$139 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 5/22. 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.
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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$482
Santo Domingo
Santo Domingo1 stop$470
Montego Bay
Montego Bay1 stop$443
Oranjestad
Oranjestad1 stop$469
Nassau
Nassau1 stop$395
Kingston
Kingston1 stop$658
Simpson Bay
Simpson Bay2 stops$567
Port of Spain
Port of Spain1 stop$535
George Town
George Town1 stop$603
Puerto Plata
Puerto Plata1 stop$524
Aguadilla
Aguadilla1 stop$668
Punta Cana
Punta Cana1 stop$482
Santo Domingo
Santo Domingo1 stop$470
Montego Bay
Montego Bay1 stop$443
Oranjestad
Oranjestad1 stop$469
Nassau
Nassau1 stop$395
Kingston
Kingston1 stop$658
Simpson Bay
Simpson Bay2 stops$567
Port of Spain
Port of Spain1 stop$535
George Town
George Town1 stop$603
Puerto Plata
Puerto Plata1 stop$524
Aguadilla
Aguadilla1 stop$668

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.

Recent round-trip flight deals from Fort Myers to Caribbean Islands

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Fort Myers to Caribbean Islands.
Discover the best prices for you by selecting your travel dates on KAYAK.
 Logo
2:44 pm - 12:44 amRSW-SJU
10h 00m1 stop
 Logo
6:09 am - 4:13 pmSJU-RSW
10h 04m1 stop
Thu, May 22 - Thu, May 29
Frontier Logo
3:27 pm - 12:44 amRSW-SJU
9h 17m1 stop
Frontier Logo
8:00 am - 6:00 pmSJU-RSW
10h 00m1 stop
$273Frontier
Find Deal
Fri, Jun 6 - Sat, Jun 7
American Airlines Logo
6:27 am - 4:20 pmRSW-SJU
9h 53m2 stops
American Airlines Logo
3:55 pm - 12:12 amSJU-RSW
8h 17m1 stop
$345American Airlines
Find Deal
Tue, Sep 9 - Fri, Sep 12
JetBlue Logo
1:15 pm - 12:54 amRSW-SJU
11h 39m1 stop
JetBlue Logo
3:23 am - 12:06 pmSJU-RSW
8h 43m1 stop
$352JetBlue
Find Deal
Sat, Jun 14 - Fri, Jun 20
United Airlines Logo
1:30 pm - 9:24 pmRSW-SJU
7h 54m1 stop
United Airlines Logo
1:25 pm - 11:44 pmSJU-RSW
10h 19m1 stop
$357United Airlines
Find Deal
Sat, May 31 - Wed, Jun 4
American Airlines Logo
8:27 am - 8:10 pmRSW-SJU
11h 43m2 stops
American Airlines Logo
5:27 pm - 10:50 amSJU-RSW
17h 23m2 stops
$365American Airlines
Find Deal
Tue, Oct 7 - Fri, Oct 10
United Airlines Logo
6:00 am - 1:45 pmRSW-SJU
7h 45m1 stop
United Airlines Logo
1:25 pm - 11:58 pmSJU-RSW
10h 33m1 stop
$375United Airlines
Find Deal
Tue, Jun 3 - Sat, Jun 7
Delta Logo
6:50 am - 4:18 pmRSW-SJU
9h 28m1 stop
Delta Logo
2:28 pm - 12:35 amSJU-RSW
10h 07m1 stop
$384Delta
Find Deal
Tue, Oct 7 - Fri, Oct 10
JetBlue Logo
1:15 pm - 12:54 amRSW-SJU
11h 39m1 stop
JetBlue Logo
3:23 am - 12:06 pmSJU-RSW
8h 43m1 stop
$390JetBlue
Find Deal
Sat, Jun 14 - Fri, Jun 20
Delta Logo
5:35 am - 11:58 amRSW-NAS
6h 23m1 stop
Delta Logo
2:36 pm - 11:00 pmNAS-RSW
8h 24m1 stop
$395Delta
Find Deal
Sat, Oct 25 - Thu, Oct 30
Useful Info

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.

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 May, when tickets cost $169 (return) on average. On the other hand, the most expensive months are February and December, when the average cost of round-trip tickets is $527 and $455 respectively.

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

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

For Fort Myers to Caribbean Islands, Tuesday is the cheapest day to fly on average and Friday is the most expensive. Flying from Caribbean Islands back to Fort Myers, the best deals are generally found on Wednesday, with Thursday being the most expensive.

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 26 weeks before departure.


Good to know

Low seasonAugust
High seasonJune
Cheapest flight$139
Best time to beat the crowds with an average 0% drop in price.
Most popular time to fly with an average 17% increase in price.
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. Morning departures are around 1% more expensive than evening flights, 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.

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 4294 reviews
8.0Comfort
8.2Boarding
7.6Entertainment
7.1Food
8.6Crew
Airline reviews

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.

6.0 GoodJennifer, Apr 2025FLL - RDU
Read more Southwest reviews

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.

The flight was delayed about 20 minutes, but this was an evening flight, so it comes as no surprise. This flight came a good 1.5 days ahead of hurricane Helene which was still far out in the gulf. However, the flight never removed the seated buckle light. The staff announced from the beginning that due to the bad weather (I suppose the hurricane a day and a half away) they would have to do an abbreviated service with water and a snack. I am fine with their water and snack offering, but this was one of the smoothest flights I've had in years. If Southwest believes a flight like this requires everyone to remain seated, then all of their flights should remain buckled for the entire flight. I cannot help but wonder if things like this are a sneaky way to cut back on expenses since the airline is currently under a lot of pressure to reduce costs.

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.

Good and consistent Printer in lounge did not work for me :(

Everything is good except the dinner and breakfast. The sandwich is very delicious. Toilet is clean, I only use one of them. Flight attendants are very nice. 👍👍

A bit rush for transit. Food and entertainment are not available

Boarding was a little difficult. The gate area at O'Hare was very small and crowded due to multiple gates in the area. Could not hear the intercom, so had to rely on signage to see when my group was boarding and the signage was blocked by passengers standing in the gate. Flight was great and we arrived in Montreal on time.

Multiple delays and not straight answer from the United team

For economy, it was very good. Staff was great, they even let some of us change seats for more leg room... Put an empty seat between us which was fantastic for a 12hr flight. Onboard entertainment was excellent, I think over 200 choices of movies/tv/etc The bad was the barely/nonfunctional wifi that cost either $16.99 or 1700 miles (full flight). It was atrocious... Definitely the worst of the last 3 long haul major airlines I was on the last few months.

Stewardess spilled orange juice on my clothes/seat no help no apology just threw napkins at me to clean the mess up. Not Happy.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

The plane pushed back from the gate on time. However, it stopped on the ramp, and we waited for over 20 minutes before the aircraft pulled back to the gate. Apparently, something of importance had to be removed from the aircraft by the gate agent. I found this to be odd. The delay was not significant, but I felt that whatever was on the aircraft that had to be taken off, should’ve been done before we pushed back from the gate.

I didn’t get on plane. Passport being processed by consulate with visa application. Tried to cancel through underpricer after purchasing cacelling for any reason. No dice, they are thieves.

Food and flight attendents with positive dispositions and friendly behavior, more professional attitudes

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.

They delayed our flight by 45 minutes and then re-updated the departure time back to normal schedule with no notification, email, or app update causing probably 40 people to miss the flight as they left without us.

terrible. Because I felt very unwell during the flight. How do they leave a woman alone in the middle of 2 men? an obese man who was falling on top of me.

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.

Nice modern plane. Can use your own device for entertainment. Get a snack on the plane.

Flight was late and missed connecting flight. They could have better accommodated, but instead did an overnight and had to arrive the next afternoon.

The boarding crew was incredibly helpful getting me on an earlier flight

They have lost any customer service care and support. Terrible airline now and been for awhile.

The flight was delayed leaving Miami. When we arrived in Charlotte, we were unable to park at our scheduled gate. We had to wait another 30-45 minutes before we could park at a different gate. All in all, we were delayed by almost two hours arriving in Charlotte.

the pilot that landed this flight in Philadelphia did an amazing job, the weather was absolutely terrible and we landed safely.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

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