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$102+ 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 9/26. Fares are subject to change and may not be available on all flights or dates of travel.
RSW — SJU
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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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 September 11, 2025.

Round-trip from

$226
(Priceline)

One-way from

$113
(Priceline)

Popular in

December

Cheapest in

June

Average price

$345
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. 5% potential increase in price ($26 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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 September 11, 2025.

This Priceline deal was found by Cheapflights users on 9/9. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/267:00 amRSW - SJU
1 stop11h 34mMultiple Airlines
Sat 9/2712:28 amSJU - RSW
1 stop8h 30mMultiple Airlines
Deal found 9/9$215
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/239:11 pmRSW - SJU
1 stop13h 46mFrontier
Sun 10/262:12 amSJU - RSW
1 stop10h 03mFrontier
Deal found 9/8$223
This Priceline deal was found by Cheapflights users on 9/11. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/149:48 amRSW - SJU
1 stop13h 35mFrontier
Wed 9/241:06 pmSJU - RSW
1 stop19h 52mFrontier
Deal found 9/11$226
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/199:48 amRSW - SJU
1 stop13h 35mFrontier
Sat 9/2012:28 amSJU - RSW
1 stop8h 30mFrontier
Deal found 9/9$228
This Priceline deal was found by Cheapflights users on 9/11. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/227:00 amRSW - SJU
1 stop11h 34mMultiple Airlines
Sat 9/271:06 pmSJU - RSW
1 stop19h 52mMultiple Airlines
Deal found 9/11$243
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/189:58 amRSW - SJU
1 stop13h 25mFrontier
Sat 9/2012:28 amSJU - RSW
1 stop8h 30mFrontier
Deal found 9/9$257
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/99:11 pmRSW - SJU
1 stop13h 46mFrontier
Thu 10/1612:11 pmSJU - RSW
1 stop23h 21mFrontier
Deal found 9/9$262
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/69:25 pmRSW - SJU
2 stops14h 15mMultiple Airlines
Fri 11/1412:11 pmSJU - RSW
1 stop9h 22mMultiple Airlines
Deal found 9/8$270
This Expedia deal was found by Cheapflights users on 9/9. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/227:00 amRSW - SJU
1 stop11h 34mMultiple Airlines
Sun 9/2812:28 amSJU - RSW
1 stop8h 30mMultiple Airlines
Deal found 9/9$277
This Frontier deal was found by Cheapflights users on 9/11. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/147:24 pmRSW - SJU
2 stops14h 32mFrontier
Sat 9/2012:28 amSJU - RSW
1 stop8h 30mFrontier
Deal found 9/11$279
This JetBlue deal was found by Cheapflights users on 9/11. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/23:40 pmRSW - SDQ
1 stop9h 15mJetBlue
Thu 10/98:10 amSDQ - RSW
1 stop10h 06mJetBlue
Deal found 9/11$421
This Mytrip deal was found by Cheapflights users on 9/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/411:56 amRSW - STT
2 stops23h 32mSpirit Airlines
Sun 12/71:33 pmSTT - RSW
2 stops22h 18mSpirit Airlines
Deal found 9/10$422

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 September 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

Sun 9/14

7:24 pm-9:56 am

2 stops14h 32m

San Juan Luis Munoz Marin Intl

Sat 9/20

12:28 am-8:58 am

1 stop8h 30m

$279

Fort MyersSan Juan

RSW - SJU

RSWSJU

Fort Myers SW Florida Intl

Thu 12/4

11:38 am-12:54 am

1 stop12h 16m

San Juan Luis Munoz Marin Intl

Sun 12/7

1:59 am-10:43 am

1 stop9h 44m

$280

Fort MyersSan Juan

RSW - SJU

RSWSJU

Fort Myers SW Florida Intl

Sat 10/18

3:40 pm-12:47 am

1 stop9h 07m

San Juan Luis Munoz Marin Intl

Sat 10/25

1:25 pm-9:40 pm

1 stop8h 15m

$295

Fort MyersSan Juan

RSW - SJU

RSWSJU

Fort Myers SW Florida Intl

Tue 10/21

11:30 am-9:24 pm

1 stop9h 54m

San Juan Luis Munoz Marin Intl

Sat 10/25

1:25 pm-9:40 pm

1 stop8h 15m

$295

Fort MyersSan Juan

RSW - SJU

RSWSJU

Fort Myers SW Florida Intl

Thu 9/25

7:24 pm-9:56 am

2 stops14h 32m

San Juan Luis Munoz Marin Intl

Sat 9/27

12:28 am-8:58 am

1 stop8h 30m

$300

Fort MyersSan Juan

RSW - SJU

RSWSJU

Fort Myers SW Florida Intl

Sat 10/18

3:40 pm-12:47 am

1 stop9h 07m

San Juan Luis Munoz Marin Intl

Tue 10/21

6:00 am-5:45 pm

1 stop11h 45m

$309

Fort MyersSan Juan

RSW - SJU

RSWSJU

Fort Myers SW Florida Intl

Thu 9/25

9:58 am-11:23 pm

1 stop13h 25m

San Juan Luis Munoz Marin Intl

Sun 9/28

12:28 am-8:58 am

1 stop8h 30m

$314

Fort MyersSan Juan

RSW - SJU

RSWSJU

Fort Myers SW Florida Intl

Fri 10/17

12:27 pm-12:29 am

1 stop12h 02m

San Juan Luis Munoz Marin Intl

Sun 10/19

2:12 am-11:10 am

1 stop8h 58m

$314

Fort MyersSan Juan

RSW - SJU

RSWSJU

Fort Myers SW Florida Intl

Mon 10/20

3:40 pm-12:57 am

1 stop9h 17m

San Juan Luis Munoz Marin Intl

Sat 10/25

1:25 pm-9:40 pm

1 stop8h 15m

$325

Fort MyersSan Juan

RSW - SJU

RSWSJU

Fort Myers SW Florida Intl

Fri 10/17

3:40 pm-12:57 am

1 stop9h 17m

San Juan Luis Munoz Marin Intl

Tue 10/21

6:00 am-5:45 pm

1 stop11h 45m

$343

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Showing 1-10 of 60 results
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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 June is currently the most expensive (average of $339). 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 September 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.

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 September 11, 2025.
See what other customers who have flown with Southwest, Delta, and American Airlines from Fort Myers to Caribbean have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,248 reviews

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,960 reviews
Southwest
8.0
Very good
4,248 reviews

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,248 reviews

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
JetBlue
7.2
Good
2,913 reviews
Southwest
8.0
Very good
4,248 reviews

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,177 reviews
Southwest
8.0
Very good
4,248 reviews

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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.

  • How long is the flight from Fort Myers to Caribbean?

    A quick flight from Fort Myers to Caribbean can take about 9h 07m. Frontier provides one of the quickest options available for as low as $295. The distance between Fort Myers and Caribbean is about 1149 mi. This flight may include one or multiple stops.

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

    To fly one-way, consider booking your trip with Spirit Airlines, which is currently one of the cheapest options available, starting at $102. Frontier flights start at $118 while deals on JetBlue start at $224 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 June is currently the most expensive (average of $339). 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

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See prices for flight routes from nearby airports that may be better suited for you.
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Top 6 airlines flying from Fort Myers to Caribbean

Discover the top 6 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$122Average$204FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$254Average$521FlexibilityNo cancel feeOn-time62%
DeltaCheapest$301Average$564FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$335Average$577FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$359Average$579FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$494Average$648FlexibilityNo cancel feeOn-time69%

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