$274 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 7/20. 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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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$699
Santiago de los Caballeros
Santiago de los Caballeros2 stops$695
Nassau
Nassau1 stop$536
Saint Thomas Island
Saint Thomas Island1 stop$550
Kingston
Kingston2 stops$719
Simpson Bay
Simpson Bay2 stops$3,555
Montego Bay
Montego Bay2 stops$699
Santiago de los Caballeros
Santiago de los Caballeros2 stops$695
Nassau
Nassau1 stop$536
Saint Thomas Island
Saint Thomas Island1 stop$550
Kingston
Kingston2 stops$719
Simpson Bay
Simpson Bay2 stops$3,555

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, Oct 14 - Tue, Oct 20
Delta Logo
11:06 am - 9:59 pm
OAJ
-
SJU
10h 53m
1 stop
Delta Logo
7:30 am - 5:44 pm
SJU
-
OAJ
10h 14m
1 stop
$436Delta
Wed, Oct 14 - Tue, Oct 20
American Airlines Logo
6:03 pm - 11:05 am
OAJ
-
SJU
17h 02m
2 stops
American Airlines Logo
3:50 pm - 8:20 am
SJU
-
OAJ
16h 30m
1 stop
$441American Airlines
Fri, Oct 16 - Mon, Oct 19
Delta Logo
6:00 am - 4:33 pm
OAJ
-
SJU
10h 33m
1 stop
Delta Logo
12:46 pm - 10:15 pm
SJU
-
OAJ
9h 29m
1 stop
$506Delta
Fri, Oct 16 - Mon, Oct 19
American Airlines Logo
8:34 pm - 12:40 pm
OAJ
-
SJU
16h 06m
2 stops
American Airlines Logo
5:50 pm - 12:25 pm
SJU
-
OAJ
18h 35m
2 stops
$511American Airlines
Fri, Oct 16 - Mon, Oct 19
American Airlines Logo
8:34 pm - 12:40 pm
OAJ
-
SJU
16h 06m
2 stops
American Airlines Logo
3:50 pm - 8:20 am
SJU
-
OAJ
16h 30m
1 stop
$541American Airlines
Mon, Jul 20 - Sun, Aug 2
Delta Logo
12:00 pm - 10:29 pm
OAJ
-
SJU
10h 29m
1 stop
Delta Logo
7:30 am - 6:04 pm
SJU
-
OAJ
10h 34m
1 stop
$591Delta
Mon, Aug 10 - Fri, Aug 14
American Airlines Logo
7:09 pm - 9:43 am
OAJ
-
SJU
14h 34m
2 stops
American Airlines Logo
7:05 am - 6:38 pm
SJU
-
OAJ
11h 33m
1 stop
$604American Airlines
Mon, Jul 20 - Sun, Aug 2
American Airlines Logo
6:11 pm - 11:04 am
OAJ
-
SJU
16h 53m
2 stops
American Airlines Logo
3:40 pm - 8:28 am
SJU
-
OAJ
16h 48m
1 stop
$616American Airlines
Mon, Jul 20 - Fri, Jul 31
Delta Logo
12:00 pm - 10:29 pm
OAJ
-
SJU
10h 29m
1 stop
Delta Logo
12:56 pm - 10:29 pm
SJU
-
OAJ
9h 33m
1 stop
$636Delta
Mon, Jul 20 - Sat, Aug 1
American Airlines Logo
6:11 pm - 11:04 am
OAJ
-
SJU
16h 53m
2 stops
American Airlines Logo
7:25 am - 5:45 pm
SJU
-
OAJ
10h 20m
1 stop
$652American 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 $562, prices are generally cheapest when you fly direct.

Find deals

Good to know

Cheapest flight$274
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.

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 11662 reviews
7.5Boarding
7.2Comfort
6.9Entertainment
6.4Food
7.9Crew
Airline reviews

STOP MAKING THE SEATING SO CRAMPED. WE NEED A PASSENGER BILL OF RIGHTS!

10.0 ExcellentLJ, May 2026
CLT - OMA
Read more American Airlines reviews

STOP MAKING THE SEATING SO CRAMPED. WE NEED A PASSENGER BILL OF RIGHTS!

Flight was delayed an no one cares, or try to help passengers to get the conexión.

Had to wait for a gate for a long time, then waited on the run way for a long time before leaving. The actual flights part was good.

Airlines should be prohibited from using the seats they get away with.

Got home at 3am after deboarding the plane. No compensation offered by American

The "on the ground" A/C was not working. It was so hot while waiting to get in the air, a passenger from the rear of the plan declared "I just can't!" and waited in the gangway until time to close the doors. It was miserable. But the crew were champs and had an amazing attitude. I know they were as miserable as we were but didn't let that affect their performance.

When I booked my flight a month ago - I selected a seat. That seat was NOT the one I ended up with when I checked into my flight the day before. This is the second time this has occurred. So, I checked my next flight on Wednesday and Thursday and no seat was assigned. Poor, very poor customer service.

Cleared standby and gave up my seat. Terrible policy and boarding experience

Message about flight cancelation was received late due to being in the air. No explanation, just canceled and booked on morning flight. We had to stay in the airport overnight because there was no transportation offered to get to the hotel that AA had available. Actual inflight was fine.

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

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

Jacksonville (OAJ)