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Cheap flights from London Southend Airport to Caribbean Islands from £288

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 6/5. Fares are subject to change and may not be available on all flights or dates of travel.
SEN — SJU
20 Feb — 27 Feb1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Southend to Caribbean Islands

Enter your travel dates to find the best prices.

Cheapest flights from Southend to Caribbean Islands
Explore the most affordable flight options available from Southend to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 21 January 2026.

Sun 22/211:55
SEN
-
PUJ
3 stops32h 50m
Multiple Airlines
Sun 8/318:00
PUJ
-
SEN
2 stops16h 50m
Multiple Airlines
Deal found 19/1£698
Wed 25/207:10
SEN
-
PUJ
2 stops35h 15m
Multiple Airlines
Thu 5/321:15
PUJ
-
SEN
1 stop11h 35m
Multiple Airlines
Deal found 20/1£999
Mon 30/316:55
SEN
-
MBJ
1 stop28h 40m
Multiple Airlines
Mon 6/422:05
MBJ
-
SEN
2 stops27h 50m
Multiple Airlines
Deal found 20/1£1,099
Fri 13/210:00
SEN
-
KIN
3 stops33h 30m
Multiple Airlines
Sat 21/215:30
KIN
-
SEN
3 stops24h 20m
Multiple Airlines
Deal found 20/1£1,235
Wed 11/207:10
SEN
-
PUJ
2 stops16h 45m
Multiple Airlines
Sun 22/218:00
PUJ
-
SEN
2 stops16h 50m
Multiple Airlines
Deal found 19/1£1,306
Sat 14/207:15
SEN
-
POS
2 stops17h 15m
Multiple Airlines
Sat 21/221:55
POS
-
SEN
1 stop18h 15m
Multiple Airlines
Deal found 19/1£1,420
Sat 14/207:15
SEN
-
BGI
2 stops35h 20m
Multiple Airlines
Sat 21/214:24
BGI
-
SEN
3 stops25h 46m
Multiple Airlines
Deal found 19/1£1,726
Sat 14/207:15
SEN
-
MBJ
2 stops33h 00m
Multiple Airlines
Sun 15/213:25
MBJ
-
SEN
3 stops20h 25m
Multiple Airlines
Deal found 20/1£2,202
Fri 13/206:40
SEN
-
POS
3 stops23h 04m
Multiple Airlines
Wed 18/219:20
POS
-
SEN
1 stop17h 55m
Multiple Airlines
Deal found 19/1£2,242

Find flight deals from Southend to Caribbean Islands

Keep the following information in mind while searching for Southend to Caribbean Islands flight deals. Data was last updated 21 January 2026.

Round-trip from

£698

One-way from

£288

Popular in

December

Cheapest in

January

Average price

£673
22/2-8/3
  • 22/2-8/3
  • 5 total stops
  • 49h 40m total
  • London to Caribbean Islands
Search Deals
6/5
  • 6/5
  • 2 total stops
  • 21h 55m total
  • London to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 2% potential increase in price (£16 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (£16 potential savings vs. average return price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Cheapflights Fare Finder

 
Customise your flight search to find flights from Southend to Caribbean Islands 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 21 January 2026.
Use the filters below to find and compare flights from London Southend Airport to Caribbean Islands that are best for you.

Fly from

Southend

Fly to

Caribbean Islands

Route

Depart

Return

Price

LondonPunta Cana

SEN - PUJ

SENPUJ

London Southend

Sun 22/2

11:55-16:45

3 stops32h 50m

Punta Cana

Sun 8/3

18:00-14:50

2 stops16h 50m

£698

LondonPunta Cana

SEN - PUJ

SENPUJ

London Southend

Wed 25/2

07:10-14:25

2 stops35h 15m

Punta Cana

Thu 5/3

21:15-12:50

1 stop11h 35m

£999

LondonMontego Bay

SEN - MBJ

SENMBJ

London Southend

Mon 30/3

16:55-15:35

1 stop28h 40m

Montego Bay Sangster Intl

Mon 6/4

22:05-07:55

2 stops27h 50m

£1,099

LondonKingston

SEN - KIN

SENKIN

London Southend

Fri 13/2

10:00-14:30

3 stops33h 30m

Kingston Norman Manley

Sat 21/2

15:30-20:50

3 stops24h 20m

£1,235

LondonPunta Cana

SEN - PUJ

SENPUJ

London Southend

Wed 11/2

07:10-19:55

2 stops16h 45m

Punta Cana

Sun 22/2

18:00-14:50

2 stops16h 50m

£1,306

LondonPort of Spain

SEN - POS

SENPOS

London Southend

Sat 14/2

07:15-20:30

2 stops17h 15m

Port of Spain Piarco Intl

Sat 21/2

21:55-20:10

1 stop18h 15m

£1,420

LondonBridgetown

SEN - BGI

SENBGI

London Southend

Sat 14/2

07:15-14:35

2 stops35h 20m

Bridgetown Grantley Adams Intl

Sat 21/2

14:24-20:10

3 stops25h 46m

£1,726

LondonMontego Bay

SEN - MBJ

SENMBJ

London Southend

Sat 14/2

07:15-11:15

2 stops33h 00m

Montego Bay Sangster Intl

Sun 15/2

13:25-14:50

3 stops20h 25m

£2,202

LondonPort of Spain

SEN - POS

SENPOS

London Southend

Fri 13/2

06:40-01:44

3 stops23h 04m

Port of Spain Piarco Intl

Wed 18/2

19:20-17:15

1 stop17h 55m

£2,242

LondonSan Juan

SEN - SJU

SENSJU

London Southend

Wed 6/5

08:25-01:20

2 stops21h 55m

£288

Flights are sorted by cheapest return flights first.

Deals found on 19/1

Showing 1-10 of 39 results
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Best time to book a flight from Southend to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from Southend 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 London Southend Airport to Caribbean Islands
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 Southend to Caribbean Islands. 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 London Southend Airport to Caribbean Islands?

    The most popular flight routes from London Southend Airport to Caribbean Islands are London Southend - Punta Cana, London Southend - Bridgetown Grantley Adams Intl and London Southend - Havana Jose Marti Intl.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Southend to Caribbean Islands 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

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Alternative routes for Southend to Caribbean Islands

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Fly with Cheapflights

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

Cheapflights helps you search for flights from Southend to Caribbean Islands via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.

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

Millions of users choose and trust Cheapflights to book the best flight deals from Southend to Caribbean Islands for free. We help you search and compare prices from hundreds of airlines for the right flight just for you.

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

Cheapflights does show flights with no change fees to all users. To see these options for flights from Southend to Caribbean Islands, users can toggle the no change fees filter when performing a flight search.

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

Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Caribbean Islands from Southend today and book when prices fit your budget.

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