Award Travel: The TRUTH behind it

I recently started planning a trip with my wife for our honeymoon (albeit a year late). We’ve wanted to go to southeast Asia for a long time now, and finally have the opportunity to go. We’ve been banking points on several credit cards for the last year or so, and had about 450,000 to redeem on award travel. 

In terms of travel costs, premium cabin travel is the most out of reach for us based on our income. The most we can generally afford in cash is premium economy and oftentimes even that too is out of reach. 450k miles in this day and age is not a ton to work with, but it’s not nothing either. We knew we had to be deliberate about what we booked, and as a result we’ve learned a lot. 

You’ve probably seen videos where travel influencers brag about the extravagant air travel they geat for ‘free’. But nothings is truly free… Many of them make money and/or points off people who use their affiliate links to sign up for credit cards. As a result, it’s not in their interest to provide caveats about how they find these incredible deals. Most of them can travel wherever they want, whenever they want. Sounds pretty nice, huh? Most of us need to be able to plan our trips around life responsibilities like jobs,  pets, children etc. If you’ve been banking those points and want to travel for less, what should you expect when you go to redeem those points? As always, we want to provide practical advice towards using points, while setting expectations so you don’t get discouraged. 

Our award trip

To start, I wanted to share the shell itinerary for our trip in the fall. We have nailed down our book-end flights, but there’s a lot in the middle we still need to book. The deals we got for this itinerary so far are good and we think It represents a realistic expectation of what you can get with ~450k miles, while planning in advance.

Dates: Late October – Mid November 2024

Our plan is to fly to Tokyo and spend about 36 hours eating to our hearts content, then head to Bangkok for a few days to explore the city, hit the beach in southern Thailand for a few days before heading to Singapore to finish up our trip.

Departing award flight: 

Route: Chicago O’hare => Haneda Japan
Airline: Japan Airlines
Cabin: Premium Economy
Points/Miles: 99200
Cash: ~$1000 + $200 in a mile top off (usd)

Notes
I transferred 92k Capital One miles to BA in order to book this flight which we booked through British Airways. Booking award flights directly through JAL is extremely difficult for some reason. The advertised redemption value for two tickets was 124k miles, but BA offers two ways to book if you’re short miles:

• pay the cash difference (they give a variety of options from specific mile values + cash)
• or top off your miles balance with cash. 

You might be asking yourself “Those sound like two of the same things”, and while they do sound similar, the math doesn’t support the claim. It was actually cheaper to top off the 92k miles we had to 100k, and then pay the cash difference from 99,200, as opposed to buying the 32k miles for the full redemption value. Always play around with these options if they’re provided. They are not all equal, and oftentimes what seems ‘easier’ is more expensive. 

Returning award flight

Route: Singapore => JFK
Airline: Singapore Airways
Cabin: Business
Points: 287k
Cash: ~$150 (usd)

Notes
For this we transferred points from both our American Express MR and Chase accounts to get the needed points in one place. The point values might seem high, but if you have the points and you have to fly 17 hours, why not right? Also, there seems to be quite a lot of volume, at least more so than other airlines. Whether this is because we were really early to book, or because of the point price, I don’t know.

The Singapore Airlines website says points transfer in 48 hours, but can take up to a week. They won’t hold award seats while you wait for points to transfer, so you’re at the whim of the travel gods in the meantime. If the seats are gone when they get there, you’re just SOL. That said, we watched the dates we wanted for this flight for a month and were confident of availability. Obviously that paid off, but there is always a risk. The good thing is that you can use Singapore KrisMiles to book with StarAlliance partners if that does happen. 

What is left over

Credit Card + Airline points: ~42k (This will get us from Tokyo to Bangkok). 
Hotel: ~ 30k (This will pay for our stay in Bangkok) 

Conclusion

If I’m being honest, nearly 300,000 miles was more miles than I wanted to use for a single flight. But beggars can’t be choosers, and it’s still an amazing cash value. At $0.01/mile our tickets together are valued at $2,870. A single Singapore Airlines business class seat costs close to $5300 for that same flight. 

Additionally, the premium economy seats on JAL for our departing flight are currently listed at about $3400. Is it possible, even perhaps likely that a better deal comes around? Yes. Does it make me feel better to know well in advance that we will have access to above average travel accommodations for both long legs of our trip? Also, definitely yes. Boston is homebase for us, so we’ll still need to get to Chicago and back from New York, but these repositioning flights are a small price to pay in our opinion. 

The hard and dirty truth about award flights

We’ve learned a lot about how to search for award seats and found some good, bad and ugly parts of the industry along the way. We’re hoping sharing these things with you will help you navigate searches and hopefully save a little sanity.  

As a disclaimer, I reserve the right to over simplify and ignore caveats where they exist. I try not to be flat-out wrong, but I’ll reserve that right too. Our goal is to provide practical advice, not get too deep into the science.   

Don’t expect to find Business or First Class award seats for under 100k

Travel influencers love to share how they book amazing flights in amazing business and first class products for what seems like dirt cheap. They have a huge advantage: most of them can go anywhere they want, whenever they want. Most of us have normal lives and jobs and need to plan when we’re going to travel. More specifically where we’re going to travel. It isn’t usually practical to decide ‘I want to go to Japan’, and then wait until the right deal comes around.

Airlines generally release award seats at one of two (or both) times: either shortly before the flights, or almost immediately when the flight schedule is released. Generally you can start purchasing seats for a flight anywhere between 6 to 11 months in advance. In experimental searches, I have found long-haul business class (specifically flights over 10 hours) for anywhere between 50-80k miles, but nearly all have been within 2 months of the departure date, max. Usually much closer, like within a few days or so. So do these award seats exist at the price? Yes. Are they extremely hard to find and plan for, also big time yes.

Pro Tip: There are award seat search tools out there, here are my favorite  

Some deals aren’t as good as they sound

There are some ‘sweet spots’ where you can find business class award seats for under 60k for flights that are technically long-haul, but on the shorter side and there is a catch.

Virgin Atlantic is known for having good redemption values and highwe volume between the northeastern United States and London Heathrow. A one way ticket in business class is available from Boston to Heathrow for 45k miles. The catch is a ‘carrier charge’ of about $950 per ticket is required in addition to your points. So, $2000 dollars each way for both (in order to get this deal you usually need to book two one way tickets). 

Pro tip: Have capital one points? Virgin is running a 30% transfer bonus (April 2024)

Alternatively, the mid tier economy seat is $1600 (you get a carry on, but no extra legroom). So, for two people, 180k miles, and $800 more than a roundtrip coach ticket you can fly business class to and from the UK. If you value the points at $0.01 per, that’s $5800 cash value for the trip. Whether or not this is a good deal is something you have to decide. 

We booked this trip for a September trip in 2023 and felt like we got our money’s worth. At the time, neither of us had ever sat in a lie flat seat. We knew exactly which plane we would be on and what the business class experiences would be like. We also got to visit the Virgin Clubhouse at Heathrow which was an experience in and of itself. 

Look for purchase-and-upgrade deals

Purchase-and-upgrade deals are exactly what they sound like, and there are two ways you can do this.

Upgrade to award seats using points Immediately after purchase 

In this scenario, you purchase a ticket in a cabin below the class you’d like to fly and immediately use points to upgrade your seat. Doing this is usually predicated on the fact that an award seat is available. For example, a United flight might have an award seat available for 200,000 points in business class, but you have 150,000 points and want two seats. Most airlines will allow you to purchase a coach seat and upgrade to the premium economy or business in the same transaction. 

In most cases, to get deals like this, you need to call the airline. The fare class you purchase matters, talk to someone from the airline’s support team and tell them exactly what your intention is. If you don’t have miles in the airline’s loyalty program, wait to confirm the seat is available before transferring from your bank, and request that they hold the award seat for you (you should have a frequent flier account setup with the airline when you call). Whether or not they’ll hold the seat depends on the airline or airline partner. 

Purchase and wait

Many airlines do offer point or cash based upgrades after the purchase of an economy seat. This will depend on fare class, but if it is offered it will be seen in the airlines app, or the website when you log in. There is no guarantee of availability, and price will often vary based on this. If availability for award seats exists, you will usually be offered that price depending on the airline. In the days leading up to your flight, it is common for airlines to release unbooked seats as award seats, and sometimes offer reduced-cost cash upgrades as well.

Last April, my wife and I took a trip to Japan. We purchased a premium economy round trip (it was insanely cheap because we bought the ticket before Japan reoopened from COVID). For months the upgrade price for Delta one was around $4800, or around 500,000 miles one way per person. Insane. When I went to check in for the flight, I got an offer to upgrade to D1 for $800 per ticket on our departing flight. Still not cheap but considering how cheap the tickets we bought were, I couldn’t resist.  

Parting Advice

Decide what is important to you, what do you want to use your points on?
Do you want to fly business/first class, or do you want to get an amazing hotel stay? Both? To maximize your credit card points, build a consistent strategy that works for your spending habits, and don’t get impatient. The longer you wait, the larger that pile of points will become which will translate into better experiences for you. The experiences you’re looking for are out there, but they may not appear as advertised by your favorite travel influencers. Flexibility is always going to be your friend, whether or not you’re planning ahead, so