Cheap flights to Windward

View €294 flight on Tue, 30 Jun 2026Opens in a new window

Popular airlines to Windward

  • KLM

  • Windward Island Airways International

  • Air Caraibes

  • Corsair

  • FlexFlight

  • Tradewind Aviation

  • Cape Air

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Cheap round-trip flights to Windward

Prices were available within the past 7 days and start at €294 for one-way flights and €566 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Windward Island Airways International
Tue, 30 Jun - Sat, 4 Jul
SKB
St. Kitts
SBH
Gustavia
€566 Return, found 21 hours ago
€566
Return
found 21 hours ago
Select Windward Island Airways International flight, departing Tue, 30 Jun from St. Kitts to Gustavia, returning Sat, 4 Jul, priced at €566 found 21 hours ago
Windward Island Airways International
Tue, 30 Jun - Sat, 4 Jul
SKB
St. Kitts
SBH
Gustavia
€581 Return, found 21 hours ago
€581
Return
found 21 hours ago
Select Windward Island Airways International flight, departing Tue, 30 Jun from St. Kitts to Gustavia, returning Sat, 4 Jul, priced at €581 found 21 hours ago
Windward Island Airways International
Tue, 30 Jun - Sat, 4 Jul
SKB
St. Kitts
SBH
Gustavia
€598 Return, found 21 hours ago
€598
Return
found 21 hours ago
Select Windward Island Airways International flight, departing Tue, 30 Jun from St. Kitts to Gustavia, returning Sat, 4 Jul, priced at €598 found 21 hours ago
Windward Island Airways International
Tue, 30 Jun - Sat, 4 Jul
SKB
St. Kitts
SBH
Gustavia
€613 Return, found 21 hours ago
€613
Return
found 21 hours ago
Select Windward Island Airways International flight, departing Tue, 30 Jun from St. Kitts to Gustavia, returning Sat, 4 Jul, priced at €613 found 21 hours ago
JetBlue Airways
Thu, 2 Jul - Mon, 6 Jul
JFK
New York
SBH
Gustavia
€786 Return, found 4 days ago
€786
Return
found 4 days ago
Select JetBlue Airways flight, departing Thu, 2 Jul from New York to Gustavia, returning Mon, 6 Jul, priced at €786 found 4 days ago
JetBlue Airways
Thu, 2 Jul - Mon, 6 Jul
JFK
New York
SBH
Gustavia
€1,002 Return, found 9 hours ago
€1,002
Return
found 9 hours ago
Select JetBlue Airways flight, departing Thu, 2 Jul from New York to Gustavia, returning Mon, 6 Jul, priced at €1,002 found 9 hours ago
JetBlue Airways
Thu, 2 Jul - Mon, 6 Jul
JFK
New York
SBH
Gustavia
€1,028 Return, found 9 hours ago
€1,028
Return
found 9 hours ago
Select JetBlue Airways flight, departing Thu, 2 Jul from New York to Gustavia, returning Mon, 6 Jul, priced at €1,028 found 9 hours ago
American Airlines
Thu, 2 Jul - Mon, 6 Jul
JFK
New York
SBH
Gustavia
€1,070 Return, found 9 hours ago
€1,070
Return
found 9 hours ago
Select American Airlines flight, departing Thu, 2 Jul from New York to Gustavia, returning Mon, 6 Jul, priced at €1,070 found 9 hours ago
United
Thu, 2 Jul - Mon, 6 Jul
EWR
New York
SBH
Gustavia
€1,071 Return, found 9 hours ago
€1,071
Return
found 9 hours ago
Select United flight, departing Thu, 2 Jul from New York to Gustavia, returning Mon, 6 Jul, priced at €1,071 found 9 hours ago
British Airways
Mon, 29 Jun - Fri, 3 Jul
BUD
Budapest
SBH
Gustavia
€2,307 Return, found 1 day ago
€2,307
Return
found 1 day ago
Select British Airways flight, departing Mon, 29 Jun from Budapest to Gustavia, returning Fri, 3 Jul, priced at €2,307 found 1 day ago

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.

Aer Lingus
Fri, 4 Dec - Sun, 13 Dec
DUB
Dublin
SBH
Gustavia
€4,220 Return, found 2 days ago
€4,220
Return
found 2 days ago
Select Aer Lingus flight, departing Fri, 4 Dec from Dublin to Gustavia, returning Sun, 13 Dec, priced at €4,220 found 2 days ago

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 €566. 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 €566 and €4,220 in the last seven days. For one-way journeys from St. Kitts (SKB), the lowest amount paid during this time was €294.
How much is a plane ticket to Windward?
In the last seven days, plane fares to Windward ranged between €566 and €4,220. 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.

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About Windward

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About Windward
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