Flights To Anguilla - Cheap Flights Starting at CA $276

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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.

Wed, Nov 25 - Wed, Dec 2
SXM
Princess Juliana Intl.
AXA
Clayton J. Lloyd Intl.
CA $539 Roundtrip, found 21 hours ago
CA $539
Roundtrip
found 21 hours ago
Select World Ticket Ltd flight, departing Wed, Nov 25 from Princess Juliana Intl. to Clayton J. Lloyd Intl., returning Wed, Dec 2, priced at CA $539 found 21 hours ago
Mon, Feb 22 - Mon, Mar 1
SXM
Princess Juliana Intl.
AXA
Clayton J. Lloyd Intl.
CA $549 Roundtrip, found 2 days ago
CA $549
Roundtrip
found 2 days ago
Select World Ticket Ltd flight, departing Mon, Feb 22 from Princess Juliana Intl. to Clayton J. Lloyd Intl., returning Mon, Mar 1, priced at CA $549 found 2 days ago
Sun, Feb 14 - Sat, Feb 20
SXM
Princess Juliana Intl.
AXA
Clayton J. Lloyd Intl.
CA $550 Roundtrip, found 4 hours ago
CA $550
Roundtrip
found 4 hours ago
Select World Ticket Ltd flight, departing Sun, Feb 14 from Princess Juliana Intl. to Clayton J. Lloyd Intl., returning Sat, Feb 20, priced at CA $550 found 4 hours ago
Tue, Nov 24 - Sun, Nov 29
SKB
Robert L. Bradshaw Intl.
AXA
Clayton J. Lloyd Intl.
CA $553 Roundtrip, found 18 hours ago
CA $553
Roundtrip
found 18 hours ago
Select FlexFlight flight, departing Tue, Nov 24 from Robert L. Bradshaw Intl. to Clayton J. Lloyd Intl., returning Sun, Nov 29, priced at CA $553 found 18 hours ago
Wed, Nov 25 - Wed, Dec 2
SXM
Princess Juliana Intl.
AXA
Clayton J. Lloyd Intl.
CA $558 Roundtrip, found 21 hours ago
CA $558
Roundtrip
found 21 hours ago
Select Hahn Air Systems flight, departing Wed, Nov 25 from Princess Juliana Intl. to Clayton J. Lloyd Intl., returning Wed, Dec 2, priced at CA $558 found 21 hours ago
Tue, Nov 24 - Sun, Nov 29
SKB
Robert L. Bradshaw Intl.
AXA
Clayton J. Lloyd Intl.
CA $568 Roundtrip, found 18 hours ago
CA $568
Roundtrip
found 18 hours ago
Select FlexFlight flight, departing Tue, Nov 24 from Robert L. Bradshaw Intl. to Clayton J. Lloyd Intl., returning Sun, Nov 29, priced at CA $568 found 18 hours ago
Sun, Feb 14 - Sat, Feb 20
SXM
Princess Juliana Intl.
AXA
Clayton J. Lloyd Intl.
CA $568 Roundtrip, found 4 hours ago
CA $568
Roundtrip
found 4 hours ago
Select World Ticket Ltd flight, departing Sun, Feb 14 from Princess Juliana Intl. to Clayton J. Lloyd Intl., returning Sat, Feb 20, priced at CA $568 found 4 hours ago
Wed, Nov 25 - Wed, Dec 2
SXM
Princess Juliana Intl.
AXA
Clayton J. Lloyd Intl.
CA $575 Roundtrip, found 21 hours ago
CA $575
Roundtrip
found 21 hours ago
Select Hahn Air Systems flight, departing Wed, Nov 25 from Princess Juliana Intl. to Clayton J. Lloyd Intl., returning Wed, Dec 2, priced at CA $575 found 21 hours ago
OriginDestinationTravel datesFlights from*
SXMThe ValleyNovember 25 to December 2CA $539
BWIThe ValleyDecember 21 to December 24CA $617
BOSThe ValleyDecember 21 to December 28CA $617
EWRThe ValleyDecember 18 to December 25CA $617
MIAThe ValleyJanuary 4 to January 15CA $855
ATLThe ValleyDecember 22 to December 29CA $1,145
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Fountain Anguilla
3.5-star property

Fountain Anguilla

Jan 11 - Jan 18

7 night stay

Toronto (YYZ) to The Valley (AXA)

American Airlines • Non-stop roundtrip • Coach
Price was CA $4,972, price is now CA $4,106 per person
CA $4,106
per person
just found
Malliouhana Resort Anguilla
5.0-star property

Malliouhana Resort Anguilla

Dec 14 - Dec 19

5 night stay

Ottawa (YOW) to The Valley (AXA)

United • Coach

The Valley (AXA) to Ottawa (YOW)

Cape Air • Coach
Price was CA $9,173, price is now CA $7,206 per person
CA $7,206
per person
found 1 day ago
Quintessence Hotel Anguilla
4.5-star property

Quintessence Hotel Anguilla

Jan 9 - Jan 16

7 night stay

Ottawa (YOW) to The Valley (AXA)

United • Coach

The Valley (AXA) to Ottawa (YOW)

Tradewind Aviation • Coach
Price was CA $21,492, price is now CA $17,384 per person
CA $17,384
per person
found 1 day ago
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Travelers ❤️ These 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
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.
Opens in a new windowFour Seasons Resort and Residences Anguilla
Aurora Anguilla Resort & Golf Club

Aurora Anguilla Resort & Golf Club

5 out of 5
Rendezvous Bay Rendezvous Bay
Book a stay at this luxury resort in Rendezvous Bay. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff in our reviews. Popular attractions Meads Bay and Aurora International Golf Club are located nearby.
Opens in a new windowAurora Anguilla Resort & Golf Club
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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! (163 reviews)
"Great experience everything was perfect 🏝️"

Reviewed on Nov 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 $539 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 15 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, November 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 $539. 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 $539 and CA $1,145 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.