Travel Hacking Guide for Our Airbnb Guests

Boris Mordkovich
Quarter Life Musings
12 min readApr 2, 2016

Over the last few years, I found that whenever I bring up the idea of “flying for free”, the idea is met both with curiosity and a bit of skepticism that this is actually possible. Well, I’m happy to say that yes — it is indeed possible and in the next 25 minutes, you will actually find out how to do it yourself.

In fact, I’ll take it even a bit further and will promise that in the next 25 minutes, I will show you how you can get 2 free (excluding about $100 in taxes) roundtrip tickets anywhere in the world within the next 3–12 months — without having to sell your firstborn or your kidneys.

Airfare oftentimes is one of the largest expenses when it comes to traveling — especially if you’re looking to go further abroad or to popular destinations in Europe. My hope is that with learning these strategies, you’ll find travel to be more affordable and use this opportunity to explore further corners of the world more often.

Without further ado, let’s dive in!

The Secret

I’ll tell you the secret to free travel right off the bat — the path to free airfare lies through frequent flyer programs.

I bet you were hoping for something more exciting, like sleeping with the flight attendants, but no … alas, it’s actually a lot more simple.

It’s likely that when you’ve purchased airfare at some point in the past, you were asked to create an account with the airline’s frequent flyer program of that airline. If you did and checked it afterwards, you have likely noticed that they deposited a small amount of miles in there after your flight was completed.

Frequent flyer program have been originally created to reward primarily loyal frequent business travelers. However, today, we all benefit greatly from them. In principle, you earn miles by flying — where you get roughly 1 mile per every mile you fly (although not always).

As an example, a trip to Barcelona from New York might net you around 7,600 miles total after you complete it — equivalent to the total roundtrip distance of 7,640 miles.

Another way that you earn miles is by having a credit card associated with an airline, like Chase United or Citi American Airlines or AMEX Delta. I’m sure you’ve seen those advertised online or in the airline’s in-flight magazines.

When you have an airline-associated credit card, you also earn roughly 1 or more miles per every dollar you spend on anything. I say that it can “more” because in some cases, it can be up to 5–10 miles per $1 depending on the card and what you buy. But as this is an introduction, for our purposes, let’s keep it simple and keep it 1 mile per $1.

Now, here’s the tricky part.

Want to guess how many miles you need to actually get a free ticket?

Well, a free roundtrip award flight from New York to Spain will cost you about 60,000 miles on most airlines. You can see the problem right away.

It will take a long time and a lot of flying or “spending” on your credit cards in order to accumulate 60,000 miles — either $60,000 in spend or about 8 roundtrip flights similar to the one I described above to earn the 60,000 miles. So while you should still use airline credit cards for accruing miles and make sure that you get credited for every flight you’ve taken in the past 12 months and will take in the future, these methods don’t do the trick for us.

Is there a Free Lunch? Apparently, yes!

Now we get to the fun part!

Fortunately, we live at a time when credit card companies are competing head over heels for customers and, provided that we’re smart about this, we can take advantage of it.

Many credit cards will run promotions a few times a year where they will offer you bonuses as much as 50,000 to 100,000 miles with a specific airline (or hotel chain) for opening up a credit card with them and meeting the minimum spending limit, which can range from $1,000 to $5,000 in 3 months.

These promotions typically just last for a few months, but due to the sheer number of credit card offers out there, at any given time, you can find a few really good deals available.

Consider this — 50,000 points can get you:

  • 2 free roundtrip tickets in the continental U.S. (20–25,000 miles each),
  • 1 free roundtrip flight to Hawaii with miles left over (35–40,000 miles each), or
  • It can cover 83% off a ticket pretty much anywhere in the world (using 60,000 miles as an example).

In short, you can get over $500 to $1,000 in value — just for spending 15 minutes and opening up a credit card. That surely beats the offers we had when I was in college — of getting a free t-shirt!

Do me a favor — if you made it this far, promise me that from now on, you will never open up a credit card unless it gives you at least $500 in value.

This sounds fishy! There’s got to be the catch?

Unlike the promises of becoming a millionaire in 5 easy steps or watching a late night infomercial about a set of knives that can cut through shoes and tin cans, frequent flyer programs and free flights are actually a reality. There is a cost that you pay to this — which is time that you spend on this and a certain amount of discipline that you need to have to come out ahead. However, that’s minimal — considering the benefits at stake.

That said, before I go further, I want to dispel a few myths:

Myth #1: Opening new cards will ruin my credit score and history.

Not exactly. Yes, whenever you open up a new credit card, you do get a hard inquiry on your credit history that will temporarily reduce your score by 2–5 points. You should be aware of that.

However, credit inquiries only account for about 10% of the overall factors that go into your calculating your score. The upside is that once the card is opened, your overall credit limit will be increased by whatever amount you get on the card and that will cause your credit score to go back up within a few months.

Bottom line — you can open up 2–3 or more new cards every 3–4 months and provided that you pay everything on time, you’ll find that your credit score will either remain at the same level or even go up over time.

Myth #2: I will be on the hook for annual fees that the credit card charges.

While annual fees certainly exist, many of the credit cards offer promotions where they will waive the annual fee for the first year. After that, it does become about $90–100/year.

However, what you can do is call before your credit card is up for renewal or even within 30 days after you were charged the annual fee and either a) downgrade it to a free version of the card, or b) cancel the card altogether and have the fee canceled/refunded.

There are a lot of benefits to downgrading the card and keeping it, as it boosts your overall credit limits. But regardless of what you choose to do, the principle is the same — as long as you are disciplined and remember to handle this before (or within 30 days) after the annual fee is charged, you can easily avoid it.

Myth #3: Having too many credit cards is bad for my credit score.

Actually, having a large number of cards doesn’t really affect your credit score that much. In fact having a large overall credit limit is a good thing and increases your score. Personally, I typically suggest that you keep as many cards as you can, provided that you don’t pay the annual fee on them, as that keeps your credit line high and helps create more credit history to the lenders.

Myth #4: There must be a catch!

Well, yes:

a) You need to have a decent credit score — preferably over 700 — in order to get approved for most cards. In some cards, even 670+ is OK — but it’ll be slightly more difficult;

b) You need to sign up for the right promotions — don’t waste your time and energy on cards that offer 10–25,000 mile bonuses;

c) You need to pay off your cards on time and in full. This is incredibly important — most of the people who “play” the mile game will never carry a balance on any of their cards, as the enormous APR fees eliminate all of the benefits you gain from this.;

d) You need to track your cards to avoid annual fees. Use Mint.com to do this easily.

Other than that, this really works as described. However, before we go on, I do want to include 2 more disclaimers:

Disclaimer #1: You should only do this if you are disciplined enough to pay off whatever balance you charge to the card — every month. I want to reiterate — carrying a balance and paying the outrageous interest rates defeats the whole purpose.

Disclaimer #2: If you are planning a purchase of a new house and planning to get a mortgage in the next 1.5–2 years, you should be careful not to go overboard with this. Even though your credit score does go up over time, you don’t want to have too many hard inquiries from the credit card applications when you get considered for a mortgage.

Other than that, go wild!

How to Redeem the Miles & Airline Alliances

Let’s say that you’ll follow the ideas in this post and will open up a couple of credit cards for yourself. The next step comes with redeeming the miles for award flights.

One important thing that I want to point out is Airline Alliances.

Every major airline will typically belong to one of 3 alliances: OneWorld, Star Alliance or SkyTeam. When you get miles with, let’s say, American Airlines, you have the opportunity to redeem your miles not just on AA, but on any of the 12 airlines in the OneWorld alliance to which it belongs. With United or US Airways, you get access to 27 airlines in the Star Alliance. And so on. Here’s a good summary if you want to see who belongs to what alliance.

This is something that can confuse people at first, as airlines don’t make it particularly easy to redeem them on partner airlines. But overall, after you do it once, you’ll get the hang of it and it will be almost as easy as booking a regular flight.

As an example, I wanted to show a couple of sample itineraries and show how much they would cost with different airlines:

Boston -> Paris, France

  • AA: 60,000 miles + $82
  • United: 60,000 miles + $90
  • US Airways: 55,000 points and $148 (poor availability during peak season)
  • Chase UR Points: 77,000 points for $962 ticket

Boston -> Bangkok, Thailand

  • United: 65,000 miles and $74 in taxes
  • AA: 70,000 miles and taxes
  • US Airways: 80,000 miles and taxes
  • Chase UR Points: 102,000 points for $1,282 ticket

Boston -> Buenos Aires, Brazil

  • United: 60,000 miles and taxes
  • AA: 40,000 miles and taxes
  • US Airways: 60,000 miles and taxes
  • Chase UR Points: 97,000 points for $1,200

Boston -> San Francisco, California

  • AA: 25,000 miles + $10 in taxes
  • United: 25,000 miles + $7.50 in taxes
  • US Airways: 20,000 miles + $35 in taxes
  • Chase UR Points: 25,000 points for $315 ticket

Boston -> Honolulu, Hawaii

  • AA: 35,000 points + $10 in taxes
  • United: 40,000 miles + $7.50 in taxes
  • US Airways: 60,000 miles + $60 in taxes
  • Chase UR Points: 51,000 points for $648 ticket

Where are you going to go?

So, now let’s get to the promise I’ve made you in the beginning of the post — your 2 vacations this year.

Let’s say that this year, you’d like to do a vacation in Hawaii or Brazil and a week-long adventure trip in Asia or a cultural trip in Europe. Let’s see how this plays out.

Scenario #1 — Hawaii and Bangkok:

  • 35,000–40,000 miles for Hawaii
  • 65,000–80,000 miles for Asia

You need a total of 100,000–120,000 miles for the itinerary above. You can get most of these miles through AA and United cards.

Scenario #2 — Buenos Aires and Paris:

  • 40,000–60,000 for South America
  • 55,000–60,000 miles for Europe

You need a total of 95,000–120,000 miles for the itinerary above. You can get most of these miles through AA and United/US Airways cards.

Have any other destination in mind? There is a really great, free tool that will show you how many miles you’ll need with each program to get there. You can check it out here. As you can see above and you’ll discover through your own searches, different airlines have different strengths in different regions. Some offer the best deals for Europe, others with U.S.-based travel and so on.

Timing also plays a role — many airlines offer discounted award redemption rates for off-peak season, as well as having more availability in the first place.

More Tips:

You may have noticed that many of the international rewards require 60,000–80,000 points, but you only get 50,000–55,000 when you open a single card. How do you close the ga?:

  • Partner Up — if you have a spouse or a significant other, open the cards together to get additional points.
  • Once you have the card, put your expenses it, as you’ll typically earn 1–2 miles per person. How about paying your school loans with a card? Other bills?
  • Take a look at any flights you’ve flown in the last 12 months to see if you have any miles that you can retroactively get for them;
  • Keep your eyes open for better promotions. A few times a year, you can get as much as 75,000 to 100,000 miles by opening up a single credit card when there is a right promotion going on.
  • If you have a business, open up a business credit card to double your rewards.
  • Or worse comes to worst, you can actually purchase miles. It usually only makes sense if you just need 1,000–3,000 miles to meet the award requirement, as the airlines will typically charge $30 per 1,000 miles.

The goal is to be pro-active about this and plan ahead. You’ll find that after a year or so, you’ll have miles spread out over different programs and it will become easier to meet the award requirements.

Show Me the Money! What Are The Best Cards to Open Now?

All right — we covered the “theory”, let’s now get to action and see how we can implement this. Below are some of the best offers available as of now — and the list will be updated every couple of months.

Chase Sapphire Preferred Card

  • 50,000 points bonus. Can redeem either for $625 on any flight, hotel or car rental or convert to 50,000 United, British Airways or JetBlue points.
  • $95 annual fee, but waived during the first year.

Citi Thank You Premier Card

  • 60,000 points bonus. Can redeem for $750 on any flight, hotel or car rental.
  • $95 annual fee, but waived during the first year.

Barclays American Airlines Aviator Card

  • 60,000 American Airline miles after 1 purchase of any amount. No minimum spend required.
  • $95 annual fee, but not waived.

I want to learn more!

No problem. I actually used to teach classes on this via TravelMastersAcademy.com platform. However, while I don’t do live classes at this time, I still have the recordings of Travel Masters 101 and Travel Masters 201 classes.

Each one is about 1.5–2 hours long and if you want them both, you’ll have an extremely strong foundation for moving forward.

Travel Masters 101 Class:

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Travel Masters 201 Class:

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Before you go.

After doing this for a while myself and accumulating probably a few million miles over the last few years, I really do think that this opens up a lot of fantastic opportunities to travel affordably.

To be fair, it does take time and it does take some level of flexibility. But if it allows you to go almost anywhere in the world several times per year, I believe that it’s very much worth it.

This article is meant to be just an introduction, as there is much more to discover — both in terms of earning miles and redeeming them in the most effective ways. If you have any questions, I’m always happy to help — don’t hesitate to reach out.

Oh, and one more thing — if you found this article helpful, do me a favor and post a comment if you plan on making any trips happen with miles this year and what cards you decided to pursue.

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