Chicago (ORD) to San Juan (SJU) flight deal in economy from $191
ORDO'Hare International Airport
Chicago, United States
SJULuis Muñoz Marín International Airport
San Juan, Puerto Rico
$465 USD
-59%$191 USD
Verified about 4 hours agoDecember 2026
Mon
Tue
Wed
Thu
Fri
Sat
Sun
Rare Availability
5% of dates checked are available within 10% of the lowest price
Monday, December 21st, 2026
10 round-trip options
Returning
Sat, Dec 26, 2026•5 Day Trip
$732 USD
Returning
Sun, Dec 27, 2026•6 Day Trip
$876 USD
Returning
Mon, Dec 28, 2026•7 Day Trip
$844 USD
Returning
Tue, Dec 29, 2026•8 Day Trip
$816 USD
Returning
Wed, Dec 30, 2026•9 Day Trip
$929 USD
Returning
Thu, Dec 31, 2026•10 Day Trip
$926 USD
Returning
Fri, Jan 1, 2027•11 Day Trip
$1,024 USD
Returning
Sat, Jan 2, 2027•12 Day Trip
$1,510 USD
Returning
Sun, Jan 3, 2027•13 Day Trip
$1,467 USD
Returning
Mon, Jan 4, 2027•14 Day Trip
$1,328 USD