$405 Find Cheap Flights from Jacksonville to Caribbean Islands

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 Islands departing on 1/20. 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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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$566
Nassau
Nassau2 stops$1,354
Kingston
Kingston2 stops$668
Simpson Bay
Simpson Bay2 stops$3,660
Bridgetown
Bridgetown1 stop$641
Montego Bay
Montego Bay1 stop$566
Nassau
Nassau2 stops$1,354
Kingston
Kingston2 stops$668
Simpson Bay
Simpson Bay2 stops$3,660
Bridgetown
Bridgetown1 stop$641

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

mar., janv. 20 - ven., janv. 23
American Airlines Logo
6:07 am - 5:01 pm
OAJ
-
SJU
9h 54m2 stops
American Airlines Logo
7:12 pm - 11:11 am
SJU
-
OAJ
16h 59m2 stops
$405American Airlines
dim., févr. 1 - dim., févr. 8
Delta Logo
5:40 am - 11:13 am
OAJ
-
MBJ
5h 33m1 stop
Delta Logo
12:38 pm - 9:42 pm
MBJ
-
OAJ
9h 04m1 stop
$566Delta
dim., févr. 1 - dim., févr. 8
American Airlines Logo
7:05 pm - 12:58 pm
OAJ
-
MBJ
17h 53m2 stops
American Airlines Logo
1:58 pm - 11:11 am
MBJ
-
OAJ
21h 13m2 stops
$571American Airlines
lun., janv. 12 - lun., janv. 26
American Airlines Logo
6:07 am - 2:43 pm
OAJ
-
BGI
7h 36m1 stop
American Airlines Logo
3:46 pm - 10:58 pm
BGI
-
OAJ
8h 12m1 stop
$641American Airlines
lun., janv. 12 - lun., janv. 26
American Airlines Logo
6:07 am - 2:43 pm
OAJ
-
BGI
7h 36m1 stop
American Airlines Logo
4:25 pm - 11:11 am
BGI
-
OAJ
19h 46m2 stops
$646American Airlines
mar., févr. 24 - lun., mars 2
Delta Logo
5:40 am - 3:19 pm
OAJ
-
MBJ
9h 39m1 stop
Delta Logo
4:44 pm - 10:35 pm
MBJ
-
OAJ
5h 51m1 stop
$650Delta
lun., janv. 12 - lun., janv. 26
American Airlines Logo
6:07 am - 9:16 pm
OAJ
-
KIN
15h 09m2 stops
American Airlines Logo
7:00 am - 10:58 pm
KIN
-
OAJ
15h 58m2 stops
$668American Airlines
sam., avr. 4 - sam., avr. 11
WestJet Logo
11:50 am - 3:40 pm
OAJ
-
NAS
27h 50m2 stops
WestJet Logo
4:40 pm - 6:04 pm
NAS
-
OAJ
25h 24m2 stops
$1,354WestJet
sam., janv. 31 - mer., févr. 4
WestJet Logo
4:00 pm - 7:40 pm
OAJ
-
NAS
27h 40m2 stops
WestJet Logo
4:40 pm - 5:46 pm
NAS
-
OAJ
25h 06m2 stops
$1,389WestJet
sam., janv. 31 - sam., févr. 7
WestJet Logo
4:00 pm - 7:40 pm
OAJ
-
NAS
27h 40m2 stops
WestJet Logo
4:40 pm - 1:35 pm
NAS
-
OAJ
44h 55m2 stops
$1,399WestJet
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 $520, prices are generally cheapest when you fly direct.

Good to know

Low seasonFebruary
Cheapest flight$405
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly and prices are also 12% 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.

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 11054 reviews
6.9Entertainment
8.0Crew
7.5Boarding
6.5Food
7.2Comfort
Airline reviews

Flight was on time is the only good thing. Person loading the plane called 1-6 to board at the same time, made it chaotic. Plane was too small for even putting backpacks in overhead. Seat for normal sized people were too small. The WIFI didn't work. When we landed had to wait because not enough ground crew.

8.0 ExcellentHugh, Dec 2025
CLT - MDT
Read more American Airlines reviews

Flight was on time is the only good thing. Person loading the plane called 1-6 to board at the same time, made it chaotic. Plane was too small for even putting backpacks in overhead. Seat for normal sized people were too small. The WIFI didn't work. When we landed had to wait because not enough ground crew.

Did not understand a single word the attendant said on the pa system. I was glad it was not an emergency.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

Waaay too small plane. They also need to up the size of the overhead bins. I would love to keep me 3k with of camera equipment in my hard case baggahe instead of it being thrown into the belly of the plane

After arriving in Dallas, the aircraft taxied for an unusually long time and was unable to park at the gate, which caused a significant delay and made me miss my connecting flight. I then had to wait in a very long line to be rebooked, and I was told that no hotel or meal accommodations would be provided. What is even more unacceptable is that my luggage was mishandled and has still not been located. My suitcase contains important medications that I urgently need, and I have been unable to access them due to the airline’s mishandling. This situation has caused me considerable stress and inconvenience, and I need this issue to be resolved immediately.

I had a positive experience on American. I'm blind and traveling with a guide dog and the flight attendants were so kind, friendly, and helpful towards us. They checked in on us during the flight and they made us feel comfortable and welcomed. There was an hour delay before depature, but overall the flight was a smooth ride. I appreciate that there were no issues on this long flight back home.

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.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports