Chicago (ORD) to Santiago de los Caballeros (STI) flight deal in economy from $378

Monday, December 21st, 2026

10 round-trip options

Returning
Sat, Dec 26, 20265 Day Trip
$1,142 USD
Returning
Sun, Dec 27, 20266 Day Trip
$1,081 USD
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Mon, Dec 28, 20267 Day Trip
$1,010 USD
Returning
Tue, Dec 29, 20268 Day Trip
$1,081 USD
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Wed, Dec 30, 20269 Day Trip
$1,081 USD
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Thu, Dec 31, 202610 Day Trip
$1,152 USD
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Fri, Jan 1, 202711 Day Trip
$1,256 USD
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Sat, Jan 2, 202712 Day Trip
$1,779 USD
Returning
Sun, Jan 3, 202713 Day Trip
$1,817 USD
Returning
Mon, Jan 4, 202714 Day Trip
$1,256 USD