$288 Find Cheap Flights from Jacksonville to Caribbean Islands

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Jacksonville to Caribbean Islands departing on 7/12. 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.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Jacksonville to Caribbean Islands, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Jacksonville to Caribbean Islands, as well as popular online travel agencies
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Flights Deals

Best Caribbean Islands Flight Deals from Jacksonville

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Montego Bay
Montego Bay1 stop$519
Nassau
Nassau1 stop$506
Kingston
Kingston2 stops$616
Simpson Bay
Simpson Bay1 stop$586
Montego Bay
Montego Bay1 stop$519
Nassau
Nassau1 stop$506
Kingston
Kingston2 stops$616
Simpson Bay
Simpson Bay1 stop$586

Cheap Flights from Jacksonville to Caribbean Islands

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Jacksonville to Caribbean Islands 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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Jacksonville to Caribbean Islands

Fri, Sep 26 - Wed, Oct 1
American Airlines Logo
8:00 am - 3:52 pmOAJ-SJU
7h 52m1 stop
American Airlines Logo
4:42 pm - 8:30 amSJU-OAJ
15h 48m1 stop
$365American Airlines
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Mon, Sep 8 - Mon, Sep 15
American Airlines Logo
7:10 pm - 2:53 pmOAJ-SJU
19h 43m2 stops
American Airlines Logo
4:42 pm - 9:52 amSJU-OAJ
17h 10m1 stop
$445American Airlines
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Sun, Aug 17 - Wed, Aug 20
Delta Logo
5:55 am - 2:10 pmOAJ-STT
8h 15m1 stop
Delta Logo
3:23 pm - 10:15 pmSTT-OAJ
6h 52m1 stop
$479Delta
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Mon, Sep 8 - Mon, Sep 15
American Airlines Logo
5:22 pm - 12:46 pmOAJ-SJU
19h 24m2 stops
American Airlines Logo
7:05 pm - 9:52 amSJU-OAJ
14h 47m2 stops
$485American Airlines
Find Deal
Tue, Aug 19 - Fri, Aug 22
Delta Logo
5:55 am - 2:10 pmOAJ-STT
8h 15m1 stop
Delta Logo
3:23 pm - 10:15 pmSTT-OAJ
6h 52m1 stop
$498Delta
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Tue, Nov 4 - Tue, Nov 11
American Airlines Logo
5:01 am - 12:00 pmOAJ-MBJ
6h 59m1 stop
American Airlines Logo
4:05 pm - 8:23 amMBJ-OAJ
16h 18m2 stops
$519American Airlines
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Mon, Sep 22 - Fri, Sep 26
Delta Logo
2:25 pm - 8:00 pmOAJ-KIN
6h 35m1 stop
Delta Logo
9:00 am - 5:46 pmKIN-OAJ
7h 46m1 stop
$637Delta
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Mon, Dec 1 - Mon, Dec 8
WestJet Logo
5:40 am - 1:53 pmOAJ-MBJ
32h 13m2 stops
WestJet Logo
6:55 pm - 10:16 pmMBJ-OAJ
27h 21m2 stops
$2,381WestJet
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Sun, Sep 28 - Thu, Oct 2
WestJet Logo
6:25 pm - 1:43 pmOAJ-MBJ
20h 18m2 stops
WestJet Logo
10:30 am - 1:40 pmMBJ-OAJ
26h 10m2 stops
$3,798WestJet
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Fri, Aug 1 - Fri, Aug 8
WestJet Logo
3:26 pm - 12:33 pmOAJ-MBJ
46h 07m2 stops
WestJet Logo
10:30 am - 4:08 pmMBJ-OAJ
28h 38m2 stops
$3,828WestJet
Find Deal
Useful Info

KAYAK's insights & trends for Jacksonville to Caribbean Islands flights

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

Can I save money by flying with a layover from Jacksonville to Caribbean Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $418, prices are generally cheapest when you fly direct.


Good to know

Low seasonAugust
High seasonAugust
Cheapest flight$288
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly and prices are also 43% lower on average.
Flight from Jacksonville to San Juan

FAQs - booking Caribbean Islands flights

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

    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 Islands.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Jacksonville to Caribbean Islands 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 Islands?

    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 Islands 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 Islands?

    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 Islands 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 Islands?

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

Top airline flying from Jacksonville to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from Jacksonville to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Jacksonville to Caribbean Islands? 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.
7.2
American AirlinesOverall score based on 10000 reviews
6.5Food
7.5Boarding
8.0Crew
6.9Entertainment
7.2Comfort
Airline reviews

Long 5 hour and 45 min flight and only one drink service and cookie snack

8.0 ExcellentBlake, Jun 2025CLT - SFO
Read more American Airlines reviews

Long 5 hour and 45 min flight and only one drink service and cookie snack

Newark airport grounded inbound flight and only announced when the flight was about to start taxing.

Was a normal flight but it was delayed, and there wasn't an explanation.

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.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

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