San Juan (SJU) to Chicago (ORD) flight deal in business from $706

Monday, December 21st, 2026

8 round-trip options

Returning
Sat, Dec 26, 20265 Day Trip
$1,897 USD
Returning
Sun, Dec 27, 20266 Day Trip
$1,463 USD
Returning
Mon, Dec 28, 20267 Day Trip
$1,292 USD
Returning
Wed, Dec 30, 20269 Day Trip
$1,237 USD
Returning
Fri, Jan 1, 202711 Day Trip
$1,107 USD
Returning
Sat, Jan 2, 202712 Day Trip
$1,107 USD
Returning
Sun, Jan 3, 202713 Day Trip
$1,189 USD
Returning
Mon, Jan 4, 202714 Day Trip
$1,112 USD