$148 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 3/24. 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$480
Santo Domingo
Santo Domingo1 stop$391
Montego Bay
Montego Bay1 stop$352
Oranjestad
Oranjestad2 stops$489
Nassau
Nassau2 stops$466
Kingston
Kingston2 stops$719
Simpson Bay
Simpson Bay1 stop$428
Port of Spain
Port of Spain1 stop$730
Bridgetown
Bridgetown1 stop$697
George Town
George Town1 stop$545
Aguadilla
Aguadilla1 stop$801
Punta Cana
Punta Cana2 stops$480
Santo Domingo
Santo Domingo1 stop$391
Montego Bay
Montego Bay1 stop$352
Oranjestad
Oranjestad2 stops$489
Nassau
Nassau2 stops$466
Kingston
Kingston2 stops$719
Simpson Bay
Simpson Bay1 stop$428
Port of Spain
Port of Spain1 stop$730
Bridgetown
Bridgetown1 stop$697
George Town
George Town1 stop$545
Aguadilla
Aguadilla1 stop$801

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, Apr 25 - Mon, Apr 27
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
$284Frontier
Tue, May 5 - Tue, May 12
Frontier Logo
8:16 pm - 3:50 pm
RSW
-
SJU
19h 34m
1 stop
Frontier Logo
6:30 am - 7:16 pm
SJU
-
RSW
12h 46m
1 stop
$293Frontier
Mon, May 4 - Fri, May 8
Delta Logo
5:30 am - 4:23 pm
RSW
-
SJU
10h 53m
1 stop
Delta Logo
2:48 pm - 10:25 pm
SJU
-
RSW
7h 37m
1 stop
$296Delta
Mon, May 11 - Fri, May 15
Southwest Logo
12:55 pm - 11:25 pm
RSW
-
SJU
10h 30m
2 stops
Southwest Logo
5:35 am - 5:20 pm
SJU
-
RSW
11h 45m
1 stop
$311Southwest
Wed, Jun 3 - Tue, Jun 9
Delta Logo
3:45 pm - 10:17 pm
RSW
-
SJU
6h 32m
1 stop
Delta Logo
5:48 pm - 12:36 am
SJU
-
RSW
6h 48m
1 stop
$316Delta
Fri, Apr 24 - Wed, Apr 29
Southwest Logo
6:00 pm - 11:55 pm
RSW
-
SJU
5h 55m
1 stop
Southwest Logo
5:35 am - 3:40 pm
SJU
-
RSW
10h 05m
2 stops
$321Southwest
Tue, Apr 14 - Tue, Apr 21
JetBlue Logo
6:02 pm - 1:58 pm
RSW
-
GCM
20h 56m
1 stop
JetBlue Logo
1:55 pm - 5:00 pm
GCM
-
RSW
26h 05m
2 stops
$545JetBlue
Wed, Aug 12 - Tue, Aug 18
American Airlines Logo
8:23 am - 3:50 pm
RSW
-
PUJ
7h 27m
1 stop
American Airlines Logo
5:00 pm - 9:07 am
PUJ
-
RSW
16h 07m
1 stop
$570American Airlines
Wed, Aug 12 - Tue, Aug 18
American Airlines Logo
8:23 am - 3:50 pm
RSW
-
PUJ
7h 27m
1 stop
American Airlines Logo
3:25 pm - 11:12 am
PUJ
-
RSW
19h 47m
2 stops
$574American Airlines
Tue, Apr 14 - Tue, Apr 21
JetBlue Logo
6:02 pm - 1:58 pm
RSW
-
GCM
20h 56m
1 stop
JetBlue Logo
3:05 pm - 9:35 am
GCM
-
RSW
17h 30m
1 stop
$574JetBlue
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.

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

The average price for all round-trip flights from Fort Myers to Caribbean Islands depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

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.

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 $348, 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 $294 (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.

Good to know

Low seasonOctober
Cheapest flight$94
Best time to beat the crowds with an average 1% drop in price.
Most popular time to fly and prices are also 15% 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.

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 4321 reviews
8.1Boarding
8.6Crew
7.5Entertainment
8.0Comfort
7.0Food
Airline reviews

I was supposed to be on a later flight. When I showed up at the gate, the woman working there was extremely helpful getting moved up to this earlier flight.

10.0 ExcellentEric, Mar 2026
MCO - BNA
Read more Southwest reviews

I was supposed to be on a later flight. When I showed up at the gate, the woman working there was extremely helpful getting moved up to this earlier flight.

Long layover between flights to Long Island from BWI - need better coordination between flights

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

An entire day of delays. Cost lots of money. Meals and a hotel.

I appreciate the staff who allowed me to board though I arrived a little late! Regarding the assigned seating, I had booked my flight before this change and wasn't aware of the change at the time, and so I didn't select a seat at booking as I didn't realize it was relevant. Better communication about the change would have been helpful for preparing.

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.

Perhaps when you’re sitting in 1st class and the crew closes the bathroom for the pilots, there could be a notification other than holding your hands up as a blockade when you get there and you’re told the restrooms are closed please turn around … especially at night when visibility is poor and you’re met by a flight attendants with their arms up

Loved flying First Class. Very comfortable. The seat was amazing. Enjoyed a movie and was able to relax so much better than in coach.

We landed and sat on the tarmac for 45 minutes because they only have one gate at the airport and there was another plane running late so we had to wait

An awesome flight crew. FC seat cushion just doesn’t cut it for a 3+ hour flight.

Delta continues to set the benchmark for traveler-friendly service with minimal disruption and clear communication within the mainland US (coast to coast). I am consistently pleased to be a Delta customer, and this experience once again met my expectations. There was a brief delay departing from MIA due to a technical issue that required the aircraft to return to the gate. However, the situation was handled professionally and transparently. Fortunately, my planned layover allowed ample buffer time, so the adjustment caused no stress. Overall, another smooth and reassuring experience.

Totally worth the miles to upgrade to Delta Comfort. Plenty of legroom.

This was my first time flying Delta ever and I had a great experience!

The flight was great as well as the airline staff

Comfort seating was on the tight side. Maybe it was a smaller plane(?)

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

Flight cancelled 2 hours prior to boarding. No explanation. No refunds.

Delayed by 1.5 hours. Terrible apologies, half hearted at best. It will be a LONG time until i book w Jet Blue again. Very disappointed.

They made me check my bag and I didn't need to as there was overhead space available. I paid for a seat towards the front of the plane and it didn't recline. I requested a refund and they declined to give me one.

I have to congratulate Kayak (and Dylan the Chatdeal agent) because because when we decided extended our trip in Florida by two days, there were many direct flights oprions back to Boston available on the Friday we wanted to fly on the JetBlue website, but once I canceled the original JetBlue flight on their website, those direct return options disappeared immediatley! I think it's a game JetBlue plays. . Luckily, I checked Kayak and they had a direct flight that wasn't appearing on JetBlue's website and so I booked it, and we were able to fly home direct through the Kayak booking when JetBlue was offering nothing (even though I have been a True Blue member for 20 years, and also am a Mosaic member). So much for loyalty- their algorithm for booking is like a shell game. JetBlue used to be a good company but now they're worse than anyone. Also I was originally booked this trip to Florida, two months before the departure date, I booked the trip on JetBlue's website and then after the payment part, they said there was a problem and that I needed to do the booking again, so when I immediately went to rebook , the price had gone up 30%! I called them and it sounded like they had heard this so many times before and the guy told me to check back in 10 minutes and the price would be back to where it was when I was booking- it but it never was. How could the price go up 30% in one minute two months before the flight???? They're playing a game with their customers. Anyways, I booked a cheaper flight then at a less convenient time. So fast forward two months the night before the 7 AM flight, they sent me an email at midnight when I was sleeping to let me know that my flight at 7 AM had been canceled. The only thing they offered was a flight that night from from a different airport (Providence) to a different airport in Florida (West Palm Beach) or a flight two days later. No compensation, nothing. They couldn't of tried to get another plane to the Boston airport? They had all night to do it. I passed on their ridiculous options and flew with Delta and it was a great experience. Of course, I had to pay a lot more booking on the same day, but JetBlue doesn't care. I put in a lengthy complaint with the agent who assured me someone would get back to me by email within three days and I haven't heard a thing. JetBlue used to be a good company but now they're among the worst. The only thing they still have is decent legroom, but the corporate bean counters will probably start taking that away too.

We were made to wait in the airport for six hours for a flight that was ultimately canceled.

Friendly crew, efficient boarding and flight arrived early. Couldn’t ask for a better experience

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.

Really good. I accidentally left my duffel on the plane and the reps were so friendly in retrieving it.

After changing the departure gate 5 times making us mo e from one side of the airport to the other and then back the flight was delayed nearly 2 hours. The male flight attendant had a bad attitude with the guest being condescending, disrespectful with people who were already on edge.

There was no beverage service and the only time I saw a crew member walk through the cabin is when we were preparing to land.

Flights were constantly delayed. CRW took 50 minutes to get bags

Appreciate having multiple food options for allergies. Nice to have an extra seat between us for comfort.

Where do I start!! I was delayed with my flight from Dallas to Tampa. On the way back from Tampa to Dallas the flight was delayed over 4 hours+. I was put on another flight that was also delayed but not as long. Traveling on American Airlines is becoming exhausing.

I didn't end up taking this flight. I got up at 4am for a flight that was supposed to board at 6am - at 5:55am you delayed the flight to 10am. The airport is under construction so I switched to a later flight as I wasn't going to sit in the airport for 4 hours. They said the delay was due to the crew needing rest from a flight coming in late the night before - if that was the case then I think you should have delayed the flight much sooner so that passengers wouldn't get up so early and get to the airport to sit and wait.

The flight attendants and the service is getting worse by the day.

Other than nearly three hour delay for maintenance issues, everything went smooth

why would I bother with this airline and pick seats when I am asked to move for a weight imbalance

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports