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Booking a stopover and open jaw -- NY to Indonesia

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I'm planning a trip to Indonesia for my husband and me for the Spring of 2016 and am really daunted by the logistics of getting there and back. We've been to India and SE Asia, and the flights were a breeze comparatively. I know this is early planning, but I love doing this, and it helps to see pricing over a period of time.

I've got a tentative plan of 3 weeks, going to Java (Yogyakarta); then Kalimantan; and finishing in Bali. I'd like a stopover on the way there (if possible) in Singapore or Hong Kong. I'd prefer to stop in Singapore because it's so much closer to our destination and it will give us a chance to acclimate. On the return, I'd consider a stopover in Hong Kong, if it made any sense, but not essential. We will clearly be booking a number of domestic or regional flights, too, so I'm trying to understand how to maximize the international flight ticket.

We will be purchasing in economy (don't have miles) and I'm trying to understand how to approach this. So many questions! I've never booked a stopover before, although I've done open jaw trips several times. I find the process overwhelming and more than a little confusing. I've just signed on to Flyertalk, too, but there is too much for me to digest at this point. Since I'm early in the planning, I'm starting here.

Questions (these are only a few of the many I have!)
1) How do you input a stopover in the booking form on a website?
2) Would it be easier or cheaper to book an open jaw to Singapore, leaving from Denpasar, and booking the other flights through local airlines?
3) I see that United, Singapore Air, Cathay Pacific, Korean Air are a few of the airlines that fly to these destinations; any others that you recommend? Any of the above that might be best?
4) Does one book the flight TO Jakarta with a stopover in Singapore? Or can one book aflight directly to Yogyakarta with Singapore as the stopover?
5) More broadly, how does one approach this and figure out which airlines are most suited to this trip?

Any and all suggestions are welcome!

Paule

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