Like putting together a jigsaw puzzle

After a few months of discussion and research, we settled on our destinations: Singapore and Indonesia. Great! Then came the hard part: Getting us there…and I’m not talking about the 19 hours in the air, plus layovers and such. I’m talking about finding a way to get three people from Chicago to Singapore and then home from Bali. In business class; two on United frequent flyer miles (preferably saver awards) and one on a paid ticket (preferably a deeply discounted business class fare). In a relatively defined timeframe from late May to the end of June. With a total trip duration of two weeks, give or take a couple of days. No problem…

It didn’t help that I was shopping for saver business class award tickets for popular international destinations about seven months out from the dates of travel. That’s kind of a “no mans land” in the world of premium saver awards. We pretty quickly realized that we might not all be flying together. That was fine, as long as we could arrive at our destinations at close to the same time.

After weeks of searching availability for a wide span of dates in late May and most of June, I was able to confirm the following:

• One on a saver business class award to Singapore via Narita on ANA; one on the same flights on a paid ticket
• One on standard business class award to Singapore via Narita on United, arriving Singapore 10 minutes before the ANA flight—not a great use of miles, but I had a hunch I might be able to convert that to a saver award closer to travel

• Two on on saver business class awards from Bali to Incheon (Asiana) to Vancouver (Air Canada) to Chicago (United)
• One on a paid ticket via Incheon (same Asiana flight) and San Francisco (United), arriving O’Hare 10 minutes after the others from Vancouver

Pretty close to perfect! It felt kind of like finishing a jigsaw puzzle.

As an aside, I started watching award tickets again about five to six weeks before we began our travel. About a week later, I found a global first class saver award on the same ANA flight to Tokyo (we would now all be on the same first flight!) and then United to Singapore—for 50,000 fewer miles than the standard business class ticket. NOW I was done!

We’ll expand on the itinerary along the way—including how/why we planned this trip as we did. For now, I’ll just share the outline of what’s coming:

3 nights in Singapore

3 nights near Borobudur in Central Java

4 nights in Yogyakarta, Central Java

5 nights in Ubud, Bali

We will travel by air (Air Asia) from Singapore to Yogyakarta and from Yogyakarta to Denpasar.