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Find cheap flights from Fort Myers to Caribbean Islands from $51

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 Islands departing on 4/12. 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
0 bags
Sun 4/28
Sun 5/5

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Best Caribbean Islands Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Punta Cana
Punta Cana2 stops$400
Montego Bay
Montego Bay2 stops$405
Santo Domingo
Santo Domingo1 stop$312
Oranjestad
Oranjestad1 stop$438
Nassau
Nassau1 stop$421
Kingston
Kingston1 stop$480
Simpson Bay
Simpson Bay2 stops$372
Port of Spain
Port of Spain2 stops$475
Bridgetown
Bridgetown1 stop$550
George Town
George Town1 stop$568
Aguadilla
Aguadilla1 stop$414

Good to know

Low season

September

High season

February

Cheapest flight

$51
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly and prices are also 15% lower on average.
Flight from Fort Myers to San Juan

FAQs - booking Caribbean Islands flights

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

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Caribbean Islands from Fort Myers 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 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 to Caribbean Islands with an airline and back to Fort Myers 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 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 to Caribbean Islands from Fort Myers up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Caribbean Islands

  • Looking for a cheap flight? 25% of our users found tickets from Fort Myers to the following destinations at these prices or less: San Juan $77 one-way - $139 round-trip

Top 4 airlines serving from Fort Myers to Caribbean Islands

Need help choosing which airline to fly with from Fort Myers 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 KAYAK reviews.
8.0
DeltaOverall score based on 11402 reviews
82boarding
86crew
79comfort
81overall
80entertainment
75food
Airline reviews

The main person that was coordinating everything was a short white/light skin Spanish man and he was very rude. It honestly made me feel like it was everyone’s First day at work. His announcements were very not reasonable and they did not make sense. The stewardess on the flight that made the announcements she didn’t even know what she was talking about she sounded inebriated. There were no snacks or drinks on our flight there wasn’t even much turbulence. This flight was not enjoyable nor was it what a Delta flight should be and just this past week I flew with Delta 3 times.

Read more about Delta

The main person that was coordinating everything was a short white/light skin Spanish man and he was very rude. It honestly made me feel like it was everyone’s First day at work. His announcements were very not reasonable and they did not make sense. The stewardess on the flight that made the announcements she didn’t even know what she was talking about she sounded inebriated. There were no snacks or drinks on our flight there wasn’t even much turbulence. This flight was not enjoyable nor was it what a Delta flight should be and just this past week I flew with Delta 3 times.

nothing Delta could do... the person sitting next to me was huge and overflowing into my seat

Crew was great! I need wheelchair assistance and they knew who I was and updated me that my chair was on its way and to just hang tight. There was some turbulence but the captain announced we would be going thru it and he handled the plane well. Landing was soft and his.

Aircraft very cramped. Check-in was great with an agent helping us. Food was almost non-existent. Pre-flight went well once I got the app reloaded on my phone since we don’t fly much anymore.

I like that it got us where we were going. Everything else needed work. It was 1/2 hour late and we took off an hour late. The plane had to be cleaned and the disabled loaded on board before we could take off which took forever and then we sat at the terminal FOREVER before we took off. The ride was so bumpy that they couldn’t serve drinks and snack but to about 1/2 the plane. Seriously we should have flown out of Fort Lauderdale. We probably would’ve gotten home several hours earlier.

Flight was on time, the staff was personable & professional, & the plane arrived on time.

Flight was great. DELTA did a fantastic job! FLL airport was chaotic!

You lost my luggage!!! How frustrating!!! Now they can’t find one of our bags!!!! I really don’t have time for this!!!

Fast boarding and exit. Different snacks other than almonds and sun chips.

The boarding agents appeared to do the minimum customer service. They did not appear to try to find solutions to problems.

Everything was good except for deplaning in NY. Took way too long!!

Jet Blue keeps getting iit wrong. 4 hour mechanical delay followed by terrible boarding experience. This is my third horrific jet blue flight in 2024. I am going to try to avoid this loser in the sky

Delayed by almost an hour - I also noticed that all JetBlue flights departing from PBI were delayed yet the weather was perfect.

My experience with JetBlue was fantastic! The service was top-notch, the flight was smooth, and the staff were friendly and helpful. I would definitely fly with them again.

The free wi-fi was great. But, the flight delay was not sustainable. It definitely impacted people schedules and JetBlue didn’t do anything to compensate clients for it

Need a 2nd round of water for a 4+ hour flight

I loved the wifi, much better than Delta. Seats were old. and bathrooms dingy.

no wifi and the aircraft was very old with tiny 4” screens.

I actually missed my first scheduled flight and caught it the next day. I think the check in procedure was mishandled by the baggage handler but the staff were very accommodating.

Has been always great except flight cancelation in the past at very last minute waiting till 2am and we when have to beg for overnight accommodation

That flight was smooth, and staff we courteous. it was a full flight so very tight. The boarding through security was not properly controlled. it was rushed and the scanning process for our bags, etc. was pilling up at the other end with no time to empty our belonging my personal items almost toppled over on the floor if i hadn't caught it rapidly. Was it just that time, or always like this - cant say. other than that all else was fine.

Boarding was friendly and quick. While the plane model was older with no live tv, the entertainment was full of movies and tv shows. All food was available. Pilots were very communicative with status of the flight. Flight landed on time.

It was terrible because the flight was delayed for 3 hours.

Crowded flight, but upbeat and kind crew. Pilot greeted us at door, flight attendant thanked a number of “special” passengers for their business, another addressed an eight-year old boy as “young man.” United obviously trying to up their game, but though all of that is nice and notable, flying still feels like moving along a human assembly line, being herded into one small space after another (boarding areas with too few seats, planes with limited personal space, shuttles (IAD) packed too full.

Did not like the seat spacing. The seat was very narrow and tight.

United domestic flight was better than international flight. There was no switch to control Ac In international united flight. Food was also average, Air canada food was much better than united.

Seat didn't recline all the way back. Very uncomfortable flight for 8 hours. The turbulence eliminated snack and food stops

Nothing exceptional but all good. Business class seats are like the domestic Mint class on Jet Blue. Comfortable but not exceptional. Food is good but not superb. Flight attendants were better than US carriers but that is to be expected. However, not the caliber of Asian or Middle Eastern airlines. Very Lufthansa like but Lufthansa has slightly better seats, even though they are hardly best in class

The flight was clean and on time, the crew were all very nice and we got the seats we booked. Plenty of food and beverages. The seats are too close so it’s very difficult to try and sleep comfortably.

Any flight that gets from point A to B with no drama is excellent.

Me and my husband experienced very bad in American Airlines. We missed our flight going to Doha. The American Airlines was delayed we arrived already 10:27pm. Supposed to be 9:40 pm. So what they did they rebooked our flight and they gave us a hotel. When we arrived at the hotel the front desk said it was fully booked already. Oh my gosh! I said why did you accept the booking if it's fully booked. The guy said that's American Airlines they just book even it's already full. That's 2am already, we have nothing to do so, we decided to go another hotel. We pay the room, food and taxi. Pls give an action on this matter. Refund our expenses and give us more compensation. Not only our room, food, taxi but also our efforts, tiredness looking for a room that can accommodate us.

Was flying in premium eco and there were around 5-6 movies I wanted to watch and none of those could I play for some reasons. Not just me we checked w the person sitting next to me. Few of the movies were only playable :( Also that was not great that we couldn't upgrade to business however tried to, many times before the flight :(

Food choice is limited, entertainment better than average, seat leg room terrible

Horrible. Flight was delayed and very bumpy. I was super unhappy

Got a much appreciated surprise upgrade to an exit row and the crew was very friendly and helpful.

I have not found it to be easy to set up on Wi-Fi with American Airlines. I don’t know if it is me or poor instructions.

Overall it was good. The plane was small and the flight attendants on the Clt to gso route were not that friendly

Late arrival due to gate being blocked by stalled truck

It was good. Flights were all on time to start and landed early. Connections were easy.

The agents at the gate were rude. The stwards were pleasant. The seats were comfortable. The tray table had crumbs on it. A passenger talked constantlt and very loudly for the entire flight annoying many passengers. The stewards did not ask her to speak in a lower voice but my travel partner did.

Book cheap flights from Fort Myers to Caribbean Islands

Recent round-trip flight deals

4/22Mon
nonstopSpirit Airlines
2h 33mRSW-SJU
4/26Fri
nonstopSpirit Airlines
3h 01mSJU-RSW
$118
4/24Wed
nonstopSpirit Airlines
2h 35mRSW-SJU
5/1Wed
nonstopSpirit Airlines
2h 59mSJU-RSW
$119
4/17Wed
1 stopDelta
6h 44mRSW-SJU
4/25Thu
1 stopDelta
9h 59mSJU-RSW
$304
4/12Fri
2 stopsAmerican Airlines
17h 52mRSW-SJU
4/14Sun
2 stopsAmerican Airlines
19h 07mSJU-RSW
$311
4/11Thu
1 stopUnited Airlines
11h 38mRSW-SJU
4/14Sun
1 stopUnited Airlines
12h 20mSJU-RSW
$324
4/17Wed
2 stopsAmerican Airlines
10h 35mRSW-SJU
4/25Thu
2 stopsAmerican Airlines
8h 56mSJU-RSW
$361
4/8Mon
1 stopDelta
6h 31mRSW-NAS
4/12Fri
1 stopDelta
5h 27mNAS-RSW
$421
5/11Sat
1 stopJetBlue
13h 30mRSW-NAS
5/18Sat
1 stopJetBlue
8h 29mNAS-RSW
$473
6/2Sun
1 stopUnited Airlines
7h 06mRSW-NAS
6/5Wed
1 stopUnited Airlines
6h 36mNAS-RSW
$491
5/22Wed
1 stopJetBlue
11h 42mRSW-SDQ
5/26Sun
1 stopJetBlue
16h 09mSDQ-RSW
$673

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Recent one-way flight deals

4/12Fri
nonstopSpirit Airlines
2h 37mRSW-SJU
$51
4/22Mon
nonstopSpirit Airlines
2h 33mRSW-SJU
$58
4/12Fri
1 stopAmerican Airlines
18h 35mRSW-SJU
$115
4/24Wed
2 stops
19h 10mRSW-SJU
$117
4/10Wed
2 stopsFrontier
15h 50mRSW-SJU
$132
4/10Wed
2 stopsFrontier
15h 50mRSW-SJU
$133
5/1Wed
3 stops
12h 42mRSW-SJU
$134
4/10Wed
1 stopAmerican Airlines
11h 05mRSW-SJU
$156
4/21Sun
1 stopDelta
6h 15mRSW-NAS
$251
6/15Sat
1 stopDelta
7h 44mRSW-SJU
$297

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Last minute flights from Fort Myers to Caribbean Islands

Last minute flight, train and bus deals

4/1Mon
nonstopSpirit Airlines
2h 38mRSW-SJU
4/3Wed
nonstopSpirit Airlines
2h 58mSJU-RSW
$285
4/3Wed
nonstop
2h 40mRSW-SJU
4/6Sat
multi-stop
30h 41mSJU-RSW
$318
4/3Wed
multi-stopAmerican Airlines
8h 23mRSW-AUA
4/10Wed
multi-stopAmerican Airlines
10h 11mAUA-RSW
$540
4/1Mon
multi-stopAmerican Airlines
6h 33mRSW-MBJ
4/3Wed
multi-stopAmerican Airlines
7h 20mMBJ-RSW
$739
4/3Wed
multi-stopDelta
12h 20mRSW-SDQ
4/7Sun
multi-stopDelta
15h 13mSDQ-RSW
$840
4/3Wed
multi-stopDelta
17h 10mRSW-SDQ
4/7Sun
multi-stopDelta
15h 13mSDQ-RSW
$845
3/29Fri
multi-stopUnited Airlines
26h 34mRSW-NAS
4/1Mon
multi-stopUnited Airlines
8h 42mNAS-RSW
$863
4/3Wed
multi-stopJetBlue
11h 38mRSW-SDQ
4/6Sat
multi-stopJetBlue
10h 33mSDQ-RSW
$914
4/1Mon
multi-stopUnited Airlines
25h 28mRSW-PUJ
4/6Sat
multi-stopUnited Airlines
27h 49mPUJ-RSW
$958
4/1Mon
multi-stopJetBlue
11h 38mRSW-SDQ
4/2Tue
multi-stopJetBlue
10h 33mSDQ-RSW
$1,335

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Fort Myers - Caribbean Islands Flights

Departure:

Fort Myers (RSW)United States

Return flight deals:

Caribbean Islands - Fort Myers

Cabin classes:

$588
$681
$381
$39