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

Friday, December 18th, 2026

10 round-trip options

Returning
Wed, Dec 23, 20265 Day Trip
$687 USD
Returning
Thu, Dec 24, 20266 Day Trip
$687 USD
Returning
Fri, Dec 25, 20267 Day Trip
$949 USD
Returning
Sat, Dec 26, 20268 Day Trip
$916 USD
Returning
Sun, Dec 27, 20269 Day Trip
$962 USD
Returning
Mon, Dec 28, 202610 Day Trip
$687 USD
Returning
Tue, Dec 29, 202611 Day Trip
$599 USD
Returning
Wed, Dec 30, 202612 Day Trip
$540 USD
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Thu, Dec 31, 202613 Day Trip
$527 USD
Returning
Fri, Jan 1, 202714 Day Trip
$487 USD