Cheapest flights from Chicago

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, Nov 5 - Mon, Nov 17

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$434 Roundtrip, found 13 hours ago

$434

Roundtrip

found 13 hours ago

Select Spirit Airlines flight, departing Wed, Nov 5 from O'Hare Intl. to Princess Juliana Intl., returning Mon, Nov 17, priced at $434 found 13 hours ago

Tue, Nov 11 - Mon, Nov 17

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$443 Roundtrip, found 13 hours ago

$443

Roundtrip

found 13 hours ago

Select Spirit Airlines flight, departing Tue, Nov 11 from O'Hare Intl. to Princess Juliana Intl., returning Mon, Nov 17, priced at $443 found 13 hours ago

Tue, Nov 11 - Fri, Nov 14

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$446 Roundtrip, found 13 hours ago

$446

Roundtrip

found 13 hours ago

Select JetBlue Airways flight, departing Tue, Nov 11 from O'Hare Intl. to Princess Juliana Intl., returning Fri, Nov 14, priced at $446 found 13 hours ago

Mon, Nov 10 - Mon, Nov 17

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$452 Roundtrip, found 13 hours ago

$452

Roundtrip

found 13 hours ago

Select Spirit Airlines flight, departing Mon, Nov 10 from O'Hare Intl. to Princess Juliana Intl., returning Mon, Nov 17, priced at $452 found 13 hours ago

Mon, Nov 10 - Fri, Nov 14

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$460 Roundtrip, found 13 hours ago

$460

Roundtrip

found 13 hours ago

Select JetBlue Airways flight, departing Mon, Nov 10 from O'Hare Intl. to Princess Juliana Intl., returning Fri, Nov 14, priced at $460 found 13 hours ago

Mon, Nov 10 - Wed, Nov 12

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$463 Roundtrip, found 13 hours ago

$463

Roundtrip

found 13 hours ago

Select Spirit Airlines flight, departing Mon, Nov 10 from O'Hare Intl. to Princess Juliana Intl., returning Wed, Nov 12, priced at $463 found 13 hours ago

Wed, Nov 5 - Fri, Nov 14

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$464 Roundtrip, found 13 hours ago

$464

Roundtrip

found 13 hours ago

Select Spirit Airlines flight, departing Wed, Nov 5 from O'Hare Intl. to Princess Juliana Intl., returning Fri, Nov 14, priced at $464 found 13 hours ago

Sat, Nov 8 - Mon, Nov 17

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$494 Roundtrip, found 13 hours ago

$494

Roundtrip

found 13 hours ago

Select Spirit Airlines flight, departing Sat, Nov 8 from O'Hare Intl. to Princess Juliana Intl., returning Mon, Nov 17, priced at $494 found 13 hours ago

Sat, Nov 8 - Fri, Nov 14

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$500 Roundtrip, found 13 hours ago

$500

Roundtrip

found 13 hours ago

Select JetBlue Airways flight, departing Sat, Nov 8 from O'Hare Intl. to Princess Juliana Intl., returning Fri, Nov 14, priced at $500 found 13 hours ago

Tue, Nov 11 - Thu, Nov 13

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$503 Roundtrip, found 13 hours ago

$503

Roundtrip

found 13 hours ago

Select JetBlue Airways flight, departing Tue, Nov 11 from O'Hare Intl. to Princess Juliana Intl., returning Thu, Nov 13, priced at $503 found 13 hours ago

Sun, Nov 9 - Mon, Nov 17

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$508 Roundtrip, found 13 hours ago

$508

Roundtrip

found 13 hours ago

Select Spirit Airlines flight, departing Sun, Nov 9 from O'Hare Intl. to Princess Juliana Intl., returning Mon, Nov 17, priced at $508 found 13 hours ago

Thu, Nov 6 - Fri, Nov 14

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$510 Roundtrip, found 13 hours ago

$510

Roundtrip

found 13 hours ago

Select Air Canada flight, departing Thu, Nov 6 from O'Hare Intl. to Princess Juliana Intl., returning Fri, Nov 14, priced at $510 found 13 hours ago

Sun, Nov 9 - Wed, Nov 12

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$518 Roundtrip, found 13 hours ago

$518

Roundtrip

found 13 hours ago

Select Spirit Airlines flight, departing Sun, Nov 9 from O'Hare Intl. to Princess Juliana Intl., returning Wed, Nov 12, priced at $518 found 13 hours ago

Wed, Nov 5 - Sat, Nov 15

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$521 Roundtrip, found 13 hours ago

$521

Roundtrip

found 13 hours ago

Select Spirit Airlines flight, departing Wed, Nov 5 from O'Hare Intl. to Princess Juliana Intl., returning Sat, Nov 15, priced at $521 found 13 hours ago

Thu, Nov 6 - Mon, Nov 17

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$522 Roundtrip, found 13 hours ago

$522

Roundtrip

found 13 hours ago

Select Spirit Airlines flight, departing Thu, Nov 6 from O'Hare Intl. to Princess Juliana Intl., returning Mon, Nov 17, priced at $522 found 13 hours ago

Fri, Nov 7 - Sat, Nov 15

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$527 Roundtrip, found 13 hours ago

$527

Roundtrip

found 13 hours ago

Select Air Canada flight, departing Fri, Nov 7 from O'Hare Intl. to Princess Juliana Intl., returning Sat, Nov 15, priced at $527 found 13 hours ago

Sun, Nov 9 - Tue, Nov 18

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$587 Roundtrip, found 13 hours ago

$587

Roundtrip

found 13 hours ago

Select Delta flight, departing Sun, Nov 9 from O'Hare Intl. to Princess Juliana Intl., returning Tue, Nov 18, priced at $587 found 13 hours ago

Sat, Jan 3 - Sat, Jan 31

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$602 Roundtrip, found 4 days ago

$602

Roundtrip

found 4 days ago

Select American Airlines flight, departing Sat, Jan 3 from O'Hare Intl. to Princess Juliana Intl., returning Sat, Jan 31, priced at $602 found 4 days ago

Sat, Jan 3 - Sat, Jan 31

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$663 Roundtrip, found 4 days ago

$663

Roundtrip

found 4 days ago

Select American Airlines flight, departing Sat, Jan 3 from O'Hare Intl. to Princess Juliana Intl., returning Sat, Jan 31, priced at $663 found 4 days ago

Sat, Nov 8 - Sat, Nov 15

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$752 Roundtrip, found 13 hours ago

$752

Roundtrip

found 13 hours ago

Select United flight, departing Sat, Nov 8 from O'Hare Intl. to Princess Juliana Intl., returning Sat, Nov 15, priced at $752 found 13 hours ago