This post contains references to products from one or more of our advertisers. We may receive compensation when you click on links to those products. For an explanation of our Advertising Policy, visit this page.

We talk a lot about a little something called “award redemptions” here — but I’m going to let you in on a secret: For the first few weeks that I worked here at The Points Guy, I had negative clue what that meant. And if you’re anything like menew to points and miles with no idea where to start — it can be really intimidating when people are throwing around all these terms left and right, and let’s be real, shun you for asking questions and not knowing all the answers (looking at you, comments section. Be nice or leave).

But I’ve been in your shoes before, and while I’ve definitely come a long way, I’m still only a few steps ahead of a lot of you. Now, though, I’m going to walk you through a few things you should know before you book your trip, step by step.

But first, what even is an “award redemption”? Glad you asked. An award redemption is a fancy points and miles term that means “using your points.” Once you understand that, everything else starts to make sense.

Points aren’t all created equal (use our valuations guide to get a sense of what yours are worth). Having a sense of what each point or mile is worth helps you decide when it makes sense to redeem vs. pay cash — since if a particular redemption gets you significantly less value per point/mile than how you value that point/mile, you’re better off saving those rewards for another time. In regular terms: Your points are worth money. Don’t pay more for a flight with points than you would pay if you just booked it outright using your credit card, or vice versa.

So, let’s say you want to book a trip from JFK to New Orleans (MSY) on Delta. In cash, the flight is $438 round-trip, and in miles, it’s 29,000. So to find out how much value you’re getting per mile with this redemption, you simply divide the cash price by the number of points: $438/29,000 = 1.5 cents per mile. Since we value Delta miles at 1.2 cents apiece, this is a pretty solid redemption.

You still with me? Cool. I promise there’s a method to this madness.

Now that we have the basics down, I’ll explain how I booked my vacation to Croatia and from Budapest using magical sorcery and wizardry — also known as points.

Once I decided where I wanted to go, I consulted the sage advice of my “personal Google,” colleagues Nick Ellis and Julian Kheel. They suggested I check Aeroplan, Air Canada’s loyalty program. Aeroplan shows “award availability,” or where you can use your points to book flights, on Star Alliance airlines such as United, Turkish Airlines, Lufthansa and Swiss Air. Good call, guys.

I ended up finding a one-way business-class flight from JFK to Dubrovnik with a short layover in Istanbul on Turkish Airlines for only 57,500 miles + about $12 in taxes. To book, I transferred 58,000 Amex points to Aeroplan by logging in to Amex’s website, going to “Membership” –> “Rewards” –> and then “Transfer Points.” 1 Amex point is equal to 1 Aeroplan point, which is called a 1:1 transfer ratio. When you do this, your points should transfer instantaneously into your Aeroplan account and voila! You’ll be on your way. This actually ended up being my first international business-class flight and it was SO relaxing, not to mention they served literally the best grilled artichokes I’ve ever had in my life.

Photo by Zsolt Hlinka/Getty Images
Budapest. Photo by Zsolt Hlinka/Getty Image

To get home, I found a seasonal, nonstop flight on American Airlines from Budapest to Philly, which worked perfectly for my itinerary. Ironically, the airline is launching what will be the US’ only nonstop flight to Croatia next summer. And here’s where things get interesting: I was very generously gifted an American Airlines Systemwide Upgrade that I wanted to use, but knew I would have to find the right fare class availability for it to clear. Airlines group cabins into fare classes, which determines how you’ll earn miles as well as your chances of getting an upgrade. I used ExpertFlyer to look for C fare class availability on a handful of dates, and lo and behold, one was waiting for me. C fare class availability means that the upgrade will automatically clear once it was applied (and it did!), which made me *quite* the happy camper.

But that’s not all: I booked my $1,000 economy flight — which was later upgraded to business — and my friend’s $2,000 business-class flight on my Platinum Card® from American Express, where I get 5x points on airline purchases made directly with the airline or through Amex Travel. So, a little bit of math again: $3,000 worth of flights x 5x points = 15,000 points! And remember those 58,000 Amex points I used to book my flight to Croatia? Well, this helped me recoup about 15,000 of them.

Like I said: Sorcery. So, all in all, I paid about $1,000 + 43,000 points for two business-class flights to and from Europe. Not bad, huh?

For a lot of you, I know your head is probably spinning right about now. Booking something like this can be somewhat of a long process, and you definitely need to have some patience, persistence and, truth be told, a little luck. But keep at it, and soon these things will start to make more and more sense; I’ll be there with you every step of the way.

Oh, and while we’re on the subject: Go to Croatia and Budapest. You’ll thank me later.

Feature image by @betterxtogether via Twenty20

Know before you go.

News and deals straight to your inbox every day.

2018 TPG Award Winner: Mid-Tier Card of the Year
Chase Sapphire Preferred® Card

NEW INCREASED OFFER: 60,000 Points

TPG'S BONUS VALUATION*: $1,200

CARD HIGHLIGHTS: 2X points on all travel and dining, points transferrable to over a dozen travel partners

*Bonus value is an estimated value calculated by TPG and not the card issuer. View our latest valuations here.

Apply Now
More Things to Know
  • Earn 60,000 bonus points after you spend $4,000 on purchases in the first 3 months from account opening. That's $750 toward travel when you redeem through Chase Ultimate Rewards®
  • 2X points on travel and dining at restaurants worldwide & 1 point per dollar spent on all other purchases.
  • No foreign transaction fees
Intro APR on Purchases
N/A
Regular APR
17.99% - 24.99% Variable
Annual Fee
$95
Balance Transfer Fee
Either $5 or 5% of the amount of each transfer, whichever is greater.
Recommended Credit
Excellent/Good

Editorial Disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airlines or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.

Disclaimer: The responses below are 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 posts and/or questions are answered.