March Update

Four out of five people sitting in first class aren’t rich—they’re smart. Enter the world of travel hacking to score rewards flights and free first-class upgrades on most of your flights. It’s all possible. Here’s how to start.

A few years ago, I flew my family of four from Portland, Maine to San Antonio, Texas for a family wedding—for free.

Had I paid for the airfare, the cost would have rung up at over $2,000.

Also awesome: I’ve gotten free first-class upgrades on about six out of the last 10 flights I’ve taken, even though I usually buy the cheapest ticket available.

Relative to consultants and sales reps who are on the road every week, I’m not a frequent traveler. I might fly four or five times a year to conferences for work.

But I still leverage travel points to get free trips and an upgraded travel experience.

If you’re not collecting travel points, this is why you should start.

This post will give you an introduction to travel hacking. We’ll start with basic things anyone can (and should) do to save money on flights. Then we’ll progress to the ways I racked up close to a million Delta SkyMiles while still in my 20s.

How to start travel hacking (Level 1): Get the best deal on every flight

Most of you aren’t living under a rock, so I don’t need to tell you that you should start your search for a flight with a site like Kayak that searches multiple travel sites for the best fares, or even Expedia or TripAdvisor. Skyscanner or Momondo are good for foreign routes.

Be as flexible as possible: If you search for alternate airports and dates to avoid peak business travel times, you can save hundreds of dollars. Priceline is still the best way to score unpublished fares and hotel rooms if you can be as flexible as possible, check out these New York jet charters.

But here are some things you might not know:

If you’re traveling on an international airline, go to the airline’s foreign website to see if the airfare is cheaper in another currency

For example, search instead of You’ll have to do some conversions, and also consider whether your credit card will charge you a foreign transaction fee. (Here are some travel cards that don’t.)

Check your destination airport to see all the airlines that fly there.

There may be some smaller airlines that cost less but don’t show up in the aggregator sites. For example, if you’re flying from New York to Continental Europe, it may cost less to fly to London and then switch to a low-fare airline to hop from London to your destination city. (But you may have to book the tickets separately.)

Call a travel agent that specializes in your destination.

Once I traveled to Croatia, Bosnia, and Herzegovina. We used a Croatian travel agency in New York that arranged a multi-stop air itinerary on different airlines that came to about $1,500 per person, which was half what we were finding on our own. Travel agents may not always be less expensive, but they’re worth a shot.

How to start travel hacking (Level 2): Collect and use frequent flyer miles

This is where it gets fun.

By travel hacker standards, my system is simple: Years ago I picked an airline (Delta) that I liked to fly and that offered a good amount of routes from my city. I became loyal, choosing to fly Delta whenever possible, even if the ticket was ~$50 more than a competitor.

At the same time, I got Delta’s affinity credit card—the Delta SkyMiles Card from American Express. Right off the bat, signing up got me bonus miles worth almost enough for a free flight, and the card comes with other perks, like free checked bags and double miles on the airfare I book.

Many of these travel rewards credit cards come with free points to get you started.

Now, for someone who can’t commit to airline loyalty, airline credit cards aren’t the best deal. Generic travel rewards credit cards offer more rewards per dollar spent, and the airline cards have annual fees and higher-than-average interest rates, which is why you should never, ever use these cards if you can’t pay the balance in full each month.

What these cards are great for, however, is accelerating how many points you can earn each year. The Platinum version of Delta’s card, for example, gives you a 10,000-mile bonus when you hit a certain spending threshold.

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