Cheap Flights to Windward

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    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.

American Airlines
Fri, 22 Aug. - Fri, 29 Aug.
ORD
Chicago
SBH
Gustavia
AU$2,110 Return, found 1 day ago
AU$2,110
Return
found 1 day ago
Select American Airlines flight, departing Fri, 22 Aug. from Chicago to Gustavia, returning Fri, 29 Aug., priced at AU$2,110 found 1 day ago
United
Sun, 24 Aug. - Sun, 31 Aug.
ORD
Chicago
SBH
Gustavia
AU$2,127 Return, found 2 days ago
AU$2,127
Return
found 2 days ago
Select United flight, departing Sun, 24 Aug. from Chicago to Gustavia, returning Sun, 31 Aug., priced at AU$2,127 found 2 days ago
American Airlines
Fri, 22 Aug. - Fri, 29 Aug.
ORD
Chicago
SBH
Gustavia
AU$2,190 Return, found 1 day ago
AU$2,190
Return
found 1 day ago
Select American Airlines flight, departing Fri, 22 Aug. from Chicago to Gustavia, returning Fri, 29 Aug., priced at AU$2,190 found 1 day ago
American Airlines
Fri, 22 Aug. - Fri, 29 Aug.
ORD
Chicago
SBH
Gustavia
AU$2,257 Return, found 1 day ago
AU$2,257
Return
found 1 day ago
Select American Airlines flight, departing Fri, 22 Aug. from Chicago to Gustavia, returning Fri, 29 Aug., priced at AU$2,257 found 1 day ago
United
Sun, 24 Aug. - Sun, 31 Aug.
ORD
Chicago
SBH
Gustavia
AU$2,314 Return, found 2 days ago
AU$2,314
Return
found 2 days ago
Select United flight, departing Sun, 24 Aug. from Chicago to Gustavia, returning Sun, 31 Aug., priced at AU$2,314 found 2 days ago
American Airlines
Fri, 22 Aug. - Fri, 29 Aug.
ORD
Chicago
SBH
Gustavia
AU$2,318 Return, found 1 day ago
AU$2,318
Return
found 1 day ago
Select American Airlines flight, departing Fri, 22 Aug. from Chicago to Gustavia, returning Fri, 29 Aug., priced at AU$2,318 found 1 day ago
United
Fri, 22 Aug. - Fri, 29 Aug.
ORD
Chicago
SBH
Gustavia
AU$2,322 Return, found 1 day ago
AU$2,322
Return
found 1 day ago
Select United flight, departing Fri, 22 Aug. from Chicago to Gustavia, returning Fri, 29 Aug., priced at AU$2,322 found 1 day ago
United
Sun, 24 Aug. - Sun, 31 Aug.
ORD
Chicago
SBH
Gustavia
AU$2,326 Return, found 2 days ago
AU$2,326
Return
found 2 days ago
Select United flight, departing Sun, 24 Aug. from Chicago to Gustavia, returning Sun, 31 Aug., priced at AU$2,326 found 2 days ago
American Airlines
Sun, 24 Aug. - Sun, 31 Aug.
ORD
Chicago
SBH
Gustavia
AU$2,368 Return, found 2 days ago
AU$2,368
Return
found 2 days ago
Select American Airlines flight, departing Sun, 24 Aug. from Chicago to Gustavia, returning Sun, 31 Aug., priced at AU$2,368 found 2 days ago
United
Fri, 22 Aug. - Fri, 29 Aug.
ORD
Chicago
SBH
Gustavia
AU$2,445 Return, found 1 day ago
AU$2,445
Return
found 1 day ago
Select United flight, departing Fri, 22 Aug. from Chicago to Gustavia, returning Fri, 29 Aug., priced at AU$2,445 found 1 day ago
American Airlines
Fri, 22 Aug. - Fri, 29 Aug.
ORD
Chicago
SBH
Gustavia
AU$2,458 Return, found 1 day ago
AU$2,458
Return
found 1 day ago
Select American Airlines flight, departing Fri, 22 Aug. from Chicago to Gustavia, returning Fri, 29 Aug., priced at AU$2,458 found 1 day ago
United
Fri, 22 Aug. - Fri, 29 Aug.
ORD
Chicago
SBH
Gustavia
AU$2,463 Return, found 1 day ago
AU$2,463
Return
found 1 day ago
Select United flight, departing Fri, 22 Aug. from Chicago to Gustavia, returning Fri, 29 Aug., priced at AU$2,463 found 1 day ago
American Airlines
Fri, 22 Aug. - Fri, 29 Aug.
ORD
Chicago
SBH
Gustavia
AU$2,465 Return, found 1 day ago
AU$2,465
Return
found 1 day ago
Select American Airlines flight, departing Fri, 22 Aug. from Chicago to Gustavia, returning Fri, 29 Aug., priced at AU$2,465 found 1 day ago
American Airlines
Sun, 24 Aug. - Sun, 31 Aug.
ORD
Chicago
SBH
Gustavia
AU$2,506 Return, found 2 days ago
AU$2,506
Return
found 2 days ago
Select American Airlines flight, departing Sun, 24 Aug. from Chicago to Gustavia, returning Sun, 31 Aug., priced at AU$2,506 found 2 days ago
United
Sun, 24 Aug. - Sun, 31 Aug.
ORD
Chicago
SBH
Gustavia
AU$2,513 Return, found 2 days ago
AU$2,513
Return
found 2 days ago
Select United flight, departing Sun, 24 Aug. from Chicago to Gustavia, returning Sun, 31 Aug., priced at AU$2,513 found 2 days ago
American Airlines
Sun, 24 Aug. - Sun, 31 Aug.
ORD
Chicago
SBH
Gustavia
AU$2,520 Return, found 2 days ago
AU$2,520
Return
found 2 days ago
Select American Airlines flight, departing Sun, 24 Aug. from Chicago to Gustavia, returning Sun, 31 Aug., priced at AU$2,520 found 2 days ago
American Airlines
Fri, 22 Aug. - Fri, 29 Aug.
ORD
Chicago
SBH
Gustavia
AU$2,527 Return, found 1 day ago
AU$2,527
Return
found 1 day ago
Select American Airlines flight, departing Fri, 22 Aug. from Chicago to Gustavia, returning Fri, 29 Aug., priced at AU$2,527 found 1 day ago
American Airlines
Sun, 24 Aug. - Sun, 31 Aug.
ORD
Chicago
SBH
Gustavia
AU$2,545 Return, found 2 days ago
AU$2,545
Return
found 2 days ago
Select American Airlines flight, departing Sun, 24 Aug. from Chicago to Gustavia, returning Sun, 31 Aug., priced at AU$2,545 found 2 days ago
United
Fri, 22 Aug. - Fri, 29 Aug.
ORD
Chicago
SBH
Gustavia
AU$2,571 Return, found 1 day ago
AU$2,571
Return
found 1 day ago
Select United flight, departing Fri, 22 Aug. from Chicago to Gustavia, returning Fri, 29 Aug., priced at AU$2,571 found 1 day ago
Air France
Fri, 17 Oct. - Thu, 30 Oct.
TLS
Toulouse
SBH
Gustavia
AU$3,394 Return, found 13 hours ago
AU$3,394
Return
found 13 hours ago
Select Air France flight, departing Fri, 17 Oct. from Toulouse to Gustavia, returning Thu, 30 Oct., priced at AU$3,394 found 13 hours 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
American Airlines, United, Air France
Roundtrip price
from AU$2,110

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$2,110. 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$2,110 and AU$3,394 in the last seven days. For one-way journeys from (), the lowest amount paid during this time was .
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$2,110 and AU$3,394. 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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