Cheap Flights to Leeward from $135

View $135 flight on Mon, Mar 2, 2026Opens in a new window

Popular airlines to Leeward

  • FlexFlight

  • KLM

  • Windward Island Airways International

  • Corsair

  • Air Caraibes

  • Tradewind Aviation

  • Cape Air

How much is the cheapest flight to Leeward?

Prices were available within the past 7 days and start at $135 for one-way flights and $193 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

FlexFlight
Sun, Feb 15 - Thu, Feb 19
SXM
Saint Martin
SBH
Gustavia
$193 Roundtrip, found 11 hours ago
$193
Roundtrip
found 11 hours ago
Select FlexFlight flight, departing Sun, Feb 15 from Saint Martin to Gustavia, returning Thu, Feb 19, priced at $193 found 11 hours ago
FlexFlight
Mon, Mar 2 - Fri, Mar 6
SXM
Saint Martin
SBH
Gustavia
$195 Roundtrip, just found
$195
Roundtrip
just found
Select FlexFlight flight, departing Mon, Mar 2 from Saint Martin to Gustavia, returning Fri, Mar 6, priced at $195 just found
FlexFlight
Wed, Mar 11 - Wed, Mar 18
SXM
Saint Martin
SBH
Gustavia
$213 Roundtrip, found 2 hours ago
$213
Roundtrip
found 2 hours ago
Select FlexFlight flight, departing Wed, Mar 11 from Saint Martin to Gustavia, returning Wed, Mar 18, priced at $213 found 2 hours ago
FlexFlight
Mon, Mar 2 - Fri, Mar 6
SXM
Saint Martin
SBH
Gustavia
$255 Roundtrip, just found
$255
Roundtrip
just found
Select FlexFlight flight, departing Mon, Mar 2 from Saint Martin to Gustavia, returning Fri, Mar 6, priced at $255 just found
FlexFlight
Wed, Feb 18 - Tue, Feb 24
SXM
Saint Martin
SBH
Gustavia
$258 Roundtrip, found 15 hours ago
$258
Roundtrip
found 15 hours ago
Select FlexFlight flight, departing Wed, Feb 18 from Saint Martin to Gustavia, returning Tue, Feb 24, priced at $258 found 15 hours ago
Windward Island Airways International
Tue, Feb 24 - Sun, Mar 8
SXM
Saint Martin
SBH
Gustavia
$317 Roundtrip, found 5 days ago
$317
Roundtrip
found 5 days ago
Select Windward Island Airways International flight, departing Tue, Feb 24 from Saint Martin to Gustavia, returning Sun, Mar 8, priced at $317 found 5 days ago
JetBlue Airways
Fri, Apr 17 - Sun, Apr 19
FLL
Fort Lauderdale
SBH
Gustavia
$544 Roundtrip, found 5 days ago
$544
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Fri, Apr 17 from Fort Lauderdale to Gustavia, returning Sun, Apr 19, priced at $544 found 5 days ago
JetBlue Airways
Sat, Feb 21 - Tue, Feb 24
ATL
Atlanta
SBH
Gustavia
$578 Roundtrip, found 4 hours ago
$578
Roundtrip
found 4 hours ago
Select JetBlue Airways flight, departing Sat, Feb 21 from Atlanta to Gustavia, returning Tue, Feb 24, priced at $578 found 4 hours ago
United
Fri, Mar 20 - Wed, Mar 25
EWR
New York
SBH
Gustavia
$583 Roundtrip, found 6 days ago
$583
Roundtrip
found 6 days ago
Select United flight, departing Fri, Mar 20 from New York to Gustavia, returning Wed, Mar 25, priced at $583 found 6 days ago
interCaribbean Airways
Fri, Jun 5 - Tue, Jun 16
SJU
San Juan
SBH
Gustavia
$781 Roundtrip, found 1 day ago
$781
Roundtrip
found 1 day ago
Select interCaribbean Airways flight, departing Fri, Jun 5 from San Juan to Gustavia, returning Tue, Jun 16, priced at $781 found 1 day 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 $256
SXM
Princess Juliana Intl.
Cheapest
Flights from $256
Select flight to Clayton J. Lloyd Intl. AXA. Flights from $718
AXA
Clayton J. Lloyd Intl.
Flights from $718
Select flight to Gustaf III SBH. Flights from $901
SBH
Gustaf III
Flights from $901

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

*Flight schedules are subject to change.

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 $193. 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 $193 and $781. If you were journeying one way out of Saint Martin (SXM), you could have picked up a fare from just $135.
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 $193 to $781 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.

*Flight schedules are subject to change.

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.

JetBlue Airways
Fri, Apr 17 - Sun, Apr 19
FLL
Fort Lauderdale
SBH
Gustavia
$544 Roundtrip, found 5 days ago
$544
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Fri, Apr 17 from Fort Lauderdale to Gustavia, returning Sun, Apr 19, priced at $544 found 5 days ago
*Available to One Key members.