Cheap Flights to Windward from $135

How much is the cheapest flight to Windward?

Prices were available within the past 7 days and start at $135 for one-way flights and $255 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Thu, Apr 16 - Fri, Apr 17

SXM

Saint Martin

SBH

Gustavia

$255 Roundtrip, found 1 hour ago

$255

Roundtrip

found 1 hour ago

Select FlexFlight flight, departing Thu, Apr 16 from Saint Martin to Gustavia, returning Fri, Apr 17, priced at $255 found 1 hour ago

Wed, Apr 22 - Sun, Apr 26

SXM

Saint Martin

SBH

Gustavia

$265 Roundtrip, found 3 hours ago

$265

Roundtrip

found 3 hours ago

Select FlexFlight flight, departing Wed, Apr 22 from Saint Martin to Gustavia, returning Sun, Apr 26, priced at $265 found 3 hours ago

Sun, Apr 26 - Wed, Apr 29

SXM

Saint Martin

SBH

Gustavia

$268 Roundtrip, found 5 days ago

$268

Roundtrip

found 5 days ago

Select FlexFlight flight, departing Sun, Apr 26 from Saint Martin to Gustavia, returning Wed, Apr 29, priced at $268 found 5 days ago

Thu, Apr 16 - Mon, Apr 20

SXM

Saint Martin

SBH

Gustavia

$290 Roundtrip, found 1 hour ago

$290

Roundtrip

found 1 hour ago

Select FlexFlight flight, departing Thu, Apr 16 from Saint Martin to Gustavia, returning Mon, Apr 20, priced at $290 found 1 hour ago

Thu, Apr 16 - Fri, Apr 17

SXM

Saint Martin

SBH

Gustavia

$293 Roundtrip, found 1 hour ago

$293

Roundtrip

found 1 hour ago

Select Windward Island Airways International flight, departing Thu, Apr 16 from Saint Martin to Gustavia, returning Fri, Apr 17, priced at $293 found 1 hour ago

Sun, Apr 26 - Wed, Apr 29

SXM

Saint Martin

SBH

Gustavia

$297 Roundtrip, found 5 days ago

$297

Roundtrip

found 5 days ago

Select Windward Island Airways International flight, departing Sun, Apr 26 from Saint Martin to Gustavia, returning Wed, Apr 29, priced at $297 found 5 days ago

Thu, Apr 16 - Fri, Apr 17

SXM

Saint Martin

SBH

Gustavia

$319 Roundtrip, found 1 hour ago

$319

Roundtrip

found 1 hour ago

Select Windward Island Airways International flight, departing Thu, Apr 16 from Saint Martin to Gustavia, returning Fri, Apr 17, priced at $319 found 1 hour ago

Mon, Apr 13 - Thu, Apr 16

FLL

Fort Lauderdale

SBH

Gustavia

$578 Roundtrip, found 1 hour ago

$578

Roundtrip

found 1 hour ago

Select JetBlue Airways flight, departing Mon, Apr 13 from Fort Lauderdale to Gustavia, returning Thu, Apr 16, priced at $578 found 1 hour ago

Sun, Apr 5 - Sat, Apr 11

STT

St. Thomas

SBH

Gustavia

$590 Roundtrip, found 1 hour ago

$590

Roundtrip

found 1 hour ago

Select Cape Air flight, departing Sun, Apr 5 from St. Thomas to Gustavia, returning Sat, Apr 11, priced at $590 found 1 hour ago

Sat, Jun 13 - Thu, Jun 18

BOS

Boston

SBH

Gustavia

$641 Roundtrip, found 3 days ago

$641

Roundtrip

found 3 days ago

Select United flight, departing Sat, Jun 13 from Boston to Gustavia, returning Thu, Jun 18, priced at $641 found 3 days ago