just for those starting their foray into points and miles — the TPG Beginner’s Guide. If you haven’t read that guide yet, give it a look. I’ll wait right here for you to get back.

The guide will talk you through some common points-and-miles terminology, beginner basics, what points are worth and why you need to care about airline alliances and partnerships to make the most of your miles.

I’m going to keep things simple in this article, but I’m also going to assume you’ve read the beginner’s guide. If you get lost in what I say next, head back to the beginner’s guide and give it (another) read.

Related: Start your award travel with the TPG Beginner’s Guide to points and miles

Run some searches

Once you know where you want to go and have at least a loose understanding of points-and-miles concepts, it’s time to run a few types of searches. First, do some Google searches for where you want to go using your points and miles.

For example, if you want to go to Bora Bora, you’ll run a Google search for “Bora Bora using points and miles” and watch the magic appear on your computer screen.

Same with “Maldives on points and miles,” “Paris on points and miles,” “Disney World on points and miles,” “Ski trips on points and miles,” “Hawaii on points and miles” or wherever you want to go. Check the dates on the articles because older, un-updated articles may lead you a bit astray, but there are many great step-by-step guides right here on TPG.

Conrad Bora Bora (Photo by Summer Hull/The Points Guy)
Conrad Bora Bora (Photo by Summer Hull/The Points Guy)

Or, let’s say your goal is to fly a specific plane or type of seat (you’re not alone). Run a Google search for that. Examples could be, “How to book Lufthansa first class with miles” or “Lufthansa first class award availability trends.” Searching for articles like that will give you an idea of what is realistically available using miles, as well as what type of miles you’ll need to book the flight.

Armed with the knowledge from those who have booked those flights before you, start running some award searches of your own. This is true even if you don’t yet have your miles in hand or know exactly when you want to travel. The goal of these searches is to see if you can find the flights you want to book and get used to searching for results and comparing the options. As quickly as things change these days with dynamic-priced programs, you want up-to-date search results in front of you before assuming you know what an award will cost.

Enough of the theoretical.

Let’s say you want to fly to Hawaii and have decided to use American Airlines miles. Head to the American Airlines website and search for flights as you would if you were paying with cash. The only difference is that you click the “Redeem miles” box on the search screen. This process will be similar with most U.S. frequent flyer programs. With some international programs, you likely need to have an account set up and be logged in to search for awards.

Screenshot courtesy of American Airlines

But, American keeps it simple; you don’t have to be logged in to search. Here are some search results for first-class award seats from Dallas – Fort Worth (DFW) to Honolulu (HNL). For January, award prices start at 45,000 American Airlines AAdvantage miles each way for first class, which is a good price. However, you’ll also find award seats that same month that are 87,500 miles each way on that same route. This is what we call YMMV (your mileage may vary).

Screenshot courtesy of American Airlines
Screenshot courtesy of American Airlines


If you are using United miles to fly from Houston (IAH) to Amsterdam (AMS) in business class, you’d search on the United homepage and again click the “Book with miles” box.

Screenshot courtesy of United Airlines
Screenshot courtesy of United Airlines

Using the flexible date calendar search view (which is what you typically want to use when searching award flights, assuming you have any flexibility) for the Houston to Amsterdam route, you’ll see that award prices for that route on this month are consistent at 60,000 miles each way — though we have seen pricing go up to 158,000 miles during other times.

Screenshot courtesy of United Airlines
Screenshot courtesy of United Airlines

These days, there’s rarely one fixed award price for a given route using your airline miles — just like there isn’t one set price with cash. In these searches, what you’re really looking for is a range of normal so you can spot a good deal versus a not-so-good deal.

Screenshot courtesy of United Airlines
Screenshot courtesy of United Airlines

Determine what’s a good deal

Because flight award prices are so variable, it can be hard to spot a good deal when you are new to this way of traveling. Assuming you have the luxury of choice, you’ll want to search a few different dates and possibilities to see the range of normal award prices, and you’ll also want to do some math.

Here’s a real-world situation from pre-coronavirus days where my family did some math to book a simple award trip. My husband decided close to the last minute to go see a Kansas City Chiefs football game with his dad in Kansas City. We live near Houston, so he needed a simple Houston (IAH) – Kansas City (MCI) round-trip award flight. Only United operates nonstop flights on that specific route, so we immediately narrowed the search down to United-operated flights.

Last-minute cash prices for the flights were about $600 round-trip. (Always start by checking the cash price so you have that baseline knowledge.) Had the cash prices been inexpensive ($150 to $250), we would have just spent cash (or fixed-value points) and earned miles on the journey.

United Airlines wanted around 56,000 MileagePlus miles for the round-trip award flights — which wasn’t a good deal at all. Not only is that a lot of points, but it’s also a return of just over 1 cent per mile, below the TPG valuations of 1.3 cents per United mile and well below what we normally get for our United miles.

Related: Here’s what your points and miles are worth

However, when pricing the trip as one-way awards, United did have the outbound flight available for 12,000 miles one-way, which was a fair price.

But on the return, United wanted 47,000 to 67,000 miles, depending on which flight we selected. Before resigning ourselves to spending anywhere near that many points, we checked another option. Since we have the Chase Sapphire Reserve card, we can transfer those Chase points to United or book flights through Chase at a fixed rate of 1.5 cents per redeemed point. Here are details on how to do that.

Related: Best credit cards for earning United miles

In this case, the return flight was on sale through Chase for about $273 or 18,000 Chase points at a value of 1.5 cents per point. An extra upside of redeeming points this way, instead of transferring them to United to book a traditional flight award, is that the flight is viewed as a “paid” flight in the eyes of United, so he’ll earn elite and redeemable miles for that flight.

In total, by doing some basic math and running a few searches with different booking methods, we spent a total of 30,000 points and miles for the two one-way United flights, which is less than if we booked it all as one traditional award flight from United.

If I’ve lost you, that’s OK, just head back through the beginner’s guide or read through when to use miles versus cash for airline tickets. It may take a minute, but it will all make sense. Before you book that first award trip, it pays to know what your options are.

United Airlines tail of plane
Photo by Vytautas Kielaitis/Shutterstock)

Keep it simple

If that all sounds dreadfully awful and you just want to keep the work of booking your first-ever award flight extra-simple, that’s fine, too. You don’t have to do math and compare different sites if you don’t want to — especially at first.

If simple is what you want the most, here are some tips for booking that first award flight.

Stick with Southwest Airlines

Southwest Airlines likes things simple just as much as you do, so if the airline serves where you want to go, focus on earning and redeeming its Rapid Reward points. Southwest points are generally worth around 1.5 cents each toward the airline’s lowest “Wanna Get Away” fares. So, if you have Rapid Rewards points and you want to use them, just use them!

On top of that, Southwest doesn’t charge bag fees, change fees, seat assignment fees, etc. making it a safe-bet with very few surprises. (Here’s how to score the best seats on Southwest.)

A quick example is this $139 Southwest flight from Oakland (OAK) to Maui (OGG).

The one-way flight is either $139 or 8,967 Rapid Rewards points + $5.60. Taking into account the $5.60 in taxes charged on the award flight, 8,967 Southwest points in this example are worth 1.49 cents each, which is right on target for the norm with Southwest. Whether you want to go to Las Vegas, Orlando, Maui or Cancun, your Southwest points are pretty much always worth the same amount on Wanna Get Away fares, making them very easy to confidently redeem.

Related: Best credit cards for earning Southwest points

If you really like Southwest and travel with a buddy, focus on earning a Companion Pass to get a yearlong BOGO deal on Southwest flights.

(Photo by Summer Hull / The Points Guy)
(Photo by Summer Hull/The Points Guy)

Get fixed-value credit card points

An even easier way to make your first award-flight booking simple and rewarding is to start with fixed-value points. These credit card points are worth a fixed amount toward flights or travel. You’ve maybe never heard that term, but you’ve heard of these types of points thanks to “double miles” Capital One commercials featuring Jennifer Garner and Samuel L.Jackson.

While the Capital One Venture Rewards Credit Card now also provides the option of airline transfer partners, you can choose to keep things simple and use the miles at a value of 1 cent each toward erasing a previous travel purchase. So charge a $300 flight to the card and wipe out that travel charge with 30,000 Venture “miles.” Here’s how.

The Capital One Venture Rewards Credit Card currently has a welcome bonus of 75,000 bonus miles when you spend $4,000 on purchases in the first three months from account opening (worth $750 in travel).

If that isn’t the right card for you, there are many fixed-value cards out there where you can just use the points at a set amount toward flights, which is an easy and rewarding way to book your first award flight.

Just book it

Once you’ve learned the basics, decided where you want to go and run your searches, just book it. It’s OK if your first award booking isn’t an around-the-world journey in business class with multiple built-in stopovers or if the math on the redemption isn’t jaw-dropping. Booking an award flight to anywhere in any cabin is a big, big step forward in your journey of traveling more for less.

Color coded boarding cards (Photo by Summer Hull / The Points Guy)
Color-coded boarding cards. (Photo by Summer Hull/The Points Guy)

When you book that all-important first award flight, just be sure to pay the taxes owed with a credit card that provides trip delay or cancellation perks, when possible. Sometimes your trip can still be protected, even if you are paying with miles or points that are earned from that card.

Armed with the basics, book that first award flight (tell us all about it) and start planning for the next trip.

Featured image by Issarawat Tattong/Getty Images

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