Deal found on November 5, 2026
Chicago to San Juan
$205$40549% off
Round trip
San Juan is $205 round trip from Chicago Midway, down from the usual $370 to $475. There are 3 date windows open across November, December, and January on Frontier. Old San Juan's beaches and historic fort make it a reliably popular Caribbean pick, and as a US territory it needs no passport for American travelers.
Travel dates
November into December
e.g. Nov 26 – Dec 5 · 9 nights
Date options
3 at this price
Lowest we've seen
$154
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