£100 Cheap Flights to Windward

View £100 flight on Mon, 13 Jul 2026Opens in a new window

Popular airlines to Windward

  • Windward Island Airways International

  • KLM

  • Corsair

  • Air Caraibes

  • FlexFlight

  • Tradewind Aviation

  • Cape Air

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Cheap round-trip flights to Windward

Prices were available within the past 7 days and start at £100 for one-way flights and £157 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

FlexFlight
Tue, 2 Jun - Fri, 5 Jun
SXM
Saint Martin
SBH
Gustavia
£157 Return, found 4 days ago
£157
Return
found 4 days ago
Select FlexFlight flight, departing Tue, 2 Jun from Saint Martin to Gustavia, returning Fri, 5 Jun, priced at £157 found 4 days ago
St Barth Executive
Wed, 27 May - Tue, 2 Jun
PTP
Pointe-à-Pitre
SBH
Gustavia
£420 Return, found 5 days ago
£420
Return
found 5 days ago
Select St Barth Executive flight, departing Wed, 27 May from Pointe-à-Pitre to Gustavia, returning Tue, 2 Jun, priced at £420 found 5 days ago
Cape Air
Sun, 15 Nov - Sun, 22 Nov
STT
St. Thomas
SBH
Gustavia
£449 Return, found 1 day ago
£449
Return
found 1 day ago
Select Cape Air flight, departing Sun, 15 Nov from St. Thomas to Gustavia, returning Sun, 22 Nov, priced at £449 found 1 day ago
JetBlue Airways
Mon, 6 Jul - Wed, 15 Jul
FLL
Fort Lauderdale
SBH
Gustavia
£478 Return, found 2 days ago
£478
Return
found 2 days ago
Select JetBlue Airways flight, departing Mon, 6 Jul from Fort Lauderdale to Gustavia, returning Wed, 15 Jul, priced at £478 found 2 days ago
World Ticket Ltd
Tue, 19 May - Wed, 20 May
AXA
The Valley
SBH
Gustavia
£500 Return, found 19 hours ago
£500
Return
found 19 hours ago
Select World Ticket Ltd flight, departing Tue, 19 May from The Valley to Gustavia, returning Wed, 20 May, priced at £500 found 19 hours ago
JetBlue Airways
Sat, 30 May - Fri, 5 Jun
JFK
New York
SBH
Gustavia
£511 Return, found 1 day ago
£511
Return
found 1 day ago
Select JetBlue Airways flight, departing Sat, 30 May from New York to Gustavia, returning Fri, 5 Jun, priced at £511 found 1 day ago
Contour Airlines
Sun, 7 Jun - Thu, 11 Jun
SJU
San Juan
SBH
Gustavia
£534 Return, found 4 days ago
£534
Return
found 4 days ago
Select Contour Airlines flight, departing Sun, 7 Jun from San Juan to Gustavia, returning Thu, 11 Jun, priced at £534 found 4 days ago
Caribbean Airlines
Thu, 4 Jun - Tue, 9 Jun
MIA
Miami
SBH
Gustavia
£719 Return, found 22 hours ago
£719
Return
found 22 hours ago
Select Caribbean Airlines flight, departing Thu, 4 Jun from Miami to Gustavia, returning Tue, 9 Jun, priced at £719 found 22 hours ago
JetBlue Airways
Sat, 22 Aug - Fri, 28 Aug
LGA
New York
SBH
Gustavia
£738 Return, found 2 days ago
£738
Return
found 2 days ago
Select JetBlue Airways flight, departing Sat, 22 Aug from New York to Gustavia, returning Fri, 28 Aug, priced at £738 found 2 days ago
Air Caraibes
Mon, 4 Jan - Mon, 11 Jan
ORY
Paris
SBH
Gustavia
£758 Return, found 4 days ago
£758
Return
found 4 days ago
Select Air Caraibes flight, departing Mon, 4 Jan from Paris to Gustavia, returning Mon, 11 Jan, priced at £758 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.

KLM
Mon, 15 Jun - Tue, 23 Jun
LCY
London
SBH
Gustavia
£1,255 Return, found 2 days ago
£1,255
Return
found 2 days ago
Select KLM flight, departing Mon, 15 Jun from London to Gustavia, returning Tue, 23 Jun, priced at £1,255 found 2 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 £157. 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 £157 and £3,179 in the last seven days. For one-way journeys from Saint Martin (SXM), the lowest amount paid during this time was £100.
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 £157 and £3,179. 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

Top tips for booking flights to Windward from UK

Get ready to fly to Windward

Prepare your luggage and book your flights to Windward with Expedia. We offer a seamless flight booking experience, with a wide range of Windward plane tickets to choose from. If you need help finding some of the best deals for cheap flights to Windward in 2026, we are always available to assist you. Book your flights to Windward today and let the adventure begin!

Find the best tickets to Windward

To find some of the best tickets to Windward in 2026, use Expedia's powerful search engine to compare dates and the different departure and arrival airports for your trip. Whether you're after direct flights to Windward or last-minute flights to Windward, you can filter and sort your search results, making it easy to find the ideal flight to Windward.

Airlines fly to Windward

There are 20 different airlines that fly to Windward including some of the most trusted names in the business. To book flights to Windward with your favourite airline, take a look at Expedia's flight listings and try out different dates to find some of the best Windward plane tickets.

Find the cheapest flights to Windward

By booking early you may find some of the best deals for Windward flights from the UK, including Windward direct flights. You can usually find affordable and cheap flights to Windward, whether one-way from £100 or round-trip from £157, with Expedia if you book your trip far enough in advance.

Find the best airports for cheap flights to Windward

Try searching for different Windward airports with Expedia to find some of the cheapest flights to Windward. Flights from Saint Martin (SXM) to Gustavia (SBH) usually have the lowest price from £100.

Why book your flights to Windward with Expedia

Expedia offers great deals on Windward air fares from £100 to cater to every budget. Not only is Expedia one of the top platforms to book flights to Windward from the UK, it is also your one-stop shop for booking hotels, car rentals, and more.

 

*Prices and availability are subject to change. Additional terms apply.

Top tips for booking flights to Windward from UK

Travel information

Windward Flights Information

Airlines serving
FlexFlight, Windward Island Airways International, Cape Air, World Ticket Ltd, JetBlue Airways, Hahn Air Systems, Contour Airlines, St Barth Executive, Caribbean Airlines, Air Caraibes
Roundtrip price
from £157
Windward Flights Information
*Available to Expedia members.