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 $206 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, Apr 29 - Wed, May 6

SXM

Saint Martin

SBH

Gustavia

$206 Roundtrip, found 12 hours ago

$206

Roundtrip

found 12 hours ago

Select FlexFlight flight, departing Wed, Apr 29 from Saint Martin to Gustavia, returning Wed, May 6, priced at $206 found 12 hours ago

Sat, Jan 31 - Sat, Feb 7

SXM

Saint Martin

SBH

Gustavia

$239 Roundtrip, just found

$239

Roundtrip

just found

Select FlexFlight flight, departing Sat, Jan 31 from Saint Martin to Gustavia, returning Sat, Feb 7, priced at $239 just found

Tue, Jan 20 - Thu, Jan 22

SXM

Saint Martin

SBH

Gustavia

$242 Roundtrip, found 11 hours ago

$242

Roundtrip

found 11 hours ago

Select FlexFlight flight, departing Tue, Jan 20 from Saint Martin to Gustavia, returning Thu, Jan 22, priced at $242 found 11 hours ago

Sat, Jan 31 - Sat, Feb 7

SXM

Saint Martin

SBH

Gustavia

$249 Roundtrip, just found

$249

Roundtrip

just found

Select FlexFlight flight, departing Sat, Jan 31 from Saint Martin to Gustavia, returning Sat, Feb 7, priced at $249 just found

Tue, Jan 20 - Thu, Jan 22

SXM

Saint Martin

SBH

Gustavia

$252 Roundtrip, found 11 hours ago

$252

Roundtrip

found 11 hours ago

Select FlexFlight flight, departing Tue, Jan 20 from Saint Martin to Gustavia, returning Thu, Jan 22, priced at $252 found 11 hours ago

Mon, Dec 29 - Sat, Jan 10

SXM

Saint Martin

SBH

Gustavia

$293 Roundtrip, just found

$293

Roundtrip

just found

Select Windward Island Airways International flight, departing Mon, Dec 29 from Saint Martin to Gustavia, returning Sat, Jan 10, priced at $293 just found

Sat, Feb 7 - Wed, Feb 11

EWR

New York

SBH

Gustavia

$556 Roundtrip, found 6 days ago

$556

Roundtrip

found 6 days ago

Select United flight, departing Sat, Feb 7 from New York to Gustavia, returning Wed, Feb 11, priced at $556 found 6 days ago

Sun, Feb 1 - Sat, Feb 7

JFK

New York

SBH

Gustavia

$561 Roundtrip, found 1 day ago

$561

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Sun, Feb 1 from New York to Gustavia, returning Sat, Feb 7, priced at $561 found 1 day ago

Thu, Jan 1 - Sat, Jan 31

BOS

Boston

SBH

Gustavia

$566 Roundtrip, found 4 days ago

$566

Roundtrip

found 4 days ago

Select United flight, departing Thu, Jan 1 from Boston to Gustavia, returning Sat, Jan 31, priced at $566 found 4 days ago

Sun, Jan 11 - Sun, Jan 18

SJU

San Juan

SBH

Gustavia

$706 Roundtrip, found 5 hours ago

$706

Roundtrip

found 5 hours ago

Select Tradewind Aviation flight, departing Sun, Jan 11 from San Juan to Gustavia, returning Sun, Jan 18, priced at $706 found 5 hours ago