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Need booking advice for US Airways RT Boston to PR flight choices

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We have found one stop flights from Boston to PR w/ a 35 min layover - change of plane In Phili.This is for mid February.
Could this possibly be too brief a window for changing planes?
Also, we read that Monday night through Tuesday is a good time for deals from the airlines.
Should we wait till that time period to book?
Non-stop RT fare today, Sunday, is $800
1 stop " " " $755 Possibly the $45 extra fee for the non stop is worth the extra expense?
Many thanks (again),
LinB

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