Flights from Boston to Simpson Bay

Cheapest flights from Boston

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.

Sat, Oct 25 - Sat, Nov 1

BOS

Logan Intl.

SXM

Princess Juliana Intl.

$377 Roundtrip, found 1 day ago

$377

Roundtrip

found 1 day ago

Select United flight, departing Sat, Oct 25 from Logan Intl. to Princess Juliana Intl., returning Sat, Nov 1, priced at $377 found 1 day ago

Sat, Oct 25 - Sat, Nov 1

BOS

Logan Intl.

SXM

Princess Juliana Intl.

$382 Roundtrip, found 1 day ago

$382

Roundtrip

found 1 day ago

Select United flight, departing Sat, Oct 25 from Logan Intl. to Princess Juliana Intl., returning Sat, Nov 1, priced at $382 found 1 day ago

Sat, Oct 25 - Sat, Nov 1

BOS

Logan Intl.

SXM

Princess Juliana Intl.

$399 Roundtrip, found 1 day ago

$399

Roundtrip

found 1 day ago

Select United flight, departing Sat, Oct 25 from Logan Intl. to Princess Juliana Intl., returning Sat, Nov 1, priced at $399 found 1 day ago

Sun, Oct 26 - Mon, Nov 3

BOS

Logan Intl.

SXM

Princess Juliana Intl.

$400 Roundtrip, found 1 day ago

$400

Roundtrip

found 1 day ago

Select Delta flight, departing Sun, Oct 26 from Logan Intl. to Princess Juliana Intl., returning Mon, Nov 3, priced at $400 found 1 day ago

Sat, Oct 25 - Sat, Nov 1

BOS

Logan Intl.

SXM

Princess Juliana Intl.

$403 Roundtrip, found 1 day ago

$403

Roundtrip

found 1 day ago

Select United flight, departing Sat, Oct 25 from Logan Intl. to Princess Juliana Intl., returning Sat, Nov 1, priced at $403 found 1 day ago

Mon, Oct 27 - Wed, Oct 29

BOS

Logan Intl.

SXM

Princess Juliana Intl.

$409 Roundtrip, found 1 day ago

$409

Roundtrip

found 1 day ago

Select Delta flight, departing Mon, Oct 27 from Logan Intl. to Princess Juliana Intl., returning Wed, Oct 29, priced at $409 found 1 day ago

Sun, Oct 26 - Wed, Oct 29

BOS

Logan Intl.

SXM

Princess Juliana Intl.

$416 Roundtrip, found 1 day ago

$416

Roundtrip

found 1 day ago

Select Delta flight, departing Sun, Oct 26 from Logan Intl. to Princess Juliana Intl., returning Wed, Oct 29, priced at $416 found 1 day ago

Wed, Oct 22 - Wed, Oct 29

BOS

Logan Intl.

SXM

Princess Juliana Intl.

$420 Roundtrip, found 1 day ago

$420

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Wed, Oct 22 from Logan Intl. to Princess Juliana Intl., returning Wed, Oct 29, priced at $420 found 1 day ago

Wed, Oct 22 - Fri, Oct 31

BOS

Logan Intl.

SXM

Princess Juliana Intl.

$429 Roundtrip, found 1 day ago

$429

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Wed, Oct 22 from Logan Intl. to Princess Juliana Intl., returning Fri, Oct 31, priced at $429 found 1 day ago

Fri, Oct 24 - Sat, Nov 1

BOS

Logan Intl.

SXM

Princess Juliana Intl.

$432 Roundtrip, found 1 day ago

$432

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Fri, Oct 24 from Logan Intl. to Princess Juliana Intl., returning Sat, Nov 1, priced at $432 found 1 day ago

Sat, Oct 25 - Sat, Nov 1

BOS

Logan Intl.

SXM

Princess Juliana Intl.

$435 Roundtrip, found 1 day ago

$435

Roundtrip

found 1 day ago

Select United flight, departing Sat, Oct 25 from Logan Intl. to Princess Juliana Intl., returning Sat, Nov 1, priced at $435 found 1 day ago

Sat, Oct 25 - Sat, Nov 1

BOS

Logan Intl.

SXM

Princess Juliana Intl.

$436 Roundtrip, found 1 day ago

$436

Roundtrip

found 1 day ago

Select American Airlines flight, departing Sat, Oct 25 from Logan Intl. to Princess Juliana Intl., returning Sat, Nov 1, priced at $436 found 1 day ago

Fri, Oct 24 - Wed, Oct 29

BOS

Logan Intl.

SXM

Princess Juliana Intl.

$437 Roundtrip, found 1 day ago

$437

Roundtrip

found 1 day ago

Select Delta flight, departing Fri, Oct 24 from Logan Intl. to Princess Juliana Intl., returning Wed, Oct 29, priced at $437 found 1 day ago

Sat, Oct 25 - Sat, Nov 1

BOS

Logan Intl.

SXM

Princess Juliana Intl.

$439 Roundtrip, found 1 day ago

$439

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Sat, Oct 25 from Logan Intl. to Princess Juliana Intl., returning Sat, Nov 1, priced at $439 found 1 day ago

Sat, Oct 25 - Sat, Nov 1

BOS

Logan Intl.

SXM

Princess Juliana Intl.

$442 Roundtrip, found 1 day ago

$442

Roundtrip

found 1 day ago

Select American Airlines flight, departing Sat, Oct 25 from Logan Intl. to Princess Juliana Intl., returning Sat, Nov 1, priced at $442 found 1 day ago

Wed, Oct 22 - Sat, Nov 1

BOS

Logan Intl.

SXM

Princess Juliana Intl.

$450 Roundtrip, found 1 day ago

$450

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Wed, Oct 22 from Logan Intl. to Princess Juliana Intl., returning Sat, Nov 1, priced at $450 found 1 day ago

Sat, Oct 25 - Sat, Nov 1

BOS

Logan Intl.

SXM

Princess Juliana Intl.

$457 Roundtrip, found 1 day ago

$457

Roundtrip

found 1 day ago

Select United flight, departing Sat, Oct 25 from Logan Intl. to Princess Juliana Intl., returning Sat, Nov 1, priced at $457 found 1 day ago

Sun, Oct 26 - Tue, Nov 4

BOS

Logan Intl.

SXM

Princess Juliana Intl.

$490 Roundtrip, found 1 day ago

$490

Roundtrip

found 1 day ago

Select American Airlines flight, departing Sun, Oct 26 from Logan Intl. to Princess Juliana Intl., returning Tue, Nov 4, priced at $490 found 1 day ago

Sat, Oct 25 - Sat, Nov 1

BOS

Logan Intl.

SXM

Princess Juliana Intl.

$549 Roundtrip, found 1 day ago

$549

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Sat, Oct 25 from Logan Intl. to Princess Juliana Intl., returning Sat, Nov 1, priced at $549 found 1 day ago

Sat, Oct 25 - Sat, Nov 1

BOS

Logan Intl.

SXM

Princess Juliana Intl.

$572 Roundtrip, found 1 day ago

$572

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Sat, Oct 25 from Logan Intl. to Princess Juliana Intl., returning Sat, Nov 1, priced at $572 found 1 day ago