Booking Flights With Points (Overview)

Learning how to book flights with points can feel a bit overwhelming at times — there are so many options and factors to consider! This post aims to give you an overview of the process I follow. For more information on booking flights with points, review lessons 42-50 of my free course.

Know Your Routes

It’s important to take into consideration the flight routes from your home airport, as influences which strategy and sweet spots make the most sense for you to focus in on. We almost always prioritize non-stop flights and that influences how we plan our trips and destinations.

This is also important because for some destinations like Europe, flights on budget airlines are so cheap to hop around. Enjoy a day or two wherever you land (bonus mini vacation!) and then continue on to your final destination. For Europe, for instance, we often focus on getting a nonstop for the long haul portion of our flight and then using budget airlines like RyanAir or EasyJet to get to other destinations. We have done the same in SouthEast Asia.

Check non-stop routes from your home airport

Your first step is to head to FlightConnections.com and enter your home airport in the “From” box. It will then populate all the non-stop routes you can take from your home airport. You can click on different cities to find out which airlines fly that route and how frequently they fly it.

You’ll notice a lot of the routes are seasonal. From Chicago, for instance, there are only nonstop flights to Rome from about April-October.

If you have a specific destination in mind and your airport has a nonstop flight to that destination — that’s a great way to focus in on your strategy and begin to work out the cheapest way to book that route with points.

Smaller airport strategies

What if your home airport doesn’t have any non-stop flights to where you want to go? If I can’t get somewhere non-stop, I try to do it with just one connecting flight. To see the best options, I run a search on Google Flights to see some routing possibilities.

If possible, it is preferable to book your flights from departure to destination all on the same ticket. This can still be possible if you’re booking through American Airlines, United Airlines, Delta, and many other airlines.

If you find a few routings that seem like they could work for you, make a note of the airlines that fly them and the alliances the airlines are in.

Repositioning

Sometimes you can find a better routing for yourself by booking two flights separately from each other.

Repositioning is a strategy of flying yourself to a different U.S. city than your hometown in order to take a flight from that city over to Europe. Repositioning is different than booking a flight connection because you are likely booking on two different airlines and your ticket reservations are often separate.

In the miles and points world, a lot of people use Southwest Airlines (With a companion pass) to reposition.

Make sure you’re adding up your total cost if you choose to reposition! I also highly suggest booking yourself an overnight layover to account for delays. Of course you could book that overnight layover in a hotel you pay for with points. But keep in mind the overall cost to yourself.

There are some risks with repositioning: if your first flight gets cancelled or delayed, you may miss your connection to Europe and if they were on different airlines — the airlines don’t always work together to get you to your final destination.

This will make the most sense if it helps you get to a bigger airport in 1 stop and will either save you money, points, or time.

Price Compare with Google Flights

Before I discuss too many of the details of booking with miles and points, I want to emphasize you should always check prices on Google Flights!

For instance, many of the options to use airline miles to Japan cost 70,000-90,000 points plus taxes and fees.

But when prices to Japan drop, it can be much more advantageous to book other ways!

Take this fare which I just pulled up from LAX to Tokyo on ANA, which is one of the top airline experiences to Japan.

This round trip costs just $720.

If I booked this with points, the cheapest way to book would be either using ANA miles (transferred from Amex) for 55,000 points + $446. Or else to transfer other credit card points to Avianca Lifemiles for 94,000 points + $100ish in taxes.

But neither of those is my best option here.

Instead, I could book through bank portals for a lot less and have my taxes and fees incorporated into the price — less than 48,000 points in fact.

If you have a stash or Chase Ultimate Rewards® you could book this through Chase Travel℠. If you have a Chase Sapphire Reserve®, you get $150 of travel value for every 10,000 points. So for this flight you’d pay just 48,000 points round trip and nothing extra in taxes.

If you had the Chase Sapphire Preferred® Card, you’d pay 58,000 points per ticket. That’s a great price, too — but keep in mind that anytime you are going to redeem more than 60,000 points in Chase Travel℠, you will come out ahead by upgrading to a Chase Sapphire Reserve due to the higher redemption rate.

Or you could book this on Capital One Travel and you’d earn 5x points for booking via Capital One Travel. That will earn you 3600 Venture miles. Then you could use 72,000 Venture miles to cover the purchase — or even redeem part of the $300 Capital One Venture X Rewards Credit Card annual credit to help offset the cost.

Keep in mind: booking through a bank travel portal is booking through a third party and any changes need to be made via Chase Travel℠, Capital One Travel, etc. We frequently have used this to book cheap cash fares and haven’t had any serious issues.

You’ll also earn airline miles on this reservation if you add your loyalty account number to the reservation.

Learn About Transfer and Alliance Partners

Alliance and transfer partners are an all-important aspect of getting more options and better deals on your flights!

I cover both of these in depth in my free course in lessons 42-50. I also have a free guide which you can download to begin to understand. The most important overall concepts you need to understand are:

• • Airlines operate in partnerships with other airlines. These partnerships allow you to use your miles from one airline to book on another — but only when airlines open seats to their partners.

• • Flexible points credit cards (like Chase Sapphire Preferred® Card or Capital One Venture X Rewards Credit Card) allow you to transfer your points and miles to a variety of airlines

•  

Find Sweet Spots

Sweet spots are those intersections of alliance partners and pricing that offer better-than-normal value and allow you to stretch your points further.

For instance, I could book from Seattle to Tokyo on Delta for 100,000 Skymiles + $55. But if instead I book using Flying Blue miles (because Flying Blue and Delta are partnered through SkyTeam), it would cost just 67,000 + $55.

Flying Blue miles are easy to earn, too — since points from Chase, Citi, Capital One, and American Express all transfer to them.

How can you know where to start? Where are the best values for your destination?

Our team is in the process of writing up detailed guides for all the major destinations. We will continue to update this section as we add more.

Currently you can read up on sweet spots for flights to

Japan

Europe

Hawaii

Earn Points

Each airline option reference has more than one credit card that can earn you a welcome bonus and the points you need to book flights.

So how can you figure out how to earn the right points? First step: get my free airline transfer partner guide — inside I have a chart that shows which kinds of points transfer to which airlines. Then work backwards! Let’s see you figure out that you want to earn points with Flying Blue. You can look at the chart in my guide and see that American Express Membership Rewards®, Chase Ultimate Rewards®, Capital One Miles, and Citi ThankYou® Rewards all transfer 1:1 to Flying Blue. Then you could browse my Best Offers page, where I list all my favorite current offers–to see which cards currently have good bonuses and earn those kinds of points.

Many airlines also have co-branded cards which means they have a card that earns points directly with that airline.

Pro Tip: Transfer Bonuses

Most points transfer 1:1 when you transfer from a program like Chase Ultimate Rewards® to an airline or hotel. But! Banks run promos throughout the year and certain transfer may offer a bonus. I don’t currently maintain an updated list of transfer bonuses but you can find one here.

Finding Availability

A decade ago, almost all airlines priced their award flights according to an award chart. That meant you could go to a chart and see that it would cost 60,000 miles to fly from the U.S. to Europe, for instance. When airlines price using award charts, they generally offer a limited number of “award seats” per flight. So just because a flight exists didn’t mean it was available to book with airline miles.

More and more airlines are switching to “dynamic pricing.” This generally means that they allow almost all of their flights to be booked with their airline miles. It also means they change those prices up and down according to supply and demand. The price of a ticket in airline miles can vary from day to day, just like the prices do when you pay with cash.

Most of the best deals still come with airlines that use some sort of award chart — but this in turn will lead to more searching for available award seats.

Generally speaking, the earlier you book, the better chance you have to find an award seat but this isn’t always true.

In addition, it is important to emphasize that airlines only release some of their seats to their partners. With United and American, they tend to release any “saver” level seats to their partners. Delta, on the other hand, has no official “saver” awards and the ones they release to partners do not match their cheapest flights.

Tools for Award Flight Searches

When possible, I tried to note by each sweet spot in my destination guides if there is an easy way to search for it. If you already have a lot of points, specific dates, and destinations — you can use a tool that can search flights from your home airport to your desired destination and filter by the kinds of points you have.

PointsYeah.com is a free search that is fast and powerful, but won’t necessarily include all airlines. It also allows you to filter for taxes and even has an explore feature if you’re flexible as to where you want to go.

I personally prefer using searches that show me 30 days of availability at a time, because I’m generally somewhat flexible on my dates and destinations.

SeatSpy is a very user friendly tool for searching 365 days at a time — and it’s free for economy searches! It typically only works for non-stop routes. This is especially great for finding FlyingBlue promo deals and saver pricing on United and American routes.

Note: SeatSpy is currently not showing availability for United but still works for many other carriers.

United.com is a great way to find 30 day Star Alliance availability.

AA.com has 30 day functionality for oneworld availability.

Delta has a 7 day flexible calendar for its own flights. For searching for Delta flights that are bookable by partners Virgin Atlantic or Flying Blue, you can use this trick.

Check Aircraft Information

I’m not an aviation geek and never pay much attention to seat maps or stats like seat pitch or seat width. That came back to haunt me on our flight to Japan in November 2023. We had always previously flown Asian airlines to Asia (Asiana, ANA, JAL, EVA Airway) and I really underestimated how much worse United was.

Besides the abysmal food, the seats on United felt so small and tight to me and when I got home, I realized why. They truly were

In economy, United seats were 16.3-17″ wide and had a 31″ seat pitch.

In contrast, JAL has seats that are 19″ wide with a 34″ seat pitch in economy!

The JAL seats are essentially the same as United Premium Economy.

If you’re going to be on a plane more than 9 hours, it’s worth checking a few options if they are comparable in price.