$97 Find Cheap Flights from Fort Myers 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 Fort Myers to Caribbean Islands departing on 6/26. 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 Fort Myers 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 Fort Myers to Caribbean Islands, as well as popular online travel agencies
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Best Caribbean Islands Flight Deals from Fort Myers

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$386
Santo Domingo
Santo Domingo2 stops$479
Montego Bay
Montego Bay3 stops$479
Oranjestad
Oranjestad1 stop$499
Nassau
Nassau1 stop$380
Kingston
Kingston2 stops$548
Simpson Bay
Simpson Bay1 stop$684
Port of Spain
Port of Spain1 stop$526
Bridgetown
Bridgetown1 stop$505
George Town
George Town1 stop$528
Puerto Plata
Puerto Plata2 stops$544
Aguadilla
Aguadilla2 stops$603
Punta Cana
Punta Cana1 stop$386
Santo Domingo
Santo Domingo2 stops$479
Montego Bay
Montego Bay3 stops$479
Oranjestad
Oranjestad1 stop$499
Nassau
Nassau1 stop$380
Kingston
Kingston2 stops$548
Simpson Bay
Simpson Bay1 stop$684
Port of Spain
Port of Spain1 stop$526
Bridgetown
Bridgetown1 stop$505
George Town
George Town1 stop$528
Puerto Plata
Puerto Plata2 stops$544
Aguadilla
Aguadilla2 stops$603

Cheap Flights from Fort Myers to Caribbean Islands

 
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 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 Fort Myers to Caribbean Islands

Thu, Jun 26 - Tue, Jul 1
Frontier Logo
2:38 pm - 12:44 amRSW-SJU
10h 06m1 stop
Frontier Logo
8:00 am - 4:38 pmSJU-RSW
8h 38m1 stop
$183Frontier
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Fri, Aug 15 - Sat, Aug 23
Frontier Logo
2:07 pm - 12:28 pmRSW-SJU
22h 21m1 stop
Frontier Logo
1:09 pm - 10:20 amSJU-RSW
21h 11m1 stop
$189Frontier
Find Deal
Sat, Nov 8 - Sun, Nov 9
JetBlue Logo
10:20 am - 11:00 pmRSW-SJU
11h 40m1 stop
JetBlue Logo
1:59 am - 9:20 amSJU-RSW
8h 21m1 stop
$345JetBlue
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Mon, Sep 8 - Sat, Sep 13
JetBlue Logo
3:40 pm - 12:57 amRSW-SJU
9h 17m1 stop
JetBlue Logo
6:00 am - 6:05 pmSJU-RSW
12h 05m1 stop
$363JetBlue
Find Deal
Sun, Sep 14 - Fri, Sep 19
Delta Logo
5:35 am - 1:11 pmRSW-NAS
7h 36m1 stop
Delta Logo
1:19 pm - 6:52 pmNAS-RSW
5h 33m1 stop
$380Delta
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Sat, Dec 6 - Sat, Jan 10
American Airlines Logo
5:44 pm - 11:40 amRSW-SJU
16h 56m1 stop
American Airlines Logo
9:25 am - 8:06 pmSJU-RSW
11h 41m1 stop
$390American Airlines
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Mon, Oct 20 - Fri, Oct 24
Delta Logo
5:35 am - 11:58 amRSW-NAS
6h 23m1 stop
Delta Logo
2:36 pm - 9:16 pmNAS-RSW
6h 40m1 stop
$403Delta
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Sat, Nov 8 - Mon, Nov 10
American Airlines Logo
1:45 pm - 2:10 amRSW-SJU
11h 25m2 stops
American Airlines Logo
2:30 pm - 10:16 pmSJU-RSW
8h 46m1 stop
$436American Airlines
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Sat, Dec 6 - Sat, Dec 13
United Airlines Logo
1:45 pm - 2:00 pmRSW-MBJ
24h 15m1 stop
United Airlines Logo
3:20 pm - 11:19 pmMBJ-RSW
7h 59m1 stop
$492United Airlines
Find Deal
Tue, Jul 8 - Tue, Jul 15
United Airlines Logo
6:00 am - 4:40 pmRSW-AUA
10h 40m1 stop
United Airlines Logo
4:30 pm - 10:58 amAUA-RSW
18h 28m1 stop
$549United Airlines
Find Deal
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KAYAK's insights & trends for Fort Myers to Caribbean Islands flights

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

What is the cheapest Fort Myers to Caribbean Islands flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Fort Myers to Caribbean Islands.

The cheapest ticket to Caribbean Islands from Fort Myers found in the last 72 hours was to San Juan, at $290 round-trip. The most popular route is from Fort Myers (RSW) to San Juan Luis Munoz Marin Intl Airport (SJU), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $290.

Can I save money by flying with a layover from Fort Myers 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 $694, prices are generally cheapest when you fly direct.

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

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 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 Fort Myers to Caribbean Islands is June, when tickets cost $211 (return) on average. On the other hand, the most expensive months are February and April, when the average cost of round-trip tickets is $503 and $475 respectively.

How far in advance should I book a flight from Fort Myers 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 Fort Myers 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 Fort Myers to Caribbean Islands, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 8 weeks before departure.


Good to know

Low seasonAugust
High seasonMarch
Cheapest flight$97
Best time to beat the crowds but there is an average 1% increase in price.
Most popular time to fly and prices are also 9% 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 from Fort Myers 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 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 from Fort Myers 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 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 from Fort Myers 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 $119 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 $187.

Top 5 airlines serving from Fort Myers to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from Fort Myers 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 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 verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4287 reviews
8.2Boarding
8.0Comfort
7.6Entertainment
7.1Food
8.6Crew
Airline reviews

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

6.0 GoodDavid, Jun 2025BWI - COS
Read more Southwest reviews

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

WiFi on the flight was not working. Thus, entertainment options were limited.

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

Crew was great flight was great baggage claim was a failure. It took over 1 hour for bags to arrive. Poor communication poor effort when I spoke to the supervisor about the delay

Planes are aged. The wifi is unreliable and on many fights, no-existent. The flight attendants were very good.

I had a wonderful flight, but the only thing that annoyed me was how crowded TSA was. I still believe airports and all planes work together to bunch everyone together to drive up cost.

Easy to book and to get check in and get on and off.

Everything worked well. Crew was as entertaining as is possible on a plane flight. Southwest still has good legroom:

Glad flight made it out. So many delays due to hurricane. everyone did a great job.

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

Friendly flight attendants, smooth 8-9 hours flight. Economy seats are small and uncomfortable as usual.

The young man who was our flight attendant in first class was lazy and did not do his job well at all. Never offered drinks upon boarding - actually I take that back... said "are you okay with water" as if I do not want to get you anything else, only passed the snacks around once, got my drink order wrong and then never offered a second round of drinks. He was the worst I have ever seen on Delta and we fly a lot.

Flight left early and arrived early. the whole trip was excellent.

Newer plane, relatively easy boarding, not a full flight and was told that we could not be moved up because of weight and balance issues. Otherwise, a very good experience.

Everything was great. Great service, excellent communication, and early arrival

I sat in comfort plus. It was fine. Seats were comfortable. I got drinks and snacks.

it was so bad. I tried to board my flight from vancouver to saskatoon. And to my surprise they did not board me cause the flight was changed and no email was send to me. and on my boarding pass which i got from seattle says different flight. I did not knew anyone from Vancouver, air canada crew was rude, i asked for today flight but they were rude and i had early morning dental appointment in saskatoon. I was so much in pain and my whole day is wasted today. and i suffered alot. They did provide me hotel but they did not provide me any food. I am really really disappointed first time had so bad experience with air canada. I may think twice to book it again. If i can get any reply or any composition that would be great. Thanks

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

Terrible. Out flight was delayed for 21 (twenty one) hours. United is a joke.

Boarding was mayhem. Late boarding by 15 minutes because of lack of staff (missing 1 flight attendant. We had to wait for an arrival of another plane before we could board). Flight was a little rough, but cannot blame on airlines.

Impressed with the service despite turbulence because of the weather. Both flights arrived before their scheduled times.

Very comfortable (upgraded to business class). The audio on my screen didn’t work, but I managed to play the audio through my phone while watching the screen.

The food was the worst I’ve had on any flight I’ve ever been on.

Great experience…left a bit behind schedule but made up fir that in the air and landed 10 minutes early 😁

I was supposed to be on business class at first class from Denver back to Miami due to weather changes. I missed my connection and it’s put on a flight to Fort Lauderdale. Instead of honoring my business class/1st class ticket, they put me in coach, but there were two first class seats open. I think it’s absolutely disgusting that I paid for first class $1300 ticket and they put me in economy and they had to open seats available and I have still not been refunded the difference. I ended up having to eat a snack box instead of the meal I was supposed to get and did not get home till 2 AM so I think that’s a little pathetic that I had to live off crackers for dinner And my poor dog ate some cheese and salami. Oh yes, apparently when they switched me to the new flight they forgot to mention I had a service dog

Excellent service despite turbulence during the flight. Flight attendants were remarkable!

Flight was delayed several 3 hours - no reason was given and no communication what so ever.

No overhead baggage room even though I was seated in row 2. Consequently had to check in my carry on bag. Baggage carousel was jammed. Took 45 min to get my bag.

Cancelled flight with no specific instructions to get a boarding pass for another flight. The whole flight of people were in line for an hour because there was only 1 person to help at the desk. This was unusual for JetBlue.

Except for the 28 minute delay leaving and the earlier reschedule to a later takeoff time the flight was good.

Loved the leg room and tvs screens on the seats and free WiFi. Wish the price was lower and could save by rebooking

The flight was delayed for 4 hours. Once onboard the crew was wonderful.

Very well organized both boarding and deplaning. Very satisfied with the service I received.

I rate it is good we had a 4-hour travel delay at one point but JetBlue gave out food vouchers and travel points credits for another flight so they try to make up for it

Flight was on time arrived at the destination 10min early they kept in touch via email

My encounter with the entertainment services provided on board was moderate; the functionality of the Wi-Fi connection was either sluggish or nonoperational, while the display screens were antiquated and suffered from poor visibility. On the positive side, the cabin exuded a sense of expansiveness, and the crew exhibited amiable and accommodating behavior throughout the journey.

It was one of my worst flight ever. First they were changing the gate for at least 4 times, changing from gate D7 to D12 to D44. Considering the size of the Miami Airport, we are talking about long distance and the train at the airport was not working. Then the flight was delayed around one hour. Then finally we boarded into the plane and when everybody was seated, there was an announcement that there is an issue with one of the tire of the plane, so we all had to get out of the plane with our belongings, to replace the tire. So we had around 2.5-hour delay

No entertainment yatem in flight at seat 51H. Would not shut down either leaving a self moving and openin and changing menus with changes in colors,images brightness levels sort of the type when you get sleep deprivation and image overload when being tortured during an interrogation. 8 hours worth of it. Unable to place backpack underneath seat on that chair. One female stewardess was excellent as she gave up her carryon's space for my backpack but the rest of the iberia crew were very sharp an chtting during the whole flight. The plane did not have hot water so nobody had coffee nor tea. The plane was not up to par to be flying.

I was late from Jacksonville, FL but the limited interaction I had with the Philly crew was great.

The delays and cancellations kept me stuck in Miami for an additional 24 hours, and the whole thing seemed extremely disorganized

The chicken adobo was a little too spicy but good otherwise. My personal opinion. Movie selection could be improved, too many horror movies. Could add a few more chick flicks! The flight was bumpy at times. We arrived a little early too! Flight attendants friendly.

really bad they refused to check in luggages that I had purchased, even showing them the transaction receipt from british airways app the staff in miami was MEDIOCRE

The flight to Tokyo AA61 took off about two hours late, but then had to turn back. By that time the crew had to be replaced. Then they kept promising to take off in an hour, then in 3, then switch to the next day.

Uncomfortable seats and flight attendant was rude as she insisted on waking up my husband to ask him if he wanted a drink. When he said that he was sleeping, she replied “without an attitude “. He was seated at 8c

No food/snack served during the flight. Crew wasn’t interested at all. Flew American First but flying low cost with Ryanair is even better

Crew professional. Easy bag drop off. On time. Good entertainment.

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