Deal found on October 14, 2026
Boston to San Juan
$258$33824% off
Round trip
San Juan comes in at just $258 round trip on American, compared to the usual $462 fare on this route. Dates are open from now through early spring, and since Puerto Rico is a US territory, you get a full Caribbean beach trip with no passport required. That is a 44% discount on one of the easiest island getaways from the Northeast.
Travel dates
Dates in November
e.g. Nov 2 – Nov 11 · 9 nights
Date options
12 at this price
Lowest we've seen
$192
Get deals like this from Boston
Free email alerts when we find a fare worth booking. No spam.