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Caribbean Islands

$307+ Cheap flights from Jacksonville, NC (OAJ) to Caribbean Islands

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 9/23. Fares are subject to change and may not be available on all flights or dates of travel.
OAJ — SJU
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheap flight deals from Jacksonville to Caribbean Islands

Keep the following information in mind while searching for Jacksonville to Caribbean Islands flight deals. Data was last updated August 14, 2025.

Round-trip from

$365
(American Airlines)

One-way from

$307
(Delta)

Popular in

December

Cheapest in

February

Average price

$565
From Jacksonville Albert J Ellis to Caribbean Islands
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One-way flight from Jacksonville Albert J Ellis to Caribbean Islands
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Highest demand for flights based on searches. 28% potential increase in price ($249 potential increase over avg. RT price).
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Cheapest flight prices on average. 13% potential price decrease ($72 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find flight deals from Jacksonville to Caribbean Islands

Cheapest flights from Jacksonville to Caribbean Islands
Explore the most affordable flight options available from Jacksonville to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 14, 2025.

This American Airlines deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/179:00 amOAJ - SJU
1 stop14h 54mAmerican Airlines
Sun 10/197:10 amSJU - OAJ
1 stop6h 06mAmerican Airlines
Deal found 8/13$365
This American Airlines deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/77:02 pmOAJ - SJU
1 stop17h 02mAmerican Airlines
Tue 11/116:42 pmSJU - OAJ
2 stops17h 26mAmerican Airlines
Deal found 8/13$390
This American Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1510:59 amOAJ - ELH
2 stops26h 16mAmerican Airlines
Sat 11/221:00 pmELH - OAJ
1 stop6h 18mAmerican Airlines
Deal found 8/12$403
This American Airlines deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/127:10 pmOAJ - SJU
2 stops17h 40mAmerican Airlines
Fri 9/194:43 pmSJU - OAJ
1 stop6h 25mAmerican Airlines
Deal found 8/13$430
This American Airlines deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/206:10 amOAJ - SJU
1 stop9h 42mAmerican Airlines
Sat 9/274:45 pmSJU - OAJ
1 stop15h 49mAmerican Airlines
Deal found 8/13$455
This American Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/46:19 amOAJ - MBJ
1 stop8h 31mAmerican Airlines
Tue 11/114:02 pmMBJ - OAJ
2 stops19h 06mAmerican Airlines
Deal found 8/12$527
This American Airlines deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/287:24 pmOAJ - ELH
2 stops15h 59mAmerican Airlines
Fri 10/3112:05 pmELH - OAJ
2 stops25h 11mAmerican Airlines
Deal found 8/13$531
This American Airlines deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/17:00 amOAJ - SJU
1 stop15h 56mAmerican Airlines
Mon 9/87:05 pmSJU - OAJ
2 stops21h 52mAmerican Airlines
Deal found 8/14$534
This American Airlines deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/276:10 amOAJ - SJU
2 stops9h 55mAmerican Airlines
Sat 8/307:05 pmSJU - OAJ
2 stops22h 30mAmerican Airlines
Deal found 8/13$550
This American Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2810:19 amOAJ - ELH
2 stops25h 04mAmerican Airlines
Thu 10/3012:05 pmELH - OAJ
2 stops21h 49mAmerican Airlines
Deal found 8/11$576
This American Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/78:02 pmOAJ - CUR
2 stops19h 22mAmerican Airlines
Sun 9/144:25 pmCUR - OAJ
2 stops24h 32mAmerican Airlines
Deal found 8/12$592
This American Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/85:00 amOAJ - CUR
1 stop8h 10mAmerican Airlines
Thu 12/113:30 pmCUR - OAJ
1 stop7h 08mAmerican Airlines
Deal found 8/11$609

Cheapflights Fare Finder

 
Customize your flight search to find flights from Jacksonville 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 2,558,603 searches. Data last updated August 14, 2025.
Use the filters below to find and compare flights from Jacksonville to Caribbean Islands that are best for you.

Fly from

Jacksonville

Fly to

Caribbean Islands

Route

Depart

Return

Price

JacksonvilleSan Juan

OAJ - SJU

OAJSJU

Jacksonville Albert J Ellis

Fri 10/17

9:00 am-11:54 pm

1 stop14h 54m

San Juan Luis Munoz Marin Intl

Sun 10/19

7:10 am-1:16 pm

1 stop6h 06m

$365

JacksonvilleSan Juan

OAJ - SJU

OAJSJU

Jacksonville Albert J Ellis

Fri 11/7

7:02 pm-1:04 pm

1 stop17h 02m

San Juan Luis Munoz Marin Intl

Tue 11/11

6:42 pm-11:08 am

2 stops17h 26m

$390

JacksonvilleGregory Town

OAJ - ELH

OAJELH

Jacksonville Albert J Ellis

Sat 11/15

8:04 pm-11:26 am

2 stops15h 22m

Gregory Town North Eleuthera

Sat 11/22

1:55 pm-10:33 am

2 stops20h 38m

$403

JacksonvilleSan Juan

OAJ - SJU

OAJSJU

Jacksonville Albert J Ellis

Sat 9/20

7:10 pm-2:53 pm

2 stops19h 43m

San Juan Luis Munoz Marin Intl

Sat 9/27

4:45 pm-8:34 am

1 stop15h 49m

$430

JacksonvilleSan Juan

OAJ - SJU

OAJSJU

Jacksonville Albert J Ellis

Fri 9/12

7:10 pm-11:11 am

2 stops16h 01m

San Juan Luis Munoz Marin Intl

Fri 9/19

12:01 pm-11:08 pm

2 stops11h 07m

$430

JacksonvilleMontego Bay

OAJ - MBJ

OAJMBJ

Jacksonville Albert J Ellis

Tue 11/4

6:19 am-2:50 pm

1 stop8h 31m

Montego Bay Sangster Intl

Tue 11/11

4:02 pm-11:08 am

2 stops19h 06m

$527

JacksonvilleGregory Town

OAJ - ELH

OAJELH

Jacksonville Albert J Ellis

Tue 10/28

10:19 am-11:23 am

2 stops25h 04m

Gregory Town North Eleuthera

Fri 10/31

12:05 pm-11:33 am

2 stops47h 28m

$531

JacksonvilleSan Juan

OAJ - SJU

OAJSJU

Jacksonville Albert J Ellis

Mon 9/1

8:03 pm-11:09 am

2 stops15h 06m

San Juan Luis Munoz Marin Intl

Mon 9/8

7:05 pm-4:57 pm

2 stops21h 52m

$534

JacksonvilleGregory Town

OAJ - ELH

OAJELH

Jacksonville Albert J Ellis

Tue 10/28

10:19 am-11:23 am

2 stops25h 04m

Gregory Town North Eleuthera

Thu 10/30

12:05 pm-9:54 am

2 stops21h 49m

$576

JacksonvilleWillemstad

OAJ - CUR

OAJCUR

Jacksonville Albert J Ellis

Sun 9/7

8:02 pm-3:24 pm

2 stops19h 22m

Willemstad Hato Int.

Sun 9/14

4:25 pm-4:57 pm

2 stops24h 32m

$592

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/14

Showing 1-10 of 23 results
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Best time to book a flight from Jacksonville to Caribbean Islands

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

Cheapflights Insights

Everything you need to know about your flight from Jacksonville to Caribbean Islands

What is the cheapest month to book a flight from Jacksonville, North Carolina to Caribbean Islands?

Currently, September is the cheapest month in which you can book a flight from Jacksonville, North Carolina to Caribbean Islands (average of $254). Flying from Jacksonville, North Carolina to Caribbean Islands in June is currently the most expensive (average of $339). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from OAJ to EPX?

Find hourly flight availability from Jacksonville to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 14, 2025.

When flying from Jacksonville, North Carolina to Caribbean Islands, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Reviews of airlines servicing Caribbean Islands

Get insights into the airlines that provide service to Caribbean Islands. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean Islands. Reviews last updated August 14, 2025.
Get a feel of what it's like to fly with American Airlines from Jacksonville to Caribbean Islands by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
10,000 reviews

Crew

8.0

Boarding

7.5

Food

6.5

Overall

7.2

Entertainment

6.9

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Crew

8.0

Boarding

7.5

Food

6.5

Overall

7.2

Entertainment

6.9

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.

Related info for your journey

Find useful and relevant information for your journey from Jacksonville 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 airport do you fly from for flights from Jacksonville to Caribbean Islands?

    Located just 11.3 mi from the city center, Jacksonville Albert J Ellis (OAJ) is the airport most travelers will use when flying to Caribbean Islands from Jacksonville.

  • What are the most popular routes from Jacksonville, North Carolina to Caribbean Islands?

    The most popular flight routes from Jacksonville, North Carolina to Caribbean Islands are Jacksonville Albert J Ellis - Varadero Juan Gualberto Gomez, Jacksonville Albert J Ellis - San Juan Luis Munoz Marin Intl and Jacksonville Albert J Ellis - Bridgetown Grantley Adams Intl.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Jacksonville 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.

  • What is the cheapest month to book a flight from Jacksonville, North Carolina to Caribbean Islands?

    Currently, September is the cheapest month in which you can book a flight from Jacksonville, North Carolina to Caribbean Islands (average of $254). Flying from Jacksonville, North Carolina to Caribbean Islands in June is currently the most expensive (average of $339). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Top 2 airlines flying from Jacksonville to Caribbean Islands

Discover the top 2 airlines that operate flights from Jacksonville to Caribbean Islands. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$323Average$687FlexibilityNo cancel feeOn-time71%
DeltaCheapest$335Average$514FlexibilityNo cancel feeOn-timeN/A

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