Flights from Cleveland to Simpson Bay

Cheapest flights from Cleveland

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, Jul 10 - Sat, Jul 19

CLE

Hopkins Intl.

SXM

Princess Juliana Intl.

$373 Roundtrip, found 23 hours ago

$373

Roundtrip

found 23 hours ago

Select Frontier Airlines flight, departing Thu, Jul 10 from Hopkins Intl. to Princess Juliana Intl., returning Sat, Jul 19, priced at $373 found 23 hours ago

Thu, Jul 10 - Fri, Jul 18

CLE

Hopkins Intl.

SXM

Princess Juliana Intl.

$383 Roundtrip, found 23 hours ago

$383

Roundtrip

found 23 hours ago

Select Frontier Airlines flight, departing Thu, Jul 10 from Hopkins Intl. to Princess Juliana Intl., returning Fri, Jul 18, priced at $383 found 23 hours ago

Sat, Jul 12 - Sat, Jul 19

CLE

Hopkins Intl.

SXM

Princess Juliana Intl.

$407 Roundtrip, found 23 hours ago

$407

Roundtrip

found 23 hours ago

Select Frontier Airlines flight, departing Sat, Jul 12 from Hopkins Intl. to Princess Juliana Intl., returning Sat, Jul 19, priced at $407 found 23 hours ago

Sat, Jul 12 - Fri, Jul 18

CLE

Hopkins Intl.

SXM

Princess Juliana Intl.

$417 Roundtrip, found 23 hours ago

$417

Roundtrip

found 23 hours ago

Select Frontier Airlines flight, departing Sat, Jul 12 from Hopkins Intl. to Princess Juliana Intl., returning Fri, Jul 18, priced at $417 found 23 hours ago

Mon, Jul 14 - Sat, Jul 19

CLE

Hopkins Intl.

SXM

Princess Juliana Intl.

$426 Roundtrip, found 23 hours ago

$426

Roundtrip

found 23 hours ago

Select Frontier Airlines flight, departing Mon, Jul 14 from Hopkins Intl. to Princess Juliana Intl., returning Sat, Jul 19, priced at $426 found 23 hours ago

Mon, Jul 14 - Fri, Jul 18

CLE

Hopkins Intl.

SXM

Princess Juliana Intl.

$436 Roundtrip, found 23 hours ago

$436

Roundtrip

found 23 hours ago

Select Frontier Airlines flight, departing Mon, Jul 14 from Hopkins Intl. to Princess Juliana Intl., returning Fri, Jul 18, priced at $436 found 23 hours ago

Tue, Jul 15 - Fri, Jul 18

CLE

Hopkins Intl.

SXM

Princess Juliana Intl.

$506 Roundtrip, found 23 hours ago

$506

Roundtrip

found 23 hours ago

Select Spirit Airlines flight, departing Tue, Jul 15 from Hopkins Intl. to Princess Juliana Intl., returning Fri, Jul 18, priced at $506 found 23 hours ago

Tue, Jul 15 - Mon, Jul 21

CLE

Hopkins Intl.

SXM

Princess Juliana Intl.

$509 Roundtrip, found 23 hours ago

$509

Roundtrip

found 23 hours ago

Select Spirit Airlines flight, departing Tue, Jul 15 from Hopkins Intl. to Princess Juliana Intl., returning Mon, Jul 21, priced at $509 found 23 hours ago

Wed, Jul 9 - Wed, Jul 16

CLE

Hopkins Intl.

SXM

Princess Juliana Intl.

$537 Roundtrip, found 23 hours ago

$537

Roundtrip

found 23 hours ago

Select Delta flight, departing Wed, Jul 9 from Hopkins Intl. to Princess Juliana Intl., returning Wed, Jul 16, priced at $537 found 23 hours ago

Mon, Jul 14 - Wed, Jul 16

CLE

Hopkins Intl.

SXM

Princess Juliana Intl.

$551 Roundtrip, found 23 hours ago

$551

Roundtrip

found 23 hours ago

Select Delta flight, departing Mon, Jul 14 from Hopkins Intl. to Princess Juliana Intl., returning Wed, Jul 16, priced at $551 found 23 hours ago

Wed, Jul 9 - Tue, Jul 15

CLE

Hopkins Intl.

SXM

Princess Juliana Intl.

$574 Roundtrip, found 23 hours ago

$574

Roundtrip

found 23 hours ago

Select Delta flight, departing Wed, Jul 9 from Hopkins Intl. to Princess Juliana Intl., returning Tue, Jul 15, priced at $574 found 23 hours ago

Mon, Jul 14 - Tue, Jul 15

CLE

Hopkins Intl.

SXM

Princess Juliana Intl.

$581 Roundtrip, found 23 hours ago

$581

Roundtrip

found 23 hours ago

Select Delta flight, departing Mon, Jul 14 from Hopkins Intl. to Princess Juliana Intl., returning Tue, Jul 15, priced at $581 found 23 hours ago

Sat, Jul 12 - Wed, Jul 16

CLE

Hopkins Intl.

SXM

Princess Juliana Intl.

$599 Roundtrip, found 23 hours ago

$599

Roundtrip

found 23 hours ago

Select Delta flight, departing Sat, Jul 12 from Hopkins Intl. to Princess Juliana Intl., returning Wed, Jul 16, priced at $599 found 23 hours ago

Thu, Jul 10 - Wed, Jul 16

CLE

Hopkins Intl.

SXM

Princess Juliana Intl.

$627 Roundtrip, found 23 hours ago

$627

Roundtrip

found 23 hours ago

Select United flight, departing Thu, Jul 10 from Hopkins Intl. to Princess Juliana Intl., returning Wed, Jul 16, priced at $627 found 23 hours ago

Sat, Jul 12 - Tue, Jul 15

CLE

Hopkins Intl.

SXM

Princess Juliana Intl.

$627 Roundtrip, found 23 hours ago

$627

Roundtrip

found 23 hours ago

Select American Airlines flight, departing Sat, Jul 12 from Hopkins Intl. to Princess Juliana Intl., returning Tue, Jul 15, priced at $627 found 23 hours ago

Mon, Jul 14 - Sun, Jul 20

CLE

Hopkins Intl.

SXM

Princess Juliana Intl.

$629 Roundtrip, found 23 hours ago

$629

Roundtrip

found 23 hours ago

Select Delta flight, departing Mon, Jul 14 from Hopkins Intl. to Princess Juliana Intl., returning Sun, Jul 20, priced at $629 found 23 hours ago

Sun, Jul 13 - Wed, Jul 16

CLE

Hopkins Intl.

SXM

Princess Juliana Intl.

$641 Roundtrip, found 23 hours ago

$641

Roundtrip

found 23 hours ago

Select United flight, departing Sun, Jul 13 from Hopkins Intl. to Princess Juliana Intl., returning Wed, Jul 16, priced at $641 found 23 hours ago

Wed, Jul 9 - Sat, Jul 19

CLE

Hopkins Intl.

SXM

Princess Juliana Intl.

$652 Roundtrip, found 23 hours ago

$652

Roundtrip

found 23 hours ago

Select American Airlines flight, departing Wed, Jul 9 from Hopkins Intl. to Princess Juliana Intl., returning Sat, Jul 19, priced at $652 found 23 hours ago

Sun, Jul 13 - Sun, Jul 20

CLE

Hopkins Intl.

SXM

Princess Juliana Intl.

$662 Roundtrip, found 23 hours ago

$662

Roundtrip

found 23 hours ago

Select American Airlines flight, departing Sun, Jul 13 from Hopkins Intl. to Princess Juliana Intl., returning Sun, Jul 20, priced at $662 found 23 hours ago

Tue, Jul 15 - Sat, Jul 19

CLE

Hopkins Intl.

SXM

Princess Juliana Intl.

$666 Roundtrip, found 23 hours ago

$666

Roundtrip

found 23 hours ago

Select American Airlines flight, departing Tue, Jul 15 from Hopkins Intl. to Princess Juliana Intl., returning Sat, Jul 19, priced at $666 found 23 hours ago