Deal found on October 21, 2026
Chicago to San Juan
$208$40549% off
Round trip
San Juan is $208 round trip from Chicago Midway on Frontier, compared to the roughly $575 this route usually commands, nearly 64% off. Puerto Rico delivers beaches, rainforest hikes, and no passport required, all with just one stop. This is comfortably one of the best fares we have tracked on this route.
Travel dates
November into December
e.g. Nov 23 – Dec 2 · 9 nights
Date options
6 at this price
Lowest we've seen
$154
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