Cheap Flights to Windward

Popular airlines to Windward

  • Windward Island Airways International

    Windward Island Airways International

  • Tradewind Aviation

    Tradewind Aviation

  • Corsair

    Corsair

  • Air Caraibes

    Air Caraibes

  • Cape Air

    Cape Air

  • Hahn Air Systems

    Hahn Air Systems

  • Air France

    Air France

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Cheapest Flights to Windward

Prices were available within the past 7 days for one-way flights and round trip tickets for the period specified. Prices and availability are subject to change. Additional terms apply.

Windward Island Airways International
Fri, 3 July - Sun, 12 July
SXM
Saint Martin
SBH
Gustavia
AU$452 Return, found 1 day ago
AU$452
Return
found 1 day ago
Select Windward Island Airways International flight, departing Fri, 3 July from Saint Martin to Gustavia, returning Sun, 12 July, priced at AU$452 found 1 day ago
Windward Island Airways International
Thu, 16 Oct - Sun, 19 Oct
SXM
Saint Martin
SBH
Gustavia
AU$550 Return, found 7 hours ago
AU$550
Return
found 7 hours ago
Select Windward Island Airways International flight, departing Thu, 16 Oct from Saint Martin to Gustavia, returning Sun, 19 Oct, priced at AU$550 found 7 hours ago
Windward Island Airways International
Thu, 16 Oct - Sun, 19 Oct
SXM
Saint Martin
SBH
Gustavia
AU$611 Return, found 7 hours ago
AU$611
Return
found 7 hours ago
Select Windward Island Airways International flight, departing Thu, 16 Oct from Saint Martin to Gustavia, returning Sun, 19 Oct, priced at AU$611 found 7 hours ago
Windward Island Airways International
Thu, 16 Oct - Sun, 19 Oct
SXM
Saint Martin
SBH
Gustavia
AU$649 Return, found 7 hours ago
AU$649
Return
found 7 hours ago
Select Windward Island Airways International flight, departing Thu, 16 Oct from Saint Martin to Gustavia, returning Sun, 19 Oct, priced at AU$649 found 7 hours ago
Tradewind Aviation
Thu, 30 Oct - Mon, 3 Nov
SJU
San Juan
SBH
Gustavia
AU$1,118 Return, found 1 day ago
AU$1,118
Return
found 1 day ago
Select Tradewind Aviation flight, departing Thu, 30 Oct from San Juan to Gustavia, returning Mon, 3 Nov, priced at AU$1,118 found 1 day ago
Tradewind Aviation
Thu, 30 Oct - Mon, 3 Nov
SJU
San Juan
SBH
Gustavia
AU$1,265 Return, found 1 day ago
AU$1,265
Return
found 1 day ago
Select Tradewind Aviation flight, departing Thu, 30 Oct from San Juan to Gustavia, returning Mon, 3 Nov, priced at AU$1,265 found 1 day ago
interCaribbean Airways
Thu, 30 Oct - Mon, 3 Nov
SJU
San Juan
SBH
Gustavia
AU$1,267 Return, found 1 day ago
AU$1,267
Return
found 1 day ago
Select interCaribbean Airways flight, departing Thu, 30 Oct from San Juan to Gustavia, returning Mon, 3 Nov, priced at AU$1,267 found 1 day ago
Tradewind Aviation
Thu, 30 Oct - Mon, 3 Nov
SJU
San Juan
SBH
Gustavia
AU$1,380 Return, found 1 day ago
AU$1,380
Return
found 1 day ago
Select Tradewind Aviation flight, departing Thu, 30 Oct from San Juan to Gustavia, returning Mon, 3 Nov, priced at AU$1,380 found 1 day ago
JetBlue Airways
Thu, 30 Oct - Mon, 3 Nov
SJU
San Juan
SBH
Gustavia
AU$1,435 Return, found 1 day ago
AU$1,435
Return
found 1 day ago
Select JetBlue Airways flight, departing Thu, 30 Oct from San Juan to Gustavia, returning Mon, 3 Nov, priced at AU$1,435 found 1 day ago
Cape Air
Thu, 30 Oct - Mon, 3 Nov
SJU
San Juan
SBH
Gustavia
AU$1,442 Return, found 1 day ago
AU$1,442
Return
found 1 day ago
Select Cape Air flight, departing Thu, 30 Oct from San Juan to Gustavia, returning Mon, 3 Nov, priced at AU$1,442 found 1 day ago

Windward Flights

When was the last time you embarked on a grand adventure? Whether it was last month or years ago, there’s never been a better time to start planning your next big trip. Book tickets to Windward today and get ready to build your travel itinerary, from exploring the area with your family to recharging in the change of scenery. During your stay, visit the must-see attractions, chow down on the local cuisine, and relish in a holiday state of mind. However you decide to spend your upcoming trip, we’re here to make your travel plans easy and affordable.

Book Your Windward Airfare

At Expedia.com.au, it’s simple to find cheap flights to Windward that won’t cause your wallet to flinch. Browse through our inventory of Windward flights and find airfare matching your preferred times and dates. Looking for a red-eye flight or an afternoon departure? Don’t worry, we’ve got you covered. You can even take advantage of our convenient My Scratchpad online feature, which lets you track your search results with ease. No more excuses; book your travel arrangements with us today to make your dream trip a reality.

Windward Flights Information

Airlines serving
Windward Island Airways International, Tradewind Aviation, interCaribbean Airways, JetBlue Airways, Cape Air
Roundtrip price
from AU$452

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 AU$452. 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 AU$452 and AU$1,442 in the last seven days. For one-way journeys from Saint Martin (SXM), the lowest amount paid during this time was AU$282.
When is the cheapest time to fly to Windward?
Flying on a Tuesday, followed by a Monday, is usually the best way to pick up the cheapest flight. Steer clear of weekends if you can, because Saturday is typically the costliest day. Spend the funds you saved having an awesome time in Windward instead!
How much is a plane ticket to Windward?
In the last seven days, plane fares to Windward ranged between AU$452 and AU$1,442. 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.
*Available to Expedia members.