Some friends flew eastwards from New York to Singapore on a direct flight (it's one of the longest flights). I wondered what their experience of sunrises and sunsets were (they departed 10PM), I've noted down the times but haven't plotted it...
Later this year I'm flying from Europe to the West Coast of Canada, and it seems I'll be in daylight for the entirity of the flight (departing 2PM local, landing 4PM local after a 10 hour flight).
Edit: well, FR24 has a handy flight tracking that includes the daylight progression: https://www.flightradar24.com/data/flights/sq23#3de5a306
So they flew 18 hours and experienced a full daylight cycle, arriving just before the second sunrise...
I flew from central US to western asia (via moscow) and it was an interesting experience for the reasons you mentioned. I think I left early Saturday morning local time and arrived Sunday evening local time. I saw a sunrise, sunset, sunrise, sunset in 18 hours of travel time.