$64 Find Cheap Flights from Jacksonville to Caribbean Islands - Compare and Save

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 8/10. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 21% 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.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Jacksonville to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$349
Santo Domingo
Santo Domingo1 stop$371
Montego Bay
Montego Bay1 stop$369
Oranjestad
Oranjestad1 stop$414
Nassau
Nassau1 stop$306
Kingston
Kingston1 stop$456
Simpson Bay
Simpson Bay1 stop$466
Providenciales
Providenciales1 stop$535
Port of Spain
Port of Spain1 stop$580
Bridgetown
Bridgetown1 stop$636
George Town
George Town1 stop$615
Willemstad
Willemstad1 stop$685
Aguadilla
Aguadilla1 stop$326
Puerto Plata
Puerto Plata1 stop$719
St. John's
St. John's1 stop$712
Punta Cana
Punta Cana1 stop$349
Santo Domingo
Santo Domingo1 stop$371
Montego Bay
Montego Bay1 stop$369
Oranjestad
Oranjestad1 stop$414
Nassau
Nassau1 stop$306
Kingston
Kingston1 stop$456
Simpson Bay
Simpson Bay1 stop$466
Providenciales
Providenciales1 stop$535
Port of Spain
Port of Spain1 stop$580
Bridgetown
Bridgetown1 stop$636
George Town
George Town1 stop$615
Willemstad
Willemstad1 stop$685
Aguadilla
Aguadilla1 stop$326
Puerto Plata
Puerto Plata1 stop$719
St. John's
St. John's1 stop$712

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

Sat, Aug 22 - Wed, Aug 26
Frontier Logo
11:20 am - 2:29 pm
JAX
-
SJU
3h 09mnonstop
Frontier Logo
7:00 am - 10:25 am
SJU
-
JAX
3h 25mnonstop
$158Frontier
Thu, Aug 27 - Sun, Aug 30
Frontier Logo
11:20 am - 2:29 pm
JAX
-
SJU
3h 09mnonstop
Frontier Logo
7:00 am - 10:25 am
SJU
-
JAX
3h 25mnonstop
$160Frontier
Thu, Jul 2 - Tue, Jul 7
American Airlines Logo
8:17 pm - 10:01 am
JAX
-
NAS
13h 44m
1 stop
American Airlines Logo
10:17 am - 12:15 am
NAS
-
JAX
13h 58m
1 stop
$306American Airlines
Tue, Jul 7 - Thu, Jul 9
American Airlines Logo
6:18 am - 3:13 pm
JAX
-
NAS
8h 55m
2 stops
American Airlines Logo
6:45 pm - 12:15 am
NAS
-
JAX
5h 30m
1 stop
$310American Airlines
Wed, Sep 16 - Tue, Sep 22
JetBlue Logo
2:10 pm - 2:41 pm
JAX
-
STT
24h 31m
1 stop
JetBlue Logo
3:40 pm - 1:10 pm
STT
-
JAX
21h 30m
1 stop
$368JetBlue
Mon, Aug 24 - Mon, Aug 31
JetBlue Logo
7:12 am - 11:14 am
JAX
-
MBJ
5h 02m
1 stop
JetBlue Logo
12:55 pm - 7:55 pm
MBJ
-
JAX
6h 00m
1 stop
$369JetBlue
Fri, Aug 7 - Tue, Aug 11
Delta Logo
12:02 pm - 12:54 am
JAX
-
SDQ
12h 52m
2 stops
Delta Logo
2:53 pm - 11:55 pm
SDQ
-
JAX
9h 02m
1 stop
$383Delta
Fri, Jul 10 - Thu, Jul 16
Delta Logo
7:25 pm - 11:10 am
JAX
-
AUA
15h 45m
1 stop
Delta Logo
1:55 pm - 8:36 am
AUA
-
JAX
18h 41m
2 stops
$414Delta
Sat, Jul 11 - Wed, Jul 15
United Airlines Logo
7:05 am - 3:20 pm
JAX
-
AUA
8h 15m
1 stop
United Airlines Logo
3:10 pm - 11:20 pm
AUA
-
JAX
8h 10m
1 stop
$421United Airlines
Fri, Jul 10 - Thu, Jul 16
United Airlines Logo
4:55 pm - 3:00 pm
JAX
-
AUA
22h 05m
1 stop
United Airlines Logo
3:10 pm - 11:20 pm
AUA
-
JAX
8h 10m
1 stop
$429United 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.

What is the cheapest Jacksonville to Caribbean Islands flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Caribbean Islands from Jacksonville found in the last 5 days was to San Juan, at $178 round-trip. The most popular route is from Jacksonville (JAX) to San Juan Luis Munoz Marin Intl Airport (SJU), and the cheapest round-trip airline ticket found on this route in the last 5 days was $178.

What is the cheapest time of day to fly to Caribbean Islands?

The average price for all round-trip flights from Jacksonville to Caribbean Islands depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Caribbean Islands is generally in the morning, when round-trip flights cost $256 on average. Morning departures are around 22% cheaper than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally in the evening, which is peak travel time and where the average cost of a ticket is $329.

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 $320, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Jacksonville to Caribbean Islands?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Jacksonville to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Jacksonville to Caribbean Islands is March, when tickets cost $100 (return) on average. On the other hand, the most expensive months are October and November, when the average cost of round-trip tickets is $368 and $352 respectively.

What’s the cheapest day of the week to fly from Jacksonville to Caribbean Islands?

The average price of all round-trip flights from Jacksonville to Caribbean Islands clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Jacksonville to Caribbean Islands, look for departures on Sundays and avoid leaving on a Saturday, as it's usually the priciest day. When flying back from Caribbean Islands, Tuesday is the cheapest day to fly and Wednesday is the most expensive.

How far in advance should I book a flight from Jacksonville to Caribbean Islands?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Jacksonville to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Jacksonville to Caribbean Islands, you should book around 2 weeks before departure, which saves you about 19% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 4 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$64
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly with an average 1% increase in price.
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.

Top tips for finding cheap flights to Caribbean Islands

  • Looking for a cheap flight? 25% of our users found tickets from Jacksonville to the following destinations at these prices or less: San Juan $131 one-way - $226 round-trip

Reviews of the top 5 airlines serving 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.
7.8
DeltaOverall score based on 8410 reviews
8.1Boarding
7.8Comfort
8.5Crew
7.8Entertainment
7.2Food
Airline reviews

Five hour delays every hour, I wish it were all at once

2.0 MediocreAnonymous, Jun 2026
MCO - LGA
Read more Delta reviews

Five hour delays every hour, I wish it were all at once

Got rerouted from a straight flight from Orlando to Atlanta to Knoxville to a flight from Orlando to Detroit to Knoxville! Seriously!! Flight delay out of Detroit! Long day for what should have been a pretty easy travel day!

Left /arrived on time. Decent seat space. Like the wifi/plugs and entertainment. Windows and tray table were kinda gross. Attendants didn't start snack service til 40mins before landing. Two rows before us, captain came on to say there's turbulence and recalled staff to seats. So, no drink/snack. Later, attendants didn't stop to see if we had trash nor even look our way. Felt invisible! Almost all pilot announcements were not only unintelligible, but so quiet. We had no idea what she said.

Gate agent was unhelpful for handicapped boarding. Flight attendant seemed untrained.

Clean planes and not take my comfort class seat away.

Weather caused a long delay, but the efficiency and updates from the pilot were helpful. We were able to make our connection fortunately.

Planes were clean, no water or snacks on either flight.

Aside from a completely packed plane, I really have no complaints.

Much better than Latam, the worse airline company ever. I hope I don't have the need to fly Latam ever in my life again.

The flight was operated by Latam. The aircraft had a technical issue and the flight was delayed for the next day. They grounded other passengers to get their airplane assigned to my flight. Most of he ground staff don't speak English (Orlando Airport), but were very polite.The crew on the other hand could speak English and Portuguese. On board service was good.

6 1/2 hours from Tampa to SFO on a Boeing 737. Cramped. No Service. No real food. One pass for coffee at the beginning and a second pass THREE hours later. And check-in in Tampa was nasty even by United standards. And I am at almost TWO million miles on United. It's a non-stop. But terrible service.

The flight had a delay but I made it to my connection. Flight was smooth overall

It's a short hop. My carryon was checked at the gate, I didn't have to drag it all over the airport. Excellent wheelchair assist.

Flights were on time actually early service was good and crew cheerful

The boarding process was straightforward. One pertinent observation regarding all boarding procedures is that if an individual requires assistance or possesses a special status and is part of preboarding, it is advisable to limit the number of passengers who can preboard with them, rather than the entire, sometimes large, companion groups. The seats are uncomfortable, and the entertainment options are significantly inferior compared to other airlines. During the snack service, I requested an additional bag of snacks, but my request was denied. Initially, the flight attendant agreed to my request.becoming a strange accurate moment. The flight duration was four hours.

Flights were on time. Free Wifi on plane. Everything was well organized.

Experience was great - no complaints. Took off on time, landed early. Got to the gate relatively quickly - took a little bit of extra time to deplane but nothing excessive.

Economy plus was so cramped I could not use my laptop. It was beyond bad.

United is one airline which regardless of how many separate United tickets in existence, if one flight breaks down, the airline will take care of all the flights.

Everything was on time and service on the flight was great!

We sat on plane at gate delayed without communication as to why we were just sitting there

Trash. Sat on the runway for 40 mins…missed connecting flight because of it now I’m stuck. Thanks…a whole fkn lot.

Little time between flight from Dallas to flight to Gainesville. We chose this one, 43 minutes between, because the price for a connection with at least an hour between, was so much higher. Had to ask passengers on the Dallas flight to please allow us to deplane ahead of them. The economy passengers allowed this. We had to walk very fast to the next gate, 35 gates away. Thankfully all in the same terminal. Getting to the small Gainesville plane was a little confusing as you enter an area that is boarding many small planes at the same time. We stood in the wrong line for about 15 seconds before realizing it was not our Gainesville flight. Since I had boarded at this gate in the past, I knew to check the signs carefully so we weren’t lost. The first class seat experience was wonderful. I really enjoyed the upgrade. We were offered an alcohol drink as soon as we sat down. I got something different but it was a great gesture especially since we really had to hurry to make the flight. We had packed expecting we might miss this connection, but made it. Our luggage didn’t miss the flight. American Airlines delivered our bags to our home the next day. That was very convenient!

It was what i expected. I like the movies you can access from your phone. It would be nice if there was a gluten free snack offered. But I did bring my own snack knowing there would not be a gluten free option

There were flight delays making our flight arrive at our destination after midnight didn’t seem to have enough crew or airplanes for the flights laid over in Dallas should’ve had plenty of time to make it to our next flight only made it because that flight was also delayed because our plane wasn’t even at the airport yet overall have not had a good experience on American

Requested early boarding to disinfect seat, tray table, etc. before general boarding. Instructed to board after wheelchair passengers. Waited on jet bridge behind 12 wheelchair passengers. Stopped immediately after entering plane to wait for gate agent in rear of plane cleaning a seat that was wet, got to my row and found both seats adjacent to mine already occupied, with the lack of room making it impossible for me to clean my own space and defeating the purpose of my boarding early. Cleaned the armrests and tray table as best I could.

We had several flights and they were all on-time and flawless

For a 4 1/2 hour international flight all we got was 1 small pack of cookies and a drink. You had to watch movies on your own devise.

The seats need better cushioning for a nearly 5-hour flight, it was a bit uncomfortable. I'm glad American has free wi-fi but there were was a bout 30 minutes in the middle of the flight when there was no connection which was frustrating.

My original flight got delayed day of so I had to rebook it from one layover to two layovers. The flight also left earlier which was a slight inconvenience but manageable. Then my first connection flight got delayed 3 separate times for a total of 2 hours delayed, causing me to miss my second connection flight back to Santa Barbara. Now, because of this missed flight, I am missing my college classes that I pay for.

My checked in luggage cost was $59, almost ticket price. The first 13 rows were empty, but fly attendant did not alow women with little boy change her middle sit, sweet boy was crying, I am so sorry for mother and passengers. At the end of the flight the cabin became impossible cold. Only good was timing of departure and early landing, but it suppose to be normal.

I tried to book a flight with Jet Blue. Your third party company hijacked my attempt with a website that looked like I was booking with Jet Blue. I realized it when I paid. I tried to cancel and was told by a man in India that there were no refunds. $735 stolen, Thanks Kayak!

The flight out was delayed from 3:40pm to 5pm and again to 8pm. We boarded after 5pm, had to disembark because they could not get the Engine started, then we switched gates and got a new plane and did not board until after 8pm.

Boarding was easy. Provided drinks and snacks. Good aircraft and staff

Flight was quick, less time than expected, and the attendants all friendly and helpful. We had paid extra for more leg room and were very comfortable. Haven't flown JetBlue in quite a while. Glad to be back!

JetBlue not only has the most comfortable planes, but also used to have the best customer service. Lorie Wright, the lady at the gate was very rude not only to me, but to other passengers as well. Her colleague, the gentleman was also not very friendly. They both were acting like they were doing passengers a favor. The crew on board was very nice.

Direct tv did not work on flight Short flight so no good service offered Arrived early to destination and had to wait for gate to open. Deplaned LATER than if we arrived on time!! Poor planning Jet blue has had something go wrong on every flight I’ve taken with them in last five years. Terribly run airline

My experience with JetBlue was fine BUT I am very upset with Kayak! JetBlue had delayed our scheduled departure by an hour and you NEVER notified me of the change. I did not hear directly from JetBlue because the trip was booked through Kayak, a mistake I will not repeat. Your reminder of the our trip last week still had the WRONG departure time. Our return trip has also changed, and again no notice from you.

Not having an assigned seat until boarding and then having to check my bag.

I purchased ticket so our daughter ( a minor) can sit next to her mother. No help at gate after kayak insisted that this could be done. She ended sitting by herself

There weren't enough employees at check in took awhile to get bags checked. There wasn't a wheel chair for me, I was sent to someone who turns out to work for a different airline, if My flight hadn't been delayed I probably would have missed my flight as it was, by the time I arrived at my gate, they started boarding in about 15 minutes. I don't know who took me to my gate, definitely was not the normal people who take passengers to the gate. I'm guessing she may have been in a management position. I wish I knew her name, she went beyond to help me. With that said everyone was kind, and were doing the best they could. So, I choose to say it was an Adventure, stressful start, but good. In the end went well. The situation was not only difficult for passengers but the employee's.

The staff at the check in counter was so rude. Made you feel Incompetent

Frontier scheduled a 40 minute connection in DEN. What they failed to mention was that they “close the doors” 20 mins prior to departure, which means you only have 20 mins. Not enough time. Possibly against DOT regulations. Filing complaint.

Flight was scheduled at 9:40pm. Got delayed to 10 am, the next day. crazy

The bag check, flight check-in, and onboard experience convinced my wife and me that we will actively go out of our way to avoid flying Frontier Airlines in the future. At bag check, we were informed that check-in could only be completed via the Frontier mobile app. Unfortunately, the app was extremely frustrating—sending us through repetitive, confusing loops that repeatedly forced us to decline add-on services with nearly every click. While most airline apps upsell, this one felt intentionally exhausting. As the process dragged on, we became genuinely concerned that my phone battery would die before check-in could be completed. We approached the bag check staff—who were standing together talking—and explained both our frustration and our predicament. They laughed. Later, my wife described the interaction as “gaslighting,” which felt accurate. We were then informed it would cost $25 per person simply to have our boarding passes printed. From that point forward, the tone of the experience was consistently hostile. The bag check employees were condescending and combative, behaving more like bullies than customer service staff. Unfortunately, that same attitude continued onboard. One flight attendant argued with me when I attempted to stow my backpack in the overhead bin. I explained that we had each paid $75 to check our bags specifically so we would not need to use carry-on space and could have adequate legroom. She demanded to see my ticket, pointed out that it said “no carry-on”—which I acknowledged—and I reiterated that this was precisely why we paid to check our bags. Her response was, “I don’t make the rules.” She then walked away, but not before asking if I “truly wanted to fly back to Chicago today?”—an unnecessary and unmistakable threat. It is also worth noting that despite booking our tickets together in the same transaction, we were not seated together. Upon our return to Chicago—where we could once again sit together—we compared onboard experiences. We both remarked on how unhappy the flight attendants appeared and how each of us was separately asked whether we would like to purchase a beverage. We declined. At no point was water mentioned as an option, leaving us with the clear impression that even water came at a cost—or that complimentary water, if available at all, was deliberately left unmentioned. Overall, the experience was shocking and deeply disappointing, but it was also a profound learning experience—one we will not forget and will not repeat. -Steve

Plane was hot and miserable and the crew was rude!

12 hour delay required getting on and off plane 3 times - would have at least liked to have been offered a snack or drink

They didn’t offer a water, even after I asked

It was an early flight and most people napped/slept and the crew let us which was nice.

It didn’t happen. I booked it and then was told it wasn’t available and then forced to pay far higher prices for a worse option

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports