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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 1/6. Fares are subject to change and may not be available on all flights or dates of travel.
RSW — SJU
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
1 adult, Economy
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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 October 28, 2025.

This Priceline deal was found by Cheapflights users on 10/26. 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.
Sat 12/612:22 pmRSW - SJU
1 stop11h 27mMultiple Airlines
Sat 12/137:07 pmSJU - RSW
1 stop18h 13mMultiple Airlines
Deal found 10/26$239
This Mytrip deal was found by Cheapflights users on 10/26. 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.
Sat 12/68:29 pmRSW - SJU
2 stops25h 56mSpirit Airlines
Sat 12/137:07 pmSJU - RSW
1 stop18h 13mSpirit Airlines
Deal found 10/26$272
This Priceline deal was found by Cheapflights users on 10/26. 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.
Sat 12/612:22 pmRSW - SJU
1 stop11h 27mFrontier
Fri 12/121:59 amSJU - RSW
1 stop10h 28mFrontier
Deal found 10/26$274
This Priceline deal was found by Cheapflights users on 10/25. 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 11/109:28 pmRSW - SJU
1 stop13h 48mFrontier
Fri 11/1412:11 pmSJU - RSW
1 stop9h 22mFrontier
Deal found 10/25$296
This Frontier deal was found by Cheapflights users on 10/26. 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.
Sat 12/612:22 pmRSW - SJU
1 stop11h 27mFrontier
Fri 1/92:29 amSJU - RSW
1 stop9h 09mFrontier
Deal found 10/26$304
This JetBlue deal was found by Cheapflights users on 10/26. 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.
Sat 11/156:13 amRSW - SJU
1 stop8h 09mJetBlue
Wed 11/1912:30 pmSJU - RSW
1 stop10h 09mJetBlue
Deal found 10/26$315
This Frontier deal was found by Cheapflights users on 10/26. 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.
Thu 10/309:28 pmRSW - SJU
1 stop13h 29mFrontier
Sat 11/15:51 pmSJU - RSW
2 stops19h 28mFrontier
Deal found 10/26$316
This Frontier deal was found by Cheapflights users on 10/27. 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 11/169:28 pmRSW - SJU
1 stop12h 33mFrontier
Sun 11/239:30 pmSJU - RSW
2 stops18h 44mFrontier
Deal found 10/27$319
This Frontier deal was found by Cheapflights users on 10/27. 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.
Mon 11/179:28 pmRSW - SJU
1 stop13h 48mFrontier
Fri 11/286:01 amSJU - RSW
1 stop9h 56mFrontier
Deal found 10/27$324
This Frontier deal was found by Cheapflights users on 10/28. 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 11/910:21 pmRSW - SJU
1 stop11h 40mFrontier
Fri 11/1412:11 pmSJU - RSW
1 stop9h 22mFrontier
Deal found 10/28$326
This Flysmarter deal was found by Cheapflights users on 10/27. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/156:13 amRSW - AUA
1 stop9h 32mJetBlue
Sun 11/231:50 pmAUA - RSW
1 stop10h 58mJetBlue
Deal found 10/27$402
This JetBlue deal was found by Cheapflights users on 10/26. 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 11/136:13 amRSW - GCM
1 stop8h 18mJetBlue
Sat 11/2212:30 pmGCM - RSW
1 stop20h 39mJetBlue
Deal found 10/26$427

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 October 28, 2025.

Most accurate provider

Expedia
2 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$239
(Priceline)

One-way from

$102
(Priceline)

Popular in

November

Cheapest in

June

Average price

$514
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. 13% potential increase in price ($70 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

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 October 28, 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

Sat 12/6

12:22 pm-12:49 am

1 stop11h 27m

San Juan Luis Munoz Marin Intl

Sat 12/13

7:07 pm-12:20 pm

1 stop18h 13m

$239

Fort MyersSan Juan

RSW - SJU

RSWSJU

Fort Myers SW Florida Intl

Sat 12/6

8:29 pm-11:25 pm

2 stops25h 56m

San Juan Luis Munoz Marin Intl

Sat 12/13

7:07 pm-12:20 pm

1 stop18h 13m

$272

Fort MyersSan Juan

RSW - SJU

RSWSJU

Fort Myers SW Florida Intl

Mon 1/12

3:00 pm-11:44 pm

1 stop7h 44m

San Juan Luis Munoz Marin Intl

Sat 1/17

6:30 pm-12:13 am

1 stop6h 43m

$313

Fort MyersSan Juan

RSW - SJU

RSWSJU

Fort Myers SW Florida Intl

Sun 2/15

5:50 pm-12:40 am

1 stop5h 50m

San Juan Luis Munoz Marin Intl

Thu 2/19

4:10 pm-9:35 pm

1 stop6h 25m

$313

Fort MyersSan Juan

RSW - SJU

RSWSJU

Fort Myers SW Florida Intl

Wed 1/7

8:20 pm-10:59 pm

2 stops25h 39m

San Juan Luis Munoz Marin Intl

Sun 1/11

5:28 pm-6:06 pm

2 stops25h 38m

$355

Fort MyersSan Juan

RSW - SJU

RSWSJU

Fort Myers SW Florida Intl

Sat 11/15

7:00 am-5:25 pm

2 stops9h 25m

San Juan Luis Munoz Marin Intl

Wed 11/19

11:20 am-9:45 pm

2 stops11h 25m

$359

Fort MyersSan Juan

RSW - SJU

RSWSJU

Fort Myers SW Florida Intl

Mon 1/12

10:30 am-8:55 pm

2 stops9h 25m

San Juan Luis Munoz Marin Intl

Sat 1/17

5:30 am-11:25 am

1 stop6h 55m

$359

Fort MyersSan Juan

RSW - SJU

RSWSJU

Fort Myers SW Florida Intl

Tue 3/3

3:55 pm-2:47 am

1 stop9h 52m

San Juan Luis Munoz Marin Intl

Mon 3/9

12:59 am-9:20 am

1 stop8h 21m

$362

Fort MyersOranjestad

RSW - AUA

RSWAUA

Fort Myers SW Florida Intl

Sat 11/15

6:13 am-4:45 pm

1 stop9h 32m

Oranjestad Reina Beatrix

Sun 11/23

1:50 pm-11:48 pm

1 stop10h 58m

$402

Fort MyersGeorge Town

RSW - GCM

RSWGCM

Fort Myers SW Florida Intl

Thu 11/13

6:13 am-2:31 pm

1 stop8h 18m

George Town Owen Roberts Intl

Sat 11/22

12:30 pm-9:09 am

1 stop20h 39m

$427

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

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, August is the cheapest month in which you can book a flight from Fort Myers to Caribbean (average of $53). Flying from Fort Myers to Caribbean in December is currently the most expensive (average of $305). 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 October 28, 2025.

It’s typically best to fly out from Fort Myers to Caribbean at noon. Doing so could potentially save you 30% on the flight price compared to flying in the morning, which is usually more expensive.

What is the cheapest day to fly from Fort Myers to Caribbean?

Use this chart to determine the cheapest time to fly round-trip from Fort Myers to Caribbean. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Fort Myers to Caribbean flight should consider departing on Wednesday at noon when fares are most often at their lowest. Tuesday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

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 October 28, 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
4,235 reviews

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Comfort

8.0

Overall

8.0

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
4,235 reviews
Southwest
8.0
Very good
4,235 reviews

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Comfort

8.0

Overall

8.0

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
7.9
Good
7,995 reviews
Southwest
8.0
Very good
4,235 reviews

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Comfort

8.0

Overall

8.0

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
11,033 reviews
Southwest
8.0
Very good
4,235 reviews

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Comfort

8.0

Overall

8.0

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
2,907 reviews
Southwest
8.0
Very good
4,235 reviews

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Comfort

8.0

Overall

8.0

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
3,122 reviews
Southwest
8.0
Very good
4,235 reviews

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Comfort

8.0

Overall

8.0

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 5h 50m. Spirit Airlines provides one of the quickest options available for as low as $313. 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 $138 while deals on JetBlue start at $184 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 - Simpson Bay Princess Juliana 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, August is the cheapest month in which you can book a flight from Fort Myers to Caribbean (average of $53). Flying from Fort Myers to Caribbean in December is currently the most expensive (average of $305). 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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Alternative routes for Fort Myers to Caribbean

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 October 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$122Average$208FlexibilityNo cancel feeOn-time62%
DeltaCheapest$238Average$565FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$254Average$508FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$335Average$580FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$360Average$577FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$494Average$648FlexibilityNo cancel feeOn-time69%

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