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Need help with Thailand ticket. Paid vs award

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I am new to the forum, but seeking advice on my trip to Thailand in 2014.

I want to go to Chiang Mai (CNX), Bangkok (BKK) and Phuket (HKT)

I need 3 RT tickets. I have enough UA miles for 2 award tickets. I also have 150,000 Capital One points that I can use for a paid ticket and be reimbursed via Purchase Eraser.

I also have the option of trading 25k of my Skymiles for my mother in law’s 25k UA miles and purchasing the rest at about $1500 (which could also be reimbursed via Capital One) and then be able to book 3 award tickets.

Here is the dilemma.

If I go with all 3 as award tickets, I can get the routing I want. Flying into CNX and out of HKT. I also get the comfort of flying on Asiana and Thai Airways for the long haul flights.

The bad part of 3 award tickets is I won’t earn any miles on a flight. I will be out 25k Skymiles in addition to my 150k Capital One points.

If I do 2 award tickets and 1 paid ticket, I cannot do the open jaw itinerary without being charged a $4,000 fare. So I would have to go in and out of Bangkok and take an extra domestic Thailand flight. I would have the discomfort of flying a UA plane on the long haul flights. I would pay the extra to upgrade to Economy Plus, but not sure if I can even do that on an award ticket or if it would even be worth it.

The good part of 2 award and 1 paid is that I will earn about 19-20k miles on UA for the paid ticket. I will also not have to sacrifice my 25k Skymiles.

I think it comes down to what is more important.....time (comfort) or money (value)?

What would YOU do in this situation?? Or does anybody have an alternative that I have not yet considered.

Incidentally, I have over 300k miles on DL, but they want 80k to go to Thailand vs 65k on UA. What a rip off.

I will be able to book my flights in about 13 days, and I want to do it ASAP to make sure I get the routing I want. Thank you in advance for any advice!

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