Chicago (ORD) to San Juan (SJU) flight deal in economy from $237
ORDO'Hare International Airport
Chicago, United States
SJULuis Muñoz Marín International Airport
San Juan, Puerto Rico
$527 USD
-55%$237 USD
Verified 16 days agoDecember 2026
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Extremely Rare Availability
3% of dates checked are available within 10% of the lowest price
Friday, December 18th, 2026
7 round-trip options
Returning
Wed, Dec 23, 2026•5 Day Trip
$963 USD
Returning
Thu, Dec 24, 2026•6 Day Trip
$894 USD
Returning
Fri, Dec 25, 2026•7 Day Trip
$894 USD
Returning
Sun, Dec 27, 2026•9 Day Trip
$1,113 USD
Returning
Tue, Dec 29, 2026•11 Day Trip
$1,008 USD
Returning
Wed, Dec 30, 2026•12 Day Trip
$1,008 USD
Returning
Thu, Dec 31, 2026•13 Day Trip
$992 USD