How to Start Travel Hacking: Fly for Little or Nothing (Even in First Class)

Four out of 5 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.

The beginner's guide to travel hacking.This July, I’m flying my family of four from Portland, Maine to San Antonio for a family wedding…for free.

Had I paid for the airfare, the cost would ring in at over $2,000.

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

Relative to consultants and sales reps on the road every week, I’m not a frequent traveler. I might fly 4 or 5 times a year to conferences for work.

But I still manage to leverage travel points to open the door to free travel and an upgraded travel experience.

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

Travel hacking is a big deal online. You could devote hours a day to exploring sites like The Points GuyFlyerTalk and dozens of others explaining in detail how to get free points here, there and everywhere else.

Chris Guillibeau is close to visiting every country in the world…and much of his travel is gratis (or at least very very cheap).

This post will give you a basic 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): Getting 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 Expeida. Skyscanner or Momondo are others good for foreign routes.

Being as flexible as possible – searching for alternate airports and dates to avoid peak business travel times – can also save you hundreds.

But here are some things you might not know:

1. 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, instead of You’ll have to do some conversions and also take into account whether your credit card will charge you a conversion fee (here are some travel cards that don’t).

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

There may be some smaller airlines that don’t show up in the aggregator sites and are often cheaper. 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).

3. Call a travel agent that specializes in your destination.

Once I traveled to Croatia and Bosnia and Herzegovina. We used a Croatian travel agency in New York that arranged a multi-stop air itinerary on different airlines that came up 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): Collecting and using 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 offered a good amount of routes from my city. I became loyal, choosing to fly Delta whenever possible even if the ticket was $50 or so 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. (See more below.)

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, the airline cards have annual fees and higher-than-average interest rates which is why you 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 certain spending thresholds.

If you fly enough each year on one airline you can obtain elite status. Although there are other perks that come with “status” as it’s known in frequent-flyer lingo, by far the most coveted is the complementary first-class upgrade.

How travel hackers get first-class upgrades for free

Here’s how it works. Very few people pay out-of-pocket for a pricey first-class ticket. In the last few days or hours before a flight takes off, the airline begins awarding unsold first-class seats to passengers with elite status. Each airline has several tiers of status – so the passengers who fly the most get first dibs and it trickles down. Other factors, like weather delays and how much you paid for your ticket might bump a lowlier elite flyer to the top of the list.

It’s luck of the draw: But I’ve gotten first-class upgrades on 50-60 percent of my Delta flights – including some long hauls from Las Vegas to Boston – since I became a Silver Medallion three years ago.

Admittedly, my success ratio scoring upgrades fell after Delta merged with Northwest because the number of elite flyers on the combined airline grew. If I can fly enough this year, combined with the qualification miles the Delta Amex will earn me, I may be able to reach the Gold level next year.

How to get your first free flight

If you have good credit and no debt, the best place to start is with an airline credit card’s sign-up bonus. Here’s a list of some of the available bonuses right now. Many will get you enough points for your first free flight (or very very close).

Many people are concerned that signing up for new credit cards will hurt your credit.

This may be true if you have a lot of credit card debt already, but if you’re relatively debt-free and have good credit, applying for a few new cards won’t hurt as long as — you know — you don’t go crazy and max them out! What you want to avoid, however, is opening them, grabbing the bonus and then closing them, a process known as “churning”.

Bottom line: Only get cards that you’re comfortable keeping for a few years.

Enrolling in miles programs

If you’re not in a position to sign up for a card – at least sign up for a few frequent travel rewards programs (airlines and hotels) EVEN if you’re not traveling anytime soon.

Here are some of the biggest to get you started:

And hotels:

Most rewards systems have ways to earn points other than traveling. For example, I’ll get emails from Delta offering points on surveys or if I purchase something through their link. (Around holidays they send out miles deals for FTD Florist, so I can pick up a few miles by sending my wife flowers which I might do anyway).

Once you’re a member of a few rewards programs, use them! Anytime you fly or stay at a hotel, make sure you use your number. Some hotel chains, for example, allow you to “double dip”, meaning you can apply both your hotel rewards number and an airline program to your stay, earning both points and miles.

Buying or challenging for status

If the thought of free first-class upgrades has you jittery, you can get there faster. If you have the cash, U.S. Airways lets you buy status outright. Other airlines let you get there faster by taking a “points challenge”.

Basically you have to call up the airline (they don’t advertise this) and tell them you’re a frequent flyer and want to take a points challenge to earn status. It works best if you hint that you are loyal to another airline and want to switch.

There may be a fee to take the challenge, and then you have to earn so many miles within a limited time window like 90 days.

On American Airlines, you can challenge for Gold or Platinum status by calling 1-800-882-8880 and paying a fee of $120 or $240 respectively. To get Gold status you must earn 5,000 Elite Qualifying Points (EQPs) in 90 days and to get Platinum you must earn 10,000 EQPs in 90 days. Ordinarily you have to earn 25,000 or 50,000 EQPs over the course of a year.

Buying status isn’t cheap. American discounts the EQPs you earn on cheap tickets so you’ll have to fly more miles or buy higher-cost tickets to meet the challenge thresholds. But if you fly often it “pays for itself” in future upgrades if you consider the considerable money saved over paying first-class fares.

(I should also note that U.S. Airways and American are merging, meaning these options are available for another couple of months after which they may change or go away. Either option will get you status until February 2015.)

Maximizing your rewards

You can only collect points so fast – you’ll need to travel a bit to accumulate much of a balance. Credit card bonuses are obviously the fastest way to accelerate this.

But the real art of travel hacking comes not so much from collecting the points as redeeming them.

Most of the time, a single airline mile is worth somewhere between $0.01 and $0.02. It all depends on how you spend it.

You might, for example, redeem 50,000 miles for a round-trip domestic ticket that costs $300. That’s a per-mile value of just six-tenths of a penny. Not good.

Let’s say, however, that you save up 200,000 miles and redeem it for a business-class international ticket that sells for $8,000 (crazy, I know), you’re getting $0.04 per mile.

Obviously rewards are only good if you can use them – so this won’t always apply. But this is also why it makes sense to focus your efforts (at least in the beginning) on one or two airlines so you can obtain a critical mass of points more quickly.

Are you an aspiring travel hacker? What’s your favorite trick?

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About David Weliver

David Weliver is the founding editor of Money Under 30. He's a cited authority on personal finance and the unique money issues we face during our first two decades as adults. He lives in Maine with his wife and two children.


  1. This is a well-written article that gives a good introduction to the basics of travel hacking. I would like to challenge one point – “What you want to avoid, however, is opening them, grabbing the bonus and then closing them, a process known as “churning”.

    While I’ll agree there is a slight hit to a credit score for opening/closing a credit card, not every card you open you should plan on keeping for one year. Let me give you an example – the current Citi AAdvantange Executive World Mastercard gives you 100k miles if you spend $10k after 3 months. Obviously that is high but doable for some people. After the first year, though I wouldn’t keep the card since the annual fee is high.

    That 100k miles is worth 4 round trip domestic flights or 2 domestic business class flights. I would argue the small impact of closing the card to your credit is definitely worth getting thousands of dollars of free flights. So churning done on a small scale (and larger if you know what you are doing) isnt necessarily a bad thing.

    Some sites (like mine) actually offer consulting services to people to help them figure this all out

  2. I didn’t know about those first class upgrades being given out to frequent fliers! I always thought, who can possibly afford those tickets?

    Tomorrow I am flying to Europe courtesy of my first major reward card hack!