POINTS REDEMPTION -- THE BASICS
Now that you have collected a pile of points, it's time for you to put those points to use. (Fair warning there will be some very simple math in this section.)
VALUING YOUR POINTS FOR THE BEST DEAL
For this section, I'm going to assume you have 75,000 Chase Ultimate Rewards points, but the principles here also apply to other transferable points programs (Capital One Rewards Miles, American Express Membership Rewards, Citi ThankYou Points and others).
Let's say you want to fly a round trip from Chicago to Paris. The first thing you should do is go to Google Flights and figure out what it would cost you in cash. Let's say it's going to cost you $750 round trip.
Now let's figure out how you can optimally use your points to get yourself to Paris and back.
Chase will give you several options. First, you could cash out your 75,000 points at $.01/per mile. Cool! You have your $750 to pay for your ticket to Paris!
Don't do that!!! There are better ways!
Your next option would be to book your roundtrip flight through the Chase travel portal. If you have a Chase Sapphire Preferred, you can use the Chase travel portal to book your trip at a rate of $.0125/point (the Reserve gives an even better rate). So, if you book your trip through the portal, it will only cost you 60,000 points ($750/.0125 = 60,000). You just saved yourself 15,000 points!
But wait! There is likely an even better deal!
Now you need to figure out how many points it would cost for your round trip to Paris if you transfer your points to one of Chase's transfer partners. (More on doing searches for points costs below). Let's say that Flying Blue (Air France's points program) has flights for only 20,000 points each way – a total of 40,000 points round trip. You've just saved yourself 20,000-35,000 points! That's almost enough for another round-trip ticket to Paris!
In summary, your points have the following values under these three options:
Cashback = $.01/point
Travel portal = $.0125/point
Transfer to Flying Blue = $.01875/point ($750/40,000)
So, you're getting the best point value with the transfer partner. It is usually – but not always – the case that transfer partners will give you the best deal. (See the next section for an example.)
ONE COMPLICATION AND A LITTLE EXTRA MATH
Every transfer program that I know of will charge you cash for taxes and fees. These amounts can vary wildly and will affect the value of your point redemptions.
Let's say that Flying Blue is going to charge you $100 in taxes and fees if you redeem your points for a round-trip ticket to Paris. That means that you are really only saving $650 by using points instead of $750. ($750 cash ticket price - $100 taxes and fees = $650)
So, you should use $650 as the numerator on your transfer to Flying Blue. But that's still the best deal. That still values your points at $.01625/point ($650/40,000).
But let's say that Carrier B is going to charge you $300 in taxes and fees. That means that your numerator is now $450 ($750 cash ticket price - $300 taxes and fees = $450) If you divide the $450 by the 40,000 points that you would use instead, the points value drops to $.01125/point. In that case, the Chase travel portal will give you a better value per point than the transfer partner.
Whether that makes a difference is up to you, some people just want free flights no matter what the points redemption value is. Others meticulously track their points values and will not even consider booking anything with a points value of less than $.02/point. I fall somewhere in the middle.
FINDING THE BEST TRANSFER PARTNER DEAL
Students, you may put your calculators down!
At the moment, my starting place for searching for flights on points is the website pointsyeah.com. There are other good search tools out there like roame.travel, seats.aero and point.me. I like pointsyeah.com because it's free with registration and has a simple interface and easy filtering.
You should always search one-way – for example, from Chicago to Paris and then a separate search from Paris to Chicago. Pointsyeah.com will pretty much force you to do your initial search in a three or four-day window, but you can later filter it to a particular day if necessary.
Pointsyeah.com will also allow you to filter your search by bank program. So, for instance, if you have Chase points, it will only search Chase transfer partners like United, Flying Blue, British Airways etc. Programs that are not direct transfer partners (like Delta and American Airlines) will be excluded from the search. Don't be surprised if pointsyeah.com suggests some seemingly odd transfer partners. For example, pointsyeah may suggest that you book your flight from Chicago to Paris through Aeroplan (Air Canada's program) or Lifemiles (Avianca's program). These can be codeshare flights. They're the same flight; they're just ticketed by different airlines. Each program sets its own redemption rate, so some seemingly strange programs may have the best points deals.
But wait! A couple of cautionary notes. Pointsyeah is not perfect. It may show you a flight that is not actually available, so you should confirm flight availability directly with the airline before you transfer your points. (On the other hand, Pointsyeah often will show options that don't initially show up if you search directly with the airline program – meaning that you can get a better deal than what the airline initially shows you.)
TLDR: Double-check everything before you transfer your points.
And speaking of transferring points, I'm not going to get into the mechanics of that here. There are YouTube and TikTok videos that can walk you through the process.
But please be aware that sometimes points do not transfer instantaneously and point transfers are one way. That can cause problems. Let's say, for instance, that you find a fantastic points deal on Singapore Airlines, but a points transfer to Singapore Airlines is going to take 7 days. By the time your points hit your Singapore Airlines account, the flight you wanted may be gone. (Call ahead and see if they will hold a reservation for you until your points transfer. Some airlines will do it; some won't.) If the flight you wanted is gone, you may end up with a bunch of points sitting in a Singapore Airlines account because once transferred, they cannot be transferred back to Chase.
There's an incredible cheat sheet from 10x Travel that will help you figure out transfer partners and transfer times. Faster is better. (10x Travel is an amazing resource generally -- although some of its fans exhibit cult-like devotion. More on that later.)
Bottom line -- caveat emptor.
WHEN TO REDEEM YOUR POINTS AND THE IMPORTANCE OF FLEXIBILITY
Looking for great points deals isn't that different from looking for a great cash deal. Flexibility is on your side. If you are tied to very specific dates and a very specific destination, it is going to be harder to find a great deal. A number of my trips (both on points and in cash) have been the result of me just poking around, looking at interesting destinations. (For example, that's how I ended up in Peru. I found a ridiculously cheap points deal.)
Although great points deals can be found anytime, there are broadly two factors that are likely to affect your points redemptions: 1) when you travel, and 2) when you book.
On the first point -- when you travel -- if you are looking to travel over holidays or during school breaks or during the destination's high season, you're less likely to find a great deal than during the off season or shoulder season. Also, (and I'm speaking in general terms here), international weekday travel tends to be cheaper than travel on the weekends. So, if you can, keep your travel dates flexible to get the best deal.
On the second point -- when you book -- there are broadly two windows when the best deals can be found (although as I said above, great deals can happen anytime, so keep checking back). The first window is when the airline opens booking for seats that can be purchased with points. Although it varies from airline to airline, many airlines open their bookings approximately 11 months before the flight date, so if you can plan in advance, that may be a good time to check.
The second window is the period of time just before the flight. Airlines sometimes discount points starting a month or two weeks or even a few days before the flight. So, if you have flexibility and are willing to take a bit of a gamble, you can wait until more or less the last minute to book your flight. But remember, it's a gamble. There are no guarantees that the airline will discount, so if you don't have the stomach for uncertainty or have plans at your destination that can't be changed, this may not be the strategy for you.
ONE SLIGHTLY MORE ADVANCED STRATEGY
If you are traveling to or from cities that are not MAJOR transportation hubs, consider repositioning. For example, let's say you want to travel from Kansas City to Florence, Italy. Kansas City and Florence both have airports (In fact, I've heard rave reviews of the new airport in Kansas City) but searching for flights from Kansas City to Florence is not likely to give you very good points deals -- if you can find a flight with points at all. Instead, try searching from Chicago or Houston or Dallas to Rome. You might have to take a repositioning flight from Kansas City to the starting hub and then take the train from Rome to Florence, but that may be much, much cheaper and give you many more options than if you attempt to do the whole trip through points.
So, now you have the basics! You're ready to book your trip. But stay tuned for more advanced strategies!
