$114+ Cheap Flights from Anguilla

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Cheapest round-trip

The ValleyBasseterre

AXA The Valley Wallblake Intl - SKB Basseterre Robert Bradshaw Intl

AXASKB

The Valley Wallblake Intl

Sat 12/19

2:30 pm-3:00 pm

Nonstop0h 30m

Basseterre Robert Bradshaw Intl

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$115

The ValleyBasseterre

AXA The Valley Wallblake Intl - SKB Basseterre Robert Bradshaw Intl

AXASKB

The Valley Wallblake Intl

Sat 12/19

2:30 pm-3:00 pm

Nonstop0h 30m

Basseterre Robert Bradshaw Intl

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$130

The ValleyBoston

AXA The Valley Wallblake Intl - BOS Boston Logan Intl

AXABOS

The Valley Wallblake Intl

Mon 12/21

5:25 pm-9:10 pm

Nonstop4h 45m

Boston Logan Intl

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$225

The ValleyNewark

AXA The Valley Wallblake Intl - EWR Newark

AXAEWR

The Valley Wallblake Intl

Mon 2/8

7:10 pm-11:00 pm

Nonstop4h 50m

Newark

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$229

The ValleyMiami

AXA The Valley Wallblake Intl - MIA Miami

AXAMIA

The Valley Wallblake Intl

Wed 11/18

5:45 pm-8:03 pm

Nonstop3h 18m

Miami

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$252

The ValleyBasseterre

AXA The Valley Wallblake Intl - SKB Basseterre Robert Bradshaw Intl

AXASKB

The Valley Wallblake Intl

Sat 12/26

2:30 pm-3:00 pm

Nonstop0h 30m

Basseterre Robert Bradshaw Intl

Sat 1/2

5:00 pm-5:30 pm

Nonstop0h 30m

$257

Quickest round-trip

The ValleySimpson Bay

AXA The Valley Wallblake Intl - SXM Simpson Bay Princess Juliana

AXASXM

The Valley Wallblake Intl

Sat 1/30

12:30 pm-12:40 pm

Nonstop0h 10m

Simpson Bay Princess Juliana

Wed 2/3

12:15 pm-12:25 pm

Nonstop0h 10m

$285

The ValleySimpson Bay

AXA The Valley Wallblake Intl - SXM Simpson Bay Princess Juliana

AXASXM

The Valley Wallblake Intl

Mon 2/1

9:30 am-9:40 am

Nonstop0h 10m

Simpson Bay Princess Juliana

Wed 2/3

5:15 pm-5:25 pm

Nonstop0h 10m

$285

The ValleySimpson Bay

AXA The Valley Wallblake Intl - SXM Simpson Bay Princess Juliana

AXASXM

The Valley Wallblake Intl

Fri 1/29

1:30 pm-1:40 pm

Nonstop0h 10m

Simpson Bay Princess Juliana

Wed 2/3

1:15 pm-1:25 pm

Nonstop0h 10m

$285

The ValleySimpson Bay

AXA The Valley Wallblake Intl - SXM Simpson Bay Princess Juliana

AXASXM

The Valley Wallblake Intl

Tue 2/2

1:30 pm-1:40 pm

Nonstop0h 10m

Simpson Bay Princess Juliana

Wed 2/3

5:15 pm-5:25 pm

Nonstop0h 10m

$285

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/11

Showing 1-10 of 51 resultsSorted by cheapest first

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Best time to book a flight from Anguilla

Have a flexible travel schedule? Discover the best time to fly from Anguilla with our price prediction graph.

AXA-SKB

AXA-BOS

AXA-SXM

AXA-STT

AXA-MIA

Estimated round-trip price

Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Travel insights for flights from Anguilla

Get recent, data-driven insights about flights from Anguilla including ideal travel times, pricing trends, and more.

AI0-JFK

AXA-SKB

AXA-BOS

AXA-SXM

AXA-STT

What is the cheapest place to fly to from Anguilla?

The cheapest city to fly to from Anguilla is Providenciales, with prices starting at $192. Explore other affordable destinations below.

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This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/19. Fares are subject to change and may not be available on all flights or dates of travel.

Find flights from Anguilla within your budget

Best time to book a flight from Anguilla

Have a flexible travel schedule? Discover the best time to fly from Anguilla with our price prediction graph.

Travel insights for flights from Anguilla

What is the cheapest place to fly to from Anguilla?

The cheapest city to fly to from Anguilla is Providenciales, with prices starting at $192. Explore other affordable destinations below.

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Fly from Anguilla cities

Consider departing from one of these cities also located in Anguilla. Flight origins are based on user searches made on Cheapflights and were last updated on November 12, 2026.

Fly from Caribbean regions

Book your next flight out of one of these popular departure points located in Caribbean.

Popular international destinations from Caribbean

The most popular international flight routes departing from Caribbean we’ve come across at this time.

Popular Round-Trip Flight Destinations

Consider these popular destinations that Cheapflights users have chosen when departing from Caribbean. Routes are based on user searches and were last updated on November 12, 2026.

Popular flight searches

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$114+ Cheap flights from Anguilla

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/19. Fares are subject to change and may not be available on all flights or dates of travel.

Find flights from Anguilla within your budget

Best time to book a flight from Anguilla

Have a flexible travel schedule? Discover the best time to fly from Anguilla with our price prediction graph.

Travel insights for flights from Anguilla

What is the cheapest place to fly to from Anguilla?

The cheapest city to fly to from Anguilla is Providenciales, with prices starting at $192. Explore other affordable destinations below.

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Fly from Anguilla cities

Consider departing from one of these cities also located in Anguilla. Flight origins are based on user searches made on Cheapflights and were last updated on November 12, 2026.

Fly from Caribbean regions

Book your next flight out of one of these popular departure points located in Caribbean.

Popular international destinations from Caribbean

The most popular international flight routes departing from Caribbean we’ve come across at this time.

Popular Round-Trip Flight Destinations

Consider these popular destinations that Cheapflights users have chosen when departing from Caribbean. Routes are based on user searches and were last updated on November 12, 2026.

Popular flight searches

Check out other popular destinations found by fellow travelers in 2026

100% Free

Book with Flexibility

Travel Smart