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Caribbean Islands

$278+ 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 12/29. Fares are subject to change and may not be available on all flights or dates of travel.
OAJ — SJU
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheap 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 December 12, 2025.

This American Airlines deal was found by Cheapflights users on 12/11. 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 12/156:10 amOAJ - SJU
1 stop14h 59mAmerican Airlines
Fri 1/97:12 pmSJU - OAJ
2 stops16h 59mAmerican Airlines
Deal found 12/11$595
This American Airlines deal was found by Cheapflights users on 12/11. 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.
Wed 12/177:02 pmOAJ - SJU
2 stops15h 55mAmerican Airlines
Sat 1/178:20 amSJU - OAJ
1 stop7h 40mAmerican Airlines
Deal found 12/11$610
This Delta deal was found by Cheapflights users on 12/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/152:26 pmOAJ - SJU
1 stop7h 54mDelta
Fri 1/97:30 amSJU - OAJ
1 stop9h 20mDelta
Deal found 12/11$703
This American Airlines deal was found by Cheapflights users on 12/11. 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.
Thu 12/117:48 pmOAJ - STI
2 stops18h 44mAmerican Airlines
Fri 12/193:24 pmSTI - OAJ
2 stops9h 35mAmerican Airlines
Deal found 12/11$762
This American Airlines deal was found by Cheapflights users on 12/11. 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 12/2312:52 pmOAJ - SJU
1 stop8h 13mAmerican Airlines
Tue 12/306:15 pmSJU - OAJ
1 stop6h 44mAmerican Airlines
Deal found 12/11$825
This American Airlines deal was found by Cheapflights users on 12/11. 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.
Fri 12/127:02 pmOAJ - STI
2 stops19h 30mAmerican Airlines
Thu 12/183:24 pmSTI - OAJ
2 stops22h 03mAmerican Airlines
Deal found 12/11$837
This American Airlines deal was found by Cheapflights users on 12/10. 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 12/177:02 pmOAJ - SJU
2 stops17h 39mAmerican Airlines
Thu 1/15:18 amSJU - OAJ
2 stops11h 23mAmerican Airlines
Deal found 12/10$934
This American Airlines deal was found by Cheapflights users on 12/11. 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.
Fri 12/195:00 amOAJ - STI
2 stops8h 24mAmerican Airlines
Sat 12/206:17 pmSTI - OAJ
2 stops19h 10mAmerican Airlines
Deal found 12/11$1,757
This WestJet deal was found by Cheapflights users on 12/11. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/126:40 pmOAJ - POP
2 stops37h 57mWestJet
Thu 12/185:30 pmPOP - OAJ
2 stops41h 53mWestJet
Deal found 12/11$2,581
This WestJet deal was found by Cheapflights users on 12/11. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/126:40 pmOAJ - POP
2 stops37h 57mWestJet
Fri 12/195:30 pmPOP - OAJ
2 stops49h 32mWestJet
Deal found 12/11$2,698
This American Airlines deal was found by Cheapflights users on 12/11. 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.
Fri 12/126:10 amOAJ - STI
3 stops13h 23mAmerican Airlines
Fri 12/196:17 pmSTI - OAJ
2 stops17h 02mAmerican Airlines
Deal found 12/11$2,860
This WestJet deal was found by Cheapflights users on 12/11. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/112:26 pmOAJ - POP
2 stops49h 07mWestJet
Fri 12/195:30 pmPOP - OAJ
2 stops49h 32mWestJet
Deal found 12/11$4,988

Find 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 December 12, 2025.

Round-trip from

$385
(American Airlines)

One-way from

$278
(American Airlines)

Popular in

December

Cheapest in

February

Average price

$1,274
From Jacksonville Albert J Ellis to Caribbean Islands
Search Deals
One-way flight from Jacksonville Albert J Ellis to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 26% potential increase in price ($228 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 12% potential price decrease ($72 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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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 December 12, 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

Sun 1/18

11:44 am-8:58 pm

1 stop8h 14m

San Juan Luis Munoz Marin Intl

Fri 1/23

7:30 am-1:35 pm

1 stop7h 05m

$415

JacksonvilleSan Juan

OAJ - SJU

OAJSJU

Jacksonville Albert J Ellis

Sun 1/18

6:07 am-5:01 pm

2 stops9h 54m

San Juan Luis Munoz Marin Intl

Fri 1/23

8:20 am-10:58 pm

1 stop15h 38m

$430

JacksonvilleNassau

OAJ - NAS

OAJNAS

Jacksonville Albert J Ellis

Thu 3/12

11:50 am-4:45 pm

1 stop4h 55m

Nassau Intl

Mon 3/16

1:25 pm-6:04 pm

1 stop4h 39m

$497

JacksonvilleSan Juan

OAJ - SJU

OAJSJU

Jacksonville Albert J Ellis

Sun 2/8

5:40 am-5:17 pm

1 stop10h 37m

San Juan Luis Munoz Marin Intl

Thu 2/12

7:30 am-1:33 pm

1 stop7h 03m

$553

JacksonvilleSan Juan

OAJ - SJU

OAJSJU

Jacksonville Albert J Ellis

Mon 12/15

6:10 am-1:01 pm

1 stop5h 51m

San Juan Luis Munoz Marin Intl

Fri 1/9

7:12 pm-11:11 am

2 stops16h 59m

$595

JacksonvilleBridgetown

OAJ - BGI

OAJBGI

Jacksonville Albert J Ellis

Mon 1/12

6:07 am-10:28 pm

2 stops15h 21m

Bridgetown Grantley Adams Intl

Mon 1/26

3:46 pm-10:58 pm

1 stop8h 12m

$601

JacksonvilleSan Juan

OAJ - SJU

OAJSJU

Jacksonville Albert J Ellis

Wed 12/17

7:02 pm-11:57 am

2 stops15h 55m

San Juan Luis Munoz Marin Intl

Sat 1/17

8:20 am-3:00 pm

1 stop7h 40m

$610

JacksonvilleKingston

OAJ - KIN

OAJKIN

Jacksonville Albert J Ellis

Mon 1/12

5:40 am-8:00 pm

1 stop14h 20m

Kingston Norman Manley

Mon 1/26

9:00 am-5:46 pm

1 stop8h 46m

$623

JacksonvilleKingston

OAJ - KIN

OAJKIN

Jacksonville Albert J Ellis

Mon 1/12

6:07 am-9:16 pm

2 stops15h 09m

Kingston Norman Manley

Mon 1/26

7:00 am-10:58 pm

2 stops15h 58m

$628

JacksonvilleSan Juan

OAJ - SJU

OAJSJU

Jacksonville Albert J Ellis

Mon 12/15

2:26 pm-11:20 pm

1 stop7h 54m

San Juan Luis Munoz Marin Intl

Fri 1/9

7:30 am-3:50 pm

1 stop9h 20m

$703

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/9

Showing 1-10 of 20 results
1
2

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, April is the cheapest month in which you can book a flight from Jacksonville, North Carolina to Caribbean Islands (average of $218). Flying from Jacksonville, North Carolina to Caribbean Islands in October is currently the most expensive (average of $435). 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 December 12, 2025.

It’s optimal to fly from Jacksonville, North Carolina to Caribbean Islands at noon. By choosing this option you can save up to 43% on the cost of your flight, compared to a flight in the morning.

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 December 12, 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
11,050 reviews

Comfort

7.2

Boarding

7.5

Food

6.5

Crew

8.0

Entertainment

6.9

Overall

7.2

Reviews

1 / 20
10.0
Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit
American Airlines
7.2
Good
11,050 reviews
American Airlines
7.2
Good
11,050 reviews

Comfort

7.2

Boarding

7.5

Food

6.5

Crew

8.0

Entertainment

6.9

Overall

7.2

Reviews

1 / 20
10.0
Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit

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.

  • How long is the flight from Jacksonville, North Carolina to Caribbean Islands?

    A quick flight from Jacksonville, North Carolina to Caribbean Islands can take about 8h 14m. Delta provides one of the quickest options available for as low as $415. The distance from Jacksonville, North Carolina to Caribbean Islands is about 1337 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 - San Juan Luis Munoz Marin Intl, Jacksonville Albert J Ellis - Varadero Juan Gualberto Gomez 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, April is the cheapest month in which you can book a flight from Jacksonville, North Carolina to Caribbean Islands (average of $218). Flying from Jacksonville, North Carolina to Caribbean Islands in October is currently the most expensive (average of $435). 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.

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Alternative routes for Jacksonville to Caribbean Islands

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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 December 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$393Average$658FlexibilityNo cancel feeOn-time71%
DeltaCheapest$399Average$515FlexibilityNo cancel feeOn-timeN/A

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