$295 Find Cheap Flights to Anguilla - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from the United States to Anguilla departing on 1/1. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
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Book Cheap Anguilla Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights to Anguilla that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals to Anguilla

Mon, Jan 11 - Fri, Jan 15
BermudAir Logo
7:30 am - 1:10 pm
BOS
-
AXA
4h 40mnonstop
BermudAir Logo
1:25 pm - 5:10 pm
AXA
-
BOS
4h 45mnonstop
$656BermudAir
Mon, Nov 30 - Mon, Dec 7
American Airlines Logo
10:10 am - 2:18 pm
MIA
-
AXA
3h 08mnonstop
American Airlines Logo
3:01 pm - 5:26 pm
AXA
-
MIA
3h 25mnonstop
$669American Airlines
Wed, Aug 19 - Wed, Aug 26
American Airlines Logo
10:10 am - 1:32 pm
MIA
-
AXA
3h 22mnonstop
American Airlines Logo
2:12 pm - 5:20 pm
AXA
-
MIA
3h 08mnonstop
$671American Airlines
Wed, Nov 18 - Sun, Nov 22
American Airlines Logo
12:10 pm - 4:25 pm
MIA
-
AXA
3h 15mnonstop
American Airlines Logo
5:05 pm - 7:15 pm
AXA
-
MIA
3h 10mnonstop
$679American Airlines
Mon, Dec 7 - Tue, Dec 15
American Airlines Logo
5:04 pm - 2:21 pm
BWI
-
AXA
20h 17m
1 stop
American Airlines Logo
5:20 pm - 12:29 am
AXA
-
BWI
8h 09m
1 stop
$694American Airlines
Mon, Dec 7 - Tue, Dec 15
American Airlines Logo
5:04 pm - 2:21 pm
BWI
-
AXA
20h 17m
1 stop
American Airlines Logo
5:20 pm - 12:29 am
AXA
-
BWI
8h 09m
1 stop
$696American Airlines
Fri, Dec 25 - Mon, Dec 28
BermudAir Logo
7:30 am - 1:10 pm
BOS
-
AXA
4h 40mnonstop
BermudAir Logo
1:25 pm - 5:10 pm
AXA
-
BOS
4h 45mnonstop
$697BermudAir
Mon, Dec 7 - Tue, Dec 15
American Airlines Logo
5:04 pm - 2:21 pm
BWI
-
AXA
20h 17m
1 stop
American Airlines Logo
5:20 pm - 12:29 am
AXA
-
BWI
8h 09m
1 stop
$698American Airlines
Sat, Sep 19 - Sat, Sep 26
United Airlines Logo
9:00 am - 5:35 pm
IAD
-
AXA
8h 35m
1 stop
United Airlines Logo
9:46 am - 8:50 pm
AXA
-
IAD
11h 04m
1 stop
$1,166United Airlines
Fri, Oct 23 - Mon, Oct 26
United Airlines Logo
5:59 pm - 5:35 pm
CLT
-
AXA
23h 36m
2 stops
United Airlines Logo
9:46 am - 6:46 pm
AXA
-
CLT
9h 00m
2 stops
$1,502United Airlines
Booking Insights

KAYAK's insights & trends for flights to Anguilla

Get data-powered insights and trends for flights to Anguilla to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest flight to Anguilla?

These are the best round-trip prices found by users searching on KAYAK in the last 5 days.

The cheapest ticket to Anguilla from the United States found in the last 5 days was to The Valley, at $635 round-trip. The most popular route is Boston (BOS) to The Valley (AXA) and the cheapest round-trip airline ticket found on this route in the last 5 days was $635.

Good to know

Low season

September

Cheapest flight

$295
Best time to beat the crowds but there is an average 43% increase in price.
Most popular time to fly and prices are also 6% lower on average.
Flight from Boston to The Valley

FAQs - booking Anguilla flights

  • Can I fly to other Caribbean islands from the airport on Anguilla (AXA)?

    Yes. The Clayton J. Lloyd International Airport (AXA) offers many inter-Caribbean flights. For example, you can fly to San Juan or St. Thomas on Air Sunshine, to Antigua or St. Barts on Anguilla Air Services, to St. Kitts or Virgin Gorda on Trade Wind Aviation, or to St. Eustatius or Tortola on Trans Anguilla Airways.

  • Do I need a passport in order to fly to Anguilla?

    Since Anguilla is a British Territory, US citizens will need a passport in order to deplane at Anguilla. This passport must be valid at the time of entry into Anguilla and it must have at least one blank page for an entry stamp. US citizens are also required to show a return or onward ticket as proof of departure, proof that you have accommodation on Anguilla, and evidence that you have funds to maintain yourself while you are on the island; if you have all of these, then you do not need a visa.

  • Which of the New York airports is it best to depart from if I want to fly to Anguilla?

    American Airlines offers an affordable flight from LaGuardia Airport (LGA) to Anguilla (AXA) with one stop in Miami. Airlines such as American, JetBlue, Delta, United, Frontier, and others offer flights from all three major New York City airports. However, when you are booking a ticket, be sure to consider not just the price of the ticket, but also the length of the journey, which is sometimes greatly extended by stops and layover time.

  • Can I find a non-stop flight from Los Angeles to Anguilla?

    When you are booking your flight from Los Angeles to Anguilla, it is unlikely that you will be able to find a non-stop flight. However, American Airlines offers several flights from LAX to Anguilla (AXA) with just one stop in Miami (MIA).

  • Can I fly to Anguilla from any of the Washington DC major airports?

    Yes. The Ronald Reagan National Airport (DCA) tends to have the cheapest and most convenient flights available on American Airlines, with one stop in Miami. The Baltimore-Washington Thurgood Marshall International Airport (BWI) also offers a number of low-cost flights to Anguilla (AXA).

  • Where's the best place in Florida to fly from if I am headed to Anguilla?

    American Airlines offers comparable flights to Anguilla from Miami, Fort Lauderdale, Tampa, Orlando, and Jacksonville. However, there tends to be more flight options available when departing from Miami. When booking your flight from Florida to Anguilla through KAYAK, you'll find many options available in order to find the flight that works for you.

  • How does KAYAK find such low prices on flights from the United States to Anguilla?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from the United States to Anguilla.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from the United States to Anguilla?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from the United States to Anguilla is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from the United States to Anguilla?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from the United States to Anguilla with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from the United States to Anguilla?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from the United States to Anguilla up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest day to fly to Anguilla?

    Based on KAYAK data, the cheapest day to fly to Anguilla is Tuesday where round-trip tickets can be as cheap as $585. On the other hand, the most expensive day to fly is Thursday, where round-trip prices are $744 on average.

Top tips for finding cheap flights to Anguilla

  • Looking for cheap airfare to Anguilla? 25% of our users found round-trip tickets to Anguilla for the following prices or less: From Boston $724
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Anguilla flight deals.
  • When you fly directly to the Caribbean island of Anguilla, you'll be landing at the Clayton J. Lloyd International Airport (AXA), in the city The Valley, the capital of Anguilla. AXA serves The Valley, as well as Mount Fortune and Island Harbour on the north end of the island and Blowing Point and Long Bay Village on the south end.
  • You can often find a cheaper air fare to Anguilla by booking a flight from a US city to Simpson Bay in St. Maarten, Anguilla's neighboring island in the Caribbean. From St. Maarten, you can catch a ferry to Anguilla. This boat trip usually takes a little less than 30 minutes.
  • If you want to fly from the Harry Reid Las Vegas International Airport (LAS) to Anguilla (AXA), booking through KAYAK will afford you a number of options. For example, you can fly Delta with stops in Atlanta and San Juan, Puerto Rico. You can fly American with one stop in Miami or two stops in Dallas and Miami. You can fly United with two stops in Newark and in San Juan. These are just a few of the many options for flights from LAS to AXA.
  • One feasible way to book an affordable airline ticket to Anguilla is to first book a ticket to San Juan in Puerto Rico (SJU). From San Juan, you can book a separate ticket to Anguilla (AXA). The combination of these two journeys is often less expensive than a flight directly to Anguilla (AXA).
  • Affordable flights from Chicago to Anguilla can be booked through KAYAK departing from either Chicago O'Hare International Airport (ORD) or Midway International Airport (MDW). While flights from ORD can sometimes be more convenient with fewer stops, there are some flights from MDW that are quite cheap.
  • When you are booking a flight through KAYAK from the US to Anguilla, consider flying to the US Virgin Island of St. Thomas instead of directly into Anguilla, since a ticket to St. Thomas is often much cheaper. From St. Thomas, you can book a flight to Anguilla or you can catch a series of ferries to Beef Island and from there, board a flight to Anguilla.
  • If you are booking a ticket from Dallas to Anguilla, you'll find a number of flight options from Dallas-Fort Worth International Airport (DFW) to AXA. However, keep in mind that you can find some bargain flights from the Dallas Love Field Airport (DAL) as well.

Reviews of the top airlines flying to Anguilla

 
Need help choosing which airline to fly with from the United States to Anguilla? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
9.2
BermudAirOverall score based on 5 reviews
5.6Entertainment
8.8Comfort
9.6Crew
7.6Food
9.2Boarding
Airline reviews

It was perfect! Will try to use BermudAir when it works.

10.0 ExcellentDonna, Feb 2026
BWI - BDA
Read more BermudAir reviews

It was perfect! Will try to use BermudAir when it works.

They cancelled our flight two times after rebooking us for a later flight. We never got on the plane. We found another solution by driving.

Quick flight. No time to stress over it. Over before it begins.

Very good, boarded and took off on time and landed early

It was good overall but when I book my flight and seat through Kayak, AA will at times change those seats during check-in time which I don’t understand why. I always book aisle seats and had to sit at window for my flight to Austin this trip.

Mostly great. Only issue was with the WiFi. Halfway through the flight it was spotty and I was unable to work as I planned. This impacted my work products as I am traveling for business and it was an unexpected hindrance which was inconvenient. Flight here was amazing. For a 5 hour flight something more than a Biscoff would be nice but I’m just swinging at windmills I guess…

- flight was delayed several hours due to weather (understandable) - flight delayed further and we were told by attendants "we are not sure where the pilots are but they are on their way" as we have to find different pilots for the flight - announcements over the PA were somewhat unprofessional by the attendants, seems they need more training and were not reading off the script. They showed their young age and immaturity in their communications with the passengers. They were not clear and lacked professional communication language. - going from a hub to hub we were also parked at the tarmac at ohare for an additional hour and kept being told "few more minutes". Please just let the passengers know the real wait time instead of hiding the truth. We understand there is traffic and weather delays, but we just want transparency. There are several logistics of our lives that revolve around what the attendants and pilots are sharing with us but they are not being transparant.

Not good. Flight crew, was not friendly and just shoved stuff at us. Not the way I like to travel.

Booked flight at 8pm Sunday evening. Flight posted delay from 5:00 to 7:46AM Monday morning. At 12:26 AM (after I was asleep) pulled flight forward to 6:21AM. Had to scramble in morning to make the flight. Barely did

Delayed boarding because a flight attendant couldn't find the gate...sat on the plane for over an hour at the gate because AA couldn't get one of the planes behind us to move

They kept us on the tarmac for 6 hours after already delaying our flight by 2 hours. No one had any answers. They sent our gate checked stroller to baggage claim instead of giving it back at the gate.

Everything you need to know for your flight to Anguilla

Cabin class types available on flights to Anguilla

Cabin classes available on flights to Anguilla. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.