CA $184 Cheap Flight to Windward

View CA $184 flight on Thu, Jun 4, 2026Opens in a new window

Popular airlines to Windward

  • KLM

  • Windward Island Airways International

  • FlexFlight

  • Air Caraibes

  • Corsair

  • Tradewind Aviation

  • Air France

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How much is the cheapest flight to Windward?

Prices were available within the past 7 days and start at CA $184 for one-way flights and CA $290 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

FlexFlight
Thu, Jul 2 - Thu, Jul 9
SXM
Saint Martin
SBH
Gustavia
CA $290 Roundtrip, found 3 days ago
CA $290
Roundtrip
found 3 days ago
Select FlexFlight flight, departing Thu, Jul 2 from Saint Martin to Gustavia, returning Thu, Jul 9, priced at CA $290 found 3 days ago
FlexFlight
Mon, May 25 - Tue, Jun 2
SXM
Saint Martin
SBH
Gustavia
CA $291 Roundtrip, found 2 days ago
CA $291
Roundtrip
found 2 days ago
Select FlexFlight flight, departing Mon, May 25 from Saint Martin to Gustavia, returning Tue, Jun 2, priced at CA $291 found 2 days ago
FlexFlight
Thu, Jun 4 - Tue, Jun 9
SXM
Saint Martin
SBH
Gustavia
CA $302 Roundtrip, found 3 days ago
CA $302
Roundtrip
found 3 days ago
Select FlexFlight flight, departing Thu, Jun 4 from Saint Martin to Gustavia, returning Tue, Jun 9, priced at CA $302 found 3 days ago
FlexFlight
Thu, Jul 2 - Thu, Jul 9
SXM
Saint Martin
SBH
Gustavia
CA $417 Roundtrip, found 3 days ago
CA $417
Roundtrip
found 3 days ago
Select FlexFlight flight, departing Thu, Jul 2 from Saint Martin to Gustavia, returning Thu, Jul 9, priced at CA $417 found 3 days ago
FlexFlight
Thu, Jul 2 - Thu, Jul 9
SXM
Saint Martin
SBH
Gustavia
CA $418 Roundtrip, found 3 days ago
CA $418
Roundtrip
found 3 days ago
Select FlexFlight flight, departing Thu, Jul 2 from Saint Martin to Gustavia, returning Thu, Jul 9, priced at CA $418 found 3 days ago
FlexFlight
Mon, May 25 - Sun, May 31
SXM
Saint Martin
SBH
Gustavia
CA $419 Roundtrip, found 2 days ago
CA $419
Roundtrip
found 2 days ago
Select FlexFlight flight, departing Mon, May 25 from Saint Martin to Gustavia, returning Sun, May 31, priced at CA $419 found 2 days ago
Windward Island Airways International
Thu, Jun 4 - Tue, Jun 9
SXM
Saint Martin
SBH
Gustavia
CA $469 Roundtrip, found 3 days ago
CA $469
Roundtrip
found 3 days ago
Select Windward Island Airways International flight, departing Thu, Jun 4 from Saint Martin to Gustavia, returning Tue, Jun 9, priced at CA $469 found 3 days ago
St Barth Executive
Wed, Sep 23 - Sat, Sep 26
SXM
Saint Martin
SBH
Gustavia
CA $626 Roundtrip, found 2 days ago
CA $626
Roundtrip
found 2 days ago
Select St Barth Executive flight, departing Wed, Sep 23 from Saint Martin to Gustavia, returning Sat, Sep 26, priced at CA $626 found 2 days ago
JetBlue Airways
Mon, May 25 - Thu, May 28
FLL
Fort Lauderdale
SBH
Gustavia
CA $914 Roundtrip, found 6 days ago
CA $914
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Mon, May 25 from Fort Lauderdale to Gustavia, returning Thu, May 28, priced at CA $914 found 6 days ago
WestJet
Mon, Jul 20 - Wed, Aug 5
YYZ
Toronto
SBH
Gustavia
CA $914 Roundtrip, found 4 days ago
CA $914
Roundtrip
found 4 days ago
Select WestJet flight, departing Mon, Jul 20 from Toronto to Gustavia, returning Wed, Aug 5, priced at CA $914 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.

WestJet
Mon, Jul 20 - Wed, Aug 5
YYZ
Toronto
SBH
Gustavia
CA $914 Roundtrip, found 4 days ago
CA $914
Roundtrip
found 4 days ago
Select WestJet flight, departing Mon, Jul 20 from Toronto to Gustavia, returning Wed, Aug 5, priced at CA $914 found 4 days ago

Frequently asked questions

How do I find cheap flights to Windward that have flexible change policies?
At Expedia, we've been channeling our inner yogi to offer you the most flexible fares available. Simply mark the "No change fee" box right underneath the filter subheading "Flexible change policies" to find your perfect flight to Windward.
How can I find cheap tickets to Windward?
Book in advance, fly with budget airlines, avoid vacation periods — there are plenty of ways! Another one is to make the most of Expedia's "flexible dates" feature. Find your Windward flight, then compare the cheapest prices for nearby dates. In the last seven days, the lowest price for a flight to Windward was CA $290.
How much is a flight to Windward?
There were loads of affordable fares for the taking in the last seven days, with the cost of a round-trip flight to Windward ranging between CA $290 and CA $914. Many lucky vacationers scored one-way flights from Saint Martin (SXM) for just CA $184.
When is the cheapest time to fly to Windward?
Take off for Windward earlier in the week and you'll usually be rewarded with lower fares. Tuesday is generally the cheapest day to fly out, with Monday a close second. If you'd like to avoid the costliest flights, stay away from Saturdays.
How much is a plane ticket to Windward?
In the last seven days, tickets ranged between CA $290 and CA $914. Have a look at our great deals to Windward, make a booking and get ready for your next fun vacation!
What months are the cheapest to book a flight to Windward?
A great month to book well-priced airfares to Windward is February. Remember that in the United States, an expensive time to reserve a ticket is the busy month of December.

Book with confidence

Top Travel Tips for Flying to Windward

Get ready for an incredible adventure as you embark on your journey to Windward. With Expedia, finding the perfect flights is a breeze. Discover valuable travel insights and expert tips to ensure a seamless and enjoyable trip to this captivating destination.

Unleash Your Wanderlust

Pack your bags, secure your flights to Windward, and let Expedia be your trusted companion in fulfilling your travel dreams. Our wide selection of flights offers you the flexibility to explore Windward in your own unique style. Experience the trip of a lifetime with just a click, courtesy of Expedia.

Unbeatable Value with Expedia

At Expedia, we understand the importance of budget-friendly travel. That's why we are dedicated to bringing you the best deals on affordable and cheap flights from the UK to Windward. Experience the perfect balance between adventure and savings with our competitively-priced roundtrip and one-way flight options.

Endless Flight Choices

With 20 different airlines flying to Windward, you have a world of options at your fingertips. Whether you're a spontaneous traveler or a meticulous planner, find the flights that suit your schedule and preferences seamlessly. Explore last-minute deals or plan ahead with ease.

Empowering Your Decision

We believe in putting you in control of your travel choices. Our extensive range of airline tickets to Windward caters to every budget, starting from the lowest price CA $184. Enjoy the freedom to choose the perfect flights that align with your needs and desires.

Effortless Booking Process

Experience a hassle-free booking journey with Expedia. Whether you're seeking a red-eye flight, a direct route to a specific airport, or one-way flights to Windward, our streamlined booking process ensures convenience and efficiency. Download our mobile booking app to reserve your flights anytime, anywhere.

Your Adventure Awaits

It's time to make your dreams a reality. Book your airfare to Windward today with Expedia. Begin crafting your unique travel story and get ready for an unforgettable experience that caters to your tastes and budget.

Start your journey now and let the adventure unfold.

Top Travel Tips for Flying to Windward

Travel information

Windward Flights Information

Airlines serving
FlexFlight, Windward Island Airways International, St Barth Executive, JetBlue Airways, WestJet
Roundtrip price
from CA $290
Windward Flights Information
*Available to Expedia members.