Some good ideas and advice here from people who have done this or something similar but the obvious people to answer many of these detail questions are the people managing the livestock plane.Flight time from Hawaii to west coast is 5-5.5 hours. We would not use commercial as they do not have climate control.
Hoping to get them on a livestock plane.
Flight time may be 5.5 hours but what time is drop-off and how soon can you pick them up. To me that is the critical time. Whatever it is they will probably be fine without food or water for that time span unless it is ridiculous. They sleep overnight without food and water. In locations far north or south that can easily be over 16 hours.
I assume it would be a commercial flight, not a livestock flight. If a livestock flight were available I'd go that route without hesitation, though considering cost. Commercial flights have rules. For example, they are not allowed to transport dry ice in the hold with animals. Dry ice gives off CO2 which could suffocate the animal if it builds up.My concern/question is how well would they travel, and is it less stressful to take them as far east as I can with a couple of plane changes, or one plane change, land in or just past the west coast and drive them?
Again chat with the specific airline you would use to get the details but I'd think your chickens could handle either one better than you probably will. It sounds like you are a worrier. They will get over it quickly.