$287 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 8/31. 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

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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flights Deals
Booking Insights
Flights 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$515
Nassau
Nassau1 stop$715
Kingston
Kingston1 stop$611
Port of Spain
Port of Spain2 stops$673
Bridgetown
Bridgetown1 stop$566
Montego Bay
Montego Bay1 stop$515
Nassau
Nassau1 stop$715
Kingston
Kingston1 stop$611
Port of Spain
Port of Spain2 stops$673
Bridgetown
Bridgetown1 stop$566

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

Fri, Nov 7 - Tue, Nov 11
American Airlines Logo
7:02 pm - 1:41 pmOAJ-SJU
17h 39m2 stops
American Airlines Logo
6:42 pm - 11:08 amSJU-OAJ
17h 26m2 stops
$390American Airlines
Find Deal
Sat, Nov 15 - Sat, Nov 22
American Airlines Logo
8:04 pm - 11:26 amOAJ-ELH
15h 22m2 stops
American Airlines Logo
1:55 pm - 12:53 pmELH-OAJ
22h 58m2 stops
$403American Airlines
Find Deal
Sat, Nov 15 - Sat, Nov 22
American Airlines Logo
8:04 pm - 1:15 pmOAJ-ELH
17h 11m2 stops
American Airlines Logo
1:00 pm - 10:33 amELH-OAJ
21h 33m1 stop
$411American Airlines
Find Deal
Fri, Nov 7 - Tue, Nov 11
American Airlines Logo
7:02 pm - 1:04 pmOAJ-SJU
17h 02m1 stop
American Airlines Logo
6:42 pm - 11:08 amSJU-OAJ
17h 26m2 stops
$436American Airlines
Find Deal
Mon, Dec 8 - Fri, Dec 12
Delta Logo
11:06 am - 4:33 pmOAJ-MBJ
5h 27m1 stop
Delta Logo
3:32 pm - 10:16 pmMBJ-OAJ
6h 44m1 stop
$515Delta
Find Deal
Mon, Dec 8 - Fri, Dec 12
Delta Logo
5:40 am - 4:33 pmOAJ-MBJ
10h 53m1 stop
Delta Logo
3:32 pm - 10:16 pmMBJ-OAJ
6h 44m1 stop
$534Delta
Find Deal
Mon, Dec 8 - Fri, Dec 12
Delta Logo
11:06 am - 12:42 pmOAJ-MBJ
25h 36m2 stops
Delta Logo
3:32 pm - 10:16 pmMBJ-OAJ
6h 44m1 stop
$538Delta
Find Deal
Mon, Sep 15 - Mon, Sep 22
WestJet Logo
11:51 am - 12:28 pmOAJ-MBJ
25h 37m2 stops
WestJet Logo
10:30 am - 3:41 pmMBJ-OAJ
28h 11m2 stops
$3,385WestJet
Find Deal
Mon, Dec 8 - Fri, Dec 12
WestJet Logo
6:25 pm - 1:54 pmOAJ-MBJ
19h 29m2 stops
WestJet Logo
10:30 pm - 11:14 amMBJ-OAJ
12h 44m2 stops
$3,692WestJet
Find Deal
Fri, Jan 16 - Thu, Jan 22
WestJet Logo
11:06 am - 3:17 pmOAJ-CUR
51h 11m2 stops
WestJet Logo
4:10 pm - 5:43 pmCUR-OAJ
26h 33m2 stops
$3,936WestJet
Find Deal
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 $644, prices are generally cheapest when you fly direct.


Good to know

Low seasonAugust
Cheapest flight$287
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly and prices are also 41% lower on average.
Flight from Jacksonville to Montego Bay

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 10000 reviews
6.9Entertainment
7.5Boarding
7.2Comfort
6.5Food
8.0Crew
Airline reviews

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

8.0 ExcellentDeirdra, Jul 2025ILM - BOS
Read more American Airlines reviews

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.

Boarding was very efficient. Everyone got on board and we got on our way very quickly. It was frustrating that the entertainment app was not functioning properly. I was not able to activate some of the movies offered. The crew on this flight appears to be pretty grumpy. They had no smile on their faces. I felt like they were doing us a favor for being there.

Delayed because of weather in Nashville. I think God or some higher power generally has cursed me when it comes to flying out of Charlotte on American. I'm delayed pretty much everytime. We need Team Cobra Kai types to come in and "sweep the leg(s)" of the Charlotte ops people on principle. Don't let the sweet southern rocking chairs fool you, Charlotte is a sinkhole

Long 5 hour and 45 min flight and only one drink service and cookie snack

Newark airport grounded inbound flight and only announced when the flight was about to start taxing.

Was a normal flight but it was delayed, and there wasn't an explanation.

Terrible. The flight was delayed two hours due to weather. Then when we got on the plane, the first pilot ended up timing out and we had to wait for a second pilot. Second pile came on board and we tax it out. Had to return back to the gate because of an unruly passenger. Then the copilot timed out. Had to wait for new copilot. Also had to wait for maintenance to check for fuel. Then found out the second pilot timed out and we had to wait for a third pilot. Was ready to go and then needed maintenance again for another issue. In the end, it was 2 o’clock in the morning when they announced that the flight couldn’t go because the third pilot and the second copilot had timed out.

American Airlines initially postponed the flight. Then they cancelled it an rescheduled us on a flight that would take over 24 hours with multiple stops. They then changed this flight to a reasonable alternative the next day which they later cancelled and replaced with a flight that would take off with an additional 16 hour delay. They blamed weather but I noticed (at 4am) that Delta had direct flights from Charlotte to Detroit. I went on line. Booked it and was in Detroit buy 9am. The interesting thing is they did a similar thing to a family member just 2 days earlier. I don't think I will fly American unless I have to.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.