$385 Find Cheap Flights from Jacksonville to Caribbean

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Jacksonville to Caribbean departing on 5/29. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
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Best Caribbean Flight Deals from Jacksonville

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Montego Bay
Montego Bay1 stop$616
Nassau
Nassau2 stops$4,122
Simpson Bay
Simpson Bay2 stops$563
Montego Bay
Montego Bay1 stop$616
Nassau
Nassau2 stops$4,122
Simpson Bay
Simpson Bay2 stops$563

Cheap Flight Deals from Jacksonville to Caribbean (OAJ-0CB)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Jacksonville to Caribbean that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Jacksonville to Caribbean

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Jacksonville to Caribbean.
Discover the best prices for you by selecting your travel dates on KAYAK.
American Airlines Logo
5:00 am - 12:39 pmOAJ-SJU
7h 39m2 stops
American Airlines Logo
8:00 am - 11:58 pmSJU-OAJ
15h 58m1 stop
$385American Airlines
Find Deal
Thu, May 29 - Thu, Jun 5
American Airlines Logo
6:00 pm - 11:55 pmOAJ-SJU
5h 55m1 stop
American Airlines Logo
7:54 am - 12:04 amSJU-OAJ
16h 10m1 stop
$423American Airlines
Find Deal
Thu, Jul 10 - Thu, Jul 17
Delta Logo
5:40 am - 1:55 pmOAJ-STT
8h 15m1 stop
Delta Logo
3:00 pm - 10:19 pmSTT-OAJ
7h 19m1 stop
$454Delta
Find Deal
Tue, Aug 19 - Tue, Aug 26
American Airlines Logo
6:00 pm - 11:55 pmOAJ-SJU
5h 55m1 stop
American Airlines Logo
6:04 am - 10:05 pmSJU-OAJ
16h 01m2 stops
$465American Airlines
Find Deal
Thu, Jul 10 - Thu, Jul 17
American Airlines Logo
9:05 am - 8:33 pmOAJ-SJU
11h 28m1 stop
American Airlines Logo
7:15 am - 12:05 amSJU-OAJ
16h 50m1 stop
$490American Airlines
Find Deal
Wed, May 28 - Sun, Jun 1
Delta Logo
5:50 am - 1:52 pmOAJ-STT
8h 02m1 stop
Delta Logo
3:02 pm - 10:29 pmSTT-OAJ
7h 27m1 stop
$573Delta
Find Deal
Tue, Jul 29 - Sun, Aug 3
Delta Logo
5:50 am - 11:44 amOAJ-MBJ
6h 54m1 stop
Delta Logo
1:09 pm - 10:29 pmMBJ-OAJ
8h 20m1 stop
$616Delta
Find Deal
Sat, Jul 26 - Sun, Aug 3
WestJet Logo
11:54 am - 9:27 amOAJ-MBJ
22h 33m2 stops
WestJet Logo
2:55 pm - 11:14 amMBJ-OAJ
43h 19m2 stops
$3,292WestJet
Find Deal
Thu, Jun 19 - Mon, Jun 23
WestJet Logo
4:48 pm - 11:42 amOAJ-MBJ
43h 54m2 stops
WestJet Logo
1:40 pm - 6:57 pmMBJ-OAJ
28h 17m2 stops
$3,331WestJet
Find Deal
Sat, Jul 26 - Sun, Aug 3
WestJet Logo
3:26 pm - 9:27 amOAJ-MBJ
19h 01m2 stops
WestJet Logo
10:30 am - 6:54 pmMBJ-OAJ
31h 24m2 stops
$3,362WestJet
Find Deal
Tue, Jun 17 - Wed, Jun 25
Useful Info

KAYAK's insights & trends for Jacksonville to Caribbean flights

Get data-powered insights and trends into flights from Jacksonville to Caribbean to help you find the cheapest flights, the best time to fly and much more.

Which airlines provide the cheapest flights from Jacksonville to Caribbean?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Jacksonville to Caribbean were found on American Airlines ($385) and Delta ($454).


Good to know

Low seasonOctober
High seasonAugust
Cheapest flight$385
Best time to beat the crowds with an average 29% drop in price.
Most popular time to fly and prices are also 40% lower on average.
Flight from Jacksonville to San Juan

FAQs - booking Caribbean flights

  • How does KAYAK find such low prices on flights from Jacksonville to Caribbean?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Jacksonville to Caribbean.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Jacksonville to Caribbean?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Jacksonville to Caribbean is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Jacksonville to Caribbean?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Jacksonville to Caribbean with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Jacksonville to Caribbean?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Jacksonville to Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Caribbean?

    The cheapest time of day to fly to Caribbean is generally at night, when round-trip flights cost $315 on average. The most expensive time of day to fly to Caribbean is generally in the morning, which is peak travel time and where the average cost of a ticket is $458.

Top airlines flying from Jacksonville to Caribbean

Need help choosing which airline to fly with from Jacksonville to Caribbean? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
DeltaOverall score based on 7934 reviews
7.9Comfort
8.2Boarding
7.9Entertainment
8.5Crew
7.3Food
Airline reviews

Our bag was lost so that made unnecessary chaos On our trip

6.0 GoodBarbara, Apr 2025JFK - FCO
Read more Delta reviews

Our bag was lost so that made unnecessary chaos On our trip

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

It was an overnight flight and I desperately needed coffee before we landed, but Delta does only one beverage service, and that is shortly after takeoff, not before landing at 5 am.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

Terrible. The flight was delayed two hours due to weather. Then when we got on the plane, the first pilot ended up timing out and we had to wait for a second pilot. Second pile came on board and we tax it out. Had to return back to the gate because of an unruly passenger. Then the copilot timed out. Had to wait for new copilot. Also had to wait for maintenance to check for fuel. Then found out the second pilot timed out and we had to wait for a third pilot. Was ready to go and then needed maintenance again for another issue. In the end, it was 2 o’clock in the morning when they announced that the flight couldn’t go because the third pilot and the second copilot had timed out.

American Airlines initially postponed the flight. Then they cancelled it an rescheduled us on a flight that would take over 24 hours with multiple stops. They then changed this flight to a reasonable alternative the next day which they later cancelled and replaced with a flight that would take off with an additional 16 hour delay. They blamed weather but I noticed (at 4am) that Delta had direct flights from Charlotte to Detroit. I went on line. Booked it and was in Detroit buy 9am. The interesting thing is they did a similar thing to a family member just 2 days earlier. I don't think I will fly American unless I have to.

I was a little disappointed of not having an android charger. Only one it was for an iPhone. I've flown American in the past and had access to one.

At least it was a short flight. Greyhound with wings.

One of the best flights I’ve had. So smooth.

This flight didn’t happen because AA agents didn’t let us board the flight

Checking in at the counter was very disappointing. The lady had a very bad attitude and smart at me. She had no smile, did not greet me by name, or acknowledge me as a valued customer. Poor reflection of the airline.

First class flight attendant was rude and lacked any customer service skills.

Paid for a window and was assigned to a middle seat with 2 very large people on each side of me. Flight was sold out and I feel I need to be refunded foe paying for a window seat and being put in a middle one..

Would have been good to have a meal since it was a 5.5 hour flight

Everything you need to know for your flight to Caribbean

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