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How I Did It – Business Class to Thailand

Review: Bobby Vans Priority Pass Restaurant at JFK

Review: Cathay Pacific Business Class ~ New York – Hong Kong – Bangkok

Review: Hong Kong Disneyland

4 Days in Chiang Mai, Thailand

Review: Conrad Koh Samui



Welcome to the new ‘How I Did It’ series!  In this series I layout of my thought process and the steps I took to book certain award tickets.  Hopefully this helps you learn how to book more advanced award flights, highlight different award chart sweet spots, and inspire you to add to your travel bucket list.

Did you recently book a sweetspot award flight or uncover a trick or just want to brag about one of your redemptions?  I’d love to hear from you and feature you on an upcoming blog post – email me:


The Redemption

This redemption was for my family of 4 from Washington DC to Thailand in the Summer of 2018.

We had no specific flight dates/times other than sometime during school’s summer vacation.  We were targeting an approximate 2 week duration and would hopefully return home on a Saturday or Sunday for a little recovery time before heading back to work.

The Search

After a quick search on, the cheapest option was to use 50,000 Alaska Airline miles for a one way business class seat on either Cathay Pacific or Hainan Airlines.  I’ve only read amazing reviews about Cathay Pacific so I concentrated on that route.


Unfortunately Washington DC is not yet one of Cathay Pacific’s destinations from their hub in Hong Kong (although Cathay Pacific will begin service to DC in September 2018).  But Alaska Airlines will fly you on their planes to one of the cities that Cathay Pacific serves for an award ticket redemption.  AwardHacker shows there is an Alaska Airlines flight from Ronald Reagan (DCA) to Los Angeles (LAX) before switching to Cathay Pacific for the flight to Hong Kong and Bangkok.

Alternate Airports

I really didn’t want to fly 5 hours to LAX and was sure I wouldn’t be able to find 4 first class award tickets, so I checked Hong Kong International Airport on wikipedia to find which cities Cathay Pacific flies to.  I wasn’t opposed to adding a positioning flight if it made sense.


New York, Boston, and Chicago are all pretty easy to get to for me, so I started my award search for 4 seats on any of these routes.

The Long Flight

Since it’s usually hardest to find award seats on the longest segment of an award trip, I started my search for the Cathay Pacific award seats using British Airways’ site.  I first searched on my ideal travel day along with a couple of days before and after and noted which days/flights had the 4 seats available.  I was able to find 4 seats on the CX0831 JFK flight that leaves at 2:50pm which was perfect since I could then take a quick shuttle flight to JFK from Washington DC that same morning instead of having to fly in the night before and have to stay at a hotel.

The Connecting Flight

After finding the long 16 hour flight, I next searched for Hong Kong to Bangkok flight also on British Airways.  With 10 flights a day, it was very easy to find 4 business class award tickets – almost every flight had 4 seats available.  One nice thing about Alaska Airline is that one stopover is allowed on award tickets – meaning we could stop in Hong Kong for however long we wanted before continuing on our trip.  We took advantage of this, but only stopped for 2 nights so we could visit Disneyland Hong Kong.

The Positioning Flight

The last piece of the puzzle before booking this award with Alaska over the phone since you can’t book Cathay Pacific flights on Alaska’s website was to make sure the positioning flight from Washington to New York was reasonable.

I love using Google Flights – it’s so easy to filter flights.  I filtered for flights that depart after 8:00am and arrive in New York before 12:00pm.  There were a bunch of flights around $100.  I ended up using 6,000 Delta Skymiles (that I got as a welcome offer/bonus for the American Express Gold Delta Skymiles Business card) for the 10:02 am – 11:19 am flight which worked out perfectly.  Having the Amex Gold Delta card also saved me $100 on baggage fees (4 bags at $25/each).


Final Itinerary

Our final itinerary was Washington DC (IAD) – New York (JFK) – Hong Kong (HKG) – Bangkok (BKK).

Washington DC (IAD) to New York (JFK)DeltaEconomy6,000$5.60
New York (JFK) to Hong Kong (HKG)Cathay PacificBusiness50,000$26.80
Hong Kong (HKG) to Bangkok (BKK)Cathay PacificBusiness0$0

19 hours in Cathay Pacific Business class for only 50,000 Alaska Airline miles is a steal!

Getting Alaska Airline Miles

I took the easy path and signed up Bank of America’s Alaska Airlines Visa credit card (multiple times).  The signup bonus is usually 25,000 or 30,000 miles after spending $1000 in 3 months and only has a $75 annual fee.

Before Bank of America implemented the 2/3/4 rule – which means they will only approve you for 2 Bank of America credit cards in two months, 3 in twelve months, and 4 in twenty-four months.  My wife and I rotated between the personal and business versions of the card every three months and built up a stash of over 400,000 miles pretty quickly but since have slowed down since the 2/3/4 rule was implemented in late 2017.

Upgraded Points has a great article on all of the other ways to earn Alaska Airline miles.

Stayed tuned for the next installment of ‘How I Did it‘ to see how we got home.



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