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5 Ways to Score Big on Travel in the New Year

A cheaper vacation awaits.

So maybe you didn’t make that trip to Ibiza this year. Maybe work just got in the way, or you sat on a flight deal and then got fleeced by an infuriating last-minute change (that’s not supposed to happen on Tuesday!). Maybe you’re hoarding points like a rewards-card Scrooge. Whatever your holdup, 2019 waits around the corner, and so does that getaway.

Here Brian Kelly, founder and CEO of The Points Guy, helps you mine credit-card rewards, utilize points, and finally catch that airline deal in the new year. Just remember to pack sunscreen.

1. Know When to Book

You’ve probably tried this late-night travel trick before: staying up Monday or Tuesday and waiting for the price to miraculously drop at midnight—which it probably didn’t. “Though we do see more activity on Tuesdays and Wednesdays than we do on the weekend, there’s no one set rule for which day is best,” Kelly says. Back in the day when airlines filed fares and tried to match competitors, Tuesday was the day to shop. But these days, timing can be a bit all over the place.

Keeping an eye on the time

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Giving yourself an ample window from booking to flying, however, is no myth. “For international travel, which is where a lot of the deals are right now, two months-plus is usually a good time frame,” Kelly adds. As flights approach departure time, airlines try to take advantage of business travelers and begin hiking prices. But even if you’re late to booking, you can actually take advantage of an airline’s inability to fill seats. “Airlines want to fill every seat of every plane, so they will release award seats at the lowest rates possible. This can be the very best time to use your frequent flyer miles.”

Even if you’re late to booking, you can take advantage of an airline’s inability to fill seats.

As for domestic travel, Kelly’s determined a sweet spot: between two and four weeks from departure. 

2. Know How to Book

Instead of keeping that tab open for weeks, vigilantly checking prices, try apps like Hopper, Kelly advises. Hopper uses data to determine if a fare is likely to go up or down. But if you’re searching for low-cost carriers, be wary. “If the airline goes under (and some are currently in trouble) or if they cancel a flight, they won’t usually put you on another carrier,” Kelly says. Be wary too of other costs; the fare may be only one component of your purchase. Some discount airlines charge exorbitant rates for carry-on luggage. So do the math and determine the full cost before booking a low-cost carrier.

Worried couple struggle to pay credit card debt

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For those hoping to game the system with variant browser usage, you’re not doing much gaming. Flight shopping on incognito mode may help to block future ads, but won’t actually find you better deals.

3. Play the Points Game

Ultimately, smart travel these days comes down to points—how you accrue them and how you use them. Playing the points game, however, means also being a smart credit card shopper (and a responsible user), as many credit cards offer generous sign-up bonuses worth several hundred dollars in free travel. “Getting the right card can basically pay for a trip,” Kelly notes. (Some of these cards require that you spend a few thousand dollars in the first few months. Just remember that the clock starts ticking as soon as you’re approved, not when you activate the card.)

Flight attendant checking tickets in airport

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Which cards should you be getting? If you’re new to the points game, a good cash-back card presents few hoops and decent rewards. But to really maximize travel, look to get mid-level cards like the Chase Sapphire Preferred or Capital One Venture, according to Kelly. They may have an annual fee (some, though, only after the first year), but in the case of the Venture, they can give you double points on all purchases—meaning you don’t have to be a frequent traveler to accumulate serious travel points.

“Don’t pay just to have a piece of titanium in your wallet.”

Avoid airline co-branded cards that offer perks, but not-so-great point earnings, like double points on only their airline. Other cards might advertise exclusivity, but charge you large annual fees and provide unclear benefits, Kelly warns. “Don’t pay just to have a piece of titanium in your wallet.”

Pro tip: When shopping for credit cards, clear your cookies or use a private browser, Kelly adds. Credit card companies will offer you better rewards deals if they think you’re not already a customer. No one has to know.

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4. Play the Transfer Game

Okay, so you’re a veteran traveler. You know the points game. But if you’re a real points expert, Kelly says, you’re thinking about transferability. This means finding a card that allows you to transfer points to an airline’s frequent flyer program. (Mid-level cards like Capital One Venture, Chase Sapphire Preferred, and Citi ThankYou Premier all offer transferable points.)

Frequent flyer programs are based on awards charts, Kelly says, not the price of the ticket. “So let’s just say 100,000 Capital One points would be $1,000 in travel normally. You can transfer those and get 100,000 frequent flyer miles. That gets you a ticket that’s maybe $5,000 in value.”

The trick is to stop thinking of points as dollars and start thinking of them as miles. Welcome to the major leagues.

The trick is to stop thinking of points as dollars and start thinking of them as miles.

5. Make the Vacation Matter

You can crunch the numbers and transfer the points all you want, but in the end, travel isn’t just about the deals; it’s about you. In a recent survey, 70 percent of people said having a “purposeful experience” was an essential part of their travels. Eighty-two percent hope trips can be meaningful to them and their loved ones.

Father and son standing by still lake

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“We’ve wanted to elevate the conversation around this idea,” Kelly says. And so The Points Guy has gone all in on purposeful travel by partnering with the Purpose Project by Capital One. Maybe that’s a solo trip to Ibiza. Or maybe it’s adult-bonding with your parents in Bordeaux. Think about what you really want from your trip, and make those frequent flyer miles actually matter.

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