$183 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 4/9. 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 Bay2 stops$3,729
Kingston
Kingston2 stops$695
Simpson Bay
Simpson Bay1 stop$702
Bridgetown
Bridgetown2 stops$672
Montego Bay
Montego Bay2 stops$3,729
Kingston
Kingston2 stops$695
Simpson Bay
Simpson Bay1 stop$702
Bridgetown
Bridgetown2 stops$672

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

Wed, May 27 - Tue, Jun 2
Delta Logo
4:07 pm - 10:17 pm
OAJ
-
SJU
6h 10m
1 stop
Delta Logo
7:30 am - 3:27 pm
SJU
-
OAJ
7h 57m
1 stop
$436Delta
Tue, Apr 21 - Wed, Apr 29
American Airlines Logo
6:00 am - 8:51 pm
OAJ
-
SJU
14h 51m
1 stop
American Airlines Logo
7:25 am - 11:57 pm
SJU
-
OAJ
16h 32m
1 stop
$451American Airlines
Wed, May 27 - Mon, Jun 1
Delta Logo
4:07 pm - 10:17 pm
OAJ
-
SJU
6h 10m
1 stop
Delta Logo
6:15 am - 3:27 pm
SJU
-
OAJ
9h 12m
1 stop
$471Delta
Wed, May 27 - Fri, Jun 5
Delta Logo
4:07 pm - 10:17 pm
OAJ
-
SJU
6h 10m
1 stop
Delta Logo
2:48 pm - 10:04 pm
SJU
-
OAJ
7h 16m
1 stop
$536Delta
Sun, May 24 - Tue, Jun 2
American Airlines Logo
1:14 pm - 11:03 am
OAJ
-
SJU
21h 49m
2 stops
American Airlines Logo
11:55 am - 12:49 pm
SJU
-
OAJ
24h 54m
2 stops
$556American Airlines
Wed, May 27 - Wed, Jun 3
American Airlines Logo
6:41 am - 9:59 pm
OAJ
-
SJU
15h 18m
2 stops
American Airlines Logo
7:00 am - 12:49 pm
SJU
-
OAJ
5h 49m
1 stop
$561American Airlines
Sun, May 24 - Mon, Jun 1
American Airlines Logo
3:07 pm - 10:45 pm
OAJ
-
SJU
7h 38m
1 stop
American Airlines Logo
6:00 am - 11:56 pm
SJU
-
OAJ
17h 56m
2 stops
$576American Airlines
Wed, Aug 5 - Fri, Aug 7
American Airlines Logo
9:00 am - 6:15 pm
OAJ
-
SJU
9h 15m
2 stops
American Airlines Logo
8:00 am - 10:07 pm
SJU
-
OAJ
14h 07m
1 stop
$581American Airlines
Fri, Aug 7 - Mon, Aug 10
American Airlines Logo
8:03 pm - 11:09 am
OAJ
-
SJU
15h 06m
2 stops
American Airlines Logo
7:05 pm - 12:56 pm
SJU
-
OAJ
17h 51m
2 stops
$591American Airlines
Thu, May 28 - Wed, Jun 3
American Airlines Logo
6:41 am - 3:48 pm
OAJ
-
SJU
9h 07m
2 stops
American Airlines Logo
6:00 am - 2:35 pm
SJU
-
OAJ
8h 35m
2 stops
$596American Airlines
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 $354, prices are generally cheapest when you fly direct.

Good to know

Cheapest flight$183
Flight from Jacksonville to Saint Thomas Island

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.

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.
7.1
American AirlinesOverall score based on 11496 reviews
7.2Comfort
7.5Boarding
6.4Food
7.9Crew
6.9Entertainment
Airline reviews

Ceiling fell down and had to have maintenance come and duct tape it up. No WiFi on the flight.

6.0 GoodJeffrey, Mar 2026
CLT - HPN
Read more American Airlines reviews

Ceiling fell down and had to have maintenance come and duct tape it up. No WiFi on the flight.

I appreciate that I finally got the seat I paid extra for this time. Thank you

American Airlines did everything they could with the high Spring Break crowd. I was frustrated to be changed from 1st class to a middle seat at the back of the plane. This has happened before, not sure booking 1st class and paying the extra actually works.

Plane from partner PSA was filthy. Plastic needs to be thoroughly cleaned. Really disgusting to look at and wonder about cleanliness of parts less visible.

Arrived early picked up my bag in a few minutes- great trip - thank you

I like that the flight attendant was very attentive and helpful. The meal menu could have more of an variety of food choices.

We missed our flight and got stranded in Miami where we had to rent a hotel we could not afford. they would not work with us because they said it was weather related even though the gate attendant said it was not. I could go on but trying to get satisfaction has wore me down, which I believe is the intent. My only solution is to never fly AA again.

Overall it was a good flight. Because we traveled on a Saturday we were upgraded to FC since my wife and I are both Executive Platinum. The only areas for improvement we noted are better snack assortment and perhaps a little nicer plane as American is flying some older planes now. Everything else on this flight was excellent, which is frankly not the norm for American since we have had multiple issues on prior AA flights.

Didn't get a seat assignment until the last minute even though i picked a seat.

Flight was smooth, quick and felt safe. The 2 delays not happening would have been better but I guess that happens in the airline industry

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports