Cheap Flights to Anguilla from $152 (2026/2027)

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Jet to one of Anguilla's top cities

A beach with clear turquoise waters, white sand, and a palm tree.

Shoal Bay

Flights
Shoal Bay

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.

Mon, Sep 21 - Wed, Sep 23
SXM
Princess Juliana Intl.
AXA
Clayton J. Lloyd Intl.
$358 Roundtrip, found 18 hours ago
$358
Roundtrip
found 18 hours ago
Select World Ticket Ltd flight, departing Mon, Sep 21 from Princess Juliana Intl. to Clayton J. Lloyd Intl., returning Wed, Sep 23, priced at $358 found 18 hours ago
Sun, Nov 8 - Thu, Nov 12
DCA
Ronald Reagan Washington National
AXA
Clayton J. Lloyd Intl.
$535 Roundtrip, found 2 days ago
$535
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sun, Nov 8 from Ronald Reagan Washington National to Clayton J. Lloyd Intl., returning Thu, Nov 12, priced at $535 found 2 days ago
Sun, Nov 8 - Thu, Nov 12
BWI
Baltimore Washington Intl. Thurgood Marshall
AXA
Clayton J. Lloyd Intl.
$535 Roundtrip, found 21 hours ago
$535
Roundtrip
found 21 hours ago
Select American Airlines flight, departing Sun, Nov 8 from Baltimore Washington Intl. Thurgood Marshall to Clayton J. Lloyd Intl., returning Thu, Nov 12, priced at $535 found 21 hours ago
Fri, Nov 6 - Wed, Nov 11
MIA
Miami Intl.
AXA
Clayton J. Lloyd Intl.
$572 Roundtrip, found 5 hours ago
$572
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Fri, Nov 6 from Miami Intl. to Clayton J. Lloyd Intl., returning Wed, Nov 11, priced at $572 found 5 hours ago
Sun, Dec 13 - Thu, Dec 17
TPA
Tampa Intl.
AXA
Clayton J. Lloyd Intl.
$574 Roundtrip, found 11 hours ago
$574
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Sun, Dec 13 from Tampa Intl. to Clayton J. Lloyd Intl., returning Thu, Dec 17, priced at $574 found 11 hours ago
Sat, Jan 2 - Tue, Jan 12
IAD
Washington Dulles Intl.
AXA
Clayton J. Lloyd Intl.
$592 Roundtrip, found 2 days ago
$592
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Jan 2 from Washington Dulles Intl. to Clayton J. Lloyd Intl., returning Tue, Jan 12, priced at $592 found 2 days ago
Mon, Dec 7 - Tue, Dec 8
LGA
LaGuardia
AXA
Clayton J. Lloyd Intl.
$614 Roundtrip, found 12 hours ago
$614
Roundtrip
found 12 hours ago
Select American Airlines flight, departing Mon, Dec 7 from LaGuardia to Clayton J. Lloyd Intl., returning Tue, Dec 8, priced at $614 found 12 hours ago
Mon, Dec 7 - Tue, Dec 8
JFK
John F. Kennedy Intl.
AXA
Clayton J. Lloyd Intl.
$614 Roundtrip, found 12 hours ago
$614
Roundtrip
found 12 hours ago
Select American Airlines flight, departing Mon, Dec 7 from John F. Kennedy Intl. to Clayton J. Lloyd Intl., returning Tue, Dec 8, priced at $614 found 12 hours ago
OriginDestinationTravel DatesFlights From*
SXMThe ValleyNovember 1 to November 4$386
DCAThe ValleyNovember 8 to November 12$535
MIAThe ValleyNovember 6 to November 11$572
JFKThe ValleyDecember 7 to December 8$614
EWRThe ValleyDecember 7 to December 8$614
BOSThe ValleyDecember 18 to December 21$667
SJUThe ValleyNovember 17 to November 21$833
ATLThe ValleyNovember 7 to November 14$1,047
*Prices include taxes and fees

Best Anguilla Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Aurora Anguilla Resort & Golf Club
5.0-star property

Aurora Anguilla Resort & Golf Club

Nov 24 - Dec 1

7 night stay

Boston (BOS) to The Valley (AXA)

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $8,926, price is now $5,311 per person
$5,311
per person
found 1 day ago
Ceblue Luxury Villas
5.0-star property

Ceblue Luxury Villas

Nov 24 - Dec 1

7 night stay

Boston (BOS) to The Valley (AXA)

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $6,827, price is now $5,446 per person
$5,446
per person
found 1 day ago
6 BR Villa With Concierge Amenities Pool
2.0-star property

6 BR Villa With Concierge Amenities Pool

Nov 24 - Dec 1

7 night stay

Boston (BOS) to The Valley (AXA)

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $14,976, price is now $11,983 per person
$11,983
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.
8.2/10 Very Good! (345 reviews)
"Its a great place to unwind and relax"

Reviewed on Sep 10, 2026

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
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.
Opens in a new windowCap Juluca, A Belmond Hotel, Anguilla
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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
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 $358 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, September 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 $358. 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 $358 and $1,047 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.
What can I expect on a flight to Anguilla?
This depends mostly on your carrier and the duration of your flight. Generally, most airlines provide warm meals, drinks and entertainment on long-haul journeys. Whether you're searching for first class flights to Anguilla or cheap flights for family vacations, you'll be well looked after from boarding to touchdown.