Deal found on September 5, 2026
Chicago to San Juan
$217$40546% off
Round trip
Southwest is flying Chicago to San Juan for $217, well under the roughly $574 this route typically costs. Fall is a sweet spot in Puerto Rico: fewer crowds, warm weather, and rates that climb once winter snowbirds arrive.
Travel dates
Dates in October
e.g. Oct 19 – Oct 28 · 9 nights
Date options
10 at this price
Lowest we've seen
$154
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