The Best Tools to Take the Pain Out of the Points-and-Miles Game

The complexity of the points-and-miles landscape is intense enough to make even professionals’ heads spin. Many airlines have abandoned award charts, making it harder to discern how many miles or points you need to unlock that first-class ticket to the Maldives—as well as whether your redemption value is a rip-off or a good deal. Amassing 500,000 Delta SkyMiles for a lie-flat business class seat from New York to Sydney may sound like the points and miles version of shooting for the stars, for instance—until you realize you can get it for 160,000 AAdvantage miles instead.

Even on a more fundamental scale, it’s hard to keep track of which cards to use in order to earn the most points on any given swipe.

“There is no one-card-fits-all approach,” says Adam Gwosdof, the airdesk product manager for Skylark, a luxury travel agency. “Unless you carry around a printed spreadsheet, you need an app to tell you the best card to use for each transaction you make.”

Gwosdof, who often helps people redeem their miles and points, has some favorites: The Points Guy app and the Award Hacker website are his go-tos, though the former is still in beta and not yet available to the general public. When it can be downloaded by the masses later this year, it will be a one-stop shop offering real-time tips on which cards to use for specific purchases, expert advice on how to maximize the points you’ve earned, and notifications when any of them are set to expire. It’ll also offer an “explorer” tool to let you see how transferring points among various programs can boost their value and unlock better redemptions.

Luckily for consumers, it’s just one of many tools helping them parse an increasingly complicated landscape. We review four of them to help get you started.


The Best Tools to Take the Pain Out of the Points-and-Miles Game

For crafting the perfect credit card portfolio

The general premise: Identify whether the plastic in your wallet is really working for you—and which cards to sign up for if you’re not milking your current benefits.

Why we like it: After you enter the details of everything in your wallet, Gigapoints analyzes your spending patterns to determine if you are earning the maximum reward value with the cards you have. The company uses a third-party service called Plaid to manage password authentication, and has CIA-backed safeguards for data privacy and protection.

The initial setup takes some patience, but the rewards come quickly. The app suggests credit cards that may better match your spending patterns, helping customers get an additional $1,000 a year in benefits, on average, be it through cash back, points, or miles. It also suggests cards that address big-picture points and miles goals, like prioritizing free flights, hotel redemptions, or cash back. The developers are also available for free phone consultations if the recommendations require parsing—or if you have very specific goals, like saving for a stay in an overwater bungalow—though you can also filter the results based on simpler criteria, like earning the most airline miles or hotel points.

The caveat: Users will have to wait for future versions of the app to explore valuable secondary benefits such as lounge access and retail credits. Like the Points Guy, its business model also hinges on commissions from credit card signups, which can put off some users. 

App in the Air

The Best Tools to Take the Pain Out of the Points-and-Miles Game

For earning the most miles on every flight

The general premise:  Get the most miles out of every airfare purchase. App in the Air helps you figure out which loyalty program to use when you’re shopping for flights by analyzing the oft-confusing, nitty-gritty criteria like fare class and the earning potential tied to your specific elite status.

Why we like it: If you’re loyal to one airline, you may be surprised to learn that competitors may reward you with more. App in the Air makes it easy to know if that’s the case by adding mile earnings to the traditional aviation marketplace interface. It searches routes from more than 200 airlines and shows how many miles you’d earn on any given flight, so if you’re aiming to fly from New York to Miami, for instance, you can see that a fare on American Airlines would earn five miles per dollar spent—unless you book basic economy, in which case none of those miles would be elite-qualifying. Buy the same type of basic economy flight on Delta and you’ll earn five miles per dollar spent, plus miles that work toward achieving elite status.

Over time, that could make the difference between, say, qualifying for Gold or Platinum tiers, which unlock additional earning power and travel perks. It’ll also factor in the particulars of your existing elite status on any number of loyalty programs.

The caveat: You can’t currently sort results by the number of miles earned, which means you have to scroll through a longer list to get a sense of the relative highs and lows. The company says this feature is in the works.

The Best Tools to Take the Pain Out of the Points-and-Miles Game

For putting the miles and points you already have to smarter use

The general premise: Search more than 60 loyalty programs and their transfer partners to identify the cheapest redemptions on specific flight routes and travel dates.

Why we like it: This app is the newer, fresher, faster version of Juicy Miles, a popular service that helps book award travel, and no wonder: It was created by the same founder. It will be fully released in July and will scour more airline and credit card programs for redemption values than any other tool, making it the best place to comparison shop when using hard-earned miles.

The interface is simple and makes it easy to pinpoint the cheapest redemptions of specific itineraries. For example, a New York to Istanbul redemption via Delta SkyMiles may cost 200,000 miles, but the same city pair may only take 70,000 miles via United MileagePlus. Don’t have any United miles? No worries. suggests transfer partners that allow you to convert currency and snag the deal.

The caveat: Valuable services don’t come free, and while there’s a no-cost version of the app, it’s fairly opaque and will tell you only whether award space is available on certain dates, not which redemption partner to use. To see the full details, you'll have to fork over for access. For unlimited award trip searches, the service costs $5 for a five-day pass, $12 for monthly access, or $99 for a year.

Card Curator

The Best Tools to Take the Pain Out of the Points-and-Miles Game

For determining the right card to use on every purchase

The general premise: Use geolocation data to helps users determine which credit card to use, depending on the card bonuses that may be applicable wherever you are, be it a grocery story, gas station, or restaurant.

Why we like it: Many cards offer bonuses when you spend on categories such as dining or travel—but it’s easy to forget which one’s which. Card Curator eliminates the guesswork, sending relevant text notifications to prevent the average user from leaving thousands of points and miles on the table. If you’re in a supermarket, for instance, it will remind you that your new American Express Platinum card offers 10x points on groceries in its first six months. You can use the service without geolocation data by simply selecting a category from a drop-down menu before picking the plastic to swipe at check-out. It’s a straightforward and effective proposition: We saw our point balances swell almost immediately after downloading it.

The caveat: The app’s functionality is limited: It helps you amass points but doesn’t tell you what you can do with them. A premium version coming in August will cost $6 a month and offer a goal-setting feature; you’ll be able to input a trip you’d like to book with miles and then spend strategically to save up for it. Current users will be grandfathered into the  premium version for free, so take advantage while you can.

©2021 Bloomberg L.P.

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