$152 Find Cheap Flights from Fort Myers 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 Fort Myers to Caribbean departing on 5/28. 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 Fort Myers to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$393
Santo Domingo
Santo Domingo1 stop$526
Montego Bay
Montego Bay1 stop$422
Oranjestad
Oranjestad1 stop$535
Nassau
Nassau2 stops$486
Kingston
Kingston1 stop$647
Simpson Bay
Simpson Bay1 stop$585
Port of Spain
Port of Spain1 stop$1,186
Bridgetown
Bridgetown1 stop$458
George Town
George Town1 stop$644
Aguadilla
Aguadilla1 stop$676
Puerto Plata
Puerto Plata2 stops$722
Punta Cana
Punta Cana1 stop$393
Santo Domingo
Santo Domingo1 stop$526
Montego Bay
Montego Bay1 stop$422
Oranjestad
Oranjestad1 stop$535
Nassau
Nassau2 stops$486
Kingston
Kingston1 stop$647
Simpson Bay
Simpson Bay1 stop$585
Port of Spain
Port of Spain1 stop$1,186
Bridgetown
Bridgetown1 stop$458
George Town
George Town1 stop$644
Aguadilla
Aguadilla1 stop$676
Puerto Plata
Puerto Plata2 stops$722

Book Cheap Fort Myers 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 Fort Myers 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 Fort Myers to Caribbean

su, Touko 10 - to, Touko 14
Frontier Logo
8:01 pm - 4:01 am
RSW
-
SJU
8h 00m
1 stop
Frontier Logo
6:30 am - 7:16 pm
SJU
-
RSW
12h 46m
1 stop
$220Frontier
su, Touko 10 - to, Touko 14
Frontier Logo
8:01 pm - 4:01 am
RSW
-
SJU
8h 00m
1 stop
Frontier Logo
6:30 am - 7:16 pm
SJU
-
RSW
12h 46m
1 stop
$244Frontier
pe, elo 28 - ma, elo 31
Southwest Logo
7:05 am - 2:30 pm
RSW
-
SJU
7h 25m
1 stop
Southwest Logo
10:00 am - 8:10 pm
SJU
-
RSW
10h 10m
2 stops
$321Southwest
to, elo 20 - ma, elo 31
Southwest Logo
8:55 am - 8:05 pm
RSW
-
SJU
11h 10m
2 stops
Southwest Logo
5:00 am - 4:45 pm
SJU
-
RSW
11h 45m
2 stops
$326Southwest
su, Touko 10 - to, Touko 14
Delta Logo
5:35 am - 3:17 pm
RSW
-
STT
9h 42m
1 stop
Delta Logo
1:16 pm - 12:27 am
STT
-
RSW
11h 11m
1 stop
$380Delta
su, Touko 10 - to, Touko 14
American Airlines Logo
6:00 am - 2:49 pm
RSW
-
STT
8h 49m
1 stop
American Airlines Logo
5:05 pm - 1:00 pm
STT
-
RSW
19h 55m
2 stops
$390American Airlines
la, heinä 11 - ma, heinä 13
Delta Logo
6:00 am - 4:37 pm
RSW
-
STT
10h 37m
1 stop
Delta Logo
3:33 pm - 1:00 am
STT
-
RSW
9h 27m
1 stop
$403Delta
ma, kesä 8 - pe, kesä 12
JetBlue Logo
7:04 am - 1:03 pm
RSW
-
MBJ
30h 59m
1 stop
JetBlue Logo
11:19 am - 12:07 am
MBJ
-
RSW
11h 48m
1 stop
$521JetBlue
la, Touko 30 - to, kesä 4
JetBlue Logo
6:00 am - 4:46 pm
RSW
-
AUA
10h 46m
1 stop
JetBlue Logo
4:40 pm - 11:49 am
AUA
-
RSW
19h 09m
1 stop
$535JetBlue
to, kesä 11 - ke, kesä 17
American Airlines Logo
6:16 am - 10:55 pm
RSW
-
SDQ
16h 39m
2 stops
American Airlines Logo
7:35 pm - 6:39 pm
SDQ
-
RSW
23h 04m
2 stops
$545American Airlines
Booking Insights

KAYAK's insights & trends for Fort Myers to Caribbean flights

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

What is the cheapest month to fly from Fort Myers to Caribbean?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Fort Myers to Caribbean, 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 Fort Myers to Caribbean is February, when tickets cost $138 (return) on average. On the other hand, the most expensive months are December and April, when the average cost of round-trip tickets is $314 and $268 respectively.

Good to know

Low seasonMarch
Cheapest flight$122
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly and prices are also 18% lower on average.
Flight from Fort Myers to San Juan

FAQs - booking Caribbean flights

  • How does KAYAK find such low prices on flights from Fort Myers 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 Fort Myers to Caribbean.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Fort Myers 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 Fort Myers 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 Fort Myers 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 Fort Myers 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 Fort Myers 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 5 airlines serving from Fort Myers to Caribbean

 
Need help choosing which airline to fly with from Fort Myers 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.
8.0
SouthwestOverall score based on 4314 reviews
8.6Crew
8.0Comfort
7.0Food
7.5Entertainment
8.1Boarding
Airline reviews

Communication about the delayed flight was poor. We were told to move gates three times but that was bad information. We went from gate 128 to gate 126 and then to gate 123 and back to gate 126. Communication about the delay was bad. Ended up being 1 1/2 hour late getting home.

2.0 MediocreDavid, Apr 2026
MCO - MCI
Read more Southwest reviews

Communication about the delayed flight was poor. We were told to move gates three times but that was bad information. We went from gate 128 to gate 126 and then to gate 123 and back to gate 126. Communication about the delay was bad. Ended up being 1 1/2 hour late getting home.

Southwest continues to do less for more money. Flight attendants used to be fun and friendly. But now it’s like they don’t even see you. Such a shame.

I liked it better when you were truer to your roots Am paying more for less fun

I was supposed to be on a later flight. When I showed up at the gate, the woman working there was extremely helpful getting moved up to this earlier flight.

Long layover between flights to Long Island from BWI - need better coordination between flights

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

An entire day of delays. Cost lots of money. Meals and a hotel.

I appreciate the staff who allowed me to board though I arrived a little late! Regarding the assigned seating, I had booked my flight before this change and wasn't aware of the change at the time, and so I didn't select a seat at booking as I didn't realize it was relevant. Better communication about the change would have been helpful for preparing.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

Flight was on time. Wi-fi was a little spotty/slow. Boarding and exit were efficient.

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.

Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous

The flight was very good and the staff was very friendly and helpful!

Landed without a gate ready. Plane is extremely old and dirty.

All the amenities was wonderful, if they could keep their prices that low. I'd fly with them all the time.

The WiFi was horrific. I fly delta often and love their (usually reliable and free) WiFi. On this flight it was intermittent and when it did connect was extremely slow. I couldn’t get any work done while I was on the flight which was extremely frustrating. I was also in the exit row seat where there is now immediate seat in front of you, so while the leg room was nice, I couldn’t even watch the TV when the internet wasn’t working. Finally, for the last 20 mins of the flight, the announcement indicator came on the TV screens and took them over, even though no announcement was being made. Really disappointed.

Crew was great. Near on time departure and early arrival. Snacks are always meh. Not a fan of the "pay for everything including miles " proposal unless base flight rate going to be 100 bucks.

On the return flight, flight attendant Britt went out of her way to inform passengers that several of us had tight connections.

Too many people are taking up space in the overhead bins with their extra piece of luggage. Since they cannot fit their backpacks or extra luggage piece under the seat in front of them, they store it in the overheads and thus taking up room for other passengers. It wasn’t only one or two persons; more like 12 or 13 passengers.

Kayak botched up the booking, i had to call delta and fix. In the process Delta failed to honor my comfort plus seat assignment that i had previously.

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

Terrible. There was a lot of misleading information regarding ticketing, seat upgrades, & boarding group. I also expect my seat will recline. I have back problems & it is very painful for me of the seat doesn’t recline. In addition, when I choose a fare that allows me a carry-on bag, I expect to be able to carry it on. Not be forced to check it. Thos happened on my flight to MCO & back to Boston. Not sure I will ever fly JetBlue again. Further I bought the ticket through hat deal. I will NEVER do that again. They were incapable of providing an accurate record locator # for either leg of the trip. I had to call them before each flight with me VERY stressed about whether I would actually be able to get on my flight. Who does that? Who books flight & then FAILS to give an accurate record locator? Twice!

The flight was delayed 4 hours and the JetBlue people at the counter kept lying to us and telling us it was due to weather however all other flights were going in and out of NY and FL. Then they lied that the plane had to stop to refuel. Then they lied and said the plane needed a tire change. JetBlue is the worst. Then they gave a lot of people meal vouchers however I didn’t know they did that and they didn’t offer anything to me.

Jet Blue has excellent everything, Friendly customer service and staff, clean aircraft’s and is always on time.

I was traveling with two small kids and our TV s were the only ones not working. Informed the flight attendant who did nothing about them.

I was especially impressed without efficiently the crew got passengers on and off. One of the stewards was slightly gruff, I thought. No big deal but that's what I noticed.

Onboard functioning wide-variety entertainment on a budget and having an open pantry is nice. Seats are not comfortable but go provide plenty of legroom for a 6'2" 260lbs man.

Even though the weather made a lot of flights become cancelled Jet Blue made the flight that was supposed to leave at 9 pm and we left at 12:15 am and I was so grateful- Thanks to the Senior Jet Blue Staff who made those decisions

Worst customer service ever experienced on the planet, dirty plane, no communication, and severe delays

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.

Flight: Started on time. Comfortable flight. Arrived on time. Crew: Very cordial and helpful. Drinks and snack was served with a smile. Overall enjoyed the trip. Regards, Hari Doss Chanchala Doss

I’m sure Business Class would be excellent. I feel like I got what I paid for. Overall it was good and well worth it. I would do it again.

This short sector between Miami and JFK was undertaken purely for business purposes, with efficiency as the primary objective rather than a full inflight experience. Overall, the journey met its intended purpose; however, the ground experience at Miami stood out significantly. During check-in, I was unable to link my frequent flyer details from Qatar Airways (oneworld alliance) through either the self-service kiosk or web check-in. The situation was handled exceptionally well by the check-in agent, who demonstrated remarkable ownership. She coordinated across multiple counters, ensured my frequent flyer number was correctly reflected, reissued the boarding pass, and confirmed that mileage accrual would be recognized. Additionally, she ensured the boarding pass reflected priority status, enabling a seamless priority check-in experience without delays. This level of proactive service was both commendable and impactful. Boarding and the inflight experience, operated by American Airlines under a codeshare arrangement, were efficient but largely transactional. While operational delivery was smooth, there was no visible recognition of oneworld frequent flyer status onboard. In comparison to the consistently personalized engagement typically experienced with Qatar Airways, this absence was noticeable—though understandably a potential limitation of codeshare alignment rather than a direct service shortfall. In summary, while the flight itself fulfilled its operational intent, the exceptional professionalism and commitment demonstrated at the Miami check-in counter was the defining highlight of this journey. Greater consistency in elite recognition across partner airlines would further enhance the overall experience.

Business class was very good, one of my best flights

Incredibly delayed. First delay was due to plane coming in being late. Resulted in 30 minute delay. Boarded and then had multiple mechanical issues. Was on plane for an hour until they told people they could get off if they wanted but couldn't come back. Then gate agent rushed in and said they had lost control of who went off and we would all have to deplane and then get back on. They said flight had not been cancelled. Then while sitting waiting to board again they announced it would take two hours to get new plane and to wait at new gate. New plane arrived, reboarded only to find out that pilots had timed out. Waited for new pilots. In that time one of the flight attendants timed out. Never received food or water while waiting. Was confusing mess as to what was happening. Even flight attendants and gate agents were getting frustrated. Almost 6 hours delayed. Called American to received flight credit but can't get anywhere as Kayak reservation and don't have a ticket number. Reached out to Kayak but never heard back.

The new planes (American Eagle) are beautiful and especially comfortable. The flight attendants are consistently professional and courteous. And, while it may seem inconsequential, the new liquid tube of coffee creamer—in contrast to the powdered coffee creamer—makes all the difference in a cup of coffee.

Flight was delayed and they gave up my seat on my connection, even when I could still make the flight

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

This company socks. It's fraud. They canceled our flight yesterday, and today we were late because of a really long line at the check in bag. At the rebook station, there was ton of people. The workers were all rude. I am gonna make a report to FTC.

Flight got delayed for 5 hours no good explanation was offered ;(

There was no one at the counter to assist with our check in. The app didn’t work, so I arrived at the airport with time to check in and I couldn’t because no employees were there. When I finally got someone on the phone, it was inside the 60min rule and they said I could no longer check in and they could sell me another ticket. We had to scramble and pay an additional $800 for tickets and THEN AFTER (about 60 min from my original convo with customer service and 10min after original departure time) I had boarded my new flight, there was email saying my original flight from Frontier was delayed and leaving 2hr 50min later, but I STILL wouldn’t have been able to check in. Which means customer service should have been able to see it and let me check in because I was well within my check in time. When I call Frontier, they hang up on me. So their app didn’t work and they employees left and they take zero responsibility or assistance with their “customer service”

Everyone seemed to be in zone 1 for boarding. Maybe break it up a little. Otherwise, smooth flight.

The experience was good. No frills but I got there safe and sound and on time.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports