HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean

$139+ Cheap flights from Fort Myers (RSW) to Caribbean

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/22. Fares are subject to change and may not be available on all flights or dates of travel.
RSW — SJU
Apr 16 — Apr 231
Wed 4/16
Wed 4/23
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Fort Myers to Caribbean with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Fort Myers to Caribbean

Keep the following information in mind while searching for Fort Myers to Caribbean flight deals. Data was last updated April 11, 2025.

Most accurate provider

Expedia
1 star

Most trusted provider

Expedia
3 stars

Round-trip from

$258
(Frontier)

One-way from

$139
(Frontier)

Popular in

February

Cheapest in

May

Average price

$336
Provider with most accurate pricing for Fort Myers SW Florida Intl-San Juan flight deals.
Search Deals
Provider most trusted by Cheapflights users for Fort Myers SW Florida Intl-San Juan flights.
Search Deals
From Fort Myers SW Florida Intl to Caribbean
Search Deals
One-way flight from Fort Myers SW Florida Intl to Caribbean
Search Deals
Highest demand for flights based on searches. 16% potential increase in price ($67 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
Search Deals

Find flight deals from Fort Myers to Caribbean

Cheapest flights from Fort Myers to Caribbean
Explore the most affordable flight options available from Fort Myers to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 11, 2025.

This Frontier deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/162:51 pmRSW - SJU
1 stop9h 24mFrontier
Sun 4/2012:59 amSJU - RSW
1 stop9h 18mFrontier
Deal found 4/9$258
This FlightHub deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/103:46 pmRSW - SJU
1 stop8h 58mMultiple Airlines
Mon 6/2311:35 amSJU - RSW
1 stop25h 35mMultiple Airlines
Deal found 4/9$317
This Delta deal was found by Cheapflights users on 4/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/33:18 pmRSW - SJU
1 stop7h 57mDelta
Sat 5/106:15 amSJU - RSW
1 stop7h 47mDelta
Deal found 4/11$335
This Mytrip deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/165:09 pmRSW - SJU
2 stops31h 45mSpirit Airlines
Sat 5/248:12 pmSJU - RSW
2 stops19h 51mSpirit Airlines
Deal found 4/9$345
This American Airlines deal was found by Cheapflights users on 4/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/117:48 pmRSW - SJU
2 stops18h 59mAmerican Airlines
Tue 9/161:55 pmSJU - RSW
2 stops19h 12mAmerican Airlines
Deal found 4/11$355
This JetBlue deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/912:50 pmRSW - SJU
1 stop9h 13mJetBlue
Sat 6/143:25 amSJU - RSW
1 stop8h 41mJetBlue
Deal found 4/9$369
This Southwest deal was found by Cheapflights users on 4/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/36:40 amRSW - SJU
2 stops11h 15mSouthwest
Sat 5/1010:20 amSJU - RSW
1 stop11h 35mSouthwest
Deal found 4/10$399
This Booking.com deal was found by Cheapflights users on 4/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/147:10 pmRSW - PUJ
1 stop21h 25mFrontier
Wed 4/165:03 pmPUJ - RSW
1 stop31h 56mFrontier
Deal found 4/10$442
This American Airlines deal was found by Cheapflights users on 4/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/137:58 pmRSW - STT
1 stop14h 47mAmerican Airlines
Thu 11/206:15 pmSTT - RSW
2 stops17h 34mAmerican Airlines
Deal found 4/10$445
This Delta deal was found by Cheapflights users on 4/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/225:35 amRSW - NAS
1 stop8h 19mDelta
Sat 7/265:15 pmNAS - RSW
1 stop6h 18mDelta
Deal found 4/10$455
This Delta deal was found by Cheapflights users on 4/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/3012:15 pmRSW - SDQ
1 stop12h 35mDelta
Sat 5/37:00 amSDQ - RSW
2 stops15h 56mDelta
Deal found 4/10$464
This United Airlines deal was found by Cheapflights users on 4/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/252:26 pmRSW - SJU
1 stop9h 28mUnited Airlines
Tue 4/297:00 amSJU - RSW
1 stop8h 44mUnited Airlines
Deal found 4/10$475

Cheapflights Fare Finder

Customize your flight search to find flights from Fort Myers to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 11, 2025.
Use the filters below to find and compare flights from Fort Myers to Caribbean that are best for you.

Fly from

Fort Myers

Fly to

Caribbean

Route

Depart

Return

Price

Fort MyersSan Juan

RSW - SJU

RSWSJU

Fort Myers SW Florida Intl

Wed 4/30

8:45 pm-1:51 am

1 stop29h 06m

San Juan Luis Munoz Marin Intl

Sun 5/4

12:05 am-8:00 pm

1 stop19h 55m

$268

Fort MyersSan Juan

RSW - SJU

RSWSJU

Fort Myers SW Florida Intl

Tue 6/10

3:46 pm-12:44 am

1 stop8h 58m

San Juan Luis Munoz Marin Intl

Mon 6/23

11:35 am-1:10 pm

1 stop25h 35m

$317

Fort MyersSan Juan

RSW - SJU

RSWSJU

Fort Myers SW Florida Intl

Sat 5/3

3:18 pm-11:15 pm

1 stop7h 57m

San Juan Luis Munoz Marin Intl

Sat 5/10

6:15 am-2:02 pm

1 stop7h 47m

$335

Fort MyersSan Juan

RSW - SJU

RSWSJU

Fort Myers SW Florida Intl

Fri 5/16

5:09 pm-12:54 am

2 stops31h 45m

San Juan Luis Munoz Marin Intl

Sat 5/24

8:12 pm-4:03 pm

2 stops19h 51m

$345

Fort MyersSan Juan

RSW - SJU

RSWSJU

Fort Myers SW Florida Intl

Thu 9/11

7:48 pm-2:47 pm

2 stops18h 59m

San Juan Luis Munoz Marin Intl

Tue 9/16

1:55 pm-9:07 am

2 stops19h 12m

$355

Fort MyersSan Juan

RSW - SJU

RSWSJU

Fort Myers SW Florida Intl

Mon 6/9

12:50 pm-10:03 pm

1 stop9h 13m

San Juan Luis Munoz Marin Intl

Sat 6/14

3:25 am-12:06 pm

1 stop8h 41m

$369

Fort MyersSan Juan

RSW - SJU

RSWSJU

Fort Myers SW Florida Intl

Sat 5/3

6:40 am-5:55 pm

2 stops11h 15m

San Juan Luis Munoz Marin Intl

Sat 5/10

10:20 am-9:55 pm

1 stop11h 35m

$399

Fort MyersNassau

RSW - NAS

RSWNAS

Fort Myers SW Florida Intl

Tue 7/22

5:35 am-1:54 pm

1 stop8h 19m

Nassau Intl

Sat 7/26

5:15 pm-11:33 pm

1 stop6h 18m

$455

Fort MyersSanto Domingo

RSW - SDQ

RSWSDQ

Fort Myers SW Florida Intl

Wed 4/30

12:15 pm-12:50 am

1 stop12h 35m

Santo Domingo Las Americas

Sat 5/3

7:00 am-10:56 pm

2 stops15h 56m

$464

Fort MyersSan Juan

RSW - SJU

RSWSJU

Fort Myers SW Florida Intl

Sun 5/4

6:00 am-1:45 pm

1 stop7h 45m

San Juan Luis Munoz Marin Intl

Thu 5/8

1:05 am-11:14 am

1 stop10h 09m

$465

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/10

Showing 1-10 of 52 results
1
2
3
...
6

Best time to book a flight from Fort Myers to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean from Fort Myers with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Fort Myers to Caribbean

What is the cheapest month to book a flight from Fort Myers to Caribbean?

Currently, September is the cheapest month in which you can book a flight from Fort Myers to Caribbean (average of $254). Flying from Fort Myers to Caribbean in December is currently the most expensive (average of $336). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from RSW to CB?

Find hourly flight availability from Fort Myers to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 11, 2025.

When flying from Fort Myers to Caribbean, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Rainfall in Caribbean by month

Plan your trip to Caribbean by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean when rainfall is around 2.2 in.

Temperature in Caribbean by month

Plan your trip to Caribbean by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated April 11, 2025.
Southwest
8.0
Very good
4,279 reviews

Comfort

8.0

Boarding

8.2

Crew

8.6

Food

7.1

Overall

8.0

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,279 reviews
Southwest
8.0
Very good
4,279 reviews

Comfort

8.0

Boarding

8.2

Crew

8.6

Food

7.1

Overall

8.0

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,910 reviews
Southwest
8.0
Very good
4,279 reviews

Comfort

8.0

Boarding

8.2

Crew

8.6

Food

7.1

Overall

8.0

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Finnair
7.6
Good
1,269 reviews
Southwest
8.0
Very good
4,279 reviews

Comfort

8.0

Boarding

8.2

Crew

8.6

Food

7.1

Overall

8.0

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
8,636 reviews
Southwest
8.0
Very good
4,279 reviews

Comfort

8.0

Boarding

8.2

Crew

8.6

Food

7.1

Overall

8.0

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
JetBlue
7.3
Good
2,925 reviews
Southwest
8.0
Very good
4,279 reviews

Comfort

8.0

Boarding

8.2

Crew

8.6

Food

7.1

Overall

8.0

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Related info for your journey

Find useful and relevant information for your journey from Fort Myers to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Fort Myers to Caribbean?

    Most people fly from Fort Myers SW Florida Intl (RSW) if they book a flight from Fort Myers to Caribbean. Fort Myers SW Florida Intl is conveniently located just 10.0 mi from Fort Myers’s city center.

  • What are the cheapest airlines to fly from Fort Myers to Caribbean one-way?

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $139. Spirit Airlines flights start at $142 while deals on Southwest start at $201 one-way.

  • What are the most popular routes from Fort Myers to Caribbean?

    When deciding which route to take from Fort Myers to Caribbean consider Fort Myers SW Florida Intl - San Juan Luis Munoz Marin Intl, Fort Myers SW Florida Intl - Oranjestad Reina Beatrix or Fort Myers SW Florida Intl - Punta Cana as they are the most popular.

  • Can I find deals for flights from Fort Myers to Caribbean that include hotel bookings?

    Yes. In addition to deals on Fort Myers to Caribbean flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Fort Myers to Caribbean?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Fort Myers to Caribbean.

  • Can I find deals for business class flights from Fort Myers to Caribbean?

    Yes. Cheapflights offers flight deals from Fort Myers to Caribbean by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Fort Myers to Caribbean?

    Currently, September is the cheapest month in which you can book a flight from Fort Myers to Caribbean (average of $254). Flying from Fort Myers to Caribbean in December is currently the most expensive (average of $336). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Fort Myers to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
Fort Lauderdale to Newark flights
Orlando to LaGuardia flights
Fort Lauderdale to LaGuardia flights
Orlando to Newark flights
Miami to LaGuardia flights
Miami to John F Kennedy Intl flights
Miami to Newark flights
Orlando to Luis Munoz Marin Intl flights
Fort Lauderdale to John F Kennedy Intl flights
Miami to Madrid flights
Tampa to Newark flights
Orlando to John F Kennedy Intl flights
West Palm Beach to John F Kennedy Intl flights
Orlando to Seattle flights
Miami to Jose Maria Cordova Intl flights
Tampa to John F Kennedy Intl flights
Miami to Los Angeles flights
Tampa to Seattle flights
Miami to Lima flights
Orlando to Las Vegas flights
Tampa to LaGuardia flights
Fort Lauderdale to Luis Munoz Marin Intl flights
Fort Lauderdale to Las Vegas flights
Fort Lauderdale to Atlanta flights
Orlando to Los Angeles flights
Tampa to Las Vegas flights
West Palm Beach to Newark flights
Fort Lauderdale to Jose Maria Cordova Intl flights
Miami to Heathrow flights
Orlando to Cancún flights
Miami to Leonardo da Vinci/Fiumicino flights
Orlando to Dallas/Fort Worth flights
Miami to Mexico City flights
Orlando to Denver flights
Miami to Cancún flights
Fort Lauderdale to Dallas/Fort Worth flights
Fort Lauderdale to O'Hare Intl flights
Orlando to Boston flights
Miami to Seattle flights
Jacksonville to Newark flights
Orlando to Heathrow flights
Miami to Barcelona-El Prat flights
Orlando to O'Hare Intl flights
Tampa to Luis Munoz Marin Intl flights
Orlando to Dulles Intl flights
Fort Lauderdale to Los Angeles flights
Fort Lauderdale to Seattle flights
Miami to Charles de Gaulle flights
Tampa to Dallas/Fort Worth flights
Miami to Boston flights

Top 7 airlines flying from Fort Myers to Caribbean

Discover the top 7 airlines that operate flights from Fort Myers to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$107Average$169FlexibilityNo cancel feeOn-time65%
FrontierCheapest$122Average$190FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$224Average$576FlexibilityNo cancel feeOn-time71%
DeltaCheapest$224Average$610FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$324Average$583FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$346Average$558FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$418Average$664FlexibilityNo cancel feeOn-time62%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.