Cheap Flights to Leeward from $135

View $135 flight on Mon, Jun 22, 2026Opens in a new window

Popular airlines to Leeward

  • KLM

  • Windward Island Airways International

  • FlexFlight

  • Corsair

  • Tradewind Aviation

  • Air Caraibes

  • 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 $301 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

FlexFlight
Thu, May 14 - Wed, May 20
SXM
Saint Martin
SBH
Gustavia
$301 Roundtrip, found 10 hours ago
$301
Roundtrip
found 10 hours ago
Select FlexFlight flight, departing Thu, May 14 from Saint Martin to Gustavia, returning Wed, May 20, priced at $301 found 10 hours ago
FlexFlight
Fri, Jul 24 - Fri, Jul 31
SXM
Saint Martin
SBH
Gustavia
$311 Roundtrip, found 16 hours ago
$311
Roundtrip
found 16 hours ago
Select FlexFlight flight, departing Fri, Jul 24 from Saint Martin to Gustavia, returning Fri, Jul 31, priced at $311 found 16 hours ago
Windward Island Airways International
Thu, May 14 - Wed, May 20
SXM
Saint Martin
SBH
Gustavia
$335 Roundtrip, found 10 hours ago
$335
Roundtrip
found 10 hours ago
Select Windward Island Airways International flight, departing Thu, May 14 from Saint Martin to Gustavia, returning Wed, May 20, priced at $335 found 10 hours ago
FlexFlight
Wed, Jul 1 - Thu, Jul 2
SXM
Saint Martin
SBH
Gustavia
$336 Roundtrip, found 9 hours ago
$336
Roundtrip
found 9 hours ago
Select FlexFlight flight, departing Wed, Jul 1 from Saint Martin to Gustavia, returning Thu, Jul 2, priced at $336 found 9 hours ago
Windward Island Airways International
Thu, May 14 - Wed, May 20
SXM
Saint Martin
SBH
Gustavia
$390 Roundtrip, found 10 hours ago
$390
Roundtrip
found 10 hours ago
Select Windward Island Airways International flight, departing Thu, May 14 from Saint Martin to Gustavia, returning Wed, May 20, priced at $390 found 10 hours ago
St Barth Executive
Wed, Sep 30 - Thu, Oct 1
SXM
Saint Martin
SBH
Gustavia
$448 Roundtrip, found 16 hours ago
$448
Roundtrip
found 16 hours ago
Select St Barth Executive flight, departing Wed, Sep 30 from Saint Martin to Gustavia, returning Thu, Oct 1, priced at $448 found 16 hours ago
JetBlue Airways
Mon, May 18 - Thu, May 21
FLL
Fort Lauderdale
SBH
Gustavia
$598 Roundtrip, found 6 days ago
$598
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Mon, May 18 from Fort Lauderdale to Gustavia, returning Thu, May 21, priced at $598 found 6 days ago
United
Sun, May 24 - Wed, May 27
BOS
Boston
SBH
Gustavia
$661 Roundtrip, found 5 days ago
$661
Roundtrip
found 5 days ago
Select United flight, departing Sun, May 24 from Boston to Gustavia, returning Wed, May 27, priced at $661 found 5 days ago
JetBlue Airways
Wed, May 27 - Thu, Jun 4
JFK
New York
SBH
Gustavia
$691 Roundtrip, found 4 hours ago
$691
Roundtrip
found 4 hours ago
Select JetBlue Airways flight, departing Wed, May 27 from New York to Gustavia, returning Thu, Jun 4, priced at $691 found 4 hours ago
JetBlue Airways
Wed, Sep 9 - Mon, Sep 14
PHL
Philadelphia
SBH
Gustavia
$701 Roundtrip, found 19 hours ago
$701
Roundtrip
found 19 hours ago
Select JetBlue Airways flight, departing Wed, Sep 9 from Philadelphia to Gustavia, returning Mon, Sep 14, priced at $701 found 19 hours 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 $906
SXM
Princess Juliana Intl.
Cheapest
Flights from $906

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 6 days ago
$598
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Mon, May 18 from Fort Lauderdale to Gustavia, returning Thu, May 21, priced at $598 found 6 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 $301. 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 $301 and $701. 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 $301 to $701 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.