Let's talk booking on points! This is my absolute favorite thing to do. It has become second nature for me, and I love the game of it all. However, it took a while to get to that point.

When you're first starting out, earning is usually the easy half. Most people can open a rewards credit card, hit a minimum spend on eligible purchases, and watch a pile of points land in their account. The part that usually stops people cold is sitting down in front of a blank search bar with 200,000 points and absolutely no idea where to start.

So I am going to walk you through my ACTUAL booking process. Not a theoretical one. This is the exact order of operations I use when someone books a one-on-one call with me, and it is the same thing I do for our own family trips, and it's the process I've used for years, really (although the technology has changed, so more on that below). It works for any destination, any program, economy or business class, whether you have one hundred thousand points or two million.

Ten steps. That's it. Run them in order and you will not get lost.

And some real talk before we begin: there are going to be times when using points does not work out, because it does happen but almost nobody talks about it. Knowing when to walk away and pay cash is a skill, and it is part of the process, and I have a step to help you confirm whether you should use points or cash.

One quick note before we dive in. This post is about the booking process, not about how to earn points or how transfer partners work, etc. If you are still fuzzy on the earning side, go grab our free Points and Miles Crash Course first and then come back here. This is the "I have the points, now what" post.

If you need help earning points, check out the 4 cards I will ALWAYS have in my wallet here! You can not go wrong with these cards, and they will help you earn so many points.

Decide: Are You Booking Flights Or Hotels First?

The order of the steps I use below is what I do most of the time. But it is not a rule, and you should switch up the steps based on what is actually driving your trip.

Book your hotels first if the property IS the trip. If you are trying to snag availability at the Park Hyatt Maldives or the Conrad Bora Bora, or any other really aspirational property, and you find open dates that work for you, book the hotel first and flights second. Award availability at some properties is genuinely limited; it can disappear fast, and you build your flights around your hotel or resort.

Book your flights first if your dates are locked and you are flexible on where you stay. Spring break with kids is the classic version of this. Everybody is trying to fly on the exact same six days, award seats on those dates go quickly, and you can almost always find somewhere good to sleep once you know you can actually get there.

Everything else in this post works the same either way. Just start with whichever piece is harder to get.

Before You Search Anything: Set Up Your Loyalty Accounts

I know. This is the least exciting instruction on the internet. Do it anyway.

Before you go looking for award tickets, go create a loyalty account with any airline and hotel program that might POSSIBLY be an option for your trip. World of Hyatt®, Marriott Bonvoy®, Hilton Honors™, IHG One Rewards, Delta SkyMiles®, Alaska Mileage Plan™, Flying Blue, Virgin Atlantic Flying Club, etc... All of it. It will take some time upfront, but it will save you a genuine headache later.

Here is why. A handful of airline loyalty programs require that your account has been open for a certain number of days, or that you have some activity on it, before they will let you receive a points transfer. Not many, but enough that you do not want to discover it at 11pm when you have finally found the one seat you need. Award availability disappears while you are filling out a signup form.

The second thing I want you to do is keep track of all of your usernames, member numbers, and passwords. Google Doc, password manager, whatever you will actually use. There are six of us in our family. That is a gazillion frequent flyer programs and loyalty accounts across my husband, my kids, and me, and if I did not keep it all in one place I would lose my mind. I would also lose about forty minutes per booking to password resets and two-factor codes, which, side note, I understand why we need, and I still resent every single time.

Pro Tips When Setting Up Accounts:

Make sure that the name on your loyalty accounts matches both the name on your credit card as well as on your passport. We have seen some transfers and transactions held up because these don't match!

Step 1: Start With AI To Build Your Hotel Shortlist

This is the newest piece of my process, and it has saved me SO much time.

I want to be very clear up front, though, because I will not have you thinking AI is going to book your trip for you. AI is wrong a lot right now, especially on specific point redemptions. I had a client come to me not that long ago convinced that ChatGPT had told her she could get her whole family to Japan for 15,000 points RT each and that it was okay to book her child as an infant in arms even though she was over the age of two because Chat told her she could. When you get into the nitty-gritty of what things actually cost and some of the policies, do not trust it and always verify. It often pulls from old data or old comments on a Reddit thread.

But as a starting place to narrow a huge field down to a short list? It is excellent.

Here is my exact prompt. Copy it and swap in your city and your programs.

Claude (or Chat or whatever you use), we are going to (DESTINATION). I need you to give me a list of all the properties I can book on these points: (THE PROGRAMS YOU USE OR THAT YOU CAN TRANSFER TO). Include Small Luxury Hotels for Hilton and Mr & Mrs Smith hotels for Hyatt. Exclude (OR INCLUDE depending on if it's an adult trip or a family trip) any adults only properties. I only want properties in or near the city center (OR ANY OTHER INSTRUCTION YOU WANT TO GIVE IT).

A few things about why that prompt is built the way it is.

The adults only exclusion is obviously a family travel thing. If you are traveling as a couple, delete it. Replace it with whatever your actual constraint is. "Prioritize hotels with connecting rooms" is another good one to add if you have kids.

And "in or near the city center" is doing a LOT of work. Without it you get a list that includes the airport property and the one out by the convention center, and you have to individually check every single address. You can tailor this based on what you want, like show any beachfront properties, etc...

What you should get back is a short, workable list of properties across your programs, plus a few notes about what it left out and why. Read those notes. And then verify. Always. Use AI as a tool but don't 100% bank on what it gives you.

Step 2: Price Out The Cash Cost Of Your Flights FIRST

I know you came here to spend points. Price the cash first anyway. Every time.

I start at Google Flights or Skyscanner. And I search in a very specific way that I think a lot of people get wrong.

Search one way, one passenger, flexible dates. Not round trip, not your whole family, not your exact dates. You are not booking anything yet. You are gathering information about what this route actually costs and which airlines fly it. Round trip searches with four passengers hide the interesting stuff.

You are looking for two things here. First, the cash number, because that is what every points option gets measured against. Second, the list of airlines that actually fly your route. That second one tells you which frequent flyer programs are even worth searching, so you are not wasting an hour poking around a program that does not serve your city.

Write both down. You will need them in a minute.

Step 3: Search Award Availability On A Search Aggregator

Now we go looking for the award tickets. My two favorite tools here are PointsYeah and seats.aero.

PointsYeah is where I start, and it is far and away the best free award search tool out there right now. It is easy to navigate, it covers a lot of programs, and the free version is genuinely usable. If you are not doing this every day, start here. You do not need to pay for anything to get real value out of it.

seats.aero is what I use on the paid plan, and its single best feature is that you can search "anywhere in the USA" as your origin. That matters enormously if you are open to positioning, which just means flying yourself to a bigger hub city first and starting your international trip from there. It surfaces the big hubs and shows you which airline alliances are actually playing on that route. It also color codes results, and green means nonstop, which is the flag my eye goes to first. When I am building an itinerary for a client I want nonstop wherever I can get it.

Search the same way you did on Google Flights: one way, one passenger, all cabins, all airline programs, over a flexible window.

Use both tools, not one. These aggregators do not have complete coverage, and I mean that literally. I regularly find flights on Google Flights that simply do not appear in an award search, same route, same dates, same aircraft, just missing. Not because the seats do not exist, but because the tool does not see them. Running two searches catches most of what one search misses.

Quick note on the subscriptions, because I get asked. Both of these have monthly options. I pay for the year because this is literally our job. If you take one or two big trips a year, do NOT do that. Pay for one month, block off an afternoon or two, book everything you are working on, and cancel. That is the smart way to use these. No need to pay for something for a year that you aren't consistently using.

Step 4: Do The Math Before You Transfer Anything

This is the step people skip, and it is the most important one in this entire post.

You now have two numbers: the cash price and the points price. Put them next to each other and figure out what you are actually paying per point. Then compare that to what those points are reasonably worth. If your points are pulling their weight, book it. If they are not, pay cash and keep your points for a redemption where they actually stretch.

Do not forget to add the taxes and fees on the award ticket into your math. An award booking is almost never free, and on some international routes those fees are high enough to change your answer completely.

We built a free calculator to do this part for you so you are not doing decimal math in your head at midnight. 

If the math works, widen the search before you go any further. Everything up to this point has been one way, one passenger, on purpose, because that is the fastest way to find out whether a route is even worth your time. The second you find an option that looks like it works, go back and run that same search as either round-trip or with a return with the total number of people you are booking for. Availability at that price for one seat does not mean availability at that price for five, and a redemption that looked perfect at one passenger falls apart all the time at four. Much better to find that out now than after you have moved your points.

And please hear me on this: sometimes cash wins. That is not a failure. On rare occasions, paying cash can be the better move. When that happens you have some good options. Pay cash outright, use a flexible travel credit to erase the charge, or book through your card issuer's travel portal with your transferable points instead of transferring them out.

The whole skill here is knowing which of those to reach for. Run the math and the answer is usually obvious.

Step 5: Verify On The Airline's Own Website

Every single time. No exceptions. Before you transfer one point.

Search aggregators show ghost availability. It is a real and common phenomenon: the tool says the seat is there, you transfer your points, and the seat is gone or never existed. Transfers are almost always one way and permanent. You do not get to undo it.

So before I do any transferring, I go straight to the airline's own site and search the route I liked from the point search aggregator. A few things I always do here:

Toggle "shop with miles" or the award search option. Sounds obvious. People forget.

Search flexible dates. Moving your departure by a single day can change the number of points dramatically. Sometimes by half.

Load in the real number of passengers again. Same as step 4. This is your last chance to catch a seat count problem before your points are gone, so do not eyeball it.

Check whether your card gets you a discount. Some airline co-branded credit cards knock a percentage off award redemptions in that airline's program. Worth knowing before you book, and worth knowing that these discounts often do NOT apply when the flight is operated by a partner airline rather than the airline itself.

One personal note. I usually do not book the lowest fare tier on any airline. I want to choose our seats. I want to KNOW my kids are sitting with me and not scattered across four rows. I want my miles back if something falls apart. That preference costs a little more, and I am at peace with it, but I always leave that call to the client, because plenty of people would rather have the cheaper fare and take their chances. So decide what works for you!

If the seats are live and the math worked, THIS is the moment you transfer. Not before. Transfer, then book immediately.

If The Round Trip Falls Apart, Price The Return Separately

This happens constantly. You widen to round trip and the flight out is beautiful and the flight home is nowhere to be found, or it doubles in points.

Do not give up on it. Run steps 2 through 5 again for the return as its own completely separate search. Two one ways in two different programs is often the better booking anyway, out on one airline's miles and home on another's. That is normal, and once you know to check for it you will use it all the time.

Step 6: Search Your Hotels

Now I take that AI shortlist from step one and actually go shopping.

I like to start at MaxMyPoint because it lets me see a lot at once, and then I open the individual program sites in separate tabs. Search them in order of how many points you actually have. 

Then go one level deeper, because this is the part that matters and almost nobody does it. Click into the actual room types. The search results page shows you a rate. It does not show you that the property has connecting rooms, or a king plus twin configuration, or a suite with a separate living area and a rollaway bed available on request. That last one can mean a family of four does not need to book two rooms at all, which cuts your points cost in half. You will never see any of that from the results page.

Do the same math you did on flights. Points cost versus cash rate, taxes and fees included.

Step 7: Go Back To AI For The Location Question

Once you have it narrowed to two or three properties, go back and ask a second question. Because "city center" is not precise enough, and I want to know what the walk actually feels like.

Between (HOTEL A) and (HOTEL B), which is the better location and why? We will have two young children with us.

The kids detail changes the answer, which is the whole point. If you are traveling with little ones, you want to know what is stroller-friendly and what is walkable to a park. If it is just adults, ask a different question. "I want to be close to really local coffee and chocolate shops" is a completely valid thing to type. Ask for what YOU actually want out of a neighborhood.

You will often find that the cheaper property is a solid ten or fifteen minute walk further out. Sometimes that is completely fine and worth the points you save. Sometimes you would rather walk out your front door into the postcard version of the city. Only you can make that call, and that is exactly why I ask the question before booking instead of after.

Step 8: Confirm Availability, Transfer & Book Your Hotel

Once you've decided on a hotel, go straight to the hotel brand's website to search that property's point availability, confirm, transfer, and book! There is nothing that I love more than grabbing an $800+ room a night for zero dollars and booking it for my family!

Step 9: Handle The Little In-Country Hopper Flights Last

If your trip has internal legs, do those separately and do them at the very end, once your big international flights and your hotels are locked in.

I start these at Skyscanner rather than Google Flights, because Skyscanner does a noticeably better job of catching the tiny regional carriers that Google just does not surface.

And I will tell you plainly: it is usually NOT worth using points on these short hops. The cash fares are low and your miles are worth more elsewhere. I still check every time, because occasionally I am wrong and I would rather look. But go in expecting to pay cash, and play with your departure times instead, because on these routes flying later in the evening is often meaningfully cheaper.

Step 10: Confirm Everything And File It

Book it, then take five minutes to save your confirmation numbers, your loyalty numbers, and your seat assignments in the same secure document you built at the beginning. Add your hotel confirmations to it too.

Future you, standing at a check-in counter in another country, will be very grateful.

If You're Super Techy: Two Chrome Extensions That Speed This Way Up

Everything above works with zero add-ons. But if you like tinkering, these two live in my browser and they collapse steps 2 and 3 into one screen.

The seats.aero Chrome extension. Pulls seats.aero award availability into the pages you are already looking at, so you are not bouncing between tabs comparing dates by hand. If you are already paying for seats.aero, install it. There is no reason not to.

Points Path for Google Flights. This one is my favorite for beginners, weirdly, even though it sounds like the advanced option. It overlays award pricing directly onto your Google Flights search results. So you run one normal cash search and you see the cash price and the points price side by side on the same row. That comparison, cash versus points, is the single most important judgment call in this entire process, and this extension puts it right in front of you instead of making you hold two numbers in your head across four browser tabs.

Neither of these replaces step 5. You still verify on the airline's own site before you transfer anything. They just get you to that point faster.

Where AI Still Gets It Wrong (Please Read This Part)

I use AI throughout this process and I want to be equally loud about where it fails.

It is behind on program changes. One of the major hotel programs overhauled its award chart and category pricing recently, and when I asked AI about it shortly after, it confidently handed me the OLD structure. It did not know. It did not know that it did not know. Award charts, transfer ratios, and elite status requirements change constantly, and AI is frequently working from information that is a year stale.

It is bad at specific point costs. Not sort of bad. Like so bad. Never let it tell you what a flight or a night costs in points. That is what PointsYeah, seats.aero, and the program's own website are for.

It is great at exactly two things here. Narrowing a big list of properties down to a manageable shortlist, and answering location and neighborhood questions. Use it for those. Verify everything else.

The Whole Process, Start To Finish

1. Set up your loyalty accounts and put your logins somewhere secure.
2. Ask AI for a hotel shortlist. Name the partner brands. Add your own constraints.
3. Price the cash flights on Google Flights or Skyscanner. One way, one passenger, flexible dates.
4. Search award availability on PointsYeah and then seats.aero. Use both.
5. Do the math. If cash wins, pay cash and keep your points.
6. Verify on the airline's own site with the real passenger count, then transfer, then book immediately.
7. Search Hotels if the round trip does not hold, and check whether two one ways beat it.
8. Ask AI the location question to break a tie.
9. Book hotels from your shortlist. Click into the room types.
10. Do the little in-country flights last, on Skyscanner, probably in cash. Then save all your confirmations.

That is it. That is the entire thing. I do not have a secret tool. I do not have a hidden database. I just run these same steps over and over, for clients and for our own family, and I have run them enough times that I am fast at it.

You will hit hiccups. Search tools will time out on you. Flights will be available on the exact dates the hotel is not. You will find ghost availability and have to move to your second option. That is not you doing it wrong, that is just what this looks like from the inside.

And once you have run it once, all the way through, on a real trip? It stops being intimidating. It becomes a thing you do on a Tuesday night.

If you get stuck partway through, just remember you've got this! If you would rather have someone do the work for you, you can book a one-on-one session with me here!

Now go book something. I can't wait to see where points and miles take you!