$333 Find Cheap Flights from Jacksonville to Caribbean

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 departing on 6/25. 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

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Cheap Flights from Jacksonville to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Montego Bay
Montego Bay2 stops$551
Nassau
Nassau2 stops$645
Saint Thomas Island
Saint Thomas Island2 stops$398
Kingston
Kingston2 stops$724
Simpson Bay
Simpson Bay1 stop$672
Port of Spain
Port of Spain2 stops$934
Bridgetown
Bridgetown2 stops$3,925
Montego Bay
Montego Bay2 stops$551
Nassau
Nassau2 stops$645
Saint Thomas Island
Saint Thomas Island2 stops$398
Kingston
Kingston2 stops$724
Simpson Bay
Simpson Bay1 stop$672
Port of Spain
Port of Spain2 stops$934
Bridgetown
Bridgetown2 stops$3,925

Book Cheap Jacksonville to Caribbean 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 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

Tue, Oct 6 - Mon, Oct 12
American Airlines Logo
6:03 pm - 12:40 pm
OAJ
-
STT
18h 37m
2 stops
American Airlines Logo
1:50 pm - 12:25 pm
STT
-
OAJ
22h 35m
2 stops
$398American Airlines
Sun, Nov 1 - Wed, Nov 4
Delta Logo
6:00 am - 2:21 pm
OAJ
-
SJU
7h 21m
1 stop
Delta Logo
7:30 am - 1:39 pm
SJU
-
OAJ
7h 09m
1 stop
$446Delta
Tue, Oct 6 - Mon, Oct 12
American Airlines Logo
8:34 pm - 10:40 am
OAJ
-
STT
14h 06m
1 stop
American Airlines Logo
1:50 pm - 8:20 am
STT
-
OAJ
18h 30m
2 stops
$464American Airlines
Sat, Sep 5 - Fri, Sep 11
Delta Logo
6:00 am - 4:38 pm
OAJ
-
SJU
10h 38m
1 stop
Delta Logo
12:56 pm - 10:22 pm
SJU
-
OAJ
9h 26m
1 stop
$481Delta
Tue, Jul 21 - Tue, Jul 28
American Airlines Logo
6:11 pm - 11:04 am
OAJ
-
SJU
16h 53m
2 stops
American Airlines Logo
6:00 am - 10:16 pm
SJU
-
OAJ
16h 16m
2 stops
$486American Airlines
Thu, Dec 10 - Tue, Dec 15
American Airlines Logo
7:48 pm - 10:35 am
OAJ
-
SJU
13h 47m
2 stops
American Airlines Logo
6:00 am - 7:18 pm
SJU
-
OAJ
14h 18m
2 stops
$491American Airlines
Sat, Aug 8 - Sat, Aug 15
American Airlines Logo
7:09 pm - 1:49 pm
OAJ
-
MBJ
19h 40m
2 stops
American Airlines Logo
12:47 pm - 8:32 am
MBJ
-
OAJ
18h 45m
2 stops
$504American Airlines
Thu, Oct 8 - Fri, Oct 23
WestJet Logo
11:06 am - 11:10 am
OAJ
-
NAS
24h 04m
2 stops
WestJet Logo
12:00 pm - 10:15 pm
NAS
-
OAJ
34h 15m
2 stops
$3,452WestJet
Mon, Oct 26 - Mon, Nov 2
WestJet Logo
11:06 am - 3:40 pm
OAJ
-
NAS
28h 34m
2 stops
WestJet Logo
4:50 pm - 10:15 pm
NAS
-
OAJ
29h 25m
2 stops
$3,482WestJet
Mon, Dec 7 - Thu, Dec 10
WestJet Logo
6:00 am - 3:40 pm
OAJ
-
NAS
33h 40m
2 stops
WestJet Logo
11:20 am - 1:39 pm
NAS
-
OAJ
26h 19m
2 stops
$3,492WestJet
Booking Insights

KAYAK's insights & trends for Jacksonville to Caribbean flights

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

Which airlines provide the cheapest flights from Jacksonville to Caribbean?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 5 days.

In the past 5 days, the cheapest round-trip tickets from Jacksonville to Caribbean were found on Delta ($446) and American Airlines ($464).

Find deals

Good to know

Cheapest flight$333
Flight from Jacksonville to San Juan

FAQs - booking Caribbean flights

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

    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.

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

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

    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 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?

    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 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

 
Need help choosing which airline to fly with from Jacksonville to Caribbean? 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 11688 reviews
7.9Crew
7.2Comfort
6.4Food
7.5Boarding
6.8Entertainment
Airline reviews

Awfully rude American worker at door when we started boarding flight. Then, walk into a blazing hot airplane with no air conditioning until twenty minutes into the flight. Free entertainment was non existent! My husband, along with the fellow passenger in our row, and I could not get entertainment to work, no WIFI! Really?? Been flying American a long time. Was very disappointed.

2.0 MediocreKimberly, Jun 2026
RDU - DFW
Read more American Airlines reviews

Awfully rude American worker at door when we started boarding flight. Then, walk into a blazing hot airplane with no air conditioning until twenty minutes into the flight. Free entertainment was non existent! My husband, along with the fellow passenger in our row, and I could not get entertainment to work, no WIFI! Really?? Been flying American a long time. Was very disappointed.

Two hours delay, probably one hour because they didn’t bring catering and they had to bring water in board. There a change of aircraft. But delays galore at CLT so it must be a CLT and/or AA operation issue. The 1 hr additional delays because nobody could bring 2 packs of water sooner is probably the best example of this airline operates

Our flight was repeatedly delayed for maintenance problems: scheduled for 9.30am, eventually delayed to 7pm! Very very inconvenient! AA should have provided a substitute plane much earlier.. On the other hand, Customer Service crew in Charlotte helped us to reach NY (LGA) by late afternoon. Thank you Patricia!! The actual flight was quick and very comfortable. As always a. excellent, professional crew. [no food on a a short hop).

The flight was peaceful, just s slight turbulence, pilots and crews were all nice and made a great job! Arrived safely in the Philippines. Thank you ya’ll!

Flight left on time. Captain provided relevant announcements. We had to wait 45 minutes to desembark due to the ramp closed because of lightening.

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

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports

Jacksonville (OAJ)