I was wondering if using United miles, I could book: Chicago-Frankfurt-Singapore-Male(destination) Male-Singapore-Tokyo-Chicago My thought is that it would be cool to fly Lufthansa there and then Singapore on the way back (trying to get some a380 time). I have looked on some of the forums about trying to cross one ocean on the way there and another on the way back. It seems to have mixed results. Or is it mostly not able to happen on one reward? Since United offers one reward booking, does it really matter if I book it as two separate one way redemptions? And then by doing two separate one way redemptions, would I also be able to create a stopover in Singapore on the way there and a stopover in Tokyo on the way back? Looking at the United Award chart, it would cost 60,000 miles each way correct? Even if I change the final destination from Male to Singapore, South Asia and Indian Sub-continent are both 60,000 for using United miles on Star Alliance airlines? I feel like there are so many rules out there on this stuff that I must be missing something somewhere.