Flights To Anguilla - Cheap Flights Starting at CA $297

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West End Village

Flights
West End Village

How Much Does it Cost To Fly To Anguilla?

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

Tue, Aug 18 - Sat, Aug 22
SXM
Princess Juliana Intl.
AXA
Clayton J. Lloyd Intl.
CA $503 Roundtrip, found 5 days ago
CA $503
Roundtrip
found 5 days ago
Select World Ticket Ltd flight, departing Tue, Aug 18 from Princess Juliana Intl. to Clayton J. Lloyd Intl., returning Sat, Aug 22, priced at CA $503 found 5 days ago
Tue, Aug 18 - Sat, Aug 22
SXM
Princess Juliana Intl.
AXA
Clayton J. Lloyd Intl.
CA $522 Roundtrip, found 5 days ago
CA $522
Roundtrip
found 5 days ago
Select World Ticket Ltd flight, departing Tue, Aug 18 from Princess Juliana Intl. to Clayton J. Lloyd Intl., returning Sat, Aug 22, priced at CA $522 found 5 days ago
Tue, Aug 18 - Sat, Aug 22
SXM
Princess Juliana Intl.
AXA
Clayton J. Lloyd Intl.
CA $539 Roundtrip, found 5 days ago
CA $539
Roundtrip
found 5 days ago
Select Hahn Air Systems flight, departing Tue, Aug 18 from Princess Juliana Intl. to Clayton J. Lloyd Intl., returning Sat, Aug 22, priced at CA $539 found 5 days ago
Sun, Nov 22 - Tue, Nov 24
SXM
Princess Juliana Intl.
AXA
Clayton J. Lloyd Intl.
CA $542 Roundtrip, found 5 hours ago
CA $542
Roundtrip
found 5 hours ago
Select World Ticket Ltd flight, departing Sun, Nov 22 from Princess Juliana Intl. to Clayton J. Lloyd Intl., returning Tue, Nov 24, priced at CA $542 found 5 hours ago
Sun, Nov 22 - Tue, Nov 24
SXM
Princess Juliana Intl.
AXA
Clayton J. Lloyd Intl.
CA $562 Roundtrip, found 5 hours ago
CA $562
Roundtrip
found 5 hours ago
Select Hahn Air Systems flight, departing Sun, Nov 22 from Princess Juliana Intl. to Clayton J. Lloyd Intl., returning Tue, Nov 24, priced at CA $562 found 5 hours ago
Fri, Nov 13 - Sat, Nov 14
SXM
Princess Juliana Intl.
AXA
Clayton J. Lloyd Intl.
CA $576 Roundtrip, found 1 day ago
CA $576
Roundtrip
found 1 day ago
Select World Ticket Ltd flight, departing Fri, Nov 13 from Princess Juliana Intl. to Clayton J. Lloyd Intl., returning Sat, Nov 14, priced at CA $576 found 1 day ago
Sun, Nov 22 - Tue, Nov 24
SXM
Princess Juliana Intl.
AXA
Clayton J. Lloyd Intl.
CA $579 Roundtrip, found 5 hours ago
CA $579
Roundtrip
found 5 hours ago
Select Hahn Air Systems flight, departing Sun, Nov 22 from Princess Juliana Intl. to Clayton J. Lloyd Intl., returning Tue, Nov 24, priced at CA $579 found 5 hours ago
Sun, Nov 22 - Tue, Nov 24
SXM
Princess Juliana Intl.
AXA
Clayton J. Lloyd Intl.
CA $581 Roundtrip, found 5 hours ago
CA $581
Roundtrip
found 5 hours ago
Select Windward Island Airways International flight, departing Sun, Nov 22 from Princess Juliana Intl. to Clayton J. Lloyd Intl., returning Tue, Nov 24, priced at CA $581 found 5 hours ago
Sat, Jan 9 - Sat, Jan 16
YYZ
Pearson Intl.
AXA
Clayton J. Lloyd Intl.
CA $957 Roundtrip, found 3 days ago
CA $957
Roundtrip
found 3 days ago
Select BermudAir flight, departing Sat, Jan 9 from Pearson Intl. to Clayton J. Lloyd Intl., returning Sat, Jan 16, priced at CA $957 found 3 days ago
Sat, Feb 13 - Sat, Feb 20
YYZ
Pearson Intl.
AXA
Clayton J. Lloyd Intl.
CA $959 Roundtrip, found 2 days ago
CA $959
Roundtrip
found 2 days ago
Select BermudAir flight, departing Sat, Feb 13 from Pearson Intl. to Clayton J. Lloyd Intl., returning Sat, Feb 20, priced at CA $959 found 2 days ago
Sat, Jan 23 - Sat, Feb 13
YYZ
Pearson Intl.
AXA
Clayton J. Lloyd Intl.
CA $960 Roundtrip, found 1 day ago
CA $960
Roundtrip
found 1 day ago
Select BermudAir flight, departing Sat, Jan 23 from Pearson Intl. to Clayton J. Lloyd Intl., returning Sat, Feb 13, priced at CA $960 found 1 day ago
Fri, Mar 19 - Tue, Mar 30
YYZ
Pearson Intl.
AXA
Clayton J. Lloyd Intl.
CA $1,021 Roundtrip, found 10 hours ago
CA $1,021
Roundtrip
found 10 hours ago
Select American Airlines flight, departing Fri, Mar 19 from Pearson Intl. to Clayton J. Lloyd Intl., returning Tue, Mar 30, priced at CA $1,021 found 10 hours ago
OriginDestinationTravel datesFlights from*
SXMThe ValleyNovember 13 to November 14CA $543
SJUThe ValleyNovember 15 to November 19CA $1,128
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Zemi Beach House, LXR Hotels & Resorts
5.0-star property

Zemi Beach House, LXR Hotels & Resorts

Aug 16 - Aug 21

5 night stay

Toronto (YYZ) to The Valley (AXA)

WestJet • Coach

The Valley (AXA) to Toronto (YYZ)

American Airlines • Coach
Price was CA $3,591, price is now CA $3,268 per person
CA $3,268
per person
found 8 hours ago
Aurora Anguilla Resort & Golf Club
5.0-star property

Aurora Anguilla Resort & Golf Club

Oct 24 - Oct 30

6 night stay

Toronto (YTO) to The Valley (AXA)

American Airlines • Coach

The Valley (AXA) to Toronto (YTO)

Cape Air • Coach
Price was CA $5,654, price is now CA $3,973 per person
CA $3,973
per person
found 1 day ago
Malliouhana Resort Anguilla
5.0-star property

Malliouhana Resort Anguilla

Oct 24 - Oct 30

6 night stay

Toronto (YTO) to The Valley (AXA)

American Airlines • Coach

The Valley (AXA) to Toronto (YTO)

Cape Air • Coach
Price was CA $6,477, price is now CA $5,337 per person
CA $5,337
per person
found 1 day ago
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Travelers ❤️ These Anguilla 🏨

Four Seasons Resort and Residences Anguilla

Four Seasons Resort and Residences Anguilla

5 out of 5
Barnes Bay West End Village
Book a stay at this luxury resort in West End Village. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the helpful staff in our reviews. Popular attractions Meads Bay and Meads Bay Beach are located nearby.
9.6/10 Exceptional! (260 reviews)
"I love the four seasons in Anguilla!! This is my 3rd time going to the island and I wouldn't stay anywhere else!’Nothing but top notch service!! Amazing time!!"

Reviewed on Jul 28, 2026

Opens in a new windowFour Seasons Resort and Residences Anguilla
Anguilla Great House Beach Resort

Anguilla Great House Beach Resort

3.5 out of 5
Rendezvous Bay Rendezvous Bay
Book a stay at this beach hotel in Rendezvous Bay. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Meads Bay and Rendezvous Bay Beach are located nearby.
Opens in a new windowAnguilla Great House Beach Resort
Zemi Beach House, LXR Hotels & Resorts

Zemi Beach House, LXR Hotels & Resorts

5 out of 5
Shoal Bay East Shoal Bay
Book a stay at this luxury resort in Shoal Bay. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the helpful staff in our reviews. Popular attractions Shoal Bay Beach and Scrub Island are located nearby.
Opens in a new windowZemi Beach House, LXR Hotels & Resorts
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Cap Juluca, A Belmond Hotel, Anguilla

Cap Juluca, A Belmond Hotel, Anguilla

5 out of 5
Maundays Bay Maunday's Bay
Book a stay at this luxury resort in Maunday's Bay. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Meads Bay and Maundays Bay are located nearby.
9.6/10 Exceptional! (160 reviews)
"Perfection situated on stunning Mandauys Bay. Everything was top notch! Grounds were beautiful, room clean and nicely appointed. We were upgraded to a Premium Beachfront room on the 2nd floor of our Villa with a gorgeous view of the crystal clear water and white sandy beach. Daily breakfast with ..."

Reviewed on Aug 5, 2026

Opens in a new windowCap Juluca, A Belmond Hotel, Anguilla
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

How much is the cheapest flight to Anguilla?
A roundtrip flight to Anguilla cost as little as CA $503 over the last seven days. When you're ready to book, we'll help you find an amazing deal. This price was available on Travelocity for flights to Anguilla departing within the next year. Prices and availability are subject to change. Additional terms apply.
Which airlines fly to Anguilla?
Find your ideal fare with one of the 20 airlines that fly to Anguilla. If you're staying in The Valley, let Anguilla Air Services whisk you away to this lively city to explore its top sights. This popular carrier offers 30 flights there per month.
What is the cheapest month to fly to Anguilla?
If you've been dreaming of a break in Anguilla, August is the cheapest month to make your way there. This is according to Travelocity's direct return flight demand between January and December last year. Pick your preferred travel dates and lock in your seat today.
How can I check my flight status to Anguilla?
There are a couple of handy ways to look up your flight status. You can find all the necessary info in our "Trips" portal, which is located at the top right of our homepage. Log in or open a new account — you'll then be able to browse and manage your bookings whenever you need. If you're already on the go, the Travelocity app can also help you look up the status of your flight to Anguilla, as well as share details with any members of your family flying with you.
How do I find the best deals on flights to Anguilla?
Being flexible with your travel dates is one way to land an awesome deal. Travelocity makes it a piece of cake to find your ideal fare through the "Flexible dates" function. First, search for your flight to Anguilla, then compare prices for surrounding days by clicking the "Flexible dates" dropdown box above. Booking earlier and avoiding vacation periods are some other suggestions. In the last seven days, the best price for a return flight to Anguilla was CA $503. 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 Anguilla with Travelocity?
Pack your bags and get set for an awesome vacation with Travelocity. It's our job to track down fantastic deals on cheap flights to Anguilla. Whether you're seeking flexible airfares or cheap family flights from low-cost carriers, we've got you covered.
How much is a flight to Anguilla on average?
Passengers were picking up roundtrip flights to Anguilla for between CA $503 and CA $1,128 with Travelocity in the last seven days. Whether you're planning to fly economy or first class, we'll help you get a fantastic deal. These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.