A coastal town with colorful buildings, a marina with boats, and a mountainous backdrop.

Cheap Flights to Leeward from $212

View $212 flight on Wed, Nov 18, 2026Opens in a new window

Popular airlines to Leeward

  • Air France

  • KLM

  • Windward Island Airways International

  • Corsair

  • Cape Air

  • Tradewind Aviation

  • Air Caraibes

How much is the cheapest flight to Leeward?

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.

Bargain Flight
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
Cape Air
Fri, Sep 18 - Fri, Sep 25
STT
St. Thomas
SBH
Gustavia
$615 Roundtrip, found 4 hours ago
$615
Roundtrip
found 4 hours ago
Select Cape Air flight, departing Fri, Sep 18 from St. Thomas to Gustavia, returning Fri, Sep 25, priced at $615 found 4 hours ago
Contour Airlines
Fri, Sep 4 - Sun, Sep 6
SJU
San Juan
SBH
Gustavia
$778 Roundtrip, just found
$778
Roundtrip
just found
Select Contour Airlines flight, departing Fri, Sep 4 from San Juan to Gustavia, returning Sun, Sep 6, priced at $778 just found
United
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
JetBlue Airways
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
American Airlines
Tue, Jan 26 - Tue, Feb 2
DCA
Washington
SBH
Gustavia
$940 Roundtrip, found 4 days ago
$940
Roundtrip
found 4 days ago
Select American Airlines flight, departing Tue, Jan 26 from Washington to Gustavia, returning Tue, Feb 2, priced at $940 found 4 days ago
United
Mon, Jan 4 - Mon, Feb 1
BWI
Baltimore
SBH
Gustavia
$956 Roundtrip, found 2 days ago
$956
Roundtrip
found 2 days ago
Select United flight, departing Mon, Jan 4 from Baltimore to Gustavia, returning Mon, Feb 1, priced at $956 found 2 days ago
JetBlue Airways
Sat, Aug 22 - Fri, Aug 28
FLL
Fort Lauderdale
SBH
Gustavia
$957 Roundtrip, found 6 days ago
$957
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Sat, Aug 22 from Fort Lauderdale to Gustavia, returning Fri, Aug 28, priced at $957 found 6 days ago
United
Fri, Jan 22 - Tue, Jan 26
RDU
Raleigh
SBH
Gustavia
$984 Roundtrip, found 3 days ago
$984
Roundtrip
found 3 days ago
Select United flight, departing Fri, Jan 22 from Raleigh to Gustavia, returning Tue, Jan 26, priced at $984 found 3 days ago
JetBlue Airways
Thu, Oct 29 - Mon, Nov 2
MCO
Orlando
SBH
Gustavia
$1,011 Roundtrip, found 6 days ago
$1,011
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Thu, Oct 29 from Orlando to Gustavia, returning Mon, Nov 2, priced at $1,011 found 6 days ago

Airports in Leeward

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Princess Juliana Intl. SXM. Cheapest option available. Flights from $481
SXM
Princess Juliana Intl.
Cheapest
Flights from $481

Trending flights to Leeward

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
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

Frequently asked questions

How do I find cheap flights to Leeward that have flexible change policies?
It's as easy as counting 1-2-3 with Expedia. Step 1: Enter your travel details and click "Search." Step 2: Check "No change fee" directly underneath the "Flexible change policies" filter to the left of the screen. Step 3. Reserve your flexible and cheap flight to Leeward.
How can I find cheap tickets to Leeward?
One of the best ways to get your hands on cheap tickets to Leeward is to be flexible with your travel dates. Search for your flights, then click "flexible dates" at the top of your results. You'll see the cheapest prices for nearby days. The best price for a flight to Leeward in the last seven days was $366. Booking well ahead of time will usually help you get an even bigger bargain.
How much is a flight to Leeward?
The price of a round-trip journey to Leeward in the last seven days ranged between $366 and $1,011. If you were journeying one way out of Saint Martin (SXM), you could have picked up a fare from just $212.
When is the cheapest time to fly to Leeward?
If you can be flexible with what date you jet off to Leeward, fly out early on in the week. The most economical day to take off is usually Tuesday, closely followed by Monday. Saturday is typically the priciest day, with many vacationers preferring to fly on weekends.
How much is a plane ticket to Leeward?
Plane tickets to Leeward ranged from $366 to $1,011 in the last seven days. Typically, the earlier you make a reservation, the bigger the bargain.
What months are the cheapest to book a flight to Leeward?
Snap up a ticket in February for bargain flight deals to Leeward. December is often the most expensive time to buy a seat.

Book with confidence

Enjoy extra legroom, flight flexibility, and a seamless travel experience.

Travel information

*Flight schedules are subject to change.

*Available to One Key members.

 

*Flight schedules are subject to change.

*Available to One Key members.