Travelers know it all too well: Youre never really done planning a trip. Whether its dinner reservations, trains, or digging into those tiny logistical details that can make or break a trip, theres always something more to do in the lead-up to a vacation. But even for the big, important, and expensive aspects of a trip – like flights – Im rarely done booking and re-booking until I head to the airport that day.

The way I constantly massage my flight itineraries in the months, days, and even hours before flying causes raised eyebrows from my friends and family over the years, but I swear by it. Thats because, in the end, some of my favorite flights ever were not the ones I initially booked.

My travel-booking pattern goes something like this: I book a cheap economy flight using points and miles to get the trip in motion. Then, over time, I keep looking and booking better and better flights until I get the one I actually want in the end – ideally, flying in a lie-flat, business class seat. Thats how I turned what was initially a grueling, 12-hour flight in economy to Tokyo last month into a seat in the worlds best business class cabin.

Booking flexible, one-way fights using points and miles sometimes eating some modest change or cancellation fees in order to do so makes it possible.

Why I Rebook ( Rebook) Flights Last year, I wrote about my most drastic example of my rebooking pattern, but lets recap.

I rebooked my flights to Croatia four times, eventually landing myself and my wife lie-flat seats in the fantastic United Polaris business class cabin thanks to some last-minute award space not the Air France economy seats we initially booked.

It wasnt the first time, or the last time, that I moved things around until I found the best possible way to fly somewhere within my (typically tight) budget. But the latest example might be my greatest. It was simple, cost-effective, and landed me on the best flight of my life flying to Tokyo.

Last March, I leaned on our favorite workaround for booking Delta flights, using 35,000 Virgin Atlantic points per person to book two the two nonstop Delta flights to Tokyo-Haneda (HND) from Minneapolis-St. Paul (MSP) for my wife and myself. Sadly, you wont find that low rates anymore after Virgin recently hiked award rates on most Delta routes.

We booked flights home the same way, for the same amount.

We were happy to take these nonstop economy flights to Tokyo. But at the same time, I was watching closely for some business class award availability which was nonexistent at the time we began planning our trip to see if we could upgrade our situation, especially into a lie-flat seat for that long flight to Tokyo.

Throughout the year, I kept getting Thrifty Traveler Premium award alerts for Japan, but none perfectly matched what we were looking for. There was Japan Airlines business class availability that came up, but we didnt have the right points to book. Other times, United Polaris or All Nippon Airways (ANA) business class seats opened up, but we were short points to get two of those seats.

I probably checked for alternatives about twice a month leading up to our January 2024 departure. And I noticed a clear pattern: If youre trying to book ANA business class, the award availability to actually book those seats typically starts to open up two or three weeks before departure. Youll get down to the wire, but it can be done.

After noticing that clear pattern, I was feeling confident enough to make a bet. About a month before our trip, I booked a pair of cheap, flexible positioning flights from Minneapolis to Chicago just in case we were able to secure these last-minute business class for ourselves.

And then it happened: About nine days before our trip, I found the award space for two seats flying ANAs fancy The Room business class from Chicago-OHare (ORD) to Tokyo-Haneda (HND).

These flights were bookable for 47,5000 points per person through ANAs partner airline, Virgin Atlantic Flying Club. So I quickly transferred 95,000 American Express points to Virgin enough to book two seats called a helpful Virgin representative, and boom: Instead of flying economy, we were going to Japan in one of the best business class seats in the world.

But what about that Delta economy flight to Tokyo? I could have had that same phone agent cancel our one-way tickets first for a $50 award cancellation fee, get my 70,000 Virgin points back, and transfer just 25,000 more Amex points to book ANA business class instead. But I had to act fast before someone else beat me to it, so I simply had my Virgin agent cancel our Delta flight to Tokyo after booking our new ANA flight, banking those 70,000 Virgin points for a future trip.

Plus, we still were able to take our nonstop Delta flight home from Tokyo without changing anything with that itinerary we booked two one-ways separately.

Heres the moral of the story: Booking flights with points and miles gives you far more flexibility to get a better deal later on down the line or snag a better seat. Sure, you can cancel many cash flights for a voucher but then youve got $1,000 or more in airline credits to use and a year (or less) to do so before they expire.

Plus, using points allowed me to book an amazing experience that I couldnt otherwise afford: Flying ANAs The Room business class was far and away the best flight of my life. And it was all possible because I originally booked flexible award tickets and my persistence in searching for better options.

The Keys to Rebooking Award Flights Theres no one-size-fits-all method to doing this. A lot will depend on your departure airport, your desired destination, the transferrable points you have, and much more.

But if you rebook your flights to spend fewer points on your next trip or fly in a business class (or even first class) seat, there are a few things you need to make sure to do.

Always Book One-Way Flights with Your Miles This is the most crucial part of this equation. When it comes to award flights, booking one-way is going to be your best bet if you need to rebook down the line. While there are a few exceptions like the roundtrip savings when booking through ANA Mileage Club or Emirates and discounted Delta SkyMiles flash sales booking one-ways wont cost you more miles. It might cost you more in taxes and fees, but that could be worth it.

Thats because booking one-way flights gives you the flexibility to act if a better option for just one leg of your journey comes up, like with my flights to Japan. Its much, much easier to simply cancel a one-way flight you no longer need than to have an airline agent rework your roundtrip reservation if thats even an option.

Consider Your Positioning Flight Options Getting a great deal on business class flights is often restricted to departures from major airports: Think New York City (JFK), Newark (EWR), Washington, D.C.-Dulles (IAD), Chicago-OHare (ORD), or Los Angeles (LAX). So if youre hoping to rebook your flights to score a lie-flat seat, you may need to also book another, separate flight just to get there.

Theyre called positioning flights, and theyre a staple when it comes to getting a great deal using points.

For my recent trip to Japan, I knew I was angling for ANA business class but this Japanese airline doesnt fly from my home airport of Minneapolis-St. Paul (MSP). It does, however, fly to and from Chicago-OHare (ORD). So I booked my wife and myself two, one-way tickets to Ohare ahead of time while the prices were still low just in case I managed to find that last-minute award availability for ANAs The Room. Worse comes to worse, I could have canceled those flights and gotten a voucher to put towards a future trip.

In the past, Ive leveraged airline credits, Delta companion certificates, and other methods to take the sting out of those last-minute positioning flights. Ive also used programs like British Airways Avios to book American Airlines flights for as little as 8,250 points each way, or Virgin Atlantic to book Delta flights for as little as 7,500 each way to do the same.

If you can avoid flying by snagging a one-way rental car or a train to position for your flight, thats even better!

Monitor Airfare Award Availability Like a Hawk As a flight deal analyst for Thrifty Traveler Premium, I spend hours every day searching for cheap flights and award availability. Theres no doubt that gives me a leg up when it comes to finding good deals its the best perk of my job!

But even if you have just a few minutes a month to do some award searches around your upcoming trip, it could put you in a position to rebook your flights effectively.

Heres what I do: I find a few ideal routes (like I did for ANAs The Room) and just build in a single search a week for the day of my existing reservation or the day or two around it. If you want to expand that to a few routes and few searches, go right ahead! But take stock of the points and miles you have and then search around that.

If you dont have time for that, I dont blame you! Thats where we come in: Thrifty Traveler Premium sends you award availability alerts to use your points and miles daily. When you get an alert, see if it lines up with your desired travel days, transfer some points, and get to rebooking!

I also use Premium alerts for inspiration. If you didnt already know that you could book ANAs The Room Business Class using Virgin Atlantic points, the experts at Thrifty Traveler Premium did! In the most recent deals we sent to members, we outlined this practice in detail, including giving you the exact phone number to call to make sure you can get these seats booked.

While you may not book this exact deal, youll have the tools you need to do this on your own in the future.

Be Willing to Eat Some Change or Cancellation Fees This practice of rebooking isnt always free. To secure my ANA flights, I had to eat a $50 cancellation fee from Virgin Atlantic for dumping my initial Delta economy flights, but I was more than willing to do that for the opportunity to book ANA business class seats that typically cost thousands of dollars. Plus, they just deducted that $50 from the taxes and fees that were coming back my way anyway.

It all depends on the airline program, though. While some dont charge any change and cancellation fees for award tickets, others like Avianca LifeMiles hit you with a $200 fee to alter or cancel your flights at all. Ouch.

Booking your award tickets through airline programs that charge low (or no) fees to change or cancel a reservation is key. Here are a few that stand out as solid options:

Air France/KLM Flying Blue: Most award tickets can be changed or canceled for a flat 50 euro fee Alaska Airlines: Any award ticket booked using Alaska Mileage Plan miles can be changed or canceled for free to get your miles back. American Airlines: American has completely eliminated its $150 redeposit fees for all award tickets, and canceling online is easy. Just beware that if you book a partner award ticket, you may have to call the airline to cancel and get your miles back. British Airways: Flights booked with British Airways Avios can be changed or canceled for a $55 fee Delta: Only main cabin award tickets can be canceled without fee – youll get your miles and taxes and fees back automatically. For Deltas basic economy awards, youll forfeit 9,900 SkyMiles when canceling a domestic award trip (or to Mexico, Canada, Central America, or the Caribbean) and a whopping 19,900 SkyMiles for major international journeys. Iberia: Flights booked with Iberia Avios can be changed or canceled for just a 25 euro fee. United: United allows you to change a mileage redemption without paying a fee, and it will waive redeposit fees for all award travel so long as you cancel more than 30 days before departure. Virgin Atlantic: Flying Club award tickets can be canceled for a $50 fee and if you paid less than that in taxes and fees when booking the original ticket, youll simply forfeit that amount. Have Enough Points for Both Bookings to Be Safe For some points and miles programs, canceling your reservation leads to an immediate redeposit of your points into your account. That way, you can rebook your new flight using those existing points.

But beware: Not all programs (and not the best ones) work like this. In some cases, it can take hours or even days to get your miles back after canceling an award ticket, throwing your plans into the blender.

Thats why its wise to ensure you have all the points you need to rebook before pulling the trigger. While I could have put those 70,000 Virgin points I had already used to book Delta economy flights toward my new ANA business class reservation, I didnt want to risk the award space disappearing while I waited for those points to make it back into my account. Because I use points and miles for almost all flights I book these days, I know Ill be able to put those stranded points to use for a future trip no problem.

Thrifty Tip: Call a customer service representative and keep them on the line until your points are back in your account. They may even be able to hold your new flights so you can use those points to rebook.

Bottom Line Theres no rule that says once you book your flights, youre stuck with them. In fact, thats one of the best reasons to book your flights with points and miles.

Unless youre already flying lie-flat business class or scored the best deal you possibly could for your points, dont let that be the end of the story. By booking flexible one-way award tickets, travelers can set themselves up to continue upgrading their travels until they get exactly what they want.

Thats why I never stop rebooking my flights.