$84 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 11/16. 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
Travelers love KAYAK
41 299 237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
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 Cana2 stops$422
Santo Domingo
Santo Domingo2 stops$440
Montego Bay
Montego Bay2 stops$519
Oranjestad
Oranjestad1 stop$465
Nassau
Nassau1 stop$432
Kingston
Kingston1 stop$496
Simpson Bay
Simpson Bay1 stop$457
Port of Spain
Port of Spain2 stops$758
Bridgetown
Bridgetown1 stop$537
George Town
George Town1 stop$479
Puerto Plata
Puerto Plata1 stop$518
Aguadilla
Aguadilla1 stop$509
Punta Cana
Punta Cana2 stops$422
Santo Domingo
Santo Domingo2 stops$440
Montego Bay
Montego Bay2 stops$519
Oranjestad
Oranjestad1 stop$465
Nassau
Nassau1 stop$432
Kingston
Kingston1 stop$496
Simpson Bay
Simpson Bay1 stop$457
Port of Spain
Port of Spain2 stops$758
Bridgetown
Bridgetown1 stop$537
George Town
George Town1 stop$479
Puerto Plata
Puerto Plata1 stop$518
Aguadilla
Aguadilla1 stop$509

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

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
$138Frontier
Find Deal
Fri, Dec 5 - Sun, Dec 7
Frontier Logo
12:32 pm - 12:49 amRSW-SJU
11h 17m1 stop
Frontier Logo
1:59 am - 11:37 amSJU-RSW
10h 38m1 stop
$168Frontier
Find Deal
Fri, Nov 14 - Tue, Nov 18
JetBlue Logo
6:13 am - 6:20 pmRSW-SJU
11h 07m1 stop
JetBlue Logo
12:30 pm - 8:44 pmSJU-RSW
9h 14m1 stop
$336JetBlue
Find Deal
Sat, Nov 15 - Tue, Nov 18
JetBlue Logo
6:13 am - 9:54 pmRSW-SJU
14h 41m1 stop
JetBlue Logo
12:30 pm - 8:44 pmSJU-RSW
9h 14m1 stop
$339JetBlue
Find Deal
Wed, Apr 22 - Wed, Apr 29
Southwest Logo
9:20 am - 9:05 pmRSW-SJU
11h 45m2 stops
Southwest Logo
5:05 am - 5:35 pmSJU-RSW
12h 30m1 stop
$359Southwest
Find Deal
Sun, Apr 26 - Sun, May 3
Southwest Logo
6:20 am - 4:30 pmRSW-SJU
10h 10m1 stop
Southwest Logo
5:00 am - 7:35 pmSJU-RSW
14h 35m1 stop
$365Southwest
Find Deal
Thu, Jan 8 - Mon, Jan 12
Delta Logo
5:35 am - 12:42 pmRSW-STT
6h 07m1 stop
Delta Logo
4:25 pm - 12:15 amSTT-RSW
8h 50m1 stop
$449Delta
Find Deal
Tue, Mar 3 - Wed, Mar 4
Delta Logo
5:35 am - 12:00 pmRSW-NAS
6h 25m1 stop
Delta Logo
6:10 pm - 12:37 amNAS-RSW
6h 27m1 stop
$475Delta
Find Deal
Thu, Jan 8 - Mon, Jan 12
American Airlines Logo
6:35 pm - 2:02 pmRSW-STT
18h 27m2 stops
American Airlines Logo
6:39 pm - 12:22 pmSTT-RSW
18h 43m2 stops
$479American Airlines
Find Deal
Fri, Jan 16 - Sun, Jan 18
American Airlines Logo
6:35 pm - 12:21 pmRSW-SDQ
16h 46m2 stops
American Airlines Logo
3:00 pm - 10:20 amSDQ-RSW
20h 20m2 stops
$497American Airlines
Find Deal
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 $298, 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 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 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, 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$84
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 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 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 4245 reviews
8.0Comfort
7.0Food
8.1Boarding
8.6Crew
7.5Entertainment
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.

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.

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

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.

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

The person I bought the ticket for didn’t make the flight.

Lately I like the planes have been exceptionally filthy. There’s lines of dust and dirt all across the ceiling in the vents, and the cracks in between the seats are literally full of food. It’s definitely not the quality of service that I was used to with United. I’m also very disappointed with the Wi-Fi! All I wanna do is knock out a few work jobs while I’m trapped in my seat And it spools so bad. They did provide me with a refund, but the process of getting that refund is so complicated. It’s unfortunate.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.

The worst landing I have ever had on a domestic flight. Thought we would lose the landing gear on landing in Newark. Then we spent 40 minutes trying to position the plane in the right place to be able to get the jet way to the plane. The plane arrived stopped. The announcer was that we were there. Everybody got up, then we were told to sit back down because they had to have us towed to a different position. We got towed and then everyone stood up and they told us we were in the wrong position to sit back down again, and then we got towed to a different position This did not happen immediately. It was 30 minutes while we wandered around a small section of the tarmac in Newark close to the gate, but apparently not close enough. Horrifying experience The CAB should be investigating that flight

Boarding was organized. Plane seats comfortable and service was attentive. Food options were good.

It is clear that someone knew, and competent, is in charge of food at United Airlines at least for the international flights. I was flying in coach, but the choices of the dinner were excellent. Tasty, and appropriate size. I had the beef, which was a little bit like a shepherds pie, and it was good. Nothing comparable has been served on a United flight in years. It will not be confused with three star food, but it is very good for airline food. Even better was the breakfast choice between a cinnamon roll and a breakfast sandwich. I chose the breakfast sandwich which was absolutely delicious and which I would happily order again at my local Starbucks or Panera. It is clear that someone knew indifferent is in charge of the food and it’s about time.

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

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.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.