One of the key learnings of the points-savvy traveller is that miles and points shouldn't be treated as "free". Points have inherent value for a couple of reasons: there's an inherent opportunity cost to using the point as you could've been able to use it for something else in the future, and there was most likely a cost to you acquiring the point, whether it be through spending, a sign-up bonus, or otherwise.

Many loyalty schemes will operate a "pay with points" scheme, which is when you'll be able to use an assigned value of the point to redeem for cash, perhaps in the form of a ticket. HeyMax offers FlyAnywhere, where you can redeem your points for the cash fare of any flight at the rate of 1.8¢ per mile. Some other loyalty programmes may allow you to use your points for non-flying applications as well, though in this case we'll talk about flight tickets, as you'll generally get a higher return on investment per point this way.

In this post I'll talk about the types of "pay with points" schemes available, as well as how you can leverage pay-with-points programmes such as FlyAnywhere to maximise your miles.

What is a "pay with points" scheme?

"Pay with points" schemes allow you to pay for the cash price a flight ticket using your points at a certain cash-per-mile, as opposed to using cash outright. This is different from redeeming award space for a flight.

Some airlines have their own pay-with-points schemes. Singapore Airlines is one of these airlines. For example, let's say I wanted to fly from Singapore to Perth in November. I can either pay 65,000 miles (I can actually pay 45,000 miles if I found Saver award space, though I couldn't for this dummy booking). This would have been on the "redemption" page on Singapore Airlines' website.

However, I can also book the flight with cash, then select to pay with my KrisFlyer miles. In this case, I would've gotten a flat rate of S$1 back per 100 miles (I didn't have enough miles in my account to show you the full spectrum). This would've cost a total of 224,350 miles if I used the "Pay with Miles" section.

Obviously in this case, "Pay with miles" is a terrible deal, given that I'm spending 3.5x more miles on the same flight. However, the "Pay with miles" option isn't award space dependent, which means that you can fly any flight you want with the airline, and use miles to pay for your travel. Other airlines that use a "Pay with miles" option will have a similar concept with a similar rate discrepancy.

There are a few different stakeholders that will have a pay-with-points scheme:

• Airlines will have a "pay with points" scheme, where you'd be able to pay with points directly with the airline (like Singapore Airlines) – these will let you book with the redemption programme's "parent" airline only
• Open-loop loyalty programmes may have a pay-with-points option – HeyMax's FlyAnywhere programme is one of these programmes
• Credit cards will also have options to pay with points, and you might get a better rate if you have a paid card (e.g. AmEx Platinum cardholders get a preferential pay-with-points rate) – these will also let you redeem points for travel on any airline

How does HeyMax's FlyAnywhere programme work?

HeyMax's FlyAnywhere programme works similarly in principle to the above, though as an open-loop loyalty programme, you can redeem your Max Miles for the cash fare of any flight. Simply go onto the app, book your flight and pay the fare, submit your redemption onto the FlyAnywhere portion of the app, and you'll be reimbursed the cash fare of your flight within 5 business days (including taxes and fees).

Generally, redeeming for award space will represent a better deal

Earlier on in the post, I shared an example where a pay-with-points scheme would be the less valuable way to use your miles. This is often going to be the case. Airlines generally release reward seats to retain customers for their loyalty programme, and fill low-season seats. Generally, they aren't incentivised to provide valuable redemption opportunities outside of the reward seats that they release.

However, there are definitely sweet spots you can leverage when it comes to pay-with-points programmes. For example, in 2023, I used Singapore Airlines' "Pay with points" scheme to pay for my flight from Barcelona to Milan, which otherwise offers zero award space. Instead of paying 517 SGD, I paid 35,700 KrisFlyer miles plus 150 SGD in taxes, which was also so I could use some KrisFlyer miles that were expiring at the end of that year.

In this guide, I'm going to talk about what I consider when I use pay with points programmes, such as KrisFlyer's "Pay with miles" or HeyMax's FlyAnywhere programme.

Tip #1: Determine how much you value a point

My first tip to make sure you know how much you value a point. While I don't think you must know exactly how much each of your points are worth, here are a few considerations I'd think about before using a Pay with miles programme:

• How easy is it to accrue a mile (is your mileage accrual optimised based on your daily spending?)
• How often do you spend miles? (do you only have the PTO to travel twice a year? Or do you do frequent weekend trips?)
• Whether the miles expire, and whether you'd have opportunities to use them before they do

Sometimes, it is genuinely plausible that you'll have a better mileage strategy than you do regular financial management. In 2023, I was graduating from college and didn't have a proper income source, and had very limited amounts of time to travel outside of summer (where I'd already made plans), so I genuinely would've been a position to spend 35,700 miles over 350 SGD even if they weren't expiring. Now that I have a proper savings account and travel more regularly, I wouldn't have made the same decision.

Have a think about how much you value your miles, and whether your miles will be easily "replenished" with your everyday spending.

Tip #2: Know the ins and outs of airfare, including cheap origin airports

As pay-with-points schemes always scale with revenue, the same rules apply to pay-with-points schemes as with cheap airline pricing. Generally, you'll want to look at which origin airports in your region you can position to and fly out of, in order to make the most of cheap pay-with-points redemptions.

For example, yesterday I shared a flight from Incheon to London via Beijing that was charging 1,257 SGD one-way in business class (£694 was an OTA price, though China Southern's own website was charging £727, which is 1,257 SGD).

HeyMax's FlyAnywhere programme allows you to redeem 1 Max Mile for every 0.018 SGD on any flight, so FlyAnywhere would've charged me 69,833 Max Miles in order to fly this flight one-way.

If I had booked a flight directly out of Beijing, this would've cost 4,807 SGD, or 267,055 Max Miles. No thanks.

With programmes such as HeyMax's FlyAnywhere, you can even use miles to pay for the low-cost airline segment that you'd use to position to a cheaper origin airport. For example, if I wanted to fly Scoot's ScootPlus from Singapore to Incheon, I could do so for 422 SGD, or 23,444 Max Miles as per the conversion rate.

That would bring my total itinerary cost to 93,277 Max Miles, and this wouldn't be contingent on award space – I'd be able to fly any day this fare was available (and availability for the Incheon-London fare on China Southern is wide open).

While we're on the topic of airfare, do note that taxes and surcharges are included when you book with FlyAnywhere – this means that you'll be paying taxes such as the Air Passenger Duty tax in equivalent miles. The UK charges passengers a £224/387 SGD surcharge for flights in premium cabins out of the UK, so you would be paying 21,500 Max Miles for this tax. This would be included in your total airfare, though is something to keep in mind.

Tip #3: Know how much a redemption would cost for that cabin class on a similar route

Another tip I'd have is to think about how much a redemption would cost for a similar route in a similar cabin class. Generally, you want to make sure that your "pay with points" redemption is in the same ballpark of miles that you otherwise would've spent if you were redeeming directly for award space.

For the above example, Flying Blue doesn't show any award space on the Beijing to London route. However, 69,833 miles is lower than the 75,000 AAdvantage miles you'd need to fly between Asia and London, or even under what equivalent flights would charge when redeeming an award seat.

In order to see whether the route you're redeeming for is a good value, I'd familiarise myself with how much a one-way redemption would cost on a similar route. For example, for a one-way between Europe and Asia, I'd say that the ballpark is around:

• 30,000-40,000 miles in economy
• 45,000-60,000 miles in premium economy
• 65,000-100,000 miles in business class
• 110,000-150,000 miles in first class

If your mileage redemption is above this range, you might want to have a think about why you're spending your Max Miles instead of just paying cash, or whether there's a better alternative.

Tip #4: Know which routes are least likely to offer award space

Generally, I would recommend using a pay-with-points scheme if finding award space on a certain route and aircraft was very unlikely, and I managed to find a cash deal on it that I didn't want to pay for outright.

There are lots of routes that could fall into this category, though here are a few suggestions:

• Anything related to low-cost airlines or discounted economy class – if you have regular points accrual or a good number of points, you might want to spend some of these on low-cost airlines, especially if you are already past your points goals for premium travel
• There are some fifth-freedom flights where award space might just never open up – for example, I've never seen award space for any of Ethiopian's intra-Europe fifth-freedom flights, Singapore Airlines' fifth-freedom flight between Barcelona and Milan, etc.
• Some airlines are notorious for not releasing award space, such as Qantas, ANA on their new 777s, Chinese airlines in premium economy, etc. You might also want to look out for pay-with-points options if you're travelling during peak season

If the maths added up where I'd be using a similar number of points to the ballparks mentioned above, I'd consider using pay-with-points schemes.

Conclusion

Pay-with-points schemes such as HeyMax's FlyAnywhere aren't my default choice when I'm trying to book an airline ticket. However, they can represent great value, especially if I have a healthy accrual strategy and can find cash fare deals that translate well to the pay-with-points scheme.

Generally, I'd recommend having a good idea of how much you value your points (based not just on the opportunity cost, but also on your accrual rates), and measuring the redemption cost against the ballpark of how much a reward seat on a similar route might cost.