I agree with what you said about Darlene's dad, and I'm pretty sure that he dropped her off at the airport. Maybe the way Darlene and Alice got away with it is that they actually caught a flight to Hawaii first, then took another flight from Hawaii to Bangkok. One of my coworkers is Thai and goes there every now and then, according to him Thailand-bound flights are heading West, so Hawaii was sort of along the way for the girls. So the reason why Darlene's dad thought that Darlene was in Hawaii is because he actually saw her get on a flight to Hawaii. I remember that before 9/11 they actually let passengers' family/friends inside the terminal, I flew to London 3 weeks prior to that day and my parents sat with me right by the gate until I boarded the plane. Obviously, after 9/11, it's passengers only beyond the TSA line. Given that this movie was released in 1999, Darlene's dad could have done the same.
In regards to switching flights, it's not impossible to do so, and I'm pretty sure that airline staff by the gate can assist with that. Surely, there's no guarantee that there would be available seats on a short notice and fares would be way much higher vs. booking in advance, but if airline can accommodate you, they will happily take your money. I'm sure that Alice and Darlene had money saved up to make that trip happen.
In regards to visa, no need for one for US citizens (at least according to Department of State):
http://travel.state.gov/travel/cis_pa_tw/cis/cis_1040.html
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