San Juan (SJU) to Chicago (ORD) flight deal in economy from $307

Tuesday, December 22nd, 2026

10 round-trip options

Returning
Sun, Dec 27, 20265 Day Trip
$962 USD
Returning
Mon, Dec 28, 20266 Day Trip
$687 USD
Returning
Tue, Dec 29, 20267 Day Trip
$599 USD
Returning
Wed, Dec 30, 20268 Day Trip
$540 USD
Returning
Thu, Dec 31, 20269 Day Trip
$527 USD
Returning
Fri, Jan 1, 202710 Day Trip
$487 USD
Returning
Sat, Jan 2, 202711 Day Trip
$462 USD
Returning
Sun, Jan 3, 202712 Day Trip
$471 USD
Returning
Mon, Jan 4, 202713 Day Trip
$457 USD
Returning
Tue, Jan 5, 202714 Day Trip
$457 USD