Cheap Flights to Windward from $183 (2024/2025)

Wander Wisely with exceptional service, 24/7 support

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

How Much Does it Cost To Fly To Windward?

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Wed, May 22 - Sun, May 26
SXM
Princess Juliana Intl.
SBH
Gustaf III
$317 Roundtrip, just found
$317
Roundtrip
just found
Select Windward Island Airways International flight, departing Wed, May 22 from Princess Juliana Intl. to Gustaf III, returning Sun, May 26, priced at $317 just found
Thu, May 16 - Wed, May 22
FDF
Martinique Aime Cesaire Intl.
SBH
Gustaf III
$606 Roundtrip, found 5 days ago
$606
Roundtrip
found 5 days ago
Select Windward Island Airways International flight, departing Thu, May 16 from Martinique Aime Cesaire Intl. to Gustaf III, returning Wed, May 22, priced at $606 found 5 days ago
Sun, May 12 - Fri, May 17
EWR
Liberty Intl.
SBH
Gustaf III
$675 Roundtrip, found 1 day ago
$675
Roundtrip
found 1 day ago
Select United flight, departing Sun, May 12 from Liberty Intl. to Gustaf III, returning Fri, May 17, priced at $675 found 1 day ago
Mon, Jun 3 - Sat, Jun 8
JFK
John F. Kennedy Intl.
SBH
Gustaf III
$705 Roundtrip, found 1 hour ago
$705
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Mon, Jun 3 from John F. Kennedy Intl. to Gustaf III, returning Sat, Jun 8, priced at $705 found 1 hour ago
Sat, Sep 7 - Sat, Sep 14
BOS
Logan Intl.
SBH
Gustaf III
$732 Roundtrip, found 8 hours ago
$732
Roundtrip
found 8 hours ago
Select JetBlue Airways flight, departing Sat, Sep 7 from Logan Intl. to Gustaf III, returning Sat, Sep 14, priced at $732 found 8 hours ago
OriginDestinationTravel DatesFlights From*
SXMSt. BarthelemyMay 20 to May 24$317
SJUSt. BarthelemyMay 27 to May 30$686
JFKSt. BarthelemyJune 1 to June 7$705
JFKSt. BarthelemyJune 1 to June 7$705
MIASt. BarthelemyJune 3 to June 8$802
EWRSt. BarthelemyJuly 6 to July 20$807
LAXSt. BarthelemyMay 31 to June 6$815
ATLSt. BarthelemyAugust 11 to August 18$970
ORYSt. BarthelemyMay 26 to June 10$1,351
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
SXMSt. BarthelemyMay 10 to May 14$317
EWRSt. BarthelemyMay 12 to May 17$675
EWRSt. BarthelemyMay 12 to May 17$675
SJUSt. BarthelemyMay 12 to May 15$705
JFKSt. BarthelemyMay 10 to May 12$878
MIASt. BarthelemyMay 12 to May 16$885
LAXSt. BarthelemyMay 10 to May 15$1,107
CDGSt. BarthelemyMay 11 to May 20$1,652
*Prices include taxes and fees

Travelers ❤️ These Windward 🏨

Tropical Hotel St Barth

Tropical Hotel St Barth

Baie de St. Jean, St. Barthelemy
Book a stay at this beach hotel in St. Barthelemy. Enjoy free WiFi, free valet parking, and a 24-hour front desk. Our guests praise the property condition in our reviews. Popular attractions Gustavia Harbor and St. Jean Beach are located nearby.
9.6/10 Exceptional! (49 reviews)
"The Tropical is one of the best hotels on the island. The property is pristine, the rooms are amazing and the staff is incredible!!"

Reviewed on Apr 27, 2024

Tropical Hotel St Barth
Rosewood Le Guanahani St Barth

Rosewood Le Guanahani St Barth

Grand Cul De Sac, St. Barthelemy
Book a stay at this beach hotel in St. Barthelemy. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Gustavia Harbor and Grand Cul de Sac are located nearby.
9.6/10 Exceptional! (29 reviews)
"Rosewood Le Guanahani St Barth by far the nicest property in Anse du Grand Cul-de-Sac and possibly even the island (I can say the because we explored Le Barthelmy, Eden Roc and others). We enjoyed the properties many amenities, including great beachfront pool and water activities. Easy to paddle ..."

Reviewed on Apr 7, 2024

Rosewood Le Guanahani St Barth
Le Barthélemy Hotel & Spa

Le Barthélemy Hotel & Spa

5 out of 5
Baie de Grand Cul de Sac, St. Barthelemy
Stay at this 5-star luxury hotel in St. Barthelemy. Enjoy free breakfast, free WiFi, and free valet parking. Popular attractions Gustavia Harbor and Grand Cul de Sac are located nearby.
9.6/10 Exceptional! (60 reviews)
"Overall met all of our needs w a special shout out to the service. A superb staff The food could be a click better( still very good) w one exception- room service which was terrible across board. Then again the lesson is to not stay in room!"

Reviewed on Feb 24, 2024

Le Barthélemy Hotel & Spa
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Le Sereno

Le Sereno

5 out of 5
Grand Cul de Sac BP 19, St. Barthelemy
Stay at this 5-star luxury hotel in St. Barthelemy. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Gustavia Harbor and Grand Cul de Sac are located nearby.
9.4/10 Exceptional! (50 reviews)
"Staff was helpful and great. A little removed from the action but a great place to stay"

Reviewed on Apr 21, 2024

Le Sereno
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Can I fly to Windward right now?
This will depend on a few factors, for example, where you’re leaving from and the current coronavirus restrictions in your destination. Before locking in your flight to Windward, have a look at official government websites for the latest news. Travelocity’s Covid-19 Travel Advisor also has information about travel during the pandemic, including restrictions, quarantine and physical distancing rules for your destination and others around the world.
How much is the cheapest flight to Windward?
For an idea of fares, the cheapest roundtrip flight to Windward was $317 in the last seven days. An excellent way to snap up a good deal is to be flexible with your dates. This price was available on Travelocity for flights to Windward departing within the next year. Prices and availability are subject to change. Additional terms apply.
What is the cheapest month to fly to Windward?
Spend more of your money on great adventures and less on your airline ticket by making your way to Windward in May. This is the cheapest time to travel to this place according to Travelocity’s direct return flight demand from January to December last year. Browse through our range of flights and enjoy a change of scenery without breaking the bank.
How can I check my flight status to Windward?
Get useful updates about your flight status and more with Trips. This convenient portal can be found at the top right of our homepage and is the place to view and manage your bookings. Create your account easily and quickly and you’re all set. Or, use the Travelocity app to look up the details of your flight to Windward while you’re out and about — and even when offline. The app is the travel companion in your pocket. Whether you want to arrange transportation to or from the airport or share itineraries with any members of your family flying with you, our clever app can help.
How do I find the best deals on flights to Windward?
A simple way to score the best deal is to be flexible with your dates. Start by searching for your flight to Windward, then hit the “Flexible dates” box at the top of the results. This will show you prices for the surrounding dates. Want another handy tip? Book ahead of time. To give you an idea of costs, $317 was the lowest price for a return flight to Windward in the last seven days on our site. This price was available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Why should I book my flight to Windward with Travelocity?
If you’re chasing cheap flights to Windward, you’ll track down some tempting deals with Travelocity. From cheap family flights on low-cost airlines to flexible ticket options, we’ve got it all. Enjoy a worry-free break with our 24/7 social media customer support, Price Match Guarantee and free cancellations with most hotels and activities. Start packing your case and prepare to fly away to this exciting destination.
What are the most popular flight routes to Windward?
As a favorite destination for tourists, you’ll find plenty of ways to get to Windward. Browse this list of main routes:

  • Philipsburg (SXM-Princess Juliana Intl.) to Gustaf III Airport (SBH) - 4,814 flights a month.
  • Pointe-a-Pitre (PTP-Pointe-a-Pitre Intl.) to Gustaf III Airport (SBH) - 1,538 flights a month.
  • Grand Case (SFG-L’Esperance) to Gustaf III Airport (SBH) - 736 flights a month.

How much is a flight to Windward on average?
Tickets for roundtrip flights to Windward were priced between $317 and $1,652 in the last seven days. The minute you find a fabulous deal, lock it in and prepare to take off on your next epic adventure with Travelocity. These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
How long is the average flight to Windward?
Your point of departure will usually dictate how much time your direct flight to Windward will take. Here are a handful of the more popular routes to Windward and average journey times:

  • Philipsburg (SXM-Princess Juliana Intl.) to Gustaf III Airport (SBH) - 15 minutes
  • Pointe-a-Pitre (PTP-Pointe-a-Pitre Intl.) to Gustaf III Airport (SBH) - 1 hour
  • Grand Case (SFG-L’Esperance) to Gustaf III Airport (SBH) - 15 minutes

What can I expect on a flight to Windward?
This mainly depends on your airline and how long your trip is. Typically, most airlines offer things like warm meals, drinks and entertainment on long-haul journeys. Whether you’re seeking business class flights to Windward or cheap flights for family vacations, you’ll be well taken care of from takeoff to touchdown.

Destinations in Windward

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.