Cheap flights to Windward

View €116 flight on Wed, 27 May 2026Opens in a new window

Popular airlines to Windward

  • Windward Island Airways International

  • KLM

  • FlexFlight

  • Corsair

  • Air Caraibes

  • Tradewind Aviation

  • Cape Air

  • Be in the know

    Get alerts if flight prices drop or rise*

  • Book smarter

    Save up to 15% on select hotels after you book a flight*

  • Earn twice

    Earn your airline miles on top of our rewards
    Sign in

Cheap round-trip flights to Windward

Prices were available within the past 7 days and start at €116 for one-way flights and €245 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

FlexFlight
Fri, 1 May - Sun, 3 May
SXM
Saint Martin
SBH
Gustavia
€245 Return, found 13 hours ago
€245
Return
found 13 hours ago
Select FlexFlight flight, departing Fri, 1 May from Saint Martin to Gustavia, returning Sun, 3 May, priced at €245 found 13 hours ago
FlexFlight
Thu, 14 May - Mon, 18 May
SXM
Saint Martin
SBH
Gustavia
€254 Return, found 2 days ago
€254
Return
found 2 days ago
Select FlexFlight flight, departing Thu, 14 May from Saint Martin to Gustavia, returning Mon, 18 May, priced at €254 found 2 days ago
FlexFlight
Fri, 1 May - Sun, 3 May
SXM
Saint Martin
SBH
Gustavia
€263 Return, found 13 hours ago
€263
Return
found 13 hours ago
Select FlexFlight flight, departing Fri, 1 May from Saint Martin to Gustavia, returning Sun, 3 May, priced at €263 found 13 hours ago
FlexFlight
Fri, 1 May - Sun, 3 May
SXM
Saint Martin
SBH
Gustavia
€275 Return, found 13 hours ago
€275
Return
found 13 hours ago
Select FlexFlight flight, departing Fri, 1 May from Saint Martin to Gustavia, returning Sun, 3 May, priced at €275 found 13 hours ago
FlexFlight
Thu, 14 May - Mon, 18 May
SXM
Saint Martin
SBH
Gustavia
€297 Return, found 2 days ago
€297
Return
found 2 days ago
Select FlexFlight flight, departing Thu, 14 May from Saint Martin to Gustavia, returning Mon, 18 May, priced at €297 found 2 days ago
FlexFlight
Fri, 1 May - Sun, 3 May
SXM
Saint Martin
SBH
Gustavia
€301 Return, found 13 hours ago
€301
Return
found 13 hours ago
Select FlexFlight flight, departing Fri, 1 May from Saint Martin to Gustavia, returning Sun, 3 May, priced at €301 found 13 hours ago
Windward Island Airways International
Fri, 1 May - Sun, 3 May
SXM
Saint Martin
SBH
Gustavia
€306 Return, found 13 hours ago
€306
Return
found 13 hours ago
Select Windward Island Airways International flight, departing Fri, 1 May from Saint Martin to Gustavia, returning Sun, 3 May, priced at €306 found 13 hours ago
St Barth Executive
Thu, 14 May - Mon, 18 May
SXM
Saint Martin
SBH
Gustavia
€404 Return, found 2 days ago
€404
Return
found 2 days ago
Select St Barth Executive flight, departing Thu, 14 May from Saint Martin to Gustavia, returning Mon, 18 May, priced at €404 found 2 days ago
Aer Lingus
Fri, 8 May - Tue, 12 May
DUB
Dublin
SBH
Gustavia
€1,132 Return, found 4 days ago
€1,132
Return
found 4 days ago
Select Aer Lingus flight, departing Fri, 8 May from Dublin to Gustavia, returning Tue, 12 May, priced at €1,132 found 4 days ago
KLM
Wed, 6 May - Tue, 12 May
DUB
Dublin
SBH
Gustavia
€1,608 Return, found 4 days ago
€1,608
Return
found 4 days ago
Select KLM flight, departing Wed, 6 May from Dublin to Gustavia, returning Tue, 12 May, priced at €1,608 found 4 days 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, 8 May - Tue, 12 May
DUB
Dublin
SBH
Gustavia
€1,132 Return, found 4 days ago
€1,132
Return
found 4 days ago
Select Aer Lingus flight, departing Fri, 8 May from Dublin to Gustavia, returning Tue, 12 May, priced at €1,132 found 4 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 €245. 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 €245 and €3,097 in the last seven days. For one-way journeys from Saint Martin (SXM), the lowest amount paid during this time was €116.
How much is a plane ticket to Windward?
In the last seven days, plane fares to Windward ranged between €245 and €3,097. 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.

Explore a world of travel with Expedia

*Available to Expedia members.