"3 Extravagant Flights You'll Never Be Able To Afford" and How We Flew Them All

The fool.com should stick to investing advice - over the weekend they published an article about 3 Extravagant Flights You'll Never Be Able to Afford. This article makes me laugh for a couple of reasons. First, I'm not sure what the point of the article is, perhaps other than anti-1% propaganda? Secondly, it talks about extravagant First Class flights that cost $13,000-$22,000 without mentioning the fact that you can fly them all for far less than that. It would be like writing an article about how the average person could never dream of owning a $200,000 Ferrari, while there existed sort of well-known and some lesser-known ways to own one for as little as $50.

So I guess while the premise of the article is indeed true, that your average person would never be able to afford to pay those prices for First Class tickets, it certainly does not translate to mean that the average person cannot experience these flights - in fact, we've flown all 3. 2 of them were redeemed using miles, and 1 was a paid ticket but at a 90% discount off of the $22,000 he quoted. Let me explain how we did it.

Extravagant Airline #1 - Cathay Pacific

How we did it (price for each ticket) and how we got the miles 
We have actually flown Cathay Pacific twice:

SFO-HKG: 67,500 American Airlines miles + $5 in taxes/fees
HKG-SFO: 105,000 British Airways Avios + $142 in taxes/fees

- 150,000 American Airlines miles from 2 Citi American Airlines credit cards which offered 75,000 miles as a sign-up bonus each
- 50,000 American Airlines miles from opening a Fidelity brokerage account
- 150,000 British Airways Avios from a 100,000 Chase British Airways sign-up bonus + 50,000 from spend
- 60,000 British Airways Avios transferred from Chase Ultimate Rewards which came from a Chase Ink 50,000 sign-up bonus and subsequent spend

Alternative ways to do it and how to get the miles

SFO-HKG: 105,000 Cathay Pacific Asia Miles (transfer partner of American Express Membership Rewards)

- 100,000 sign-up bonus for American Express Platinum card
- 50,000 sign-up bonus for American Express Premier Rewards Gold card

This is actually the easiest of the 3 airlines he mentioned to fly with in First Class, as Cathay opens up much of it's First Class cabin for award tickets starting approximately 11 months in advance, and then usually opens up all remaining seats starting about 2 weeks prior to departure. Each airline handles this differently in terms of protecting it's First Class cabin from award bookings, but Cathay is among the most generous in that regard and make this an easy mileage redemption.

Extravagant Airline #2 - Singapore Airlines
How we did it (price for each ticket) and how we got the miles 

SFO-HKG: 70,000 United Airlines miles + $5 in taxes/fees

- 300,000 miles from flying United as my primary airline from 2011-2012
- 50,000 United Airlines miles from Chase United Explorer card sign-up bonus
- 80,000 transferred from Chase Ultimate Rewards from 2 Chase Sapphire Preferred card bonuses of 40,000 each

Alternative ways to do it and how to get the miles

SFO-HKG: 70,125 Singapore Airlines Krisflyer miles (transfer partner of American Express Membership Rewards)

- 100,000 sign-up bonus for American Express Platinum card
- 50,000 sign-up bonus for American Express Premier Rewards Gold card

Many people consider Singapore Airlines the gold standard for all airlines and the best in the world. They are also among the stingiest in terms of allowing access to their First Class cabins, which can only be redeemed through their own frequent flyer program and is blocked from all partners.

I'm still in the process of accumulating Singapore Krisflyer miles for a future redemption, so how did we get access to the highly-protected Singapore First Class cabin? In the summer of 2012, they were converting their reservation systems and for a short period of time (about a couple days), accidentally made all First Class award space available to their Star Alliance partners. This caused an absolute frenzy among those who were in the know, and I was fortunate enough to be able to use my United miles for the Singapore First Class redemption.

Even after flying some of the other heavy hitters (Emirates, Cathay, ANA, Thai), Singapore remains our favorite and I can't wait until I've saved up enough miles to fly them again.

Extravagant Airline #3 - Emirates

How we did it (price for each ticket) and how we got the miles 

CMB-DXB-LHR-SFO: $2,140.20 for First Class; MLE-DXB-LHR on Emirates and LHR-SFO on British Airways

This is the fun one - a lot of things going on here. First of all, while it's certainly more than I would like to have paid for a 1-way ticket the value I'm getting is undeniable as it's a great fare that is a 90% discount off the price of the standard First Class ticket on Emirates that he quoted (~$22,000).

So how did I get it? I don't know how to describe it other than the "random airport in a previously dangerous location" phenomenon. For some reason, airlines screw up the logic in their pricing systems for these types of places, most notably Sri Lanka (CMB) and Yangon, Myanmar (RGN) in recent years.

In fact, if you say the letters RGN to a hardcore travel hacker, odds are that their face will light up.
This was a truly amazing deal that I got the year before, where we flew home on Korean Air First Class from Yangon, Myanmar for $250 each! In fact, the miles we accrued from those flights exceeded the cost of the tickets themselves, meaning that we essentially got paid to fly. Lisa particularly loves these crazy fares, since I would never be adventurous enough to go to Myanmar or Sri Lanka if it weren't for these amazing fares.

The second interesting thing going on here is tangentially related to the concept of hidden-city ticketing. For example, the price of the ticket with the routing CMB-DXB-LHR-SFO was $2,140, but the price for that same ticket with the routing DXB-LHR-SFO was over $8,000. You might ask yourself, why the heck would I pay quadruple the price for a shorter route that has one less flight?

This is related to the concept of hidden-city ticketing, where it can be advantageous to add on additional legs to flights in order to save money. It's a big no-no from the airline Terms and Condition's standpoint, but it's rarely (if ever) enforced. A perfect example of this, was during the couple years I was flying to Chicago regularly to visit Lisa - often times the direct route to Chicago (SFO-ORD) would actually be more expensive than the route to Milwaukee that stopped in Chicago (SFO-ORD-MKE).

The reason this is hard to enforce, is after landing at ORD and during my layover, any of the following could happen a) getting sick at at the airport and not being able to make my connection b) having a work emergency at needing to go into the Chicago office c) deciding to change plans and meet up with friends for dinner in Chicago.  Any of these are feasible, and as long as you don't make a habit out of doing it it's very easy to get away with.

So again, why am I paying less for an additional flight!? Airline pricing systems are complex and I won't pretend to be an expert, but my understanding is that it has a lot to do with supply/demand and competition among certain routes. But it works for me, as I was happy to pay significantly less to fly a routing which actually included an additional flight.

Alternative ways to do it and how to get the miles

CMB-DXB-SFO: 168,750 Emirates Skywards miles (transfer partner of American Express Membership Rewards)

- 100,000 sign-up bonus for American Express Platinum card
- 50,000 sign-up bonus for American Express Premier Rewards Gold card

CMB-DXB-SFO: 100,000 Alaska Airlines Mileage Plan miles

- 50,000 sign-up bonus for Bank of America Alaska Airlines card
- Purchase up to 10,000 Alaska Airlines miles for $0.02 each every time you purchase an Alaska Airlines ticket

As you can see above, Alaska Airlines' program provides a much better value than booking directly through Emirates' program, and would even offer a stopover in Dubai along the way.