We wanted to share a few tips on how we book our award travel and when we start thinking about where we want to go. This certainly isn’t the only way to do it, but the process has worked for us.

What awards to book first? Hotels or Flights?
There are times when this question comes up and I find I don’t have a consistent order that I book. One rule of thumb is to book based on the order of most cancelable to least cancelable. What that means is you first book what comes with a free cancelation and then you book what costs money to cancel. Logically this makes sense: why pay a cancel fee unnecessarily? Of course, this thought does oversimplify the equation a bit.
Normally, I book flights first when I’m going somewhere that has many hotel options. If I’m going somewhere to stay at a specific resort (Maldives, French Polynesia, or perhaps a safari in Africa), I’d book my hotel first. After all, if there is a specific reason you want that hotel, it’s probably a good idea you get that squared away first.
Take our trip in 2022 to the Maldives. On that trip, I had booked hotels first (originally the St. Regis Maldives) and then booked flights. Of course, the St. Regis then closed for repairs (erosion) and we were moved to the Ritz Carlton. But that was one trip where it made sense for me to book our hotel first given limited awards for hotels. The flip side would be a trip like when we went to Japan in 2024 and was less concerned about the specific hotel we would stay at so we booked flights first.

Know your options on how to book
There are plenty of paid websites out there that track award space and try to entice you into buying into their services so that you can give them money. Sometimes that is indeed helpful and worth a purchase, but you might also have access to free options and not know it. Point.me has partnered with some of the larger credit card issuers to provide free services for members of those programs. Some examples include American Express and Bilt (requires you to log into your account first and then make your way through a series of menus to get to their free version). Another free option available is Roame.travel, which can give you access to some airline award space but certainly not everything that’s out there.
However, I’m usually of the mindset of finding what I need on each airline’s own websites, which is free and generally the most accurate (assuming no phantom award space shows).
Sometimes you need to be a little creative on your award routing. I know the desire is non-stop routing between your home airport and where you need to go. Sometimes this might mean that you choose another airport nearby to unlock more options for award travel. Other times, this might encompass you departing from a different airport–or even a different country–to get that award flight you’re looking for. If you’re in San Diego, you might want to consider checking out flights out of Tijuana.

Do your research
It sounds simple enough that I just tell you to go out there and book something, but sometimes it’s just not that simple. Where can you go to find other like-minded individuals and learn from their experiences? How about checking out either FlyerTalk or Reddit, which operate message boards and you could learn from the tips from others in your shoes? I find them both to be valuable resources even after doing this for well over a decade to gain insights on what it’s like at certain hotels or tracking award flight release patterns.
Remember, you don’t have to be in this alone.
A timeline of events
15 to 12 months out: Think about where to go
This is when we get a rough idea of where we would like to go. If we’re thinking of going somewhere that has extremely limited award availability, it will give me a chance to understand award patterns—when flights or rooms get released—with enough time to know what to expect. Knowing when those elusive awards become available (this is especially true for high-demand hotels like in the Maldives) sometimes is the only way to go.
This also gives me a chance to identify the best way to get there and whether or not I have enough points to do it. For example, going to a destination that has a Star Alliance hub means it might make more sense to stock up on miles in a Star Alliance airline, especially if we’re trying to reduce the number of connections we take to get there.
12 to 11 months out: Book those flights and hotels
Generally between 330 days and 360 days from your preferred day of flight award space will be released and be bookable. There are generally two windows where you can reliably find award space—at this time or within two weeks of travel.
You might think that booking two weeks before travel is too risky, but the “trick” is that award flights can be canceled pretty easily (and sometimes for free) so you can always look to upgrade your flight even if you don’t get your preference at this time.
If you tracked release patterns, you would know when it’s time to book. In fact, there might be some hotels that you could book more than a year out. So this timing doesn’t always work for every single option out there, but think of it as the main time to do it.
This isn’t the optimal time to book paid travel that you book with cash. But there are two main exceptions that come to mind. The first is if you absolutely must fly on a certain flight and there is no other option (including where you can’t book with points). If only one thing works, you might not want to risk it going away. The other option is if you’re looking to use an upgrade, like using Delta GUCs on a KLM flight. Similar to award flights, sometimes the best availability for upgrades comes right when the flights become available for purchase.
Didn’t book the flight you wanted or get enough seats for your party? You could sign up with Expert Flyer and place an alert for when award seats open up. If you’re limited to specific dates for your travel, it might be worth the expense for a subscription.

10 to 4 months out: Prepare yourself for schedule and/or equipment changes
The one downside to booking so early is that you’re going to be prone to changes from the airline when it comes to schedule changes (when your flight now departs at a new time) and equipment changes (when a route is operated by a different plane than originally planned). Most of the time, this doesn’t impact me, but it’s important to monitor your reservation during this time in the off chance that it does.
Schedule changes similarly can be a pain, especially if it might cause you to misconnect. This is especially important if you have an important reservation that could now be in jeopardy or if you pieced together two flights that aren’t on the same itinerary (you might not get protections if you miss your connecting flight if they aren’t on the same ticket). Now, sometimes you can make an argument to an airline that the new flight time doesn’t work for you. But if you booked it as an award flight, know that it’s going to be difficult to open up new award space to change to a different flight (especially if it’s a partner award).
If you do see a schedule change of a couple of hours and are fine with it, you don’t have to “accept” the change just yet. You’re generally fine ignoring it for now and waiting to accept it later in the event you want to get a free change/cancel later.
Some airlines are a bit more notorious for equipment changes, but what you’ll need to look out for here is if the plane swaps out for one with a smaller cabin. If you’re booted from the cabin you booked, you definitely want to find out about it sooner rather than later. The earlier you find out about it, the more opportunity for you to get someone on the phone to get it resolved.
2 to 3 months: Consider trading in points flights for cash flights
I’d be remiss if I didn’t at least consider if there was a suitable cash flight available that I could take instead of using my points. Why? Well, recall that even points flights have a real cost to them. That just means if you find a better price available that will get you to where you want to go, don’t be afraid to swap it out. This might be more relevant for economy flights, but sometimes it also does apply for business class flights as well.
Cash flights tend to be cheapest about three months out for international flights and two months out for domestic flights. That’s usually when most people purchase their cash tickets for leisure flights and when airlines then want to be the most competitive to earn that business. Any closer to departure and you might see purchases for business purposes and those are less price sensitive.
Cash flights also have the benefit of earning points and potentially counting more towards elite status than award flights do, so it’s fair to add your value of that to the equation. You might have a cancel fee for your award flight if the program you used to book with doesn’t have free cancels, but if you have a schedule change as mentioned above, perhaps you could get it for free.
This is also the time to double check award prices that you booked, especially if you used a program that has a dynamic price for award tickets, since cash prices are again generally at their lowest and that might reduce the points price too.
Within the last month: Check if any last-minute options are now available
Remember when I said that there are two main windows for booking award flights? Well, when you enter the time close to departure, that’s the other window when you might find award space. Sometimes this might be on a specific airline you’re hoping to try out. This might now provide more award seats that you need for everyone in your party. This could also include a better class of service that wasn’t available before (first class). Whatever the reason, it’s worth taking a gander to see if there is something now available that works better for you.

I think of award flights a starting point, and then as an opportunity to always improve on it. You might think you have the perfect flight at the perfect price, and that’s awesome if you feel that way, but there’s no harm in window shopping just in case, right?
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