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The ultimate guide to free flights, upgrades and the best credit cards for cheap travel, by The Points Guy

by London Mail
April 12, 2025
in Travel
Reading Time: 7 mins read

After more than 15 years in the points and miles game, travel is no doubt my favorite sport. 

In fact, I wrote this on a plane from Philadelphia to Los Angeles. 

So when people like to reminisce about the Golden Age of Travel during the 1960s and ’70s, and say the best global experiences are behind us, I think their idealism is severely misguided. 

Not only is travel much safer today, it’s also more efficient and accessible than ever – and knowledge is the most important currency. 

Those who understand the lucrative ecosystem of loyalty programs and credit cards have endless opportunities to make their travel dreams a reality – take it from someone who started his own points journey at just 12 years old.

In my new book, How to Win at Travel, I reveal everything I’ve learned. Here’s a few tips to get you started.

Earning rewards

Jumping into the world of travel rewards can be daunting, but figure out a strategy that works for you, and you’ll start earning money on everyday purchases, accessing deeply discounted vacations, flying first class and unlocking even more travel benefits.

Brian Kelly caught the travel bug early, when his dad challenged him at 12 years old to book the whole family’s trip to the Caribbean using points

Brian Kelly caught the travel bug early, when his dad challenged him at 12 years old to book the whole family’s trip to the Caribbean using points

Brian and his son Dean enjoy luxurious sleeping arrangements in The Residence class of Etihad Airways

Brian and his son Dean enjoy luxurious sleeping arrangements in The Residence class of Etihad Airways

Credit cards are at the top of my points-earning hierarchy – I currently have 28 and a nearly perfect FICO score. 

They’re the quickest and cheapest way to accrue miles and points, especially in the US, where the average American has around 3.9 credit cards.

If you are able to pay off your balance each month, foregoing credit cards means you’ll be leaving valuable points and perks on the table.

The goal of credit cards in this instance is to choose those that reward you for what you spend the most on (dining, travel, groceries, etc.). 

Some of the top cards out there are American Express Gold with up to 4x points on dining and groceries, Capital One Venture X, Chase Sapphire Preferred and, if you’re paying rent, Bilt Rewards. 

But, to be clear, it’s never worth making purchases you can’t afford for the sake of earning points, because the interest you pay will greatly outweigh the value of any points earned. 

Brian and Dean visit Japan - thanks to his savvy use of airline points

Brian and Dean visit Japan – thanks to his savvy use of airline points

On safari with his parents Brian and Suzanne. 'Travel is no doubt my favorite sport,' he admits

On safari with his parents Brian and Suzanne. ‘Travel is no doubt my favorite sport,’ he admits

I always recommend checking out the bonus categories that each card offers (like 3x points on restaurants or drugstores) in addition to comparing base earning rates. 

If you’re someone that spends a lot on dining, for example, those bonus categories can really help maximize your spend.

Don’t forget to check for the best sign-on bonuses – credit card companies usually have a one-time deal when you open up a new card, like offering up to 100,000 bonus points when you meet a minimum spend within the first three months.

Maximizing your points and miles

The most challenging part about playing the points and miles game is that there isn’t a one-size-fits-all airline, hotel or credit card that will get you the best deal every single time. 

Each provider has built its own points ecosystem, which makes it confusing for consumers to compare and ensure they’re getting the most value for their points. 

Throw in the complexity of transferring points from credit card providers to a host of different travel partners, and anyone is bound to experience decision paralysis.

The first step to maximizing your rewards and earnings strategy is meticulous tracking. 

There’s a bunch of different ways you can make sense of your rewards earnings. Make your own spreadsheet or downloading a tracker like AwardWallet, which currently tracks more than 638 loyalty programs and enables you to see expiration dates, earnings, reservations and more. 

If you go the spreadsheet route, don’t forget to add a tab for any special spending requirements or perks so you remember to take advantage of them. 

I also like to create a tab for all my redemptions so I can see how much value I’m getting from each card.

When it comes to actually redeeming awards, flexibility is key. 

In today’s ecosystem, transferable bank/credit card points are the most valuable – this allows you to work with a variety of travel partners versus building up loyalty with only one airline or hotel chain. 

Flexibility also applies to the timing of your trip and the actual destination. 

Google Flights is my favorite free tool for finding the best deals. Not only can you compare rates across different travel dates, but you can also use its explore feature to price compare various destinations. 

Google Flights is Brian's favorite free tool for finding the best deals. Here, he is pictured with his son in Antelope Canyon, Utah

Google Flights is Brian’s favorite free tool for finding the best deals. Here, he is pictured with his son in Antelope Canyon, Utah

Brian and Dean's travels have also taken them to the Maldives. 'Always be mindful of the people and places around you when traveling,' he advises

Brian and Dean’s travels have also taken them to the Maldives. ‘Always be mindful of the people and places around you when traveling,’ he advises

Point.me is a similar paid tool that’s become a go-to for me when looking for the best deals across destinations and dates.

You’ll also enjoy way more flexibility in your travel plans when booking with points and miles. 

For many airlines, booking with miles is like getting a refundable ticket because they usually let you cancel free of charge (or for a nominal fee) and get your miles back. 

This can come in especially handy in the event of unexpected delays – I always use my points to book a backup flight if I’m worried about delays and cancellations.

At the very least, never hoard your points – they usually decline in value over time. 

Always use them for flights and hotels, and save your hard-earned cash for activities and experiences. 

Travel etiquette

I know travel can sometimes be a stressful experience, but being kind – especially to frontline travel employees – goes such a long way. 

It’s never productive to scream at anyone, and these agents may not even have access to the information they need to to solve your problem. 

And if you really aren’t having any luck with an agent on the phone, something I always do is hang up and call again. It’s very possible that you could get a more experienced agent or someone who has more resources to resolve your issue.

Overall, always be mindful of the people and places around you when traveling. This means not touching wildlife or cultural artifacts, not feeding animals and following ‘leave no trace’ principles. 

In terms of my absolute flying ‘don’ts’: putting your bare feet up on someone’s armrest, changing a baby’s diaper on a tray table or airline seat and eating stinky foods.

How to Win at Travel by Brian Kelly is published by Avid Reader Press

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