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Cheap flights from Caribbean to London Southend Airport from £269

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 29/9. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — SEN
9 Sep — 16 Sep1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Caribbean to Southend

Enter your travel dates to find the best prices.

Cheapest flights from Caribbean to Southend
Explore the most affordable flight options available from Caribbean to Southend. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 10 August 2026.

Tue 22/916:20 -
2 stops21h 20m
Tue 6/1006:30 -
3 stops39h 30m
Deal found 5/8£779
Tue 22/916:20 -
2 stops21h 20m
Wed 7/1018:00 -
3 stops47h 20m
Deal found 7/8£799
Tue 8/916:20 -
2 stops21h 20m
Tue 15/920:25 -
3 stops44h 55m
Deal found 9/8£917
Fri 14/821:20 -
2 stops19h 25m
Fri 21/819:40 -
2 stops26h 40m
Deal found 7/8£938
Wed 23/901:40 -
3 stops28h 05m
Tue 6/1007:00 -
3 stops36h 00m
Deal found 10/8£1,071
Sat 29/813:45 -
3 stops23h 35m
Sat 5/916:50 -
3 stops34h 25m
Deal found 7/8£1,401

Find flight deals from Caribbean to Southend

Keep the following information in mind while searching for Caribbean to Southend flight deals. Data was last updated 10 August 2026.

Round-trip from

£779

One-way from

£269

Popular in

April

Cheapest in

November

Average price

£848
22/9-6/10
  • 22/9-6/10
  • 5 total stops
  • 60h 50m total
  • Caribbean to London
Search Deals
29/9
  • 29/9
  • 2 total stops
  • 21h 20m total
  • Caribbean to London
Search Deals
Highest demand for flights based on searches. 7% potential increase in price (£53 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (£11 potential savings vs. average return price).
Search Deals
Average for round-trip flights in August 2026
Search Deals

Cheapflights Fare Finder

 
Customise your flight search to find flights from Caribbean to Southend that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 858,174 searches. Data last updated 10 August 2026.
Use the filters below to find and compare flights from Caribbean to London Southend Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest return flight

Montego BayLondon

MBJ Montego Bay Sangster Intl - SEN London Southend

MBJSEN

Montego Bay Sangster Intl

Tue 22/9

16:20-19:40

2 stops21h 20m

London Southend

Tue 6/10

06:30-16:00

3 stops39h 30m

£779

Montego BayLondon

MBJ Montego Bay Sangster Intl - SEN London Southend

MBJSEN

Montego Bay Sangster Intl

Tue 22/9

16:20-19:40

2 stops21h 20m

London Southend

Wed 7/10

18:00-11:20

3 stops47h 20m

£799

Montego BayLondon

MBJ Montego Bay Sangster Intl - SEN London Southend

MBJSEN

Montego Bay Sangster Intl

Tue 8/9

16:20-19:40

2 stops21h 20m

London Southend

Tue 15/9

20:25-11:20

3 stops44h 55m

£917

Port of SpainLondon

POS Port of Spain Piarco Intl - SEN London Southend

POSSEN

Port of Spain Piarco Intl

Wed 23/9

01:40-10:45

3 stops28h 05m

London Southend

Tue 6/10

07:00-14:00

3 stops36h 00m

£1,071
Fastest return journey

George TownLondon

GCM George Town Owen Roberts Intl - SEN London Southend

GCMSEN

George Town Owen Roberts Intl

Sat 29/8

13:45-19:20

3 stops23h 35m

London Southend

Sat 5/9

16:50-21:15

3 stops34h 25m

£1,401
Cheapest one-way

Montego BayLondon

MBJ Montego Bay Sangster Intl - SEN London Southend

MBJSEN

Montego Bay Sangster Intl

Tue 29/9

16:20-19:40

2 stops21h 20m

£269

Punta CanaLondon

PUJ Punta Cana - SEN London Southend

PUJSEN

Punta Cana

Sun 20/9

15:05-19:35

1 stop23h 30m

£345

Punta CanaLondon

PUJ Punta Cana - SEN London Southend

PUJSEN

Punta Cana

Sun 13/9

15:05-19:35

2 stops23h 30m

£362

San JuanLondon

SJU San Juan Luis Munoz Marin Intl - SEN London Southend

SJUSEN

San Juan Luis Munoz Marin Intl

Mon 14/9

03:08-22:20

3 stops38h 12m

£368
Fastest single journey

Punta CanaLondon

PUJ Punta Cana - SEN London Southend

PUJSEN

Punta Cana

Wed 9/9

16:40-16:40

2 stops19h 00m

£370

Flights are sorted by cheapest return flights first.

Deals found on 9/8

Showing 1-10 of 35 resultsSorted by cheapest first
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Best time to book a flight from Caribbean to Southend

Have a flexible travel schedule? Discover the best time to fly to Southend from Caribbean with our price prediction graph.
Estimated return 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.

Cheapflights Insights

Everything you need to know about your flight from Caribbean to London Southend Airport

No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from Caribbean to Southend. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the most popular routes from Caribbean to London Southend Airport?

    When deciding which route to take from Caribbean to London Southend Airport consider Bridgetown Grantley Adams Intl - London Southend, George Town Owen Roberts Intl - London Southend or Kingston Norman Manley - London Southend as they are the most popular.

  • Can I find deals for flights from Caribbean to Southend that include hotel bookings?

    Yes. In addition to deals on Caribbean to Southend flights, Cheapflights offers holiday packages that include both flights and hotel.

  • How can I find direct flights from Caribbean to Southend?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Caribbean to Southend.

  • Can I find deals for business class flights from Caribbean to Southend?

    Yes. Cheapflights offers flight deals from Caribbean to Southend by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Travelling to a place near London Southend Airport?

Book flights to London Southend Airport if you plan to visit one of these locations
Hounslow
Milton Keynes
Gatwick
Luton
Wembley
Slough
Ilford
Hayes
Croydon
Colchester
Eastbourne
Brentford
Watford
Southend-on-Sea
Enfield
Kingston upon Thames
Southall
Dover
Romford
Borehamwood

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.

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Fly with Cheapflights

Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Caribbean to Southend?

900+ travel sites are searched through when a user searches for a flight using Cheapflights. From the search interface, users can use filters to choose airlines, airports, flight times, cabin classes and more to their preference. Book your flight to Southend from Caribbean today with Cheapflights!

Why should you use Cheapflights to find cheap flight tickets from Caribbean to Southend?

It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Caribbean to Southend.

Can Cheapflights find flights from Caribbean to Southend with no change fees?

Yes, we can. To see specific flights from Caribbean to Southend with no change fees, users can toggle flexible booking options after using the search form above to find flights.

Can Cheapflights notify me if prices for flights from Caribbean to Southend become cheaper?

Yes! Start tracking prices for Caribbean to Southend flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.

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