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

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Jet to one of Anguilla's top cities

Anguilla featuring a sandy beach, general coastal views and landscape views

The Valley

Flights

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.

Sat, Mar 7 - Sat, Mar 14

SXM

Princess Juliana Intl.

AXA

Clayton J. Lloyd Intl.

$298

Roundtrip

found 6 hours ago

Mon, Apr 13 - Sun, Apr 19

STT

Cyril E. King

AXA

Clayton J. Lloyd Intl.

$404

Roundtrip

found 17 hours ago

Wed, Feb 25 - Fri, Mar 20

SKB

Robert L. Bradshaw Intl.

AXA

Clayton J. Lloyd Intl.

$442

Roundtrip

found 12 hours ago

Mon, May 4 - Tue, May 5

MIA

Miami Intl.

AXA

Clayton J. Lloyd Intl.

$526

Roundtrip

found 11 hours ago

Sat, Apr 11 - Wed, Apr 15

MCO

Orlando Intl.

AXA

Clayton J. Lloyd Intl.

$564

Roundtrip

found 2 days ago

Wed, Apr 8 - Wed, Apr 15

RDU

Raleigh - Durham Intl.

AXA

Clayton J. Lloyd Intl.

$572

Roundtrip

found 3 days ago

Thu, Jul 9 - Wed, Jul 15

JAX

Jacksonville Intl.

AXA

Clayton J. Lloyd Intl.

$581

Roundtrip

found 17 hours ago

Fri, May 1 - Wed, May 6

ATL

Hartsfield-Jackson Atlanta Intl.

AXA

Clayton J. Lloyd Intl.

$584

Roundtrip

found 17 hours ago

Sat, Apr 11 - Wed, Apr 15

JFK

John F. Kennedy Intl.

AXA

Clayton J. Lloyd Intl.

$594

Roundtrip

found 6 days ago

Origin	Destination	Travel Dates	Flights From*
SXM	The Valley	March 7 to March 14	$298
MIA	The Valley	April 21 to April 28	$516
ATL	The Valley	May 1 to May 6	$584
IAD	The Valley	April 11 to April 15	$593
JFK	The Valley	April 11 to April 15	$594
LGA	The Valley	April 11 to April 15	$594
BOS	The Valley	April 8 to April 18	$629
SJU	The Valley	April 23 to April 30	$826

*Prices include taxes and fees

Origin	Destination	Travel Dates	Flights From*
SXM	The Valley	February 20 to February 22	$298
BOS	The Valley	February 21 to February 28	$682
BWI	The Valley	February 20 to February 27	$682
EWR	The Valley	February 22 to February 26	$810
JFK	The Valley	February 22 to February 26	$1,140

*Prices include taxes and fees

Best Anguilla Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.

4.0-star property

Anguilla Great House Beach Resort

May 5 - May 12

7 night stay

Boston (BOS) to The Valley (AXA)

American Airlines • Non-stop roundtrip • Coach

$1,245

per person

found 1 day ago

5.0-star property

Aurora Anguilla Resort & Golf Club

May 5 - May 12

7 night stay

Boston (BOS) to The Valley (AXA)

American Airlines • Non-stop roundtrip • Coach

Save 100% on your flight

$3,021

per person

found 1 day ago

5.0-star property

Malliouhana Resort Anguilla

May 5 - May 12

7 night stay

Boston (BOS) to The Valley (AXA)

American Airlines • Non-stop roundtrip • Coach

Save 100% on your flight

$3,898

per person

found 1 day ago

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See all available trips from Boston to Anguilla

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Travelers ❤️ These Anguilla 🏨

Four Seasons Resort and Residences Anguilla

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 Beach and Meads Bay Pond are located nearby.

9.6/10 Exceptional! (247 reviews)

Great Service!!!

Reviewed on Feb 4, 2026

Anguilla Great House Beach Resort

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 Rendezvous Bay Beach and Aurora International Golf Club are located nearby.

8/10 Very Good! (285 reviews)

An ice machine would be a benefit to guests but we had a wonderful stay!

Reviewed on Feb 11, 2026

Cap Juluca, A Belmond Hotel, Anguilla

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 Maundays Bay and Cove Bay are located nearby.

9.6/10 Exceptional! (137 reviews)

Besides the obvious natural beauty of the property, the beachfront’s glorious views, the fine restaurants and food, it is the warm, inviting and outgoing staff that sets Cap Juluca apart. It is one of a kind on the island, in a class by itself.

Reviewed on Feb 2, 2026

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Aurora Anguilla Resort & Golf Club

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 Aurora International Golf Club and Rendezvous Bay Beach are located nearby.

9.6/10 Exceptional! (189 reviews)

Every staff member was amazing and went above and beyond to ensure a wonderful stay. Everything was spotless, and the amenities were excellent. Our only recommendation is regarding the spraying on the plants—we would prefer a more natural approach, as we noticed insects dying on the sidewalks afterward. ...

Reviewed on Feb 8, 2026

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.

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Frequently asked questions

How much is the cheapest flight to Anguilla?

A roundtrip flight to Anguilla cost as little as $298 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 16 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, March 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 $298. 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 $298 and $1,140 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.

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

Travelers

Jet to one of Anguilla's top cities

The Valley

Rendezvous Bay

Shoal Bay

How Much Does it Cost To Fly To Anguilla?

Best Anguilla Flight and Hotel Packages

Anguilla Great House Beach Resort

May 5 - May 12

Boston (BOS) to The Valley (AXA)

Aurora Anguilla Resort & Golf Club

May 5 - May 12

Boston (BOS) to The Valley (AXA)

Malliouhana Resort Anguilla

May 5 - May 12

Boston (BOS) to The Valley (AXA)

Travelers ❤️ These Anguilla 🏨

Four Seasons Resort and Residences Anguilla

Anguilla Great House Beach Resort

Cap Juluca, A Belmond Hotel, Anguilla

Aurora Anguilla Resort & Golf Club

More Ways To Wander Anguilla

Frequently asked questions

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