Cheap Flights to Windward

View AU$927 flight on Fri, 6 Mar 2026Opens in a new window

Popular airlines to Windward

  • Windward Island Airways International

  • KLM

  • FlexFlight

  • Air Caraibes

  • Corsair

  • Tradewind Aviation

  • Cape Air

  • Be in the know

    Get alerts if flight prices drop or rise*

  • Book smarter

    Save up to 35% on select hotels after you book a flight*

  • Earn twice

    Earn your airline miles on top of our rewards
    Sign in

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.

United
Wed, 25 Mar - Tue, 31 Mar
LGA
New York
SBH
Gustavia
AU$1,095 Return, found 4 hours ago
AU$1,095
Return
found 4 hours ago
Select United flight, departing Wed, 25 Mar from New York to Gustavia, returning Tue, 31 Mar, priced at AU$1,095 found 4 hours ago
United
Wed, 25 Mar - Tue, 31 Mar
LGA
New York
SBH
Gustavia
AU$1,137 Return, found 4 hours ago
AU$1,137
Return
found 4 hours ago
Select United flight, departing Wed, 25 Mar from New York to Gustavia, returning Tue, 31 Mar, priced at AU$1,137 found 4 hours ago
United
Wed, 25 Mar - Tue, 31 Mar
EWR
New York
SBH
Gustavia
AU$1,311 Return, found 4 hours ago
AU$1,311
Return
found 4 hours ago
Select United flight, departing Wed, 25 Mar from New York to Gustavia, returning Tue, 31 Mar, priced at AU$1,311 found 4 hours ago
United
Wed, 25 Mar - Tue, 31 Mar
EWR
New York
SBH
Gustavia
AU$1,354 Return, found 4 hours ago
AU$1,354
Return
found 4 hours ago
Select United flight, departing Wed, 25 Mar from New York to Gustavia, returning Tue, 31 Mar, priced at AU$1,354 found 4 hours ago
United
Fri, 6 Mar - Fri, 13 Mar
LGA
New York
SBH
Gustavia
AU$1,411 Return, found 4 hours ago
AU$1,411
Return
found 4 hours ago
Select United flight, departing Fri, 6 Mar from New York to Gustavia, returning Fri, 13 Mar, priced at AU$1,411 found 4 hours ago
United
Wed, 25 Mar - Tue, 31 Mar
EWR
New York
SBH
Gustavia
AU$1,590 Return, found 4 hours ago
AU$1,590
Return
found 4 hours ago
Select United flight, departing Wed, 25 Mar from New York to Gustavia, returning Tue, 31 Mar, priced at AU$1,590 found 4 hours ago
United
Wed, 25 Mar - Tue, 31 Mar
EWR
New York
SBH
Gustavia
AU$1,647 Return, found 4 hours ago
AU$1,647
Return
found 4 hours ago
Select United flight, departing Wed, 25 Mar from New York to Gustavia, returning Tue, 31 Mar, priced at AU$1,647 found 4 hours ago
Delta
Fri, 6 Mar - Fri, 13 Mar
JFK
New York
SBH
Gustavia
AU$1,872 Return, found 4 hours ago
AU$1,872
Return
found 4 hours ago
Select Delta flight, departing Fri, 6 Mar from New York to Gustavia, returning Fri, 13 Mar, priced at AU$1,872 found 4 hours ago
Delta
Wed, 1 Apr - Tue, 7 Apr
JFK
New York
SBH
Gustavia
AU$2,086 Return, found 4 days ago
AU$2,086
Return
found 4 days ago
Select Delta flight, departing Wed, 1 Apr from New York to Gustavia, returning Tue, 7 Apr, priced at AU$2,086 found 4 days ago
American Airlines
Wed, 25 Mar - Tue, 31 Mar
JFK
New York
SBH
Gustavia
AU$2,165 Return, found 4 hours ago
AU$2,165
Return
found 4 hours ago
Select American Airlines flight, departing Wed, 25 Mar from New York to Gustavia, returning Tue, 31 Mar, priced at AU$2,165 found 4 hours ago

The Annual Holiday Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Book now

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$1,095. 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$1,095 and AU$2,165 in the last seven days. For one-way journeys from New York (JFK), the lowest amount paid during this time was AU$927.
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$1,095 and AU$2,165. 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.

Book with confidence

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

Travel information

Windward Flights Information

Airlines serving
Delta, United, American Airlines, JetBlue Airways
Roundtrip price
from AU$1,095
Windward Flights Information

Explore a world of travel with Expedia

*Available to Expedia members.