Cheap Flights to Leeward from $129

View $129 flight on Thu, Jan 15, 2026Opens in a new window

Popular airlines to Leeward

  • FlexFlight

    FlexFlight

  • Windward Island Airways International

    Windward Island Airways International

  • Air Caraibes

    Air Caraibes

  • Corsair

    Corsair

  • Cape Air

    Cape Air

  • Tradewind Aviation

    Tradewind Aviation

  • Hahn Air Systems

    Hahn Air Systems

  • notification illustration

    Be in the know

    Get alerts if flight prices drop or rise*
  • deals illustration

    Book smarter

    Save up to 30% on select hotels after you book a flight*
  • trophy illustration

    Earn twice

    Earn your airline miles on top of our OneKeyCash
    Learn about One Key

How much is the cheapest flight to Leeward?

Prices were available within the past 7 days and start at $129 for one-way flights and $189 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

FlexFlight
Thu, Jan 15 - Tue, Jan 20
SXM
Saint Martin
SBH
Gustavia
$189 Roundtrip, found 1 hour ago
$189
Roundtrip
found 1 hour ago
Select FlexFlight flight, departing Thu, Jan 15 from Saint Martin to Gustavia, returning Tue, Jan 20, priced at $189 found 1 hour ago
FlexFlight
Sat, Feb 7 - Tue, Feb 17
SXM
Saint Martin
SBH
Gustavia
$206 Roundtrip, found 14 hours ago
$206
Roundtrip
found 14 hours ago
Select FlexFlight flight, departing Sat, Feb 7 from Saint Martin to Gustavia, returning Tue, Feb 17, priced at $206 found 14 hours ago
FlexFlight
Sat, Dec 13 - Sun, Dec 14
SXM
Saint Martin
SBH
Gustavia
$239 Roundtrip, found 1 hour ago
$239
Roundtrip
found 1 hour ago
Select FlexFlight flight, departing Sat, Dec 13 from Saint Martin to Gustavia, returning Sun, Dec 14, priced at $239 found 1 hour ago
FlexFlight
Wed, Feb 4 - Mon, Feb 9
SXM
Saint Martin
SBH
Gustavia
$242 Roundtrip, found 6 hours ago
$242
Roundtrip
found 6 hours ago
Select FlexFlight flight, departing Wed, Feb 4 from Saint Martin to Gustavia, returning Mon, Feb 9, priced at $242 found 6 hours ago
FlexFlight
Tue, Dec 30 - Fri, Jan 2
SXM
Saint Martin
SBH
Gustavia
$249 Roundtrip, found 10 hours ago
$249
Roundtrip
found 10 hours ago
Select FlexFlight flight, departing Tue, Dec 30 from Saint Martin to Gustavia, returning Fri, Jan 2, priced at $249 found 10 hours ago
FlexFlight
Wed, Jan 21 - Wed, Jan 28
SXM
Saint Martin
SBH
Gustavia
$252 Roundtrip, found 10 hours ago
$252
Roundtrip
found 10 hours ago
Select FlexFlight flight, departing Wed, Jan 21 from Saint Martin to Gustavia, returning Wed, Jan 28, priced at $252 found 10 hours ago
United
Sat, Jan 31 - Wed, Feb 4
EWR
New York
SBH
Gustavia
$556 Roundtrip, found 19 hours ago
$556
Roundtrip
found 19 hours ago
Select United flight, departing Sat, Jan 31 from New York to Gustavia, returning Wed, Feb 4, priced at $556 found 19 hours ago
JetBlue Airways
Sat, Jan 24 - Thu, Jan 29
JFK
New York
SBH
Gustavia
$561 Roundtrip, found 1 day ago
$561
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sat, Jan 24 from New York to Gustavia, returning Thu, Jan 29, priced at $561 found 1 day ago
Tradewind Aviation
Fri, Aug 21 - Tue, Aug 25
SJU
San Juan
SBH
Gustavia
$706 Roundtrip, just found
$706
Roundtrip
just found
Select Tradewind Aviation flight, departing Fri, Aug 21 from San Juan to Gustavia, returning Tue, Aug 25, priced at $706 just found
Cape Air
Thu, Apr 9 - Sun, Apr 12
STT
St. Thomas
SBH
Gustavia
$814 Roundtrip, found 1 hour ago
$814
Roundtrip
found 1 hour ago
Select Cape Air flight, departing Thu, Apr 9 from St. Thomas to Gustavia, returning Sun, Apr 12, priced at $814 found 1 hour 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 $934
SXM
Princess Juliana Intl.
Cheapest
Flights from $934

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

Leeward Flights Information

Airlines serving
FlexFlight, Windward Island Airways International, United, JetBlue Airways, Accessrail, Tradewind Aviation, Cape Air
Roundtrip price
from $189

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 $189. 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 $189 and $814. If you were journeying one way out of Saint Martin (SXM), you could have picked up a fare from just $129.
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 $189 to $814 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.

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
Sat, Jan 31 - Wed, Feb 4
EWR
New York
SBH
Gustavia
$556 Roundtrip, found 19 hours ago
$556
Roundtrip
found 19 hours ago
Select United flight, departing Sat, Jan 31 from New York to Gustavia, returning Wed, Feb 4, priced at $556 found 19 hours ago
*Available to One Key members.