Chicago (ORD) to San Juan (SJU) flight deal in economy from $218

Extremely Rare Availability
4% of dates checked are available within 10% of the lowest price

Friday, December 25th, 2026

6 round-trip options

Returning
Wed, Dec 30, 20265 Day Trip
$759 USD
Returning
Thu, Dec 31, 20266 Day Trip
$748 USD
Returning
Fri, Jan 1, 20277 Day Trip
$1,053 USD
Returning
Sat, Jan 2, 20278 Day Trip
$1,053 USD
Returning
Sun, Jan 3, 20279 Day Trip
$1,053 USD
Returning
Mon, Jan 4, 202710 Day Trip
$889 USD