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Caribbean

$463+ Cheap flights from Jacksonville, NC (OAJ) to Caribbean

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/16. Fares are subject to change and may not be available on all flights or dates of travel.
OAJ — SJU
Feb 26 — Mar 51
Thu 2/26
Thu 3/5
1 adult, Economy
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Cheap flight deals from Jacksonville to Caribbean

Cheapest flights from Jacksonville to Caribbean
Explore the most affordable flight options available from Jacksonville to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 27, 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 1/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/155:00 am
OAJ
-
NAS
1 stop8h 16m
American Airlines
Sun 7/1911:02 am
NAS
-
OAJ
1 stop12h 53m
American Airlines
Deal found 1/25$567
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
2 stops15h 40m
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 1/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/195:00 am
OAJ
-
STT
1 stop9h 53m
American Airlines
Thu 2/261:00 pm
STT
-
OAJ
1 stop7h 26m
American Airlines
Deal found 1/25$578
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 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
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.
Tue 2/36:07 am
OAJ
-
MBJ
2 stops8h 05m
American Airlines
Tue 2/104:16 pm
MBJ
-
OAJ
2 stops18h 55m
American Airlines
Deal found 1/26$745
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 3/264:11 pm
OAJ
-
STT
2 stops24h 18m
American Airlines
Sun 4/55:25 pm
STT
-
OAJ
2 stops17h 08m
American Airlines
Deal found 1/27$745
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.
Sun 6/75:40 am
OAJ
-
NAS
1 stop6h 15m
Delta
Fri 6/125:20 pm
NAS
-
OAJ
1 stop4h 57m
Delta
Deal found 1/25$758

Find flight deals from Jacksonville to Caribbean

Keep the following information in mind while searching for Jacksonville to Caribbean flight deals. Data was last updated January 27, 2026.

Round-trip from

$426
(Delta)
From Jacksonville Albert J Ellis to Caribbean
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Jacksonville 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 2,558,603 searches. Data last updated January 27, 2026.
Use the filters below to find and compare flights from Jacksonville to Caribbean that are best for you.

Fly from

Jacksonville

Fly to

Caribbean

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

JacksonvilleSan Juan

OAJ - SJU

OAJSJU

Jacksonville Albert J Ellis

Thu 4/16

2:20 pm-11:12 pm

1 stop8h 52m

San Juan Luis Munoz Marin Intl

Mon 4/20

6:15 am-1:40 pm

1 stop7h 25m

$476

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

JacksonvilleSaint Thomas Island

OAJ - STT

OAJSTT

Jacksonville Albert J Ellis

Thu 2/19

5:00 am-2:03 pm

2 stops8h 03m

Saint Thomas Island Cyril E King

Thu 2/26

1:00 pm-7:26 pm

1 stop7h 26m

$578

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

JacksonvilleSan Juan

OAJ - SJU

OAJSJU

Jacksonville Albert J Ellis

Thu 3/5

2:15 pm-11:58 pm

1 stop8h 43m

San Juan Luis Munoz Marin Intl

Sun 3/8

6:15 am-1:40 pm

1 stop7h 25m

$705

JacksonvilleSaint Thomas Island

OAJ - STT

OAJSTT

Jacksonville Albert J Ellis

Thu 3/26

5:43 am-11:38 am

1 stop5h 55m

Saint Thomas Island Cyril E King

Tue 4/7

3:00 pm-10:33 pm

1 stop7h 33m

$719

JacksonvilleSaint Thomas Island

OAJ - STT

OAJSTT

Jacksonville Albert J Ellis

Fri 3/27

5:43 am-11:38 am

1 stop5h 55m

Saint Thomas Island Cyril E King

Tue 4/7

1:55 pm-10:33 pm

1 stop8h 38m

$780

JacksonvilleSaint Thomas Island

OAJ - STT

OAJSTT

Jacksonville Albert J Ellis

Thu 3/26

5:00 am-11:06 am

1 stop6h 06m

Saint Thomas Island Cyril E King

Mon 4/6

5:25 pm-6:44 pm

2 stops25h 19m

$815

JacksonvilleSaint Thomas Island

OAJ - STT

OAJSTT

Jacksonville Albert J Ellis

Thu 3/26

4:11 pm-11:12 am

2 stops19h 01m

Saint Thomas Island Cyril E King

Fri 4/3

3:40 pm-10:33 am

2 stops18h 53m

$846

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/26

Showing 1-10 of 18 results
1
2

Best time to book a flight from Jacksonville to Caribbean

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

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

Currently, February is the cheapest month in which you can book a flight from Jacksonville, North Carolina to Caribbean (average of $217). Flying from Jacksonville, North Carolina to Caribbean 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

Get insights into the airlines that provide service to Caribbean. 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. Reviews last updated January 27, 2026.
Peruse reviews from past customers who have flown with American Airlines from Jacksonville to Caribbean to help guide your decision. 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
11,197 reviews

Boarding

7.5

Comfort

7.2

Overall

7.2

Food

6.4

Crew

8.0

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
11,197 reviews
American Airlines
7.2
Good
11,197 reviews

Boarding

7.5

Comfort

7.2

Overall

7.2

Food

6.4

Crew

8.0

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. 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?

    Jacksonville Albert J Ellis (OAJ), located 11.3 mi from the city center, is the airport you fly out of when you book flights from Jacksonville to Caribbean.

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

    Departing from Jacksonville, North Carolina to Caribbean will take you 8h 52m. The distance from Jacksonville, North Carolina to Caribbean is about 1337 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    Most travelers choose Jacksonville Albert J Ellis - Varadero Juan Gualberto Gomez, Jacksonville Albert J Ellis - San Juan Luis Munoz Marin Intl or Jacksonville Albert J Ellis - Nassau Intl when deciding on the best route from Jacksonville, North Carolina to Caribbean.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Jacksonville 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.

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

    Currently, February is the cheapest month in which you can book a flight from Jacksonville, North Carolina to Caribbean (average of $217). Flying from Jacksonville, North Carolina to Caribbean 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

Discover the top airline that operate flights from Jacksonville to Caribbean. 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 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$425Average$661FlexibilityNo cancel feeOn-time71%

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