My Single Best Tip For Maximizing Points Redemptions (& More)!

Filed Under: Advice, Travel

Book something you’re happy with and always check back to see if you can improve on it.

That’s my best piece of advice for truly getting the most value out of travel, especially when you’re redeeming miles & points. It goes beyond miles & points, though, and is true of “revenue” travel as well, especially for hotel stays.

More than ever before it’s important to be flexible when redeeming miles. Airlines are holding back more and more award space, so ideally you lock in something you’re happy with when you’re ready to plan, and then just keep checking back. Over and over and over again. Let me give a few examples of “successes” I’ve had with this method recently.

Business class award space opened up

I’m going somewhere to New Year’s which is typically nearly impossible to find award space to. I only booked a few months out, and was shocked space was available. The “catch” is that the second flight was in economy. Ultimately it wasn’t a huge deal, given that it was an A330, meaning we could snag two window & aisle seats together.


Not only was there no business class award space when we booked, but business class was completely sold out. Not surprisingly, a couple of people have canceled their business class seats as the departure date approaches, as is usually the case.

When I checked back this morning, I was surprised to see that business class award space had opened up for the flight. There were exactly two business class seats for sale, and both become award seats. Yay! I would have never predicted the space would have opened more than a couple of days before departure, but checking back every day paid off.

Snagging better economy seats

Ford and I are taking a domestic flight this weekend on an American A321. The chances of the upgrade clearing are very low, and at the time of booking we weren’t even able to snag two Main Cabin Extra seats together. Well, not only did two Main Cabin Extra seats open up yesterday, but the exit row where there are just two seats opened up, meaning we’ll have unlimited legroom and won’t have a third person in our row. Add in the free snack & drink for Executive Platinums, and it’s almost like first class.


Hyatt Diamond Suite Upgrade availability opened

I recently stayed at the Grand Hyatt Hong Kong, which I booked using Points + Cash.


I only booked a few days before the arrival date, and at the time there were no suites available, which was unfortunate, since I wanted to apply a Diamond Suite Upgrade to the stay.

I checked back at the standard cancellation time for the hotel (24 hours before arrival), and sure enough a suite opened up, which I was able to confirm immediately.

Grand-Hyatt-Hong-Kong-Grand-Suite - 12

Grand-Hyatt-Hong-Kong-Grand-Suite - 23

I wouldn’t have been able to snag that suite for our five night stay if I didn’t keep checking back.

Saving $80 per night on a hotel

I’m staying at a hotel this coming week, which I booked for $199 per night several weeks ago. I checked back last week and saw that the rate had dropped to $119. Given that I booked a flexible rate, I could cancel and rebook the reservation to save $80. Woohoo!

It gets even better, though. Over the weekend I noticed that the hotel was available with a non-refundable “Hot Escapes” rate for $99. At that point I was happy booking a non-refundable rate and saving a further $20!

Bottom line

While there are lots of great tips for minimizing the cost of travel and maximizing miles & points, I think checking back on my reservations often is the one which adds the most value to my travels. Of course different people will define “checking back often” differently — some will check a reservation once a week, some once a day, and some once every few hours (in general I check more often as the travel date approaches).

To consolidate my advice…

For hotels:

  • If you’re booking far in advance try to book a flexible rate, so that you can take advantage of any rate drops as the arrival date approaches
  • If you’re looking for points availability to open up, keep checking back; it’s very likely people will cancel reservations, and therefore space will open up; arguably this is most likely to happen around the cancellation deadline for the hotel, which is often a day before arrival

For flights:

  • If you’re looking for a better economy seat, your best odds at that are around the same time that the upgrade window opens; as people get upgraded, often the better “premium” seats in economy will open up
  • For international premium cabin award flights, you’ll often have the most luck booking very last minute, even in the hours up to departure; this is especially true for airlines like Cathay Pacific, Etihad, and Lufthansa, which often even open space day of departure (you’ll probably have the best luck booking Etihad’s A380 First Class Apartment within 24 hours of departure)


Anyone use a similar technique of always checking back to see if they can improve on their travels as the departure date approaches? If so, what success have you had?

  1. I keep checking for better options all the time and most if the time it pays off – either I can save money or get a better experience.

    Just today, 3+ First Class seats on EY opened up two days before departure of our family’s pre-Christmas trip ZRH-AUH and I was able to upgrade an existing AA booking in Business at the cost of just 10k miles each. ^^

  2. “Book something you’re happy with and always check back to see if you can improve on it.”

    Is this something PointsPros does for its customers?

  3. I am so not in the position to travel right now but I do love how much effort you put into your posts and blogs. Keep it coming Ben 🙂

  4. Another big one is rental cars. Book early and then check back alot, including using booking codes you can get from simple Google searches. This has saved me hundreds of dollars each year.

  5. Except when you’ve booked a non-refundable rate. Then don’t keep checking – it will just make you unhappy.

  6. I booked 1 first class and 1 business class seat on Cathay’s Hong Kong to Boston flight for the return leg of my honeymoon. I planned on upgrading the business to a first when more availability opened up (cathay usually only releases 1 seat ahead of time), but then the AA devaluation happened.

    Luckily, I some how managed to find 2 first class awards available on the HKG to Chicago route and booked those at the old AA rates. The downside is that there was only economy available on the ORD to BOS domestic leg at the time. I’ve got some ExpertFlyer alerts set up to tell me when 2 first class seats open up on 3 different ORD to BOS legs that I will switch to.

    Even better than that, I’m hoping to switch back to the direct Boston flight a few days before the flight when Cathay release all (but one) of it’s unsold first class seats.

    Being open to different routings is just as important/useful has different dates/times.

  7. Hawaii is onto you! As I just discovered, the hotels there make you lock in your reservation several days to weeks in advance of the Christmas holidays.

    For normal dates, I find the Hotel Hustle award alerts to be invaluable by sending you an email when your desired hotel becomes available on points.

  8. Constantly! It drives me nuts when our friends book a trip a year out and never recheck car or hotel rates! I also switch hotels if rates drop and a good promotion shows up. (And it’s an airport hotel or something where it’s just a generic stay, not a special stay.) I save tons of money on car rentals this way.

  9. I took your advice & decided to check my Crowne Plaza bookings at Singapore Airport next March.

    The rates were a little cheaper than originally booked but then I noticed I can book with senior rates. Changed my bookings and saved a fair bit of money.

    One thing I have noticed with airport hotel bookings is that the closer to the time the reservation is required, the rates tend to increase. I noticed this first hand a couple of years ago when I pre-booked the Holiday Inn at Heathrow for 77GBP a note but at the time of the check-in I noticed the holte was quoting a walk up rate of 200GBP!

  10. This is good practice.
    I had booked an award ticket J from HKG-LHR-CDG on BA, with high charges.
    Then the direct flight HKG-CDG on CX became available, so I changed it.
    Then an earlier direct flight HKG-CDG on CX in First became available, can’t wait to fly it.

  11. I follow the same strategy. Booked business class to Brazil a few months back for $2700. Kept checking every day and voila, the date dropped to $1800. After the $300 AA change fee, they sent me a paper voucher for $600.

  12. It’s important to note here that Hyatt (for one) even allows you to rebook at a lower rate and keep a confirmed Diamond Suite Upgrade. Staying in NYC next week for a night and happened to see that the AAA rate dropped $45. Called Gold Passport customer service and they kept my suite and dropped the rate in just a few minutes.

  13. This is great advice. To a lot of people this is like a revelation, LOL, because they aren’t so money conscious I guess. For me, like the poster above, checking rental car rates has been a big wakeup and a moneysaver.

  14. This is a great tip. I was booked from Berlin to Toronto in on a 2-stopper including a connection in Lisbon with the transatlantic leg in just Premium Economy, and a few days beforehand was able to move on to Lufthansa Business with a single connection in Frankfurt for the cost of a small change fee. It really pays to keep checking.

  15. I think as time goes on and award seats become more scarce the majority of award bookings will be last minute. Trillions of miles chasing fewer and fewer award seats.

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