Cheap Flights to Windward from $129

How much is the cheapest flight to Windward?

Prices were available within the past 7 days and start at $129 for one-way flights and $189 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, Feb 6 - Thu, Feb 12

SXM

Saint Martin

SBH

Gustavia

$189 Roundtrip, found 1 hour ago

$189

Roundtrip

found 1 hour ago

Select FlexFlight flight, departing Fri, Feb 6 from Saint Martin to Gustavia, returning Thu, Feb 12, priced at $189 found 1 hour ago

Tue, Feb 3 - Tue, Feb 10

SXM

Saint Martin

SBH

Gustavia

$206 Roundtrip, found 1 hour ago

$206

Roundtrip

found 1 hour ago

Select FlexFlight flight, departing Tue, Feb 3 from Saint Martin to Gustavia, returning Tue, Feb 10, priced at $206 found 1 hour ago

Fri, Jan 30 - Wed, Feb 4

SXM

Saint Martin

SBH

Gustavia

$239 Roundtrip, found 5 hours ago

$239

Roundtrip

found 5 hours ago

Select FlexFlight flight, departing Fri, Jan 30 from Saint Martin to Gustavia, returning Wed, Feb 4, priced at $239 found 5 hours ago

Fri, Jan 9 - Mon, Jan 12

SXM

Saint Martin

SBH

Gustavia

$242 Roundtrip, found 15 hours ago

$242

Roundtrip

found 15 hours ago

Select FlexFlight flight, departing Fri, Jan 9 from Saint Martin to Gustavia, returning Mon, Jan 12, priced at $242 found 15 hours ago

Fri, Jan 30 - Wed, Feb 4

SXM

Saint Martin

SBH

Gustavia

$293 Roundtrip, found 5 hours ago

$293

Roundtrip

found 5 hours ago

Select Windward Island Airways International flight, departing Fri, Jan 30 from Saint Martin to Gustavia, returning Wed, Feb 4, priced at $293 found 5 hours ago

Wed, Apr 8 - Wed, Apr 15

FLL

Fort Lauderdale

SBH

Gustavia

$547 Roundtrip, found 12 hours ago

$547

Roundtrip

found 12 hours ago

Select JetBlue Airways flight, departing Wed, Apr 8 from Fort Lauderdale to Gustavia, returning Wed, Apr 15, priced at $547 found 12 hours ago

Mon, Feb 9 - Tue, Feb 10

EWR

New York

SBH

Gustavia

$551 Roundtrip, found 16 hours ago

$551

Roundtrip

found 16 hours ago

Select United flight, departing Mon, Feb 9 from New York to Gustavia, returning Tue, Feb 10, priced at $551 found 16 hours ago

Thu, Jan 8 - Thu, Jan 15

JFK

New York

SBH

Gustavia

$561 Roundtrip, found 3 days ago

$561

Roundtrip

found 3 days ago

Select JetBlue Airways flight, departing Thu, Jan 8 from New York to Gustavia, returning Thu, Jan 15, priced at $561 found 3 days ago

Tue, Jan 27 - Sat, Jan 31

BOS

Boston

SBH

Gustavia

$566 Roundtrip, found 16 hours ago

$566

Roundtrip

found 16 hours ago

Select United flight, departing Tue, Jan 27 from Boston to Gustavia, returning Sat, Jan 31, priced at $566 found 16 hours ago

Thu, Jan 1 - Mon, Jan 12

AXA

The Valley

SBH

Gustavia

$568 Roundtrip, found 1 day ago

$568

Roundtrip

found 1 day ago

Select World Ticket Ltd flight, departing Thu, Jan 1 from The Valley to Gustavia, returning Mon, Jan 12, priced at $568 found 1 day ago