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 $306 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, Jun 24 - Sun, Jun 28

SXM

Saint Martin

SBH

Gustavia

$306 Roundtrip, found 5 days ago

$306

Roundtrip

found 5 days ago

Select FlexFlight flight, departing Wed, Jun 24 from Saint Martin to Gustavia, returning Sun, Jun 28, priced at $306 found 5 days ago

Wed, Jun 24 - Tue, Jun 30

SXM

Saint Martin

SBH

Gustavia

$324 Roundtrip, found 4 days ago

$324

Roundtrip

found 4 days ago

Select Windward Island Airways International flight, departing Wed, Jun 24 from Saint Martin to Gustavia, returning Tue, Jun 30, priced at $324 found 4 days ago

Wed, Jun 24 - Sat, Jun 27

SXM

Saint Martin

SBH

Gustavia

$346 Roundtrip, found 5 days ago

$346

Roundtrip

found 5 days ago

Select FlexFlight flight, departing Wed, Jun 24 from Saint Martin to Gustavia, returning Sat, Jun 27, priced at $346 found 5 days ago

Tue, Aug 25 - Sat, Aug 29

SXM

Saint Martin

SBH

Gustavia

$456 Roundtrip, found 6 hours ago

$456

Roundtrip

found 6 hours ago

Select St Barth Executive flight, departing Tue, Aug 25 from Saint Martin to Gustavia, returning Sat, Aug 29, priced at $456 found 6 hours ago

Thu, Sep 10 - Sun, Sep 13

FLL

Fort Lauderdale

SBH

Gustavia

$616 Roundtrip, found 6 days ago

$616

Roundtrip

found 6 days ago

Select JetBlue Airways flight, departing Thu, Sep 10 from Fort Lauderdale to Gustavia, returning Sun, Sep 13, priced at $616 found 6 days ago

Sun, Dec 27 - Fri, Jan 1

SJU

San Juan

SBH

Gustavia

$620 Roundtrip, found 6 days ago

$620

Roundtrip

found 6 days ago

Select Contour Airlines flight, departing Sun, Dec 27 from San Juan to Gustavia, returning Fri, Jan 1, priced at $620 found 6 days ago

Mon, Jul 20 - Fri, Jul 24

JFK

New York

SBH

Gustavia

$647 Roundtrip, found 3 hours ago

$647

Roundtrip

found 3 hours ago

Select JetBlue Airways flight, departing Mon, Jul 20 from New York to Gustavia, returning Fri, Jul 24, priced at $647 found 3 hours ago

Sat, Jul 25 - Tue, Jul 28

EWR

New York

SBH

Gustavia

$672 Roundtrip, found 6 days ago

$672

Roundtrip

found 6 days ago

Select United flight, departing Sat, Jul 25 from New York to Gustavia, returning Tue, Jul 28, priced at $672 found 6 days ago

Thu, Sep 17 - Thu, Sep 24

ORD

Chicago

SBH

Gustavia

$678 Roundtrip, found 5 days ago

$678

Roundtrip

found 5 days ago

Select JetBlue Airways flight, departing Thu, Sep 17 from Chicago to Gustavia, returning Thu, Sep 24, priced at $678 found 5 days ago

Thu, Aug 27 - Mon, Aug 31

PHL

Philadelphia

SBH

Gustavia

$692 Roundtrip, found 5 days ago

$692

Roundtrip

found 5 days ago

Select JetBlue Airways flight, departing Thu, Aug 27 from Philadelphia to Gustavia, returning Mon, Aug 31, priced at $692 found 5 days ago