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

Wednesday, December 23rd, 2026

8 round-trip options

Returning
Mon, Dec 28, 20265 Day Trip
$621 USD
Returning
Tue, Dec 29, 20266 Day Trip
$615 USD
Returning
Wed, Dec 30, 20267 Day Trip
$632 USD
Returning
Thu, Dec 31, 20268 Day Trip
$621 USD
Returning
Fri, Jan 1, 20279 Day Trip
$926 USD
Returning
Sat, Jan 2, 202710 Day Trip
$926 USD
Returning
Sun, Jan 3, 202711 Day Trip
$926 USD
Returning
Mon, Jan 4, 202712 Day Trip
$762 USD