How to win at travel: The Points Guy Brian Kelly on frequent flier miles and travelling with kids

Extra nights in cushy hotel suites, free premium air travel and even stays on private islands.

Loyalty points and frequent flier miles, when strategically collected, can fund trips well beyond a traveller’s usual expectations and budget.

But it is not easy to get these deals. Luckily, there is an entire universe of experts who share their savvy in booking award travel, and at the forefront is Mr Brian Kelly, who founded the travel website The Points Guy in 2010.

For the 41-year-old, it started with the childhood challenge of booking travel for his family.

At 12, he planned an entire vacation to the Grand Cayman for his family of six, booking all the flights with miles earned by his father. This successful trip laid the groundwork for his career as a travel expert, he said. Deals still dictate his travel.

In his new book, How To Win At Travel, he shares advice on everything from understanding points and miles to handling flight disruptions and flight anxiety.

Here are some of his tips on how to strategise purchases with credit cards – he has 29 – flying with children in business class and the evolving world of award travel.

You have researched points and miles for decades. What is still fun about it?

I love solving the puzzle. Yes, it is a little bit difficult, but that is also the point. If it was so easy for everyone in the world to use, it would not exist. For those who want to put in a little bit of work, I think there is still a really high reward.

Some examples: I have been to the Maldives, Paris and Japan on rewards points.

What is the best travel you ever scored?

Airline technology can sometimes mess up in your favour. When US Airways was getting acquired by American back in 2013 or so, I had redeemed 130,000 points for a first-class, round-trip flight to Australia. I was flying during the tech transition, and it ended up refunding all of my points. I flew to Australia for absolutely free.

Navigating points and miles requires a lot of legwork. Travellers must compare the value of miles and dollars and points on different websites. Is it getting harder to nab good deals?

The technology makes it really interesting these days.

Before, you had to be an expert and know how to use 10 different airline websites. There are tools now, like seats.aero and Thrifty Traveler, that are a little wonky but not that hard to use. Award redemption is shifting, but with these technologies, it is easier today to find those sweet spots than before.

Certain airlines and partnerships still have really great value. Mostly the foreign programmes, like Air Canada’s Aeroplan or Air France. You can fly business class to Japan on Japan Airlines with 60,000 American Airlines miles.

You write that the best redemptions for US airlines are generally on international partners because these are not as tethered to dynamic pricing.

The foreign airlines are eventually going to catch on. I just think they are several years behind. The prices will rise. Use points now and maximise the sweet spots.

What is the No. 1 thing you would suggest rewards novices do?

It is important for everyone to understand credit.

Start with one card – it is about getting credit cards with the big sign-up bonuses. But, really, the key is making sure you are strategic about where you are charging your dining, groceries and rent. You want to have a credit card portfolio, even if it is just three cards. Start small, engage in the programmes and then expand from there and put together a strategy that is points and perks like trip disruption coverage.

I pay every bill in full every month.

When and where was the last time you flew economy?

I still fly economy. Preferably for flights under an hour.

You advise caution when booking travel with online travel agencies (OTAs). Why?

Some OTAs are better than others, but a lot of their customer service is abysmal. Be careful which ones you choose.

I have talked to hotel front desk agents: For hotel bookings, your OTAs are generally looked upon as sort of the last priority. So, do not treat yourself poorly on purpose. If the price is the same, book direct.

You no longer have elite status on a US carrier. How is this points-only approach working for you?

When we are chasing elite status, we are often spending more than we have to, or inconveniencing ourselves because we feel we have to keep up on the hamster wheel. I love being a free agent. I will fly the best flight for me and my family to get us there the most comfortably. I pretty much use points for all of my airfare.

People mistakenly assume all planes are the same, but different planes can be the dramatically much better or worse experiences: legroom, noise, amenities. Cheap is expensive, too, when you account for fees and a bad experience.

What is it like to travel frequently with young children?

My older son is two and has been to 16 countries. My second son was born in December. We are heading to Thailand for a month in April, flying with points on the Etihad Residence, where you get your own bedroom on the plane. It will be my second son’s first international flight.

Later in 2025, we are going on a cruise in Antarctica. (The cruise itself is not on points, but all of the flights and hotels before and after will be.)

I think the younger you start, the better they are about travelling. When they are young, it is easy. It is about preparation. Snacks, activities and timing flights to sleep schedules has worked for me.

Will your sons be able to fly in the main cabin after experiencing luxury flying?

I plan on giving them this character-building experience when I don’t have to be there with them.

Is the golden age for rewards over?

There are so many credit cards and ways to earn points. It is constantly evolving. It is pivoting towards a more stable valuation for miles and points as more and more people get in.

This might mean that points and miles will kind of land at a lower overall value. Potentially less sweet spots overall, but more easy to attain value. Because if airlines do not become more clear about how consumers can get their value, I think they do face regulation from the government, which they obviously want to avoid.

It is not just airlines that have these new pricing technologies; consumers do too. There are all sorts of new tools and tricks. It goes both ways. NYTIMES