It’s January and I’m seeing lots of posts online in award-travel groups about people wanting to book trips on points for spring break to Hawaii and Europe in July … this year. 

I mean … I guess it’s possible? But that’s not likely to happen unless you get extremely, extremely lucky. For popular destinations or popular times of the year to travel (or a combo of both at the same time), you’ll find a lot more availability using points and miles the earlier in advance you can book. Looking in January for a March or April trip is pretty last-minute when you’re talking points.

People who are used to booking travel paying out of pocket sometimes have a hard time wrapping their heads around how early they need to book award flights and award nights, so it’s worth breaking that down for anyone who’s new to travel with miles and points. Airlines and hotels usually only release a limited number of award seats or rooms, and while those do fluctuate some, your chances are usually better the sooner you start looking. It’s not always a “once the award space is gone, it’s gone” situation, but any lucky availability that opens up closer in time to your trip is going to be just that: lucky. You can’t count on it. So if you’re a planner like I am, you need to know when to be looking so you get the trip you want and not the trip you have to settle for.

So when should you be thinking about booking trips? 

Here’s some general advice on when to think about booking award trips could be really useful, so here’s what I, a Type A planner who regularly travels with a family of four would do. 

The more inflexible you are about the dates you’re traveling or the place you want to go (or both), the earlier you should start looking.

So if you only have a week of spring break to travel in and you want to go to a super-popular place like Kaua’i, you’re going to need to book as far in advance as humanly possible. For the in-demand Alila Ventana Big Sur, that’s going to mean 13 months in advance: as soon as Hyatt opens the points calendar. If you don’t find availability the day the calendar opens, keep looking from day to day (or set an alert—OpenHotelAlert is a good option). 

But if you’re open to the destination or can fly on lots of days within a certain two-month window, then you don’t need to plan ahead as much; you have more flexibility and will be able to jump on whatever you happen to see that fits your parameters.

Likewise, if you’re traveling alone, you’re more likely to find one business-class seat at any given time than you are to find four or five business-class seats. Traveling as just one or two people is going to make it easier to find award seats than it would be if you’re traveling in a bigger group. If you need an ADA-accessible room, you will also have more luck booking that on points the earlier you look.

Basic rule: The more specific requirements you have, the further in advance you should start looking.

These two charts show my own personal guidelines for when to start looking into finding award flights and award nights. 

First, booking plane tickets.

Second, booking hotel nights.

Do I really have to book so far in advance?!

I mean … yeah. If you want a basically free trip using miles and points, you need to plan ahead to get what you want. Or you can wing it and wait longer to book, but then you’ll need to be more flexible with where you go, how you get there, what layovers you have to deal with, etc.

It’d be awesome if we could live in a world where you could get free hotel stays and free flights and also not have to plan in advance for them! And sometimes when all the stars align, that might happen. Airlines do sometimes release last-minute business-class seats at reasonable points prices. Hotels have cancellations at the last minute. 

But is that likely to happen? No. And is that something you can reliably plan your kids’ Thanksgiving break around? Also no.

You can have a trip to your desired destination on ideal flights, you can have it be almost free, or you can book it last-minute. But you have to choose two of those three things. Getting all three at once is rare. But I’d argue that getting trips for nearly free makes the annoyance of having to plan so far in advance more than worth it!

Bonus content: If you subscribe to my free email newsletter, you can download my free chart laying out when each hotel program and airline open their calendars. It’s helpful when you’re trying to figure out when to start looking for award travel.