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.

Fri, Oct 31 - Wed, Nov 5

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$388 Roundtrip, found 6 days ago

$388

Roundtrip

found 6 days 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 6 days ago

Fri, Oct 31 - Fri, Nov 7

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$396 Roundtrip, found 6 days ago

$396

Roundtrip

found 6 days 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 6 days ago

Sat, Nov 1 - Wed, Nov 5

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$401 Roundtrip, found 6 days ago

$401

Roundtrip

found 6 days 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 6 days ago

Sat, Nov 1 - Fri, Nov 7

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$409 Roundtrip, found 6 days ago

$409

Roundtrip

found 6 days 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 6 days ago

Mon, Oct 27 - Wed, Nov 5

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$410 Roundtrip, found 6 days ago

$410

Roundtrip

found 6 days 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 6 days ago

Mon, Oct 27 - Fri, Nov 7

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$418 Roundtrip, found 6 days ago

$418

Roundtrip

found 6 days 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 6 days ago

Mon, Oct 27 - Tue, Nov 4

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$467 Roundtrip, found 6 days ago

$467

Roundtrip

found 6 days ago

Select JetBlue Airways flight, departing Mon, Oct 27 from O'Hare Intl. to Princess Juliana Intl., returning Tue, Nov 4, priced at $467 found 6 days ago

Mon, Oct 27 - Thu, Nov 6

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$477 Roundtrip, found 6 days ago

$477

Roundtrip

found 6 days ago

Select JetBlue Airways flight, departing Mon, Oct 27 from O'Hare Intl. to Princess Juliana Intl., returning Thu, Nov 6, priced at $477 found 6 days ago

Wed, Oct 29 - Mon, Nov 3

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$489 Roundtrip, found 6 days ago

$489

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 $489 found 6 days ago

Thu, Oct 30 - Tue, Nov 4

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$489 Roundtrip, found 6 days ago

$489

Roundtrip

found 6 days ago

Select JetBlue Airways flight, departing Thu, Oct 30 from O'Hare Intl. to Princess Juliana Intl., returning Tue, Nov 4, priced at $489 found 6 days ago

Thu, Oct 30 - Thu, Nov 6

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$499 Roundtrip, found 6 days ago

$499

Roundtrip

found 6 days ago

Select JetBlue Airways flight, departing Thu, Oct 30 from O'Hare Intl. to Princess Juliana Intl., returning Thu, Nov 6, priced at $499 found 6 days ago

Wed, Oct 29 - Sat, Nov 8

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$509 Roundtrip, found 6 days ago

$509

Roundtrip

found 6 days ago

Select JetBlue Airways flight, departing Wed, Oct 29 from O'Hare Intl. to Princess Juliana Intl., returning Sat, Nov 8, priced at $509 found 6 days ago

Tue, Oct 28 - Wed, Nov 5

ORD

O'Hare Intl.

SXM

Princess Juliana Intl.

$623 Roundtrip, found 6 days ago

$623

Roundtrip

found 6 days ago

Select Copa flight, departing Tue, Oct 28 from O'Hare Intl. to Princess Juliana Intl., returning Wed, Nov 5, priced at $623 found 6 days ago