Browsing Posts tagged frequent flyer miles

Bolivia to Chile

Sometimes you have to make your own path…

Why do some people always seem to travel for cheap and others search in vain for deals that elude them? Often it comes down to a combination of patience, persistence, and creativity. As creative thinking author Roger Von Oech advised, often you need to find “the second right answer.”

Next week I’m traveling from Mexico to South Carolina on a Delta frequent flier ticket. Their miles are often derisively referred to as “Skypesos” because they’re so hard to cash in compared to most other airlines. Getting the lowest level awards are next to impossible. But…this is the fourth time I’ve flown Delta for free, so it’s close to impossible, not completely so.

I managed this, as I’ve done the other times, by basing my travel dates on when Delta had availability, not when it was most convenient for me. I’ll make all kinds of changes in my travel schedule if it’s the difference in paying $50 in cash-in fees or $550 to buy a ticket.

Over the past few years, due to some smart travel hacking efforts, I’ve flown for free (except for taxes and fees) to four continents, plus a few domestic flights. Rarely was this as simple as punching in my dates and hitting the booking button. Here are a few contortions that were required to cash in all those miles for almost-free tickets:

  • I flew American to Bolivia and LAN back from Chile because neither had openings both ways.
  • I started and ended my four-country tour of Eastern Europe not in Sofia, as I’d planned, but in Budapest because that’s where I could get a mileage ticket flight the time of year I wanted.
  • My family returned from Southeast Asia on a different airline than me.
  • My daughter and I moved to Guanajuato a week earlier than my wife because we were paying and she was using mileage.
  • I got an extra cheap hotel room one night in Salt Lake City because the date I wanted to fly out on mileage wasn’t available. The next day was.

Be a Travel Deals Detective

This kind of willingness to be flexible also applies when you’re paying. I recently got quoted in this Reuters article about flying an unaccompanied minor because they liked my story about how I avoided paying United Airlines $300 to put my daughter in a seat by herself. I accompanied her up and back on Allegiant, then she returned on JetBlue. It took some time and a calculator to figure all that out, but we saved a a few hundred bucks and it all went smoothly. creative travel savings

Hotels? Go beyond the typical booking engines everyone uses. For normal hotel deals, try and get a look at what everyone is charging. If you just need a chain hotel in a certain area, use Hotwire or Priceline bidding. Try the HotelTonight app if it’s last-minute.

If all else fails, use none of them and go old school, researching independent options that don’t want to pay the big booking sites. Look at guidebooks, destination websites, and the third page of TripAdvisor for hidden gems. Ask friends of friends. Or if you’re staying a while, rent a home or apartment.

If you’re coming up empty finding a reasonably priced way to get from A to B, make sure you’re looking at all the options. From Megabus to Amtrak, Easyjet to AirAsia, one-way rental cars to alternate airports, there multiple possibilities to try before giving up.

Travel is so much easier than it was when I started 20 years ago, but it’s also easier than ever to overspend. It’s easier to mistake info that pops up in your first search as the final word. Really, it’s just a starting point. Dig deeper and wider to find a better answer.

This year I’m flying round-trip to Budapest, round-trip to Southeast Asia, and probably to South America and back—without buying plane tickets. No, I’m not going to any of those places on a press trip: I’m cashing in miles.

Many people are surprised to hear that I’ve never attained elite status on any airline. I rarely see the front cabin of the plane. It’s not that I don’t fly a fair bit, but it’s generally a mix of different airlines and there aren’t enough really long-haul flights in there to add up to 25,000 or more miles accrued in one year.

It’s also partly because I get a lot of free flights by the judicious earning and use of frequent flier miles. In the past I’ve flown gratis to Argentina, Peru, Mexico, and a half-dozen places in the U.S. This year I’m flying for free round-trip to Eastern Europe and Southeast Asia. Here’s how much Continental says just my second leg from Hanoi to New York would have cost if I’d bought this route (on Singapore Air) outright:

free flight

Yowza! Obviously I wouldn’t have taken that route and spent so much on my own dime, but that fact I was able to do it for 32,500 miles shows what kind of value you can get out of travel hacking. It can make a massive difference in how much it’s going to cost you to take an international journey.

How I did it – quick case studies

1) Free flight to Europe. My first free flight is going to be in April/May, when I’m going to Budapest and back and visiting three other countries overland. That was 40,000 miles on American Airlines. This barely put a dent in my AAdvantage balance. Sure, I’ve flown them and their partners now and then, but I pumped up the balance in a huge way by getting both a personal and business AA credit card from Citibank. The first gave me a bonus of 30,000 miles after spending a few hundred bucks on it. The second one took more effort—I had to spend $4,000 in six months on it—but I used it to buy things I was going to pay for anyway and put my rent on there one month to get over the hump. For that I earned a staggering 75,000 miles bonus.

Now I’ve got enough left to fly to South America and back (or one-way in business class) and still have leftovers. And I keep earning miles when I use the card, miles when I fly, miles when I dine out at the right restaurants, etc. Join the Travel Hacking Cartel and you’ll get regular updates on how to cash in regularly.

Hungary travel

2) Free flight to Bangkok and back from Hanoi. The carrier I use most often (besides Southwest) has traditionally been Continental, now merged with United. That’s because it has better Latin America coverage than most, especially Mexico, going through Houston on the way. Because of the great Star Alliance they belong to, you can cash in Continental/United miles for all kinds of other great airlines. So I’m flying from Tampa to Bangkok with my family—all of us free—on a combination of United and Thai Airways. They’re having to buy a one-way home, but I’m coming back from Hanoi on mileage. It’s going to be a very long trip via Singapore and Frankfurt, but on the best airline if you’re going to be stuck in economy: Singapore Airlines. I couldn’t get any closer to home than D.C. though, so I took the flight to NYC and will see a couple friends before the last leg on a cheap one-way ticket to Florida.

How did I manage this? Again, a mix of flying, credit cards, and other moves. All three of us have been saving up miles for a while, so my wife was able to transfer some from her account to my daughter’s for $75. And I had to spend $35 to top off my account to get to 65,000. And we each paid the taxes, which were around $40 each way. But considering even a one-way flight from where we live to Bangkok is $1,400 and rising, not bad. What put both my wife and I over the top on miles though was getting an airline credit card from Chase that gave us 30,000 miles each. (And it lets us check in one bag free on domestic flights.) Almost enough on its own for a one-way flight to Southeast Asia and close to what you need for a round-trip to South America or Europe.

I also have regularly bought things through their mileage mall online, taken advantage of special promotions, and earned a bit here and there from car rentals and hotel stays. I even got 1,000 miles once from installing a shopping toolbar then taking it down a couple months later. I found out about some of these opportunities from blogs, others from the Cartel.

3) South America in the Fall. I’m going on a tour through Bolivia and the Atacama Desert of Chile in November. I’m having trouble finding a free flight into Bolivia at any time, but if nothing else I know I can get home from Chile on miles as there is plenty of availability. Once again, a little extra effort up front will dramatically reduce my travel costs when it’s time to fly. With the price of oil continuing to go up and the U.S. economy improving, flight prices are unlikely to get any cheaper. It pays big dividends to use another currency besides your income.

Atacama Chile

The Travel Hacking Cartel

As I’ve said before, if you’re experienced at this and don’t mind browsing lots of different blogs and message boards on a weekly basis, you can find lots of tips and tricks for free. If your time is precious though and you’d like for it all to just land in your inbox—with some hotel points deals as well—then a Travel Hacking Cartel subscription is an easy investment to justify. They guarantee you enough points to get four free domestic tickets a year or you get your  money back. Where would you go with 100,000 miles? And is it worth less than 10 bucks a month to get there?

As most of the frequent flier programs get more transparent on the web and more savvy travelers get clued in to the wonders of travel hacking, all kinds of comparisons keep popping up for which programs are the best and worst. It’s hard to do this without the exercise making a DSLR camera manual look fun to read in comparison. The airlines’ programs all have different points quirks, different elite level perks, and different credit card alliances.

So this information is ripe for an infographic—a way to see the whole array visually so it all makes more sense than a string of numbers and costs. Here are two worth checking out.

This first FindtheBest airline infographic is pretty bare-bones visually, but it collects a lot of info in one place once you figure out that you can click through many boxes to see more detail. Right away I saw things that make me scratch my head, however, like valuing Delta “Sky Pesos” at 4 cents per mile for domestic flights, even though every mileage guru will tell you Delta’s are the hardest miles to actually redeem for anything worthwhile. They’ve got a poor record on redemptions and make it harder to find the info you need for cashing in with partners.

Still, I immediately bookmarked this site because it provides a lot of info in one place that usually requires pecking around on each airline website to find. You can see in one place who the partners are for earning miles, how many miles it takes to get to Europe or Asia, expiration window, and how the airline stacks up to a competitor one-on-one. Tabs take you to elite level perks and more mileage charts.

I would have liked to see more on fees, like how much they charge you to call them, what the fuel surcharges are (some airlines charge them on “free” flights, others don’t), and how much they ream you on baggage. But hey, for a free service, this is quite comprehensive.

Next, this cool frequent flier rundown from really puts the “graphic” in infographic. That section I cut out and stuck in at the top of this post is a sampling of how a bit of information can really pop if you frame it the right way in a picture. Let’s see, I can earn a flight in one year on Southwest and in eight years on Continental. Hmmm, which one has a better payback you think? (Factor in free bag checking and the spending-to-reward gap is even wider.)

The graphic kicks off with a great illustration of annual fees on the lowest level of airline credit cards: $45 on JetBlue, $95 on Delta, for example. With banks paying close to zero on interest yet collecting more than 14% in interest, they’re all loan sharks in that department.

Keep scrolling down though and the differences are more stark, especially in how many points/miles you can actually earn in the first year with any of these cards and how far that will take you. This is mostly about earning miles from credit cards, but since that’s how you can often earn enough for a flight in one shot, that’s the quickest way to travel hacking payoffs. It’s also the way to keep earning miles on the ground paying for things you had to buy and bills you needed to cover anyway. See the full comparison here.


I did a big long post about the Travel Hacking Cartel program from author Chris Guillebeau when it launched back in late February. Go check that out to get the details on how it works. But the general gist is that it takes most of the current mileage deals on offer out there for airlines and hotel loyalty programs and bundles them into one pretty package for members. You can get mileage deal updates by e-mail or text.

There are also tutorials on how to maximize frequent flier miles and hotels points—both from the acquiring standpoint and the using standpoint. Last, he guarantees you’ll earn 4 free plane trips per year if you spend sufficient time on the site.

Based on what I’ve experienced so far, the site may not yet meet that guarantee for experienced frequent fliers who already have a bundle of mileage credit cards. If you don’t fit that profile though, or you’re a business traveler on the move a lot, you’ll probably make the guarantee. Either way, you can’t lose really.

So far I’ve gotten more hotel points than airline miles out of the deal, especially by finding out about some deals I didn’t know about through Intercontinental Hotel Group’s Priority Club.

The airline deals have been a few hundred miles here, a thousand miles there through surveys, bonus offers for mile transfers from Amex, or following an airline on Facebook. That’s not going to add up to 25K miles in three months, unfortunately. Most of the advice in the tutorials—dining for miles, using the mileage credit card for regular bills, and taking advantage of mileage transfer bonuses—I was already doing.

Where you really get the maximum miles is through churning credit cards and charging everything you can on those cards. I’ve done a fair bit of that in the past with good results. So I tried again with one offer I only saw through the Cartel. It offered 50K Continental miles after sign-up and charging a certain amount after getting the card, which would have been enough for two round-trip domestic trips or one to South America.

Alas, I got turned down. My credit rocks these days, but I’m not a homeowner since I sold my house in the fall and I already have three Chase credit cards, one an older version of Continental’s. (Combined credit limit from the three—enough to buy a new Mercedes.) Who knows the reason, but I got struck down. Had that card been approved, I would have gotten what was promised easily. [Update – I tried again a few months later and got one with a 30,000 bonus instead. Not too shabby.]

I’m sticking with the Travel Hacking Cartel and watching how it develops. I still feel like you can find more deals out there on your own if you have the time to hunt and peck through mileage blogs and the FlyerTalk message board. But do you enjoy doing that? (Some people do—the thrill of the hunt.) If not, how much is your time worth? If you like to have it all dished up to you in one place in a pretty package that you can act on immediately, the Cartel delivers.

The beauty of this program is, it’s a monthly subscription (starting at $15). You can try it for 14 days for $1, then after that you can cancel anytime if it’s not working for you. Give it a whirl here.

Have you used the cartel yourself? How’s it going so far?

Bob has a problem. He never misses an opportunity to gain frequent flier miles or hotel points, which is good. But he’s got mileage balances in nine different programs and is worried that some will expire because he’s not on top of things.

Sure, as I advised in the Make Your Travel Dollars Worth a Fortune book, you should focus your efforts on two or three airlines tops and one main hotel program, but life is messy. Different destinations are served by different airlines, for a start. Or maybe your business flights have to be on the cheapest choice no matter what.

I talked last week about the Travel Hacking Cartel and how it promises to help you rack up enough miles for four free flights per year, or maybe a couple international ones. A free flight can make a huge difference for budget travelers. After all, while India, Indonesia, and Ecuador may be screaming bargains after arrival, you have to spend real money to fly there. Accumulate enough miles, however, and that part of your budget could disappear.

If you’re accumulating frequent flier miles and hotel points in multiple programs though, how do you keep track of all that without logging into a slew of individual sites regularly? Or maintaining a spreadsheet? Or both?

That’s where mileage tracking programs come in. The most basic  will just keep tabs on your miles and tell you where you stand. Others will flag ones about to expire, alert you to bonus opportunities, and even tell you if you’re better off buying a ticket than cashing in mileage.

Paid Mileage Tracking Programs

I signed up for MileBlaster after seeing their presentation at the PhoCusWright travel tech conference and think it’s certainly worth the minimal price of $9 a year. (For the moment it’s on sale for $7.99 even!) It keeps most of your mileage balances in one place, in a nice handy mobile-friendly interface—see the screen shot at the top. There are a few holes in all these trackers, like Southwest’s program, but it’s got most of them. Once you spend the ten minutes setting it up with your numbers and log-ins, it automatically updates your totals. The cool part is, it alerts you when you have points/miles that are about to expire, as with the short window on USAir. Then you can go get a magazine subscription or buy something from the online mileage mall to reset the clock.

Mileblaster will also help you calculate the mileage for a trip, see if there are any bonus opportunities available, and tell you how close you are to elite status. It’s a handy program that is dead easy once you set it up. If your time spent tracking this stuff is worth more than $8, jump on it.

There’s a competing program with a twist on the way from FlyMuch, but it’s just in beta right now. It looked promising from what I saw though.

Free Mileage Tracking Programs

AwardWallet has been around for years and has one big advantage: no subscription fees. I haven’t used it personally though and there’s very little info on their site: you have to register to get past the very basic intro. There’s also a paid version to eliminate some of the restrictions, but no pricing info listed on their site for this.

If you’re willing to put up with lots of ads, USA Today’s MileTracker program also covers the basics, keeping track of your accounts in a web-based interface. Here’s how it works.

There are also tracking programs available through American Express and Fidelity if you do business with either of them.

Insider Info Sites

If you’re racking up a lot of miles and manage to hit elite status on one of the airlines, that’s when you start getting the real goodies, like upgrades to business class or first class. Hey, you didn’t think all those people sitting in the front of the plane actually paid three times as much as you, did you? No, most of them got upgraded.

I’ve been giving ExpertFlyer a whirl lately and though I’m not able to take advantage of a lot of the information, I can see it’s a gold mine for road warriors with elite status. It’ll give you the upgrade availability before you book the flight, so you know if you can move up a level. It’ll also show you how full a flight is, what the seat options are, and what the change penalties will be. I also found one key piece of info for an upcoming trip: a flight to South America on Copa is allowed one free stopover in Panama City. That info does not show up in the booking process on Copa Air’s site, so I’m picking up the phone and saying, “I want my free stopover!” The ExpertFlyer price is $5-$10 a month depending on the level you choose, or $99 for a year. You can try it for free on a five-day trial.

FirstClassFlyer is a source for getting into business class for the price of economy, scoring upgrades, and taking advantage of “mistake fares” that pop up regularly and then disappear quickly. They’re offering a free 14-day free trial, but after that you need to pony up. How much? I have no idea since their sneaky site doesn’t tell you until you register. offers a lot of the same info, with more transparent pricing. Or you can just wade through the forums at for free.

How do you keep track of all your mileage and points?