Deal found on September 19, 2026
Chicago to San Juan
$201$40550% off
Round trip
San Juan is $201 round trip from Chicago Midway, usually around $400 on this route, roughly a 50% drop. Puerto Rico's old town, beaches, and rainforest hikes are easy to reach without a passport, with availability stretching into the winter months.
Travel dates
Dates in October
e.g. Oct 11 – Oct 20 · 9 nights
Date options
8 at this price
Lowest we've seen
$154
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