This is utterly unscientific, but I suspect that when it comes to my points-and-miles “strategy,” I am a lot like you. I have a couple of travel rewards cards (including the Chase Sapphire Reserve card) and I dutifully enter my airline mileage number every time I book a flight. I subscribe to a couple of flight deals newsletters and have made valiant attempts to use my credit card points, with mixed results. But I have this niggling feeling I could do more to maximize my spending—and more importantly, my redeeming—when it comes to travel points and miles.
It’s just that it seems so . . . exhausting. Where to start? What to prioritize? Quite frankly, I’d rather watch the latest season of The White Lotus. Then I read Brian Kelly’s new book, How to Win at Travel, as part of my prep for an interview that’s featured in a recent episode of our Unpacked podcast. In the book, he’s offering exactly what I was looking for: a place to begin and tips on what to prioritize—plus a lot more. So whether you’re a total newbie, a half-hearted points-er like me, or a total pro, there’s something to gain. Here’s what I learned.
Don’t Be Afraid to Play the Credit Card Game
Kelly has 28 credit cards—and he says that’s on the low end for someone in his profession. (Some pros have as many as 40 or 50 credit cards.) But if you want to rack up points and miles, using credit cards is the “quickest and cheapest way,” according to Kelly.
Don’t go out and sign up for 20 cards at once. He recommends starting with two cards: one with transferable points (such as the Chase Sapphire Preferred or Reserve cards), and a cobranded card from the airline (and or hotel company) you use the most. If you want to continue to add cards to get those valuable sign-up bonuses, don’t open more than four cards per year.
To stay on top of his cards, Kelly sets up auto-pay, at least for the minimum amount due. He also has a spreadsheet where he tracks sign-up bonuses, annual fees, and other details to make sure he extracts maximum value from each card. Finally, he says to keep a card open for at least one year: The longer your credit history, the better your credit score.
Speaking of credit scores, contrary to popular opinion, having multiple credit cards won’t hurt you. “Your score will go down maybe 5 points. Now, out of 850, that’s negligible,” Kelly says. “That’s not tanking your score.” Because as long as you pay off your balance in full every month, the more cards you have, the more available credit you have. That will improve your score over time, if you keep your utilization rate under 30 percent.
“If you were to have one credit card [with a] $5,000 credit line, and even if you paid off on the due date, but it’s $3,000 a month that you’re paying off, it can report as, like, 75 percent utilization, and your score can drop really far,” Kelly explains. “But if you had $50,000 through five different credit cards and you were using $3,000, your utilization is super low. Your score will shoot up.”
But Don’t Leave Rewards on the Table
These days, there are rewards pretty much everywhere you look. Most major travel companies have online shopping portals, where you can register your information, click to shop at your preferred retailer, and accrue airline miles, points, or other rewards for free. If you use a rewards credit card to make a purchase, you get double the rewards, Kelly says—the miles or points through the retailer, and then the miles or rewards you earn through your card.
“This is a prime example of double-dipping, as you can earn two types of points or rewards for the same purchase,” he writes. Examples include Alaska Airlines Mileage Plan Shopping, Delta SkyMiles Shopping, and the Chase shopping portal (only for cardholders).
Also consider registering your cards in the Rewards Network, which automatically earns you miles at participating restaurants. Watch for rewards-earning partnerships, like those between Uber and Marriott, Delta and Instacart, and American Airlines and Hyatt.
When It Comes to Redeeming, Invest in a Few Key Travel Apps and Services
If there’s one chapter I know I’ll read again and again, it’s “How to Win at Redeeming Rewards.” Even Kelly admits that redeeming can be difficult and complex, in part because there “isn’t one unified system that tells you the best way to redeem them.” So take a deep breath and invest in these tools.
AwardWallet: Organize Your Travel Loyalty Programs
This site (and app) tracks more than 600 loyalty programs. It tells you when your miles expire, tracks your credit card and loyalty points, and even incorporates flight details and travel itineraries. There’s a free version and a paid version ($49.99/year).
AwardHacker: Find the Best Loyalty Program for Your Route
Enter the route you want to fly into this free site and get advice on the best loyalty programs for that route.
Point.me: Find the Best Points-Based Flight
A paid tool that Kelly says he can’t live without, Point.me costs $129 a year (though it’s free for Bilt and AmEx Membership Rewards cardholders). It will search the route you want to fly, as well as dates, and suggest options that you can filter by points, number of stops, etc.
Seats.aero: Search Within a Specific Loyalty Program
Another paid tool in Kelly’s wallet, this app ($9.99/month) allows you to search a full year’s worth of dates and points on a specific route. “Where Point.me goes far and wide on a certain date,” Kelly writes, “Seats.aero can search far and wide on dates with a single loyalty program.”
If redemption still seems beyond you, you can pay pros to do it for you through sites such as Award Magic and Point.me.
Don’t Make Airline Status Your Goal
Honestly, this one surprised me. But Kelly says chasing airline elite status isn’t necessarily worth it these days. The airlines have changed their programs so much—many requiring upwards of $30,000 in annual spending to qualify—that “the opportunity cost of elite status . . . has never been higher,” he says.
So unless you fly so much on a single airline that it makes sense to book using its cobranded card, it makes more sense to get a transferable points card and use points to upgrade your seats to business or first class on any airline you want.
In contrast, Kelly says it’s still worth going after elite status when it comes to hotels, especially if you use a cobranded credit card, most of which automatically offer generous sign-up bonuses and elite status (and that translates into free room upgrades, late checkout, and more).
Read the Fine Print—and Always, Always Be Nice
Have you ever read an airline’s contract of carriage? It’s the little box you check saying you agree to fare rules, terms and conditions, etc. And, yeah, I’ve never read one either. But Kelly says we should be reading them, because they spell out what an airline will do when things go wrong. Honestly, it’s usually not much—beyond refunding the cost of your ticket, which is now required by law.
Yes, airlines will rebook you, but for most of them, that means they will rebook you on the next available flight to your destination, provided seats are available. And that could be hours (or days) from the time of the incident. So, like it or not, when flights get canceled or delayed and we’re trying to get out of the airport as quickly as possible most of the time, we’re asking for a favor. Kelly recommends approaching a gate agent with a very specific ask (“I see X seats available on X flight and I don’t mind flying through X. Can you please look for me?”)—and the utmost politeness.
“If you were behind that counter and someone’s being a jerk to you, are you going to go above and beyond and even stick your neck out on the line?” he says. “Because agents now can get in trouble for bending the rules. So think, Am I giving this agent a really good reason to help me? Because they have all the power.”
Finally, Use Points as an Insurance Policy
Kelly says that having a pool of flexible points on different airlines and with different credit cards can also help you when, say, your flight is canceled.
That way, he explains, “when your flight’s canceled on one airline, you can book using points on another as a backup option,” he says. “One of the most beautiful things to happen out of the pandemic is [that on] almost every airline loyalty program, you can redeem your points and cancel up until departure and get all your miles and points back free of charge.”
The day before his flight, he starts tracking where his plane is coming from and weather patterns (he likes FlightAware). The moment he “smells a delay”—if the incoming flight is delayed, he knows his flight is likely to be delayed too—he uses points to book another flight on a different airline. “If I don’t need that backup option, if my flight doesn’t end up being delayed, I cancel it, get all my points back, no cash out of pocket,” he says.
And that, my friends, smells like winning to me.
