Traveling on points can be a fun experience and a great way to save money, but finding the best deals can often feel like mining for gold. Award availability, as it’s called, often seems like it has no rhyme or reason; except that the larger airports or cities always get the best options.

This happens because these cities often have the most routes going to/from them and also the largest planes on those routes. Larger planes equal more seats and more seats typically means more award availability. Not to mention, it’s more likely for a larger city/airport to be a hub for at least one airline.

So, what can you do if you live in a small city or near an airport that doesn’t get many flights per day? Should you just accept that you’ll never get good cash or point deals on your flights?

Absolutely not.

While it may seem like your options are limited, there is a strategy that can unlock some fantastic deals. As a matter of fact, I take advantage of this quite often and it’s called taking a repositioning flight.

What Is A Repositioning Flight?
A repositioning flight is when you take a flight to another city to get a great fare (cash or points) to your final destination. This allows you to split your flight costs between cash and points or save a considerable amount of money when booking straight cash.

For example, let’s say you find an amazing non-stop flight deal to Athens from New York for only $333 round-trip in March, but you live in Nashville. However, when you search for a flight from Nashville to Athens on the same days, all the fares are $1100 and up. Clearly a huge price difference.

Why should you have to pay an extra $800 just because you live in Nashville? You shouldn’t.

Instead, it’s likely that you could put together your own itinerary by buying a round-trip repositioning flight from Nashville to New York for closer to $200 and then book the deal from New York to Athens. This makes your total trip to Athens less than $600 instead of the quoted $1100 if you had booked the paired itinerary suggested by the airline when trying to book it together via one of the online booking sites.

Here’s the screenshots for the scenario above:

Nashville to Athens

Nashville to New York

New York to Athens

So why can’t you just get this deal without booking separate tickets?

Well, there’s potentially a couple reasons, but the most common is that your repositioning flight is often on a different airline than your second flight. Therefore, it’s impossible to book it as one itinerary due to ticketing rules and many airlines not working together.

When Should You Book A Repositioning Flight?
It probably goes without saying, but you should consider booking repositioning flights when there’s a huge difference in the cash cost of the fare. As you can see above, it can be quite lucrative.

The other time it makes sense is when you’d like to use points to get to your destination and there’s no reasonable options out of your current location. This usually applies to international flights since domestic ones don’t usually have a large discrepancy in pricing.

Recently, I used this strategy for my trip to Italy. KLM Airlines had promo pricing on business class flights to Europe from Chicago O’hare airport. These seats were going for a meager 26k points plus $240 one way and I couldn’t pass up that deal knowing those same tickets go for about $2000 each way. That breaks down to getting 6.7 cents per point in value which is a tremendous value.

To capitalize on this promotion, I booked a round-trip ticket from Orlando to Chicago for about $250 in addition to booking my long-haul international flight via points. That allowed me to spend 8 hours crossing the pond in this seat, instead of being cramped up in Economy for very little cash out of pocket.

It looks like my dad appreciated it too.

Using Repositioning Flights Like A Pro
While using repositioning flights can unlock massive opportunity, there are some critical things that you must know in order to prepare yourself to utilize them with no issue. Here are some considerations you should keep in mind to take full advantage:

Schedule Appropriate Layover Times
The largest potential downside to booking your own multi-stop itinerary is that you are responsible for making your connections. When an airline books connecting flights for you, they are constantly monitoring your connections so that if one flights is delayed and will cause you to miss your next flight, you will be automatically rebooked.

However, when you are booking your own connections independently, you won’t have this luxury. This usually isn’t a big deal, but you’ll definitely want to take this into consideration and book layovers that give you plenty of time just in case something should go awry.

Therefore, it’s a good idea to make sure that you have a travel credit card that gives you lounge access. You’ll be able to relax in a comfortable environment and enjoy free food and drinks while you wait to board your next flight.

Don’t Forget About Your Baggage
Another potential inconvenience when booking multi-stop itineraries on different airlines is that you’ll be unable to check your bags through to your final destination. That means that you’ll have to leave security and claim your bags and then re-check them for your next flight. Depending on the airport, this could be a pain. So, you’ll want to budget enough time to handle this.

Fortunately, if you aren’t checking your luggage and only bring a carry-on, this won’t be an issue. You can stay inside the secure side of the airport (called airside) and simply make your way to the lounge or your next gate.

Conclusion
Repositioning flights can be a great way to save tons of cash or get the best point deals to international destinations. By simply knowing how to create and book your own connecting itineraries you can unlock countless options that suit your needs. Just don’t forget to schedule your layovers with plenty of time between flights and everything will be smooth sailing (or flying in this case).