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I'm not very good at sleeping on airplanes (at least in cattle class - I've never flown overnight on higher classes), and I don't fancy the prospect of sleeping for a couple of hours in an airport transit lounge either. If it happened on the way to my tourist destination it'd be fine, but unfortunately it's on the way back home (probably because my tourist destinations are further to the west of me than my home city), and I don't want to be half-asleep when I go back to work. Usually it takes me more than one day to recover from a red-eye flight, so spending two days flying non-red-eye may actually be better than spending a single day and night flying red-eye.

I looked up kayak.com for flying from Ulaan Baator to Sydney, or from Osaka to Sydney, without using a red-eye flight, and it said that there weren't any.

Is it possible to fly from city X to city Y during the daytime, have a good night's rest at city Y, and then fly from city Y to city Z during the daytime? How do I search for the most suitable flights, in terms of cost, and start and end times for each flight, and can I ensure that if the first flight is delayed for reasons beyond my control and I miss the second flight, I can get another flight without paying any extra?

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    I can certainly find you such a flight, but it's 3 times the cost! – Michael Hampton Apr 17 '16 at 6:30
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    This question would be a lot more concise if it were just the third paragraph and a brief sentence explaining the context. – Urbana Apr 17 '16 at 7:07
  • @davidvc I'm not sure you can make this question quite so generic. The problem here is that the final leg of this journey is a very long flight (10-12 hours). – Michael Hampton Apr 17 '16 at 7:10
  • @davidvc mainly written to avoid people adding "just take the red-eye flight" as a comment without any more information. – Andrew Grimm Apr 17 '16 at 8:07
  • @AndrewGrimm: As a general rule, we answer the question you ask, even if it doesn't fit our personal travel style. I don't think you need to triple the size of your question for that defense. Especially for something that practically everyone wants to avoid. – Flimzy Apr 18 '16 at 9:19
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How do I search for the most suitable flights, in terms of cost, and start and end times for each flight, and can I ensure that if the first flight is delayed for reasons beyond my control and I miss the second flight, I can get another flight without paying any extra?

Since you want a good night's sleep, let's call that 8 hours , you want at least 8 hours of layover.

So go to ITA and specify a minimum connection by clicking advanced routing codes and typing "/minconnect 480":

enter image description here

Remove "night" departures and "early morning" and "morning" arrivals from the results. Still you will get a few misfires but not many. This is your best bet, I think. Tinker with minconnect to see whether you get significant changes in price.

Edit: sorry, this was Tokyo, doesn't matter, same approaches for Osaka. Here are the results for a random day pair:

enter image description here

The price difference on this day is minimal: this flight is 72 460 JPY, the cheapest ITA finds without any restrictions is 69 060 JPY. Of course, other days it might be different.

Since you are flying with a single airline, if you have a connection problem, it's up to the airline to solve it. You might end up on a redeye still in this case -- it very much depends on the airline, how much flexibility they have in this case. Of course, if you pick an airline like Thai which only have one daily flight to Sydney then they can't put you on a redeye but then you might need to wait a day. When you try to book with the airline they typically will give you a lot of time variants and you will see whether a redeye occurs. You can also try to look up on flightstats and similar sites what flights exist between a pair of cities to see this. Even if you do that there's a very small chance of getting an entirely different route -- but not between Japan and Australia as all airlines will connect through their hub, Cathay Hong Kong, Thai Bangkok etc. That's more of a problem in the generic case.

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