Struggling To Redeem Travel Rewards Points? You Can Make It Easier

by John Harper

Many people encounter a lot of difficulties redeeming credit card points and miles. Equally as many have trouble figuring out what to do with their frequent flyer miles. A recent piece of virality, titled “The Surprising Reason You Should Cut Your Rewards Card Into Tiny Pieces,” documents one woman’s frustration.

After finding no seats on the dates she planned her overseas vacation, one frustrated United MileagePlus Explorer Cardholder is quoted saying: “they can keep the miles, I want my money back.”

My, how that makes me cringe. Here at Point Me To The Plane, we are obsessed with travel rewards. It’s written in our name. But no one said this was going to be as easy as picking some vacation dates and clicking a few buttons on a screen.

Still, most anyone should be able to get incredible value from travel rewards, making them oh-so-much more valuable than cash back rewards. Searching for awards can be time-consuming, but there are increasingly inexpensive tools and services out there to help anyone with any schedule get outsize value from travel rewards.

There are, however, a few things that make things that can make booking travel rewards flights and hotel rooms more difficult.

Frustrated using points and miles

Yes, you can enjoy the suite seats using Points and Miles, but frustration and narrow thinking can make the task feel impossible.


1. Plan Rewards Trips in Pieces – Not All At Once

Do not plan travel rewards trips in one fell swoop, and do not expect to be able to get good value whenever you can drop a pin on a calendar.

Most airlines and hotel rewards programs release a limited number of seats/rooms to award bookers and do so at irregular intervals throughout the year. That might mean waiting for the opportunity to book seats that fit within your schedule availabilities. That also means nailing down the harder parts — typically the flights — before planning a full itinerary.

2. Employ Persistence

Just because seats aren’t available now, doesn’t mean they won’t be in one week. Airlines continuously adjust award inventories to consider changes in ticket sales. If sales slump for a week while seats remain open, the seats you need on your perfect flight could become available.

Beyond just logging in and checking seats through an airline website, some tools can track available award seats for you. ExpertFlyer allows paying users to set award seat alerts for about 40 different airlines.

3. Be Flexible

Remember that airlines consider award seats to be freebies. They aim to give away seats, particularly to partners at so-called “Saver Level” pricing, that they otherwise wouldn’t sell at a profitable cash fare.

If there’s one daily nonstop flight to your chosen destination, don’t count on getting a points and miles seat there. It doesn’t hurt to monitor the seats and be persistent, but book the available connection. It’s a free seat.

4. Defer to Transferable Programs, When Possible

Many airlines are moving frequent flyer programs to dynamic pricing models. Like cash airfare, mileage awards priced this way can vary wildly from one date to the next. If you have a specific flight you’re trying to book with points, a friend’s wedding or birthday celebration lets say, an airline program may force you into an uncomfortably pricy redemption.

Migrating credit card spending to flexible programs can alleviate much consternation. American Express, Capital One, Citi and Chase all offer rewards credit cards that allow direct transfers to multiple frequent flyer programs. If one of the dozen-or-so programs has high redemption rates on the day you’re trying to travel, there’s a decent chance other airlines will offer something more reasonable.

5. Don’t Sweat The Small Stuff

When booking with points and miles, stay open-minded about trying different airlines and different routes than you might be used to flying on business. Don’t let perfect be the enemy of great, or even great be the enemy of good.

Whether you’re booking economy, business or first class rewards, you should be saving hundreds or thousands of dollars on a trip by redeeming points and miles. Taking an extra connection or flying on an unfamiliar airline doesn’t matter enough to risk a perfectly adequate flight that’s available, considering the alternative might be $1,000, $3,000 or even $10,000 out-of-pocket.

Moreover, it’s much easier to change points and miles flights if a more direct flight opens up in the same airline network. Fees are more modest than on discounted economy tickets, and some airlines don’t even charge change fees on award tickets if the destination remains the same.

Secure a good flight first, then train your eyes to look for the perfect flight, prepared to switch if seats open. In other words, don’t let your pursuit of the perfect flight ruin a chance to secure a good flight. You may not get a second chance.


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