Flights from Pittsburgh to Simpson Bay

Cheapest flights from Pittsburgh

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, Dec 31 - Thu, Jan 8

PIT

Pittsburgh Intl.

SXM

Princess Juliana Intl.

$478 Roundtrip, found 3 days ago

$478

Roundtrip

found 3 days ago

Select JetBlue Airways flight, departing Wed, Dec 31 from Pittsburgh Intl. to Princess Juliana Intl., returning Thu, Jan 8, priced at $478 found 3 days ago

Sun, Jan 4 - Thu, Jan 8

PIT

Pittsburgh Intl.

SXM

Princess Juliana Intl.

$487 Roundtrip, found 3 days ago

$487

Roundtrip

found 3 days ago

Select JetBlue Airways flight, departing Sun, Jan 4 from Pittsburgh Intl. to Princess Juliana Intl., returning Thu, Jan 8, priced at $487 found 3 days ago

Thu, Jan 1 - Thu, Jan 8

PIT

Pittsburgh Intl.

SXM

Princess Juliana Intl.

$496 Roundtrip, found 3 days ago

$496

Roundtrip

found 3 days ago

Select JetBlue Airways flight, departing Thu, Jan 1 from Pittsburgh Intl. to Princess Juliana Intl., returning Thu, Jan 8, priced at $496 found 3 days ago

Wed, Dec 31 - Fri, Jan 9

PIT

Pittsburgh Intl.

SXM

Princess Juliana Intl.

$504 Roundtrip, found 3 days ago

$504

Roundtrip

found 3 days ago

Select JetBlue Airways flight, departing Wed, Dec 31 from Pittsburgh Intl. to Princess Juliana Intl., returning Fri, Jan 9, priced at $504 found 3 days ago

Fri, Jan 2 - Thu, Jan 8

PIT

Pittsburgh Intl.

SXM

Princess Juliana Intl.

$510 Roundtrip, found 3 days ago

$510

Roundtrip

found 3 days ago

Select JetBlue Airways flight, departing Fri, Jan 2 from Pittsburgh Intl. to Princess Juliana Intl., returning Thu, Jan 8, priced at $510 found 3 days ago

Wed, Dec 31 - Sat, Jan 10

PIT

Pittsburgh Intl.

SXM

Princess Juliana Intl.

$512 Roundtrip, found 3 days ago

$512

Roundtrip

found 3 days ago

Select Delta flight, departing Wed, Dec 31 from Pittsburgh Intl. to Princess Juliana Intl., returning Sat, Jan 10, priced at $512 found 3 days ago

Tue, Jan 6 - Thu, Jan 8

PIT

Pittsburgh Intl.

SXM

Princess Juliana Intl.

$513 Roundtrip, found 3 days ago

$513

Roundtrip

found 3 days ago

Select JetBlue Airways flight, departing Tue, Jan 6 from Pittsburgh Intl. to Princess Juliana Intl., returning Thu, Jan 8, priced at $513 found 3 days ago

Thu, Jan 1 - Fri, Jan 9

PIT

Pittsburgh Intl.

SXM

Princess Juliana Intl.

$522 Roundtrip, found 3 days ago

$522

Roundtrip

found 3 days ago

Select JetBlue Airways flight, departing Thu, Jan 1 from Pittsburgh Intl. to Princess Juliana Intl., returning Fri, Jan 9, priced at $522 found 3 days ago

Fri, Jan 2 - Fri, Jan 9

PIT

Pittsburgh Intl.

SXM

Princess Juliana Intl.

$536 Roundtrip, found 3 days ago

$536

Roundtrip

found 3 days ago

Select JetBlue Airways flight, departing Fri, Jan 2 from Pittsburgh Intl. to Princess Juliana Intl., returning Fri, Jan 9, priced at $536 found 3 days ago

Thu, Jan 1 - Sat, Jan 10

PIT

Pittsburgh Intl.

SXM

Princess Juliana Intl.

$537 Roundtrip, found 3 days ago

$537

Roundtrip

found 3 days ago

Select Delta flight, departing Thu, Jan 1 from Pittsburgh Intl. to Princess Juliana Intl., returning Sat, Jan 10, priced at $537 found 3 days ago

Tue, Jan 6 - Mon, Jan 12

PIT

Pittsburgh Intl.

SXM

Princess Juliana Intl.

$581 Roundtrip, found 4 days ago

$581

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Tue, Jan 6 from Pittsburgh Intl. to Princess Juliana Intl., returning Mon, Jan 12, priced at $581 found 4 days ago

Wed, Dec 31 - Mon, Jan 12

PIT

Pittsburgh Intl.

SXM

Princess Juliana Intl.

$582 Roundtrip, found 4 days ago

$582

Roundtrip

found 4 days ago

Select Delta flight, departing Wed, Dec 31 from Pittsburgh Intl. to Princess Juliana Intl., returning Mon, Jan 12, priced at $582 found 4 days ago

Mon, Jan 5 - Mon, Jan 12

PIT

Pittsburgh Intl.

SXM

Princess Juliana Intl.

$583 Roundtrip, found 4 days ago

$583

Roundtrip

found 4 days ago

Select Air Canada flight, departing Mon, Jan 5 from Pittsburgh Intl. to Princess Juliana Intl., returning Mon, Jan 12, priced at $583 found 4 days ago

Sat, Jan 3 - Mon, Jan 12

PIT

Pittsburgh Intl.

SXM

Princess Juliana Intl.

$585 Roundtrip, found 4 days ago

$585

Roundtrip

found 4 days ago

Select Air Canada flight, departing Sat, Jan 3 from Pittsburgh Intl. to Princess Juliana Intl., returning Mon, Jan 12, priced at $585 found 4 days ago

Sun, Jan 4 - Wed, Jan 7

PIT

Pittsburgh Intl.

SXM

Princess Juliana Intl.

$602 Roundtrip, found 3 days ago

$602

Roundtrip

found 3 days ago

Select American Airlines flight, departing Sun, Jan 4 from Pittsburgh Intl. to Princess Juliana Intl., returning Wed, Jan 7, priced at $602 found 3 days ago

Mon, Jan 5 - Sat, Jan 10

PIT

Pittsburgh Intl.

SXM

Princess Juliana Intl.

$604 Roundtrip, found 3 days ago

$604

Roundtrip

found 3 days ago

Select Delta flight, departing Mon, Jan 5 from Pittsburgh Intl. to Princess Juliana Intl., returning Sat, Jan 10, priced at $604 found 3 days ago

Sat, Jan 3 - Sat, Jan 10

PIT

Pittsburgh Intl.

SXM

Princess Juliana Intl.

$607 Roundtrip, found 3 days ago

$607

Roundtrip

found 3 days ago

Select Delta flight, departing Sat, Jan 3 from Pittsburgh Intl. to Princess Juliana Intl., returning Sat, Jan 10, priced at $607 found 3 days ago

Fri, Jan 2 - Wed, Jan 7

PIT

Pittsburgh Intl.

SXM

Princess Juliana Intl.

$627 Roundtrip, found 3 days ago

$627

Roundtrip

found 3 days ago

Select American Airlines flight, departing Fri, Jan 2 from Pittsburgh Intl. to Princess Juliana Intl., returning Wed, Jan 7, priced at $627 found 3 days ago

Sat, Jan 3 - Sun, Jan 11

PIT

Pittsburgh Intl.

SXM

Princess Juliana Intl.

$646 Roundtrip, found 3 days ago

$646

Roundtrip

found 3 days ago

Select American Airlines flight, departing Sat, Jan 3 from Pittsburgh Intl. to Princess Juliana Intl., returning Sun, Jan 11, priced at $646 found 3 days ago

Sun, Jan 4 - Sun, Jan 11

PIT

Pittsburgh Intl.

SXM

Princess Juliana Intl.

$647 Roundtrip, found 3 days ago

$647

Roundtrip

found 3 days ago

Select American Airlines flight, departing Sun, Jan 4 from Pittsburgh Intl. to Princess Juliana Intl., returning Sun, Jan 11, priced at $647 found 3 days ago