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Caribbean Islands

$290+ 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 7/22. Fares are subject to change and may not be available on all flights or dates of travel.
OAJ — SJU
Feb 27 — Mar 61
Fri 2/27
Fri 3/6
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 January 28, 2026.

This American Airlines deal was found by Cheapflights users on 1/26. 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 4/167:55 pm
OAJ
-
SJU
2 stops14h 58m
American Airlines
Mon 4/203:44 pm
SJU
-
OAJ
2 stops18h 05m
American Airlines
Deal found 1/26$463
This Delta deal was found by Cheapflights users on 1/26. 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.
Thu 4/162:20 pm
OAJ
-
SJU
1 stop8h 52m
Delta
Mon 4/206:15 am
SJU
-
OAJ
1 stop7h 25m
Delta
Deal found 1/26$476
This American Airlines deal was found by Cheapflights users on 1/27. 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 5/167:55 pm
OAJ
-
STT
1 stop14h 52m
American Airlines
Tue 5/264:48 pm
STT
-
OAJ
2 stops19h 50m
American Airlines
Deal found 1/27$570
This American Airlines deal was found by Cheapflights users on 1/27. 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 7/226:10 pm
OAJ
-
KIN
2 stops18h 16m
American Airlines
Tue 8/116:00 am
KIN
-
OAJ
2 stops16h 55m
American Airlines
Deal found 1/27$610
This American Airlines deal was found by Cheapflights users on 1/27. 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 7/226:10 pm
OAJ
-
KIN
2 stops18h 16m
American Airlines
Mon 8/106:00 am
KIN
-
OAJ
2 stops16h 55m
American Airlines
Deal found 1/27$620
This American Airlines deal was found by Cheapflights users on 1/27. 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 7/226:10 pm
OAJ
-
KIN
2 stops18h 16m
American Airlines
Sun 8/911:59 am
KIN
-
OAJ
2 stops19h 36m
American Airlines
Deal found 1/27$640
This Delta deal was found by Cheapflights users on 1/27. 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.
Wed 7/222:25 pm
OAJ
-
KIN
1 stop6h 35m
Delta
Wed 8/129:00 am
KIN
-
OAJ
1 stop7h 52m
Delta
Deal found 1/27$670
This American Airlines deal was found by Cheapflights users on 1/27. 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 3/265:00 am
OAJ
-
STT
2 stops9h 46m
American Airlines
Mon 4/65:25 pm
STT
-
OAJ
2 stops25h 19m
American Airlines
Deal found 1/27$680
This American Airlines deal was found by Cheapflights users on 1/27. 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 3/267:55 pm
OAJ
-
STT
2 stops15h 17m
American Airlines
Tue 4/712:25 pm
STT
-
OAJ
2 stops24h 36m
American Airlines
Deal found 1/27$681
This American Airlines deal was found by Cheapflights users on 1/27. 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 7/218:55 am
OAJ
-
KIN
2 stops11h 44m
American Airlines
Tue 8/116:00 am
KIN
-
OAJ
2 stops16h 55m
American Airlines
Deal found 1/27$700
This Delta deal was found by Cheapflights users on 1/25. 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.
Thu 3/52:15 pm
OAJ
-
SJU
1 stop8h 43m
Delta
Sun 3/86:15 am
SJU
-
OAJ
1 stop7h 25m
Delta
Deal found 1/25$705
This Delta deal was found by Cheapflights users on 1/27. 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.
Thu 3/265:43 am
OAJ
-
STT
1 stop5h 55m
Delta
Tue 4/73:00 pm
STT
-
OAJ
1 stop7h 33m
Delta
Deal found 1/27$719

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 January 28, 2026.

Round-trip from

$463
(American Airlines)

One-way from

$290
(Delta)
From Jacksonville Albert J Ellis to Caribbean Islands
Search Deals
One-way flight from Jacksonville Albert J Ellis to Caribbean Islands
Search Deals

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 January 28, 2026.
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

Thu 4/16

7:55 pm-10:53 am

2 stops14h 58m

San Juan Luis Munoz Marin Intl

Mon 4/20

3:44 pm-9:49 am

2 stops18h 05m

$463

JacksonvilleSaint Thomas Island

OAJ - STT

OAJSTT

Jacksonville Albert J Ellis

Sat 5/16

7:55 pm-11:35 am

2 stops15h 40m

Saint Thomas Island Cyril E King

Tue 5/26

4:48 pm-12:38 pm

2 stops19h 50m

$570

JacksonvilleKingston

OAJ - KIN

OAJKIN

Jacksonville Albert J Ellis

Wed 7/22

6:10 pm-11:26 am

2 stops18h 16m

Kingston Norman Manley

Tue 8/11

6:00 am-11:55 pm

2 stops16h 55m

$610

JacksonvilleKingston

OAJ - KIN

OAJKIN

Jacksonville Albert J Ellis

Wed 7/22

6:10 pm-11:26 am

2 stops18h 16m

Kingston Norman Manley

Wed 8/12

11:59 am-8:35 am

2 stops19h 36m

$610

JacksonvilleKingston

OAJ - KIN

OAJKIN

Jacksonville Albert J Ellis

Wed 7/22

6:10 pm-11:26 am

2 stops18h 16m

Kingston Norman Manley

Mon 8/10

6:00 am-11:55 pm

2 stops16h 55m

$620

JacksonvilleKingston

OAJ - KIN

OAJKIN

Jacksonville Albert J Ellis

Thu 7/23

6:10 pm-11:26 am

2 stops18h 16m

Kingston Norman Manley

Mon 8/10

6:00 am-11:55 pm

2 stops16h 55m

$620

JacksonvilleKingston

OAJ - KIN

OAJKIN

Jacksonville Albert J Ellis

Wed 7/22

6:10 pm-11:26 am

2 stops18h 16m

Kingston Norman Manley

Sun 8/9

11:59 am-8:35 am

2 stops19h 36m

$640

JacksonvilleKingston

OAJ - KIN

OAJKIN

Jacksonville Albert J Ellis

Wed 7/22

2:25 pm-8:00 pm

1 stop6h 35m

Kingston Norman Manley

Wed 8/12

9:00 am-5:52 pm

1 stop7h 52m

$670

JacksonvilleSaint Thomas Island

OAJ - STT

OAJSTT

Jacksonville Albert J Ellis

Thu 3/26

7:55 pm-11:12 am

2 stops15h 17m

Saint Thomas Island Cyril E King

Tue 4/7

12:25 pm-1:01 pm

2 stops24h 36m

$681

JacksonvilleKingston

OAJ - KIN

OAJKIN

Jacksonville Albert J Ellis

Tue 7/21

8:55 am-7:39 pm

2 stops11h 44m

Kingston Norman Manley

Tue 8/11

6:00 am-11:55 pm

2 stops16h 55m

$700

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 32 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, February is the cheapest month in which you can book a flight from Jacksonville, North Carolina to Caribbean Islands (average of $217). Flying from Jacksonville, North Carolina to Caribbean Islands in October is currently the most expensive (average of $471). 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.

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 January 28, 2026.
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
11,201 reviews

Crew

8.0

Food

6.4

Comfort

7.2

Overall

7.2

Boarding

7.5

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.
American Airlines
7.2
Good
11,201 reviews
American Airlines
7.2
Good
11,201 reviews

Crew

8.0

Food

6.4

Comfort

7.2

Overall

7.2

Boarding

7.5

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.

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 43m. American Airlines provides one of the quickest options available for as low as $705. 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 - Varadero Juan Gualberto Gomez, Jacksonville Albert J Ellis - San Juan Luis Munoz Marin Intl and Jacksonville Albert J Ellis - Kingston Norman Manley.

  • 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, February is the cheapest month in which you can book a flight from Jacksonville, North Carolina to Caribbean Islands (average of $217). Flying from Jacksonville, North Carolina to Caribbean Islands in October is currently the most expensive (average of $471). 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 airline flying from Jacksonville to Caribbean Islands

Discover the top airline 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 January 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$425Average$661FlexibilityNo cancel feeOn-time71%

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