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During oceanic crossings, there are limited to no terrestrial radio communications available, so I would think that most flight routes are designed to minimize ocean crossing time.

Which commercial flight route have the longest oceanic crossing?

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    $\begingroup$ Most of the flight routes are designed to minimize fuel burn and if it takes the plane over the ocean, so be it. Communication is restricted, but HF radio works and so do satellite links. $\endgroup$ – Jan Hudec Jun 24 '15 at 9:54
  • $\begingroup$ Related: Are there diversion points for southern Pacific great circle route flights? $\endgroup$ – fooot Jun 24 '15 at 19:54
  • $\begingroup$ As a sidenote there is notion called ETOPS which may modify the optimal flight path (along with the weather), depending on the aircraft and airline and they may need to use different routing because of ETOPS certificate $\endgroup$ – Bela Vizer Jul 16 '18 at 9:18
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For the longest Oceanic Crossing, the following are the top three contenders:

  1. Sydney to Vancouver
  2. Melbourne to Los Angeles
  3. Auckland to Vancouver

Out of this, 1 and 2 pass over a few islands on their way, 3 does not pass over any landmass.

Have a look at this : www.gcmap.com

Image :

GCMAP of flights
(Image Source: www.gcmap.com)

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    $\begingroup$ It's worth noting that the actual routes flown by aircraft reflect current weather patterns, and can vary considerably from the great circle path. For example, AKL-YVR frequently goes west of Hawaii. $\endgroup$ – Greg Hewgill Jun 24 '15 at 22:51
  • $\begingroup$ The Air Canada Melbourne-Vancouver is probably the longest. Quibbling as to whether it might pass over an island is pointless! $\endgroup$ – David Heath Jul 16 '18 at 9:06
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In the past, Singapore Airlines used to have service from Newark Liberty to Singapore Changi Airport and back. Flights 21 and 22 respectively. The travel time from one point to the other was 18.5 hours long...the longest ever passenger flight time in all of history. This was discontinued in 2013.

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    $\begingroup$ Note, though, that that flight didn't actually cross as much water as you might think. It went over the Arctic Ocean, not the Pacific. $\endgroup$ – reirab Oct 26 '15 at 18:38
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There are also SIN-LAX or SIN-SFO handled by Singapore airlines or United. The flight time is around 17h. Singapore to New York would be even longer, but I am not sure if they fly over Pacific Ocean...

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