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Cheap flights from London Southend Airport to Caribbean from £215

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 5/9. Fares are subject to change and may not be available on all flights or dates of travel.
SEN — SJU
14 Sep — 21 Sep1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Southend to Caribbean

Enter your travel dates to find the best prices.

Cheapest flights from Southend to Caribbean
Explore the most affordable flight options available from Southend to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 15 August 2026.

Sun 27/920:05 -
2 stops26h 15m
Sun 4/1015:05 -
2 stops23h 30m
Deal found 13/8£588
Sun 13/920:05 -
2 stops26h 15m
Sun 20/915:05 -
2 stops23h 30m
Deal found 14/8£623
Mon 21/916:00 -
3 stops29h 35m
Tue 29/916:20 -
2 stops21h 20m
Deal found 10/8£658
Fri 13/1108:30 -
3 stops33h 20m
Sun 22/1112:35 -
3 stops26h 40m
Deal found 11/8£678
Sat 26/916:50 -
2 stops32h 40m
Tue 29/916:20 -
2 stops21h 20m
Deal found 11/8£711
Mon 19/1020:05 -
3 stops26h 15m
Sun 25/1017:45 -
2 stops17h 05m
Deal found 14/8£736
Tue 15/920:25 -
3 stops44h 55m
Tue 13/1016:20 -
2 stops21h 20m
Deal found 12/8£739
Sat 17/1016:50 -
3 stops33h 40m
Tue 27/1019:05 -
2 stops19h 35m
Deal found 14/8£750
Mon 19/1007:00 -
3 stops38h 35m
Thu 29/1013:55 -
2 stops22h 20m
Deal found 14/8£770
Sat 29/816:50 -
3 stops31h 45m
Sun 6/915:05 -
2 stops23h 30m
Deal found 11/8£785
Fri 28/806:30 -
2 stops17h 55m
Sun 6/915:05 -
2 stops23h 30m
Deal found 12/8£785
Sat 3/1016:50 -
2 stops26h 30m
Fri 9/1021:20 -
2 stops19h 25m
Deal found 10/8£799

Find flight deals from Southend to Caribbean

Keep the following information in mind while searching for Southend to Caribbean flight deals. Data was last updated 15 August 2026.

Round-trip from

£588

One-way from

£215

Popular in

December

Cheapest in

June

Average price

£865
27/9-4/10
  • 27/9-4/10
  • 4 total stops
  • 49h 45m total
  • London to Caribbean
Search Deals
5/9
  • 5/9
  • 1 total stop
  • 34h 35m total
  • London to Caribbean
Search Deals
Highest demand for flights based on searches. 3% potential increase in price (£19 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (£14 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 Southend to Caribbean 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 15 August 2026.
Use the filters below to find and compare flights from London Southend Airport to Caribbean that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest return flight

LondonPunta Cana

SEN London Southend - PUJ Punta Cana

SENPUJ

London Southend

Sun 27/9

20:05-17:20

2 stops26h 15m

Punta Cana

Sun 4/10

15:05-19:35

2 stops23h 30m

£588

LondonPunta Cana

SEN London Southend - PUJ Punta Cana

SENPUJ

London Southend

Sun 13/9

20:05-17:20

2 stops26h 15m

Punta Cana

Sun 20/9

15:05-19:35

2 stops23h 30m

£623

LondonPunta Cana

SEN London Southend - PUJ Punta Cana

SENPUJ

London Southend

Fri 13/11

08:30-13:50

3 stops33h 20m

Punta Cana

Sun 22/11

12:35-19:15

3 stops26h 40m

£678

LondonMontego Bay

SEN London Southend - MBJ Montego Bay Sangster Intl

SENMBJ

London Southend

Sat 26/9

16:50-19:30

2 stops32h 40m

Montego Bay Sangster Intl

Tue 29/9

16:20-19:40

2 stops21h 20m

£711

LondonPunta Cana

SEN London Southend - PUJ Punta Cana

SENPUJ

London Southend

Mon 19/10

20:05-17:20

3 stops26h 15m

Punta Cana

Sun 25/10

17:45-14:50

2 stops17h 05m

£736

LondonMontego Bay

SEN London Southend - MBJ Montego Bay Sangster Intl

SENMBJ

London Southend

Tue 15/9

20:25-11:20

3 stops44h 55m

Montego Bay Sangster Intl

Tue 13/10

16:20-19:40

2 stops21h 20m

£739

LondonMontego Bay

SEN London Southend - MBJ Montego Bay Sangster Intl

SENMBJ

London Southend

Sat 17/10

16:50-20:30

2 stops33h 40m

Montego Bay Sangster Intl

Tue 27/10

19:05-19:40

2 stops19h 35m

£767

LondonMontego Bay

SEN London Southend - MBJ Montego Bay Sangster Intl

SENMBJ

London Southend

Mon 19/10

16:00-15:35

2 stops29h 35m

Montego Bay Sangster Intl

Thu 29/10

13:55-17:15

2 stops22h 20m

£777

LondonPunta Cana

SEN London Southend - PUJ Punta Cana

SENPUJ

London Southend

Fri 28/8

06:30-19:25

2 stops17h 55m

Punta Cana

Sun 6/9

15:05-19:35

2 stops23h 30m

£785

LondonPunta Cana

SEN London Southend - PUJ Punta Cana

SENPUJ

London Southend

Sat 3/10

16:50-14:20

2 stops26h 30m

Punta Cana

Fri 9/10

21:20-21:45

2 stops19h 25m

£799

Flights are sorted by cheapest return flights first.

Deals found on 10/8

Showing 1-10 of 53 resultsSorted by cheapest first
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Best time to book a flight from Southend to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean 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

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. 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?

    The most popular route from London Southend Airport to Caribbean is London Southend - Montego Bay Sangster Intl. You may also consider London Southend - Havana Jose Marti Intl or London Southend - St. George's Point Saline Intl.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Southend to Caribbean 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

See prices for flight routes from nearby airports that may be better suited for you.
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Fly with Cheapflights

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

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

Millions of users choose and trust Cheapflights to book the best flight deals from Southend to Caribbean 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 with no change fees?

Yes! Cheapflights helps users easily find flights from Southend to Caribbean with no change fees.

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

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

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