Flights from Chicago to Simpson Bay

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 6 days ago

$434

Roundtrip

found 6 days 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 6 days ago

Tue, Nov 11 - Mon, Nov 17

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$443 Roundtrip, found 6 days ago

$443

Roundtrip

found 6 days 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 6 days ago

Fri, Nov 7 - Sat, Nov 15

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$447 Roundtrip, found 6 days ago

$447

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Fri, Nov 7 from O'Hare Intl. to Princess Juliana Intl., returning Sat, Nov 15, priced at $447 found 6 days ago

Mon, Nov 10 - Mon, Nov 17

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$452 Roundtrip, found 6 days ago

$452

Roundtrip

found 6 days 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 6 days ago

Sun, Nov 9 - Mon, Nov 17

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$462 Roundtrip, found 6 days ago

$462

Roundtrip

found 6 days ago

Select Spirit Airlines flight, departing Sun, Nov 9 from O'Hare Intl. to Princess Juliana Intl., returning Mon, Nov 17, priced at $462 found 6 days ago

Wed, Nov 5 - Fri, Nov 14

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$464 Roundtrip, found 6 days ago

$464

Roundtrip

found 6 days 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 6 days ago

Tue, Nov 11 - Fri, Nov 14

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$473 Roundtrip, found 6 days ago

$473

Roundtrip

found 6 days ago

Select Spirit Airlines flight, departing Tue, Nov 11 from O'Hare Intl. to Princess Juliana Intl., returning Fri, Nov 14, priced at $473 found 6 days ago

Mon, Nov 10 - Fri, Nov 14

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$482 Roundtrip, found 6 days ago

$482

Roundtrip

found 6 days ago

Select Spirit Airlines flight, departing Mon, Nov 10 from O'Hare Intl. to Princess Juliana Intl., returning Fri, Nov 14, priced at $482 found 6 days ago

Wed, Nov 5 - Sat, Nov 15

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$491 Roundtrip, found 6 days ago

$491

Roundtrip

found 6 days ago

Select Spirit Airlines flight, departing Wed, Nov 5 from O'Hare Intl. to Princess Juliana Intl., returning Sat, Nov 15, priced at $491 found 6 days ago

Thu, Nov 6 - Mon, Nov 17

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$492 Roundtrip, found 6 days ago

$492

Roundtrip

found 6 days ago

Select Spirit Airlines flight, departing Thu, Nov 6 from O'Hare Intl. to Princess Juliana Intl., returning Mon, Nov 17, priced at $492 found 6 days ago

Sat, Nov 8 - Mon, Nov 17

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$494 Roundtrip, found 6 days ago

$494

Roundtrip

found 6 days 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 6 days ago

Tue, Nov 11 - Sat, Nov 15

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$500 Roundtrip, found 6 days ago

$500

Roundtrip

found 6 days ago

Select Spirit Airlines flight, departing Tue, Nov 11 from O'Hare Intl. to Princess Juliana Intl., returning Sat, Nov 15, priced at $500 found 6 days ago

Thu, Nov 6 - Wed, Nov 12

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$503 Roundtrip, found 6 days ago

$503

Roundtrip

found 6 days ago

Select Spirit Airlines flight, departing Thu, Nov 6 from O'Hare Intl. to Princess Juliana Intl., returning Wed, Nov 12, priced at $503 found 6 days ago

Mon, Nov 10 - Sat, Nov 15

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$509 Roundtrip, found 6 days ago

$509

Roundtrip

found 6 days ago

Select Spirit Airlines flight, departing Mon, Nov 10 from O'Hare Intl. to Princess Juliana Intl., returning Sat, Nov 15, priced at $509 found 6 days ago

Sat, Nov 8 - Tue, Nov 18

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$576 Roundtrip, found 6 days ago

$576

Roundtrip

found 6 days ago

Select JetBlue Airways flight, departing Sat, Nov 8 from O'Hare Intl. to Princess Juliana Intl., returning Tue, Nov 18, priced at $576 found 6 days ago

Sun, Nov 9 - Tue, Nov 18

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$587 Roundtrip, found 6 days ago

$587

Roundtrip

found 6 days ago

Select Delta flight, departing Sun, Nov 9 from O'Hare Intl. to Princess Juliana Intl., returning Tue, Nov 18, priced at $587 found 6 days ago

Sat, Jan 3 - Sat, Jan 31

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$602 Roundtrip, found 3 hours ago

$602

Roundtrip

found 3 hours 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 3 hours ago

Sat, Jan 3 - Sat, Jan 31

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$663 Roundtrip, found 3 hours ago

$663

Roundtrip

found 3 hours 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 3 hours ago

Sat, Nov 8 - Sat, Nov 15

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$753 Roundtrip, found 6 days ago

$753

Roundtrip

found 6 days ago

Select United flight, departing Sat, Nov 8 from O'Hare Intl. to Princess Juliana Intl., returning Sat, Nov 15, priced at $753 found 6 days ago

Sat, Jan 3 - Sat, Jan 31

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$915 Roundtrip, found 3 hours ago

$915

Roundtrip

found 3 hours ago

Select Air Canada flight, departing Sat, Jan 3 from O'Hare Intl. to Princess Juliana Intl., returning Sat, Jan 31, priced at $915 found 3 hours ago