Deal found on October 15, 2026
Chicago to San Juan
$173$44061% off
Round trip
San Juan usually runs around $386 from Chicago, but today's fare drops to $173, a 55% discount on one of the easiest tropical getaways for US travelers since no passport is required. Winter is peak season for Puerto Rico's beaches and Old San Juan, and this fare sits well below what we typically see heading into that stretch.
Travel dates
Dates in November
e.g. Nov 15 – Nov 24 · 9 nights
Date options
7 at this price
Lowest we've seen
$128
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