Cheap Flights to Leeward from $135

View $135 flight on Wed, Jul 1, 2026Opens in a new window

Popular airlines to Leeward

  • KLM

  • Windward Island Airways International

  • FlexFlight

  • Corsair

  • Air Caraibes

  • Tradewind Aviation

  • Cape Air

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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 $213 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

FlexFlight
Wed, Jul 1 - Fri, Jul 10
SXM
Saint Martin
SBH
Gustavia
$213 Roundtrip, just found
$213
Roundtrip
just found
Select FlexFlight flight, departing Wed, Jul 1 from Saint Martin to Gustavia, returning Fri, Jul 10, priced at $213 just found
FlexFlight
Fri, May 22 - Thu, May 28
SXM
Saint Martin
SBH
Gustavia
$277 Roundtrip, found 6 days ago
$277
Roundtrip
found 6 days ago
Select FlexFlight flight, departing Fri, May 22 from Saint Martin to Gustavia, returning Thu, May 28, priced at $277 found 6 days ago
FlexFlight
Wed, Jul 1 - Mon, Jul 6
SXM
Saint Martin
SBH
Gustavia
$302 Roundtrip, just found
$302
Roundtrip
just found
Select FlexFlight flight, departing Wed, Jul 1 from Saint Martin to Gustavia, returning Mon, Jul 6, priced at $302 just found
FlexFlight
Wed, Jul 1 - Mon, Jul 6
SXM
Saint Martin
SBH
Gustavia
$307 Roundtrip, just found
$307
Roundtrip
just found
Select FlexFlight flight, departing Wed, Jul 1 from Saint Martin to Gustavia, returning Mon, Jul 6, priced at $307 just found
Windward Island Airways International
Fri, May 22 - Thu, May 28
SXM
Saint Martin
SBH
Gustavia
$311 Roundtrip, found 6 days ago
$311
Roundtrip
found 6 days ago
Select Windward Island Airways International flight, departing Fri, May 22 from Saint Martin to Gustavia, returning Thu, May 28, priced at $311 found 6 days ago
FlexFlight
Sun, Jul 19 - Sat, Jul 25
SXM
Saint Martin
SBH
Gustavia
$312 Roundtrip, found 5 hours ago
$312
Roundtrip
found 5 hours ago
Select FlexFlight flight, departing Sun, Jul 19 from Saint Martin to Gustavia, returning Sat, Jul 25, priced at $312 found 5 hours ago
Windward Island Airways International
Fri, May 22 - Thu, May 28
SXM
Saint Martin
SBH
Gustavia
$351 Roundtrip, found 6 days ago
$351
Roundtrip
found 6 days ago
Select Windward Island Airways International flight, departing Fri, May 22 from Saint Martin to Gustavia, returning Thu, May 28, priced at $351 found 6 days ago
St Barth Executive
Thu, Oct 15 - Mon, Oct 19
SXM
Saint Martin
SBH
Gustavia
$448 Roundtrip, found 4 days ago
$448
Roundtrip
found 4 days ago
Select St Barth Executive flight, departing Thu, Oct 15 from Saint Martin to Gustavia, returning Mon, Oct 19, priced at $448 found 4 days ago
JetBlue Airways
Mon, May 18 - Thu, May 21
FLL
Fort Lauderdale
SBH
Gustavia
$598 Roundtrip, found 4 days ago
$598
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Mon, May 18 from Fort Lauderdale to Gustavia, returning Thu, May 21, priced at $598 found 4 days ago
United
Sun, May 24 - Wed, May 27
BOS
Boston
SBH
Gustavia
$661 Roundtrip, found 3 days ago
$661
Roundtrip
found 3 days ago
Select United flight, departing Sun, May 24 from Boston to Gustavia, returning Wed, May 27, priced at $661 found 3 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 $700
SXM
Princess Juliana Intl.
Cheapest
Flights from $700

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
Mon, May 18 - Thu, May 21
FLL
Fort Lauderdale
SBH
Gustavia
$598 Roundtrip, found 4 days ago
$598
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Mon, May 18 from Fort Lauderdale to Gustavia, returning Thu, May 21, priced at $598 found 4 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 $213. 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 $213 and $661. 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 $213 to $661 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.

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Travel information

*Flight schedules are subject to change.

*Available to One Key members.

 

*Flight schedules are subject to change.

*Available to One Key members.

 

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