Cheap flights to Windward

View €430 flight on Thu, 22 Jan 2026Opens in a new window

Popular airlines to Windward

  • KLM

    KLM

  • Windward Island Airways International

    Windward Island Airways International

  • FlexFlight

    FlexFlight

  • Air Caraibes

    Air Caraibes

  • Corsair

    Corsair

  • Cape Air

    Cape Air

  • Air France

    Air France

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Cheap round-trip flights to Windward

Prices were available within the past 7 days and start at €430 for one-way flights and €767 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Thu, 22 Jan - Thu, 29 Jan
EWR
New York
SBH
Gustavia
€767 Return, found 5 hours ago
€767
Return
found 5 hours ago
Select United flight, departing Thu, 22 Jan from New York to Gustavia, returning Thu, 29 Jan, priced at €767 found 5 hours ago
United
Thu, 22 Jan - Thu, 29 Jan
EWR
New York
SBH
Gustavia
€831 Return, found 5 hours ago
€831
Return
found 5 hours ago
Select United flight, departing Thu, 22 Jan from New York to Gustavia, returning Thu, 29 Jan, priced at €831 found 5 hours ago
Delta
Thu, 22 Jan - Thu, 29 Jan
JFK
New York
SBH
Gustavia
€860 Return, found 5 hours ago
€860
Return
found 5 hours ago
Select Delta flight, departing Thu, 22 Jan from New York to Gustavia, returning Thu, 29 Jan, priced at €860 found 5 hours ago
American Airlines
Thu, 22 Jan - Thu, 29 Jan
JFK
New York
SBH
Gustavia
€883 Return, found 5 hours ago
€883
Return
found 5 hours ago
Select American Airlines flight, departing Thu, 22 Jan from New York to Gustavia, returning Thu, 29 Jan, priced at €883 found 5 hours ago
JetBlue Airways
Thu, 22 Jan - Thu, 29 Jan
JFK
New York
SBH
Gustavia
€885 Return, found 5 hours ago
€885
Return
found 5 hours ago
Select JetBlue Airways flight, departing Thu, 22 Jan from New York to Gustavia, returning Thu, 29 Jan, priced at €885 found 5 hours ago
United
Thu, 22 Jan - Thu, 29 Jan
EWR
New York
SBH
Gustavia
€895 Return, found 5 hours ago
€895
Return
found 5 hours ago
Select United flight, departing Thu, 22 Jan from New York to Gustavia, returning Thu, 29 Jan, priced at €895 found 5 hours ago
JetBlue Airways
Thu, 22 Jan - Thu, 29 Jan
JFK
New York
SBH
Gustavia
€910 Return, found 5 hours ago
€910
Return
found 5 hours ago
Select JetBlue Airways flight, departing Thu, 22 Jan from New York to Gustavia, returning Thu, 29 Jan, priced at €910 found 5 hours ago
JetBlue Airways
Thu, 22 Jan - Thu, 29 Jan
JFK
New York
SBH
Gustavia
€918 Return, found 5 hours ago
€918
Return
found 5 hours ago
Select JetBlue Airways flight, departing Thu, 22 Jan from New York to Gustavia, returning Thu, 29 Jan, priced at €918 found 5 hours ago
JetBlue Airways
Thu, 22 Jan - Thu, 29 Jan
JFK
New York
SBH
Gustavia
€944 Return, found 5 hours ago
€944
Return
found 5 hours ago
Select JetBlue Airways flight, departing Thu, 22 Jan from New York to Gustavia, returning Thu, 29 Jan, priced at €944 found 5 hours ago
Iberia
Mon, 29 Dec - Sat, 3 Jan
MAD
Madrid
SBH
Gustavia
€3,529 Return, found 5 days ago
€3,529
Return
found 5 days ago
Select Iberia flight, departing Mon, 29 Dec from Madrid to Gustavia, returning Sat, 3 Jan, priced at €3,529 found 5 days ago

About Windward

Expedia offers flights to Windward to meet every traveller's needs. Whatever your flight need - Expedia has the flight for you. So choose from flights to Windward or destinations around the world and discover how easy it is to make your flight reservations on Expedia.

Frequently asked questions

How do I find cheap flights to Windward that have flexible change policies?
We understand that travel plans can change in the blink of an eye, so choosing a flexible ticket with Expedia makes good sense. Simply check the "No change fee" box underneath the "Flexible change policies" filter. Your affordable, flexible flight to Windward is just a few clicks away.
How can I find cheap tickets to Windward?
One of the best ways to get your hands on cheap tickets to Windward is to be flexible with your travel dates. Search for your flights, then click "flexible dates" at the top of your results. It'll bring up the cheapest prices for nearby days. The lowest price for a flight to Windward in the last seven days was €767. Booking well ahead of time will usually help you get an even bigger bargain.
How much is a flight to Windward?
You could have locked in a round-trip flight to Windward from anywhere between €767 and €4,089 in the last seven days. For one-way journeys from New York (JFK), the lowest amount paid during this time was €430.
How much is a plane ticket to Windward?
In the last seven days, plane fares to Windward ranged between €767 and €4,089. Prices tend to rise over time, so grab a top deal today.
What months are the cheapest to book a flight to Windward?
The most cost-effective month to secure a fantastic deal to Windward is February, while the priciest month is December. Try to avoid this month if you're on a tight budget.

Trending flights to Windward

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

KLM
Thu, 8 Jan - Mon, 12 Jan
DUB
Dublin
SBH
Gustavia
€4,089 Return, found 6 hours ago
€4,089
Return
found 6 hours ago
Select KLM flight, departing Thu, 8 Jan from Dublin to Gustavia, returning Mon, 12 Jan, priced at €4,089 found 6 hours ago
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