Cheap Flights to Windward from $212

How much is the cheapest flight to Windward?

Prices were available within the past 7 days and start at $212 for one-way flights and $366 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Tue, Nov 17 - Tue, Nov 17

SXM

Saint Martin

SBH

Gustavia

$366 Roundtrip, found 4 days ago

$366

Roundtrip

found 4 days ago

Select Bargain Flight flight, departing Tue, Nov 17 from Saint Martin to Gustavia, returning Tue, Nov 17, priced at $366 found 4 days ago

Fri, Sep 18 - Fri, Sep 25

STT

St. Thomas

SBH

Gustavia

$615 Roundtrip, found 3 hours ago

$615

Roundtrip

found 3 hours ago

Select Cape Air flight, departing Fri, Sep 18 from St. Thomas to Gustavia, returning Fri, Sep 25, priced at $615 found 3 hours ago

Fri, Aug 21 - Tue, Aug 25

SJU

San Juan

SBH

Gustavia

$778 Roundtrip, just found

$778

Roundtrip

just found

Select Contour Airlines flight, departing Fri, Aug 21 from San Juan to Gustavia, returning Tue, Aug 25, priced at $778 just found

Tue, Jan 26 - Mon, Feb 1

BOS

Boston

SBH

Gustavia

$809 Roundtrip, found 3 days ago

$809

Roundtrip

found 3 days ago

Select United flight, departing Tue, Jan 26 from Boston to Gustavia, returning Mon, Feb 1, priced at $809 found 3 days ago

Mon, Aug 24 - Sun, Sep 6

JFK

New York

SBH

Gustavia

$811 Roundtrip, found 5 days ago

$811

Roundtrip

found 5 days ago

Select JetBlue Airways flight, departing Mon, Aug 24 from New York to Gustavia, returning Sun, Sep 6, priced at $811 found 5 days ago

Tue, Jan 26 - Tue, Feb 2

DCA

Washington

SBH

Gustavia

$940 Roundtrip, found 5 days ago

$940

Roundtrip

found 5 days ago

Select American Airlines flight, departing Tue, Jan 26 from Washington to Gustavia, returning Tue, Feb 2, priced at $940 found 5 days ago

Mon, Jan 4 - Mon, Feb 1

BWI

Baltimore

SBH

Gustavia

$956 Roundtrip, found 3 days ago

$956

Roundtrip

found 3 days ago

Select United flight, departing Mon, Jan 4 from Baltimore to Gustavia, returning Mon, Feb 1, priced at $956 found 3 days ago

Sat, Sep 5 - Wed, Sep 9

FLL

Fort Lauderdale

SBH

Gustavia

$998 Roundtrip, found 1 day ago

$998

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Sat, Sep 5 from Fort Lauderdale to Gustavia, returning Wed, Sep 9, priced at $998 found 1 day ago

Tue, May 4 - Tue, May 11

PWM

Portland

SBH

Gustavia

$1,012 Roundtrip, found 6 hours ago

$1,012

Roundtrip

found 6 hours ago

Select American Airlines flight, departing Tue, May 4 from Portland to Gustavia, returning Tue, May 11, priced at $1,012 found 6 hours ago

Wed, May 5 - Sun, May 9

TTN

Trenton

SBH

Gustavia

$1,041 Roundtrip, found 1 day ago

$1,041

Roundtrip

found 1 day ago

Select American Airlines flight, departing Wed, May 5 from Trenton to Gustavia, returning Sun, May 9, priced at $1,041 found 1 day ago