I’m not sure the flight times/issues are relevant.
It sounds like OP has offers for Amherst and Bowdoin.
If it was the difference of flying to Kona from Honolulu or Seattle from Honolulu, I get the comparison.
But flying to Boston, Hartford or Portland - really no point in giving one advantage over the other.
Whether through Dallas or NY or Chicago, etc. I’m sure they’ll have one stop flights.
That said, there ais a non stop HNL to BOS (which works for both schools) - on Nov 19, there’s a 9 hr 42 mins on Hawaiian, operated by Alaska although it looks like it might be ending.
There are one stops through Vegas and SLC, Denver, JFK, and Atlanta and more.
Hartford - Denver, Atlanta, Dallas, Detroit, O’Hare, Dulles, Minneapolis.
Portland had less - Detroit, Dulles, JFK, O’Hare
Bottom line - you’re going to college and home maybe 2x a year.
I don’t think travel should be a part of the decision at all.