Winkdaddy

Hey All,

I am trying to construct a work trip in September for the following: ORD-BKK, BKK-SGN, SGN-ORD. My company will likely pay for Premium Economy but not Business.

I am toying with the idea of flying UA for ORD-SFO-SIN...then take Singapore Air from SIN to BKK.. (local airlines between BKK-SGN) .and also Singapore Air for SGN back to SIN...and then UA metal from SIN-SFO-ORD

In this scenario I can try to use my Plus points to upgrade from Premium Economy to Business on SFO-SIN both ways. But how likely is that really on that route? Decent chance or total pipe dream?

I can also fly Singapore Air from a few USA cities to SIN...in Premium Economy but no chance of upgrade. (I didnt see any great options to fly to BKK directly, so using SIN seemed like a better option)

How would you guys construct such a trip if you can only buy up to Premium Economy on any airline but also had 360 Plus Points?