$268 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 3/10. 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, 0 bags

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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Flight Deals

Cheap Flights from Jacksonville to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Montego Bay
Montego Bay1 stop$531
Nassau
Nassau1 stop$475
Saint Thomas Island
Saint Thomas Island1 stop$539
Santiago de los Caballeros
Santiago de los Caballeros2 stops$452
Kingston
Kingston2 stops$616
Simpson Bay
Simpson Bay2 stops$544
Port of Spain
Port of Spain2 stops$1,173
Bridgetown
Bridgetown1 stop$651
Montego Bay
Montego Bay1 stop$531
Nassau
Nassau1 stop$475
Saint Thomas Island
Saint Thomas Island1 stop$539
Santiago de los Caballeros
Santiago de los Caballeros2 stops$452
Kingston
Kingston2 stops$616
Simpson Bay
Simpson Bay2 stops$544
Port of Spain
Port of Spain2 stops$1,173
Bridgetown
Bridgetown1 stop$651

Book Cheap Jacksonville to Caribbean Islands Plane Tickets

 
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

Mon, Apr 27 - Wed, Apr 29
Delta Logo
11:06 am - 8:06 pmOAJ-SJU
9h 00m1 stop
Delta Logo
6:15 am - 1:40 pmSJU-OAJ
7h 25m1 stop
$365Delta
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Tue, Apr 7 - Wed, Apr 8
Delta Logo
5:40 am - 12:00 pmOAJ-NAS
6h 20m1 stop
Delta Logo
2:55 pm - 10:14 pmNAS-OAJ
7h 19m1 stop
$475Delta
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Mon, Apr 27 - Wed, Apr 29
American Airlines Logo
8:26 pm - 12:35 pmOAJ-SJU
16h 09m2 stops
American Airlines Logo
6:25 am - 11:47 pmSJU-OAJ
17h 22m2 stops
$494American Airlines
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Mon, Apr 6 - Wed, Apr 8
Delta Logo
2:25 pm - 7:25 pmOAJ-MBJ
6h 00m1 stop
Delta Logo
8:00 am - 10:14 pmMBJ-OAJ
13h 14m1 stop
$531Delta
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Sat, Feb 14 - Sat, Feb 21
American Airlines Logo
7:55 pm - 11:55 amOAJ-SJU
15h 00m2 stops
American Airlines Logo
10:57 am - 11:58 pmSJU-OAJ
14h 01m2 stops
$545American Airlines
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Sat, Nov 15 - Sat, Nov 22
American Airlines Logo
1:18 pm - 11:27 amOAJ-ELH
22h 09m2 stops
American Airlines Logo
12:12 pm - 12:11 amELH-OAJ
11h 59m2 stops
$550American Airlines
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Sat, Feb 14 - Sat, Feb 21
American Airlines Logo
7:55 pm - 11:42 amOAJ-SJU
14h 47m1 stop
American Airlines Logo
10:57 am - 11:58 pmSJU-OAJ
14h 01m2 stops
$565American Airlines
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Sat, Apr 4 - Sat, Apr 11
WestJet Logo
5:40 am - 7:40 pmOAJ-NAS
38h 00m2 stops
WestJet Logo
4:40 pm - 5:43 pmNAS-OAJ
25h 03m2 stops
$1,469WestJet
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Sat, Apr 4 - Sat, Apr 11
WestJet Logo
11:06 am - 3:40 pmOAJ-NAS
28h 34m2 stops
WestJet Logo
4:40 pm - 5:43 pmNAS-OAJ
25h 03m2 stops
$1,472WestJet
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Mon, Dec 1 - Mon, Dec 8
WestJet Logo
2:26 pm - 3:50 pmOAJ-NAS
25h 24m2 stops
WestJet Logo
4:50 pm - 9:56 pmNAS-OAJ
29h 06m2 stops
$3,447WestJet
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Booking Insights

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 $481, prices are generally cheapest when you fly direct.

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Good to know

Most popular time to fly and prices are also 12% lower on average.

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.

Reviews of the 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 11040 reviews
8.0Crew
7.5Boarding
6.9Entertainment
6.4Food
7.2Comfort
Airline reviews

Flight delayed and missed connection. Rescheduled flight cancelled after 6 hrs wait. Rerouted thru ORD, flight cancelled, overnight stay in ORD. Still in the air on new flight!

2.0 MediocreAnonymous, Oct 2025RDU - DFW
Read more American Airlines reviews

Flight delayed and missed connection. Rescheduled flight cancelled after 6 hrs wait. Rerouted thru ORD, flight cancelled, overnight stay in ORD. Still in the air on new flight!

Flight was delayed because of a bird strike. They had another plane available within 45 minutes.

You can plug your phone in & use their wifi to watch movies, etc, but the plane’s wifi was disconnected for most of the flight.

The trip was smooth but the crew were very abrupt, snatching things before finished and being quite snappy when asked questions.

Very below average , plane from Dallas to Toyko was very poor designed plane. I had to sit for 13 hours next to fat man. Really bad seat and entertainment screen sucked

Boarding: Boarding was a bit of a mess. Our tickets indicated "BC" for Business Class, but we and many others were confused as that was not indicated anywhere in the airport, so we didn't know when we're supposed to board. The airplane: The airplane was nice. However, we sat near the back of the business class cabin and the flight attendants and passengers from other cabins would constantly move the curtain (which was very loud), preventing me from fallling asleep on my 8 hour flight. The flight crew: Amazing, generally. However, they nearly forgot to serve breakfast to me. The flight food: I was able to select my meal for dinner, which was really good. Breakfast was a bit of a mess, however. The crew forgot to serve me breakfast until the last minute. Very little was available by the time they remembered. The entertainment: Paltry, underwhelming, and dated. Not one new movie was available. Bottom line: For the money, you might want to consider other options for your international business class flights.

Sat on the ground in Cincinnati for 50 minutes before deplaning

Flight was delayed. Staff at the gate effectively and proactively communicated about the delay.

Overall fine, but the delay was annoying and the reasons for the delay were not communicated. The crew on board were phenomenal!

This flight never occurred because AA couldn’t get their act together.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

Jacksonville (OAJ)

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