Travel Hacking in an Unfriendly Environment

Milan Train Station - Travel Hacking

*Update: Looking for more recent travel hacking posts? They’re over here.

Six weeks ago, I went to downtown Seattle for an appointment at a big office building. The receptionist asked me to fill out a short medical history, which included questions about my self-esteem and physical appearance. After 10 minutes of waiting, I was ushered back into a small clinic down the hall.

Sounds like a personal problem, right? Well…

I was actually there for a hair-loss consultation, and as far as I can tell, my hair is doing just fine. According to the fake doctor I talked to (he wasn’t a real doctor, but wore a white coat to give the impression that he was), most of the men who come in for visits would be happy if they had half as much hair as me.

I thanked him for his time, and got out as quickly as I could. Earlier this week, six weeks after the consultation, 20,000 Delta SkyMiles posted to my account.

Yes, I went in for a hair-loss consultation to get 20,000 Frequent Flyer Miles – and so did a lot of other people. Hold that thought; we’ll come back to it at the end.

First, Let’s Look Back at the Unfriendly Travel Summer

We are now in global financial meltdown, it seems, but before the financial meltdown kicked into gear, the travel world was having its own meltdown a few months earlier.

Oil prices went to record highs, airlines started charging for any checked bags, and record numbers of flights were canceled even as planes were at high capacity.

In one of the crazier examples, United Airlines said it would start charging for meals on overseas flights from Washington, D.C. They later backed off, saying they were just “testing an idea to see how customers would respond,” a statement that a lot of travel writers had fun with. (Feel free to write your own joke about how easy it is to predict customer opinion when you take away meals on 8-hour flights.)

Meanwhile, I was happily traveling around the world, mostly on a Round-the-World ticket I had paid for nearly a year ago in the summer of 2007.

I don’t want to give the impression that it was always easy — I slept on the floor of too many airports to say that, unfortunately. But even though it wasn’t easy, for the most part I was largely unaffected by the unfriendly travel environment.

In a lot of ways, it’s easy to get frustrated with travel these days. Here are some practical things you can do to get ahead.

*Get an Elite Status Match with multiple airlines. If you have any kind of elite status with a major airline, you can use that status to get “comped” from several other airlines. To do this, make a photocopy of your status card, get a printout of a recent statement, and mail this information in to the Frequent Flyer headquarters of your preferred airline.

The catch is that you can usually only do this once in your lifetime per airline, but there are a few clever loopholes you can take advantage of. For example, right now you can get status matched with Northwest with no future penalty, since Northwest as a brand will cease to exist since they are merging with Delta.

*Get Creative with Lodging. Since most of my international travel is with Round-the-World tickets that I pay for well in advance, or Awards flights from my many Frequent Flyer miles (see below), lodging is my major expense from country to country.

I’ve adopted all of these tactics at different times to help:

  • Use Priceline to stay in nice hotels for an average of 40-60% off. Priceline is useless (mostly) for plane tickets, but helpful for hotels. I’ve lost count of the number of cheap rooms I’ve stayed in with them – at least about 20-30 so far on three continents.
  • Stay in hostels, but in your own room. Use to check for alternative lodging in your destination, including hostels, university rooms, and guesthouses.
  • Go off-the-grid. If you really want to get creative, you can stay for free with people all over the world who agree to share their couch. I usually prefer a bit more privacy, but for the desperate, this is an option.

*If your trip involves more than one international destination, consider a Round-the-World ticket or regional fare. This is how I do most of my long-haul travel now, and while it can get a bit complicated, it is hugely economical as long as you plan on doing a lot of travel. At some point I’ll create a detailed product to help people with this (there’s a lot to it), but for now if you’re out there working on a big trip and need some quick help, send me a note with the itinerary you have so far.

*Get as many bonus Frequent Flyer Miles as possible. Even though many airlines are trying their best to devalue miles, with enough planning and some persistence, you can still use them to fly for just the cost of the taxes. I do this several times a year, and I’ve used my miles to fly Upper Class on Virgin Atlantic and Business Class several times on Delta, Singapore, Lufthansa, and Korean Airlines.

Here are a few current, easy opportunities you can take advantage of to pick up miles right away with American Airlines (my preferred U.S. carrier, mostly due to how they structure their elite program):

  • One-Minute Bose Video. Watch this one-minute video, get 150 miles. If you live near a Bose store, you can get 350 more by checking out the headphones in person.
  • 1,500 Miles for Dining. Sign up here and go to a restaurant you might visit anyway. Spend more than $25 and you’ll get a 1,500 mileage bonus credited to you.

(Note that if you don’t have an American AAdvantage number, you’ll need to get one first – but you can do that here.)


These are just a few examples, and if you’re reading this later on, some of them may no longer be available. I’m not a big fan of wasting hours on surveys, but doing simple things like this every so often really adds up.

In recent years I’ve earned as many as 95,000 extra miles by the end of the year through these kinds of bonuses, not counting credit card spending or my actual flights. Since the average Business Class ticket to Asia costs at least $5,000, it’s definitely worth my time to get a free one.

880,000 Frequent Flyer Miles for a Few Close Friends

After my hair-loss consultation went well with no surprises (the total time investment was about one hour, including the ride to and from downtown), and I confirmed that the company didn’t really care who came in for the appointment, I started referring a few friends over that way. My friends reported back with the same information – it was quick and easy, and the company wasn’t offended that people were coming in just for the miles.

Next, I sent an email to the first group of customers from the Discount Airfare Guide. I figured they might be interested in 20,000 miles, and my expectation held true – reports of successful clinic visits came back from Atlanta, Vancouver, San Francisco, and elsewhere throughout the U.S. and parts of Canada.

Finally, I sent a notice out to my Twitter followers: “If anyone is willing to give up one hour for 20,000 Delta SkyMiles, write me at [email address].” A bunch of people requested the info, and several of them made their own appointments.

I asked that anyone who had their own hair-loss consultation for a free 20,000 SkyMiles let me know so that I could track how many Awards tickets I had effectively created. I don’t receive any benefit from it – I was just curious about the numbers. Judging from everyone who wrote me back, it looks like I successfully referred 44 people for a total of 880,000 Miles.

Here’s a quick overview of what 880,000 SkyMiles can be used for:

  • 4 Round-the-World Tickets
  • 18 Flights to Europe or 14 Flights to Africa
  • 7 Business Class Tickets to Asia on Singapore Airlines (nice)
  • 13 Flights to Australia (average price: $1500+)
  • 30 Flights within Asia on Korean Airlines
  • Multiple options for codeshare flights on China Airlines, Air France, and Northwest

Most people, however, will use the 20k miles for simple, domestic round-trip flights. At 25k per free ticket within the U.S. and Canada, the bonus takes you 80% of the way.

In other words, spreading the word about the hair-loss consultation earned roughly 35 free tickets for my friends, Twitter followers, and Unconventional Guide customers – and this was with very little promotion, since I didn’t write about it here on the site.

This was an experiment that seems to have worked well. I don’t mind sharing the wealth with promotions like this in the future, but I probably won’t make a lot of posts about them here since it’s not really the theme of the site. If you’re interested, follow me on Twitter, since I do post bonus opportunities over there from time to time.

Travel Survival

Note that none of these ideas are dependent on a friendly travel environment. You can still earn miles no matter what the airlines are doing, and if you can get elite status with at least one airline, you’ll avoid a lot of the new fees being charged for people who don’t travel much.

In short, travel does not have to be as difficult as some would have it. You may not be as crazy as me in terms of heading down for a hair-loss consultation, but I’m happy with my 20,000 miles. Next summer, maybe I’ll see you on a plane somewhere… and with luck, both of us will be flying for free.

For more info on Travel Hacking:

How and Why I Travel (Part One)
How and Why I Travel (Part Two)
Developing Your Own Philosophy of Travel
What I Talk About When I Talk About Travel

External Links:

Star Alliance Round-the-World Info
OneWorld Round-the-World Info
FlyerTalk Status Match thread

Finally, a Question for You:

I don’t often post practical travel information like this here. Do you like it? Is it relevant? Please tell me one way or another. Our long-promised site redesign is coming up soon (really), and having your opinion will help me.

Also, if you have any questions about the specific travel ideas mentioned, post them in the comments and I’ll do my best to answer them.


Image: Stuck in Customs

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  • Ted Hessing says:

    Hi Chris,

    “This is how I do most of my long-haul travel now, and while it can get a bit complicated, it is hugely economical as long as you plan on doing a lot of travel. At some point I’ll create a detailed product to help people with this (there’s a lot to it), ”

    Is that covered at all in the Discount travel guide?

  • Suju Vijayan says:

    I found this extremely useful and I enjoy getting practical travel info as I am already a believer in the joys of travel! We’ve used FF miles certainly within the US, but also for 2 business class round trip tix LA to Rome, and for my husband’s ticket to Barcelona and Geneva this summer (didn’t have enough for both of us, unfortunately). But what we did learn is that even though we needed to transfer some miles from my account to my husband’s (for a fee) to make up what my husband needed for his free ticket, we still saved a lot of money.

  • Jennifer Breazeale says:

    Chris –

    I don’t travel a ton, but I have friends who do and I’m definitely forwarding this article their way. One site that may be interesting to you is They’re an early stage startup in Colorado that’s working to build a travel tool that will let you manage all of your frequent flier miles (including booking trips, etc.) in one place. (FYI, I’m not affiliated with them, I just like to keep an eye on the local tech scene.)

    Thanks again for the great article!

    J. J.

  • Adrienne says:

    I will say that the main reason I myself read your blog is to learn about your travels and how you do them. The rest is just icing.

  • Chris says:

    Happy Friday, everyone.


    No, the current Discount Airfare guide does not go into too many advanced topics like RTW travel. If your trips are highly complex like mine (or even slightly less so), I wouldn’t get it for that.

  • Anca says:

    I like the practical travel info. I did the BOSE and dining miles just now. I’m also signed up for two survey sites that give me NWA miles.

  • Michael says:

    Hey Chris,

    I really appreciate the practical travel info and I hope you keep it up! It’s one thing to vicariously enjoy all the great world destinations you bring us with each installment of your newsletter, but after a while it begs the question, “How exactly could I do that?” Like a great world menu, your posts tantalize the wanderlust in us all, and make us feel a little more international. The practical info is like a valued recipe, when you’re ready to move from appreciation to participation. At least for me. So thanks.

  • Craig says:

    Chris, if you want an outlet for practical travel tips, I’m only an email away… 😛

  • Derek says:

    This is a good article. I am new to traveling overseas. I mostly fly on American Airlines. I live in Dallas and they offer so many flights from Dallas to destinations all over the world, many non-stop. Right now I travel to Europe 2 to 4 times a year. I am interested in knowing how to maximize my miles, and how to find those deals to pick up free miles all the time. I will be buying your ebook to learn more as well.

  • Nathan Hangen says:

    Free miles for a hair-loss consultation, classic! I could actually use the service, but I guess I need the card first.

    I’d say the sacrifices you’ve made have been well worth the 100 countries you have visited and the experiences you’ve been able to share.

  • Renee says:

    I agree with Adrienne above — the main reason I read your blog is for the travel info. I’m not yet able to avail myself of much of your tips, but I love them all nonetheless. As for the detailed, practical travel info — well, nothing appeals more to an accountant! 😉 Please keep it up, and thanks so much for all you share.

  • Kathy says:

    I like practical. I use my credit card for everything to rack up miles and used them this past spring to visit my daughter in Firenze, Italy. She was there for a study abroad semester. I had been saving miles for a while and if not for the miles, I would have missed this once-in-a-lifetime opportunity to see a new place through my daughter’s experiences. Any tips for adding miles is appreciated so I’ll be ready for the next adventure.I did not know about getting an elite match with other airlines – this is a tip I will definitely use in the future. Thanks for posts that encourage us to find creative ways to follow our passions.

  • Success Professor - Danny Gamache says:


    I’m very interested in the idea of using your status with one airline and getting it comped by another airline. Do you recommend doing that at this time of year, or waiting until the new year so you have longer at the higher status? Also, how long will Northwest remain a separate entity?

  • Chris says:

    Thanks again, everyone.


    Great – that’s exactly what I’m going for! I definitely want to help as many people as possible.


    Well, in terms of Northwest I’d recommend requesting the match as soon as possible, since it’s not clear how long that will still be an option. But otherwise, it’s good to do a request like this either at the beginning of the year or close to the end of the year (right around now), because they will usually give you the status for a full calendar year plus or minus a couple of months. Of course, each airline will have its own policies since this is considered an undocumented benefit – something they will usually do upon request, but they do not advertise or guarantee it.

    Make sense?

  • The Wyman says:

    Chris, getting back to The Unconventional Guide to Working For Yourself:

    As I said in my previous comments, I hesitated to buy because I know a lot about the subject already and didn’t know if it would be worth the price.

    I should have had more faith in you. I did learn a few new things and the references were worth more than the investment in the book. I take detailed notes on every book I read. Most 150-200 page books I condense down to 10-12 pages of notes. I took 15 pages of notes from your 54 page book. That means you had a lot of content and little fluff.

    Everyone who wants to have a business should have this guide. Looking forward to the non-geek idiot’s guide for the computer illiterate and the advanced strategies book.

  • Benny Lewis says:

    Excellent tips Chris!! I already follow your twitter posts so I’ll be keeping an eye out for further amazing tips!

    I’ll just add that Couchsurfing is not for the desperate. It’s a way of getting a truly different perspective on a culture by living with locals, and not even paying anything for the privilege. How you referred to it suggests that you have never even tried it – almost any country on your list of places to visit will have a host. If privacy is an issue there are actually a lot of hosts that give you private bedrooms that they aren’t using, in comfy king sized beds sometimes! The title is misleading because there are actually more hosts that don’t host you on their couch.

    I know you like being able to wonder around a place and discover it for yourself, but a lot of Couchsurfers are glad to give you a tour from a local perspective. Even if you never use it for accommodation, it’s a great means of meeting locals willing to lend a hand and share lunch or a drink with.

    I highly suggest you try (starting with an experienced and well referenced host so you have nothing to worry about). I’m sure lots of your readers (me included) would friend you through CS and make your chances of acceptance higher. here is my CS profile. If anything it would be a very different experience, and isn’t that what travelling is all about? 🙂

  • Joseph says:

    Love the tips Chris. I’m not a frequent traveler right now, but mainly because it’s an expense I can’t afford. Still, if I can get free points for some trip in the future, I’ll take advantage of every offer I can. I really can’t understand how airlines are making money doing those promotions, but who knows.

    Your posts may not always be “practical,” but they’re always interesting and thought-provoking.

  • Leigh says:

    Nice article. I clearly don’t take as much advantage of our frequent flyer miles as I could.

    One thing, I’m not sure Couchsurfing is for the desperate. While in many cases, you are literally sleeping in a busy living room, many times you have an apartment to yourself. I know one person who not only had an entire floor of a house but had a servant washing his clothes and cooking for him.

    And quite frankly, nothing quite matches having a local guide to the place your staying. We’ve made our way through Europe, Central, South and North America couchsurfing, and it’s been priceless.

  • xenia says:

    you know, I only just discovered your site, and already it has been a source of endless fascination. while I devour anything related to travel experiences – I love travel literature for escapism – I especially love practical advice. you said to let you know if we liked it, and I wanted to add my two cents that I loved it.

    I can’t travel much, as my job and my husband’s job not only don’t pay well but are fairly grounded – libraries and research. so anything we can use to shave a few more dollars off of next year’s Luxury Week, as we call it, are absolutely invaluable.

    I will continue to scour your site for hints on how to save, but in the meantime, I am loving your travel diaries! makes me want to go to uni, get a real job and find something that will sustain a travel-oriented lifestyle, just for an excuse to fly!

    thanks again for your amazing site and inspiration;


  • John says:

    Your practical travel information is the reason I first discovered and continue to return to your site.

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