$78 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 2/20. 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 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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Flight Deals

Cheap Flights from Fort Myers to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$326
Santo Domingo
Santo Domingo1 stop$365
Montego Bay
Montego Bay1 stop$354
Oranjestad
Oranjestad1 stop$401
Nassau
Nassau1 stop$463
Kingston
Kingston1 stop$593
Simpson Bay
Simpson Bay2 stops$482
Port of Spain
Port of Spain1 stop$555
Bridgetown
Bridgetown1 stop$686
George Town
George Town2 stops$526
Puerto Plata
Puerto Plata1 stop$646
Aguadilla
Aguadilla1 stop$664
Punta Cana
Punta Cana1 stop$326
Santo Domingo
Santo Domingo1 stop$365
Montego Bay
Montego Bay1 stop$354
Oranjestad
Oranjestad1 stop$401
Nassau
Nassau1 stop$463
Kingston
Kingston1 stop$593
Simpson Bay
Simpson Bay2 stops$482
Port of Spain
Port of Spain1 stop$555
Bridgetown
Bridgetown1 stop$686
George Town
George Town2 stops$526
Puerto Plata
Puerto Plata1 stop$646
Aguadilla
Aguadilla1 stop$664

Book Cheap Fort Myers 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 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, Apr 16 - Sun, Apr 19
Frontier Logo
11:40 am - 12:29 am
RSW
-
SJU
12h 49m
1 stop
Frontier Logo
1:59 am - 10:45 am
SJU
-
RSW
8h 46m
1 stop
$182Frontier
Mon, Feb 23 - Fri, Feb 27
Frontier Logo
9:31 pm - 12:45 pm
RSW
-
SJU
14h 14m
1 stop
Frontier Logo
2:54 am - 8:36 pm
SJU
-
RSW
18h 42m
1 stop
$189Frontier
Sun, Apr 26 - Fri, May 1
Southwest Logo
6:40 am - 1:10 pm
RSW
-
STT
6h 30m
1 stop
Southwest Logo
2:30 pm - 9:45 pm
STT
-
RSW
7h 15m
1 stop
$313Southwest
Sun, Apr 26 - Fri, May 1
Southwest Logo
6:40 am - 1:10 pm
RSW
-
STT
6h 30m
1 stop
Southwest Logo
2:30 pm - 9:45 am
STT
-
RSW
19h 15m
2 stops
$342Southwest
Sun, Feb 15 - Thu, Feb 19
Delta Logo
5:35 am - 12:40 pm
RSW
-
STT
6h 05m
1 stop
Delta Logo
3:10 pm - 12:33 am
STT
-
RSW
10h 23m
1 stop
$470Delta
Thu, May 28 - Sun, May 31
JetBlue Logo
6:25 am - 9:25 am
RSW
-
SDQ
27h 00m
2 stops
JetBlue Logo
8:59 pm - 11:22 am
SDQ
-
RSW
14h 23m
1 stop
$473JetBlue
Tue, Mar 3 - Tue, Mar 10
JetBlue Logo
8:52 pm - 10:56 am
RSW
-
NAS
14h 04m
1 stop
JetBlue Logo
1:42 pm - 11:52 pm
NAS
-
RSW
10h 10m
1 stop
$486JetBlue
Sun, Apr 26 - Fri, May 1
American Airlines Logo
7:41 pm - 4:15 pm
RSW
-
STT
20h 34m
2 stops
American Airlines Logo
12:25 pm - 9:36 am
STT
-
RSW
21h 11m
2 stops
$500American Airlines
Fri, May 8 - Thu, May 14
Delta Logo
8:10 am - 3:54 pm
RSW
-
NAS
7h 44m
1 stop
Delta Logo
5:08 pm - 11:02 pm
NAS
-
RSW
5h 54m
1 stop
$513Delta
Mon, Mar 2 - Mon, Mar 9
American Airlines Logo
6:00 am - 1:58 pm
RSW
-
NAS
7h 58m
1 stop
American Airlines Logo
2:58 pm - 8:42 pm
NAS
-
RSW
5h 44m
1 stop
$539American Airlines
Booking Insights

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.

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 $330, 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 $314 (return) on average. On the other hand, the most expensive months are July and November, when the average cost of round-trip tickets is $524 and $516 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 1 week before departure. For the absolute cheapest price, our data suggests you should book 24 weeks before departure.

Good to know

Low seasonOctober
Cheapest flight$78
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly and prices are also 9% lower on average.
Flight from Fort Myers to Nassau

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 afternoon, which is peak travel time and where the average cost of a ticket is $170.

Reviews of the top 4 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 4273 reviews
8.6Crew
8.1Boarding
7.5Entertainment
7.0Food
8.0Comfort
Airline reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

10.0 ExcellentAnonymous, Jan 2026
PHX - MDW
Read more Southwest reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Everything went smoothly and we even arrived a little bit early.

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.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

If we are going to have to pay for luggage, make it easier to do. Put something on the app during check-in so I don't need to do it at the kiosk. I've done it twice recently and I ended up having to pay at the desk because something went wrong at the kiosk in Tampa.

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

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.

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Connection through Atlanta was difficult. Mechanical issue on plane caused a two hour delay. New gate was a mile away.

No WiFi. Comfort plus should have alcohol provided, crew only offered water or tea. Who the heck wants tea?

I have diamond medallion status and usually we are in comfort plus . We were in main this time ( which was fine ) and my husband wanted wine . I have at least 10 vouchers for drinks that are good for this year and next! The attendant would not take the picture of the voucher as proof and never came back to check as She asked me to pull it up on delta Wi-Fi. Instead my husband just used his Amex to buy the wine . Disappointing!!!

Food is basically Sun Chips, cookies or Cheezits. I had an exit row seat so I had plenty of room. The crew was very nice and efficient. Pilot kept us informed. Pretty good flight.

The only thing nice I can say is the flight crew was really nice and apologetic about the situation. They shared as much information as they had and advised us on what we could do about missing connecting flights. The boarding process was so slow. The gate agent was working by herself and should have had someone working with her. It took almost an hour to board because she was trying to board a full flight of people and provide customer service to everyone who was flying standby and/or had questions. It was really chaotic. This didn't help the fact that we were delayed and folks were missing connections the longer it took.

The food is terrible. The staff is wonderful. Comfort is good.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

Getting to the flight was arduous and lengthy. The flight itself was good but the food option wasn’t a good selection. I need to do a Kosher option on my return. Flight crew were nice

We had a lot of really rough weather but that was not Delta's fault. Pilot was amazing.

On time on a day with lots of weather cancellations on other flights. Thank you for getting me home during a winter storm!

Don't change gate multiple times make people run across the airport. Announce delays in a timely manner. Have maintenance crew ready. Don't delay and keep passengers on the plane for 3 hrs. on tarmac.

The attendants were kind and helpful. A sugar-free drink would have been very welcome.

Little warm on the plane and delayed for an hour

UGH I HAD TO MISS MY FIRST FLIGHT TO TAMPA CAUSE OF THE 10 MINUTE DELAY OF THE ORLANDO TO MIAMI ONE SO THEY HAD ME GET ANOTHER TICKET. I AM NOT HAPPY AT ALL BECAUSE IT MADE ME MISS MY CONNECTING FLIGHT FROM TAMPA TO LONDON AND FORCED ME TO MISS A DAY AT MY ROOM IN THE UK.

Wish they didnt delay off-boarding for 10 minutes so i could connect to my flight from miami to tampa

It was fine. My connection in Charlotte to go to WPB was too late and I had to spend the night in the Charlotte Airport in the mini suites.

Boarding was organized and timely. Food was mediocre, especially for first class travel.

We were 4+ hours delayed. AA is absolutely obnoxious. They just kept pushing back the time to the point where we did not get into Vegas until after midnight when we were supposed to arrive like 845pm.

My last flight on 25 Dec, it’s Christmas Day, everyone happy and very good mood. I really enjoy traveling with Americans Airlines from Miami to Minneapolis my home town after long flight from lhe to Doha then Miami. Thank you again to make my travels comfortable and relaxed. Best regards

Horribly rude check in at airport, worst in 25 years of flying. All over a simple issue they could have googled to resolve.

1) No pilot available for 1 hour 2) no room for most passengers careyon in overhead—-> stowed below 3) when we landed we had to wait 45 min. Before docking at gate as gate was not ready

Good. No issues except a slight delay. Crew came in late.

The flight was two hours late due to a computer fault and resulting maintenance. Nothing was offered as compensation beyond bottles of water during the time we were deplaned and waiting in the terminal.

There was a fowl odour coming from the lavatory the entire flight

very difficult boarding process - aggressive passengers not the friendliest crew

WiFi was not eorkig (again) And the plane was from 1990 with the screens which were.not touch and most didn’t even work and if lucky could tune in tv

It was great. I had never flown on JetBlue before, but would be very happy to fly with them in the future.

The captain gave good announcements and the flight attendants were friendly. The WiFi was pretty good. The plane itself looked very old inside and the seats were very uncomfortable. The screens in the seat backs were the smallest I’ve ever seen. There were so many loud and obnoxious kids on this flight and the parents didn’t do much to try to quiet them down. Some had videos and games on tablets with higher than necessary volume going the whole time.

Spend hours delayed with no food, water anything sitting on the aieplane with no ability to eat or use the restroom. My entire experience was the absolute worst. I will never fly jet Blue again.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports