$102 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 1/21. 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 Cana2 stops$434
Santo Domingo
Santo Domingo1 stop$444
Montego Bay
Montego Bay2 stops$479
Oranjestad
Oranjestad1 stop$402
Nassau
Nassau1 stop$447
Kingston
Kingston1 stop$587
Simpson Bay
Simpson Bay1 stop$513
Port of Spain
Port of Spain2 stops$758
Bridgetown
Bridgetown1 stop$537
George Town
George Town2 stops$457
Puerto Plata
Puerto Plata1 stop$518
Aguadilla
Aguadilla2 stops$370
Punta Cana
Punta Cana2 stops$434
Santo Domingo
Santo Domingo1 stop$444
Montego Bay
Montego Bay2 stops$479
Oranjestad
Oranjestad1 stop$402
Nassau
Nassau1 stop$447
Kingston
Kingston1 stop$587
Simpson Bay
Simpson Bay1 stop$513
Port of Spain
Port of Spain2 stops$758
Bridgetown
Bridgetown1 stop$537
George Town
George Town2 stops$457
Puerto Plata
Puerto Plata1 stop$518
Aguadilla
Aguadilla2 stops$370

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

Sat, Dec 6 - Sat, Dec 13
Multiple Airlines Logo
12:22 pm - 12:49 amRSW-SJU
11h 27m1 stop
Multiple Airlines Logo
7:07 pm - 12:20 pmSJU-RSW
18h 13m1 stop
$239Multiple Airlines
Find Deal
Sat, Dec 6 - Sat, Dec 13
Spirit Airlines Logo
8:29 pm - 11:25 pmRSW-SJU
25h 56m2 stops
Spirit Airlines Logo
7:07 pm - 12:20 pmSJU-RSW
18h 13m1 stop
$272Spirit Airlines
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Sat, Dec 6 - Fri, Dec 12
Frontier Logo
12:22 pm - 12:49 amRSW-SJU
11h 27m1 stop
Frontier Logo
1:59 am - 11:27 amSJU-RSW
10h 28m1 stop
$274Frontier
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Sat, Dec 6 - Fri, Jan 9
Frontier Logo
12:22 pm - 12:49 amRSW-SJU
11h 27m1 stop
Frontier Logo
2:29 am - 10:38 amSJU-RSW
9h 09m1 stop
$304Frontier
Find Deal
Mon, Jan 12 - Sat, Jan 17
Delta Logo
3:00 pm - 11:44 pmRSW-SJU
7h 44m1 stop
Delta Logo
6:30 pm - 12:13 amSJU-RSW
6h 43m1 stop
$313Delta
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Mon, Jan 12 - Sat, Jan 17
Southwest Logo
10:30 am - 8:55 pmRSW-SJU
9h 25m2 stops
Southwest Logo
5:30 am - 11:25 amSJU-RSW
6h 55m1 stop
$359Southwest
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Mon, Dec 15 - Fri, Dec 19
Southwest Logo
5:10 pm - 12:35 amRSW-SJU
6h 25m1 stop
Southwest Logo
6:35 am - 2:30 pmSJU-RSW
8h 55m1 stop
$405Southwest
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Wed, Jan 7 - Sun, Jan 11
Delta Logo
5:35 am - 1:04 pmRSW-SJU
6h 29m1 stop
Delta Logo
6:15 am - 1:55 pmSJU-RSW
8h 40m1 stop
$413Delta
Find Deal
Sun, Jan 11 - Sun, Jan 18
American Airlines Logo
6:00 am - 3:06 pmRSW-STT
8h 06m1 stop
American Airlines Logo
4:12 pm - 11:33 pmSTT-RSW
8h 21m1 stop
$479American Airlines
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Mon, Mar 16 - Thu, Mar 19
American Airlines Logo
7:02 pm - 10:40 amRSW-PUJ
15h 38m2 stops
American Airlines Logo
5:05 pm - 10:49 amPUJ-RSW
17h 44m2 stops
$508American Airlines
Find Deal
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 June, when tickets cost $314 (return) on average. On the other hand, the most expensive months are November and October, when the average cost of round-trip tickets is $519 and $514 respectively.

How far in advance should I book a flight from Fort Myers to Caribbean?

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, 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, you should book around 2 weeks before departure, which saves you about 8% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 8 weeks before departure.

Good to know

Low seasonOctober
Cheapest flight$102
Best time to beat the crowds with an average 1% drop in price.
Most popular time to fly and prices are also 13% 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.

  • What is the cheapest time of day to fly to Caribbean?

    The cheapest time of day to fly to Caribbean is generally at night, when round-trip flights cost $119 on average. The most expensive time of day to fly to Caribbean is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $170.

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 4240 reviews
7.5Entertainment
8.0Comfort
8.1Boarding
8.6Crew
7.0Food
Airline reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

8.0 ExcellentGreg, Oct 2025OAK - BUR
Read more Southwest reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

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.

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.

Non stop on long haul is the way to go. Great experience

The boarding process needs to be refined. Sometimes the gate crew call out the boarding zone, and then flip to the monitor to show which zones are boarding. So unless everyone is gathered around to see the monitor there is usually confusion as wi which zones are boarding.

Passengers need to check in big baggage instead of bringing on the plane. That cause inconvenience for everyone. Otherwise flight was good.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

Quick check in. Everything went smooth. I don't know what can be done about airline food.

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

Flight was an hour late, who knows why. It was OK, nothing outstanding.

Excellent check-in. Crew was good. Excellent communication from flight deck.

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.

My flight was delayed for 17hs because the pilot forgot his passport!!! What a joke. AA used to be a great airline, now I have to think twice before flying with them again.

We had 3 flights. 1 & 2 were on the same plane but we had to de-board just to re-board 30 mins later. That may have been due to a crew change though. Our 3rd flight had a couple “maintenance” issues that held us up. They were quickly resolved but it took forever for someone to bring the paperwork needed so we could leave. Apparently there was a computer glitch so a driver had to bring a physical copy. It delayed us about 1 1/2 hrs. The flights themselves were smooth & no problems. For boarding, I don’t know why they don’t start with the back of the plane & move forward. It would eliminate the back up from people trying to find their seats & put their bags in the overhead bins. Unless you’re on an overseas flight, there is no food, you get a beverage & either a small bag of pretzels or a biscuit cookie. Take your own food or snacks of you want something more.

Lost bag and 2 days no word leaving for cruise no clothes or stuff

We will be writing a long, detailed letter to corporate about our awful experience with American airlines.

Internet was a bit expensive and did not work ask that week otherwise a good flight

Food was ok, but not as good as I have had before on AA.

Pretty good. The food was just mediocre, the boarding and crew were good.

It was very difficult to stretch my knee out and I am very short. I also had a torn tendon in my knee which made it extra uncomfortable anyways. My husband is 6'2" and I can't imagine him flying in that plane.

The plane was broken so we had to change planes.

Food was terrible, all served at once, poor quality . Wine and bread offered only once.

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.

It would have been nice if they had offered more than one set of snacks

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.

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.

After boarding and un-boarding twice over 6+hours, the flight was canceled.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

Boarding in Orlando was not good. Giant mob at the gate, should have been lines.

My flight was delayed by two hours which made it so that I would miss my layover flight. I stood in line for customer service for over an hour and when I reached the agent she told me to scan a QR code and it'll give me options. I wasn't offered any help, guidance or compensation, only told that I have options but that I had to figure it all out myself. I was refunded part of the trip and had to buy an expensive same day ticket from another airline in order to get home. I will never fly Frontier again.

The confirmation # CK8GNW and my name was not recognized/in Frontier system. I was able to check in on Frintier app so i went to the Frontier ticket agent, at time they told me that my name/ confirmation did not show up as a purchased ticket. I had to purchase a new ticket that cost $289.00 one way.

Although an hour and a half early was told by staff at check in they had overbooked and could not check us in for the flight.

The crew was delayed because they came on another flight that was delayed due to weather 10pm flight left at 1.30 am The airline made no effort to align alternate crew

Worst airline experience. They were rude and kept changing our seats and/or giving our seats away so our family didn’t get to sit with each other. Almost everyone we dealt with at both airports with this airline was rude. The app kept giving us wrong information making things take longer. Dealing with them before TSA can take close to an hour…longer than I’ve ever had to deal with before. Never using this airline again.

Everything you need to know for your flight to Caribbean

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