Flights from Chicago to Philipsburg

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.

Thu, Oct 30 - Wed, Nov 5

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$378 Roundtrip, found 19 hours ago

$378

Roundtrip

found 19 hours ago

Select Spirit Airlines flight, departing Thu, Oct 30 from O'Hare Intl. to Princess Juliana Intl., returning Wed, Nov 5, priced at $378 found 19 hours ago

Fri, Oct 31 - Wed, Nov 5

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$388 Roundtrip, found 19 hours ago

$388

Roundtrip

found 19 hours ago

Select Spirit Airlines flight, departing Fri, Oct 31 from O'Hare Intl. to Princess Juliana Intl., returning Wed, Nov 5, priced at $388 found 19 hours ago

Fri, Oct 31 - Fri, Nov 7

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$396 Roundtrip, found 19 hours ago

$396

Roundtrip

found 19 hours ago

Select Spirit Airlines flight, departing Fri, Oct 31 from O'Hare Intl. to Princess Juliana Intl., returning Fri, Nov 7, priced at $396 found 19 hours ago

Sat, Nov 1 - Wed, Nov 5

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$401 Roundtrip, found 19 hours ago

$401

Roundtrip

found 19 hours ago

Select Spirit Airlines flight, departing Sat, Nov 1 from O'Hare Intl. to Princess Juliana Intl., returning Wed, Nov 5, priced at $401 found 19 hours ago

Sat, Nov 1 - Fri, Nov 7

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$409 Roundtrip, found 19 hours ago

$409

Roundtrip

found 19 hours ago

Select Spirit Airlines flight, departing Sat, Nov 1 from O'Hare Intl. to Princess Juliana Intl., returning Fri, Nov 7, priced at $409 found 19 hours ago

Mon, Oct 27 - Wed, Nov 5

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$410 Roundtrip, found 19 hours ago

$410

Roundtrip

found 19 hours ago

Select Spirit Airlines flight, departing Mon, Oct 27 from O'Hare Intl. to Princess Juliana Intl., returning Wed, Nov 5, priced at $410 found 19 hours ago

Mon, Oct 27 - Fri, Nov 7

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$418 Roundtrip, found 19 hours ago

$418

Roundtrip

found 19 hours ago

Select Spirit Airlines flight, departing Mon, Oct 27 from O'Hare Intl. to Princess Juliana Intl., returning Fri, Nov 7, priced at $418 found 19 hours ago

Thu, Oct 30 - Wed, Nov 5

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$420 Roundtrip, found 19 hours ago

$420

Roundtrip

found 19 hours ago

Select Spirit Airlines flight, departing Thu, Oct 30 from O'Hare Intl. to Princess Juliana Intl., returning Wed, Nov 5, priced at $420 found 19 hours ago

Thu, Oct 30 - Wed, Nov 5

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$436 Roundtrip, found 19 hours ago

$436

Roundtrip

found 19 hours ago

Select JetBlue Airways flight, departing Thu, Oct 30 from O'Hare Intl. to Princess Juliana Intl., returning Wed, Nov 5, priced at $436 found 19 hours ago

Thu, Oct 30 - Wed, Nov 5

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$443 Roundtrip, found 19 hours ago

$443

Roundtrip

found 19 hours ago

Select Spirit Airlines flight, departing Thu, Oct 30 from O'Hare Intl. to Princess Juliana Intl., returning Wed, Nov 5, priced at $443 found 19 hours ago

Wed, Oct 29 - Mon, Nov 3

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$449 Roundtrip, found 6 days ago

$449

Roundtrip

found 6 days ago

Select JetBlue Airways flight, departing Wed, Oct 29 from O'Hare Intl. to Princess Juliana Intl., returning Mon, Nov 3, priced at $449 found 6 days ago

Tue, Oct 28 - Mon, Nov 3

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$452 Roundtrip, found 2 days ago

$452

Roundtrip

found 2 days ago

Select JetBlue Airways flight, departing Tue, Oct 28 from O'Hare Intl. to Princess Juliana Intl., returning Mon, Nov 3, priced at $452 found 2 days ago

Thu, Oct 30 - Wed, Nov 5

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$453 Roundtrip, found 19 hours ago

$453

Roundtrip

found 19 hours ago

Select Spirit Airlines flight, departing Thu, Oct 30 from O'Hare Intl. to Princess Juliana Intl., returning Wed, Nov 5, priced at $453 found 19 hours ago

Sat, Oct 25 - Tue, Nov 4

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$462 Roundtrip, found 2 days ago

$462

Roundtrip

found 2 days ago

Select JetBlue Airways flight, departing Sat, Oct 25 from O'Hare Intl. to Princess Juliana Intl., returning Tue, Nov 4, priced at $462 found 2 days ago

Tue, Oct 28 - Wed, Nov 5

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$587 Roundtrip, found 2 days ago

$587

Roundtrip

found 2 days ago

Select American Airlines flight, departing Tue, Oct 28 from O'Hare Intl. to Princess Juliana Intl., returning Wed, Nov 5, priced at $587 found 2 days ago

Tue, Oct 28 - Wed, Nov 5

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$623 Roundtrip, found 19 hours ago

$623

Roundtrip

found 19 hours ago

Select Copa flight, departing Tue, Oct 28 from O'Hare Intl. to Princess Juliana Intl., returning Wed, Nov 5, priced at $623 found 19 hours ago

Tue, Oct 28 - Wed, Nov 5

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$697 Roundtrip, found 2 days ago

$697

Roundtrip

found 2 days ago

Select United flight, departing Tue, Oct 28 from O'Hare Intl. to Princess Juliana Intl., returning Wed, Nov 5, priced at $697 found 2 days ago

Sun, Oct 26 - Sun, Nov 2

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$708 Roundtrip, found 2 days ago

$708

Roundtrip

found 2 days ago

Select United flight, departing Sun, Oct 26 from O'Hare Intl. to Princess Juliana Intl., returning Sun, Nov 2, priced at $708 found 2 days ago

Wed, Oct 29 - Fri, Nov 7

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$717 Roundtrip, found 2 days ago

$717

Roundtrip

found 2 days ago

Select Delta flight, departing Wed, Oct 29 from O'Hare Intl. to Princess Juliana Intl., returning Fri, Nov 7, priced at $717 found 2 days ago

Thu, Oct 30 - Wed, Nov 5

MDW

Midway Intl.

SXM

Princess Juliana Intl.

$747 Roundtrip, found 1 day ago

$747

Roundtrip

found 1 day ago

Select Delta flight, departing Thu, Oct 30 from Midway Intl. to Princess Juliana Intl., returning Wed, Nov 5, priced at $747 found 1 day ago