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$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
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

Expedia
1 star

Most trusted provider

Expedia
3 stars

Round-trip from

$273
(Frontier)

One-way from

$139
(Frontier)

Popular in

February

Cheapest in

May

Average price

$169
Provider with most accurate pricing for Fort Myers SW Florida Intl-San Juan flight deals.
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Provider most trusted by Cheapflights users for Fort Myers SW Florida Intl-San Juan flights.
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From Fort Myers SW Florida Intl to Caribbean
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One-way flight from Fort Myers SW Florida Intl to Caribbean
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Highest demand for flights based on searches. 16% potential increase in price ($68 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 1, 2025.

This Frontier deal was found by Cheapflights users on 4/29. 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.
Fri 6/63:27 pmRSW - SJU
1 stop9h 17mFrontier
Sat 6/78:00 amSJU - RSW
1 stop10h 00mFrontier
Deal found 4/29$273
This American Airlines deal was found by Cheapflights users on 4/30. 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.
Tue 9/96:27 amRSW - SJU
1 stop8h 18mAmerican Airlines
Fri 9/125:25 pmSJU - RSW
2 stops19h 44mAmerican Airlines
Deal found 4/30$345
This Booking.com deal was found by Cheapflights users on 4/30. 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 8/112:38 pmRSW - SJU
1 stop10h 21mMultiple Airlines
Fri 8/154:46 pmSJU - RSW
1 stop19h 49mMultiple Airlines
Deal found 4/30$354
This Delta deal was found by Cheapflights users on 4/30. 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.
Fri 5/161:30 pmRSW - SJU
1 stop9h 17mDelta
Sat 5/246:15 amSJU - RSW
1 stop10h 00mDelta
Deal found 4/30$370
This United Airlines deal was found by Cheapflights users on 4/30. 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.
Sat 5/36:00 amRSW - SJU
1 stop7h 45mUnited Airlines
Sat 5/311:25 pmSJU - RSW
1 stop10h 33mUnited Airlines
Deal found 4/30$387
This JetBlue deal was found by Cheapflights users on 4/30. 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.
Sun 6/86:00 amRSW - SJU
1 stop11h 30mJetBlue
Tue 6/173:23 amSJU - RSW
1 stop8h 43mJetBlue
Deal found 4/30$403
This Mytrip deal was found by Cheapflights users on 4/30. 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 5/37:25 pmRSW - SJU
1 stop25h 39mSpirit Airlines
Sat 5/318:12 pmSJU - RSW
2 stops19h 51mSpirit Airlines
Deal found 4/30$430
This Booking.com deal was found by Cheapflights users on 4/30. 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 6/93:27 pmRSW - PUJ
1 stop25h 12mFrontier
Mon 6/1611:20 amPUJ - RSW
1 stop24h 41mFrontier
Deal found 4/30$432
This Southwest deal was found by Cheapflights users on 4/30. 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.
Sun 5/258:30 amRSW - MBJ
1 stop7h 05mSouthwest
Thu 6/511:20 amMBJ - RSW
1 stop8h 00mSouthwest
Deal found 4/30$443
This American Airlines deal was found by Cheapflights users on 4/29. 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.
Wed 10/85:43 pmRSW - STT
2 stops19h 07mAmerican Airlines
Wed 10/151:45 pmSTT - RSW
2 stops21h 05mAmerican Airlines
Deal found 4/29$459
This Southwest deal was found by Cheapflights users on 4/30. 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.
Tue 7/221:40 pmRSW - SJU
2 stops10h 15mSouthwest
Tue 7/297:30 amSJU - RSW
2 stops10h 40mSouthwest
Deal found 4/30$459
This Delta deal was found by Cheapflights users on 4/30. 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 5/275:30 amRSW - MBJ
1 stop8h 28mDelta
Thu 6/52:23 pmMBJ - RSW
1 stop9h 14mDelta
Deal found 4/30$461

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 May 1, 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

Fri 6/6

3:27 pm-12:44 am

1 stop9h 17m

San Juan Luis Munoz Marin Intl

Sat 6/7

8:00 am-6:00 pm

1 stop10h 00m

$273

Fort MyersSan Juan

RSW - SJU

RSWSJU

Fort Myers SW Florida Intl

Tue 9/9

6:27 am-2:45 pm

1 stop8h 18m

San Juan Luis Munoz Marin Intl

Fri 9/12

5:25 pm-1:09 pm

2 stops19h 44m

$345

Fort MyersSan Juan

RSW - SJU

RSWSJU

Fort Myers SW Florida Intl

Mon 8/11

2:38 pm-12:59 am

1 stop10h 21m

San Juan Luis Munoz Marin Intl

Fri 8/15

4:46 pm-12:35 pm

1 stop19h 49m

$354

Fort MyersSan Juan

RSW - SJU

RSWSJU

Fort Myers SW Florida Intl

Fri 5/16

1:30 pm-10:47 pm

1 stop9h 17m

San Juan Luis Munoz Marin Intl

Sat 5/24

6:15 am-4:15 pm

1 stop10h 00m

$370

Fort MyersSan Juan

RSW - SJU

RSWSJU

Fort Myers SW Florida Intl

Sun 6/8

6:00 am-5:30 pm

1 stop11h 30m

San Juan Luis Munoz Marin Intl

Tue 6/17

3:23 am-12:06 pm

1 stop8h 43m

$403

Fort MyersPunta Cana

RSW - PUJ

RSWPUJ

Fort Myers SW Florida Intl

Mon 6/9

3:27 pm-4:39 pm

1 stop25h 12m

Punta Cana

Mon 6/16

11:20 am-12:01 pm

1 stop24h 41m

$432

Fort MyersSan Juan

RSW - SJU

RSWSJU

Fort Myers SW Florida Intl

Sun 6/1

5:09 pm-11:31 am

3 stops42h 22m

San Juan Luis Munoz Marin Intl

Fri 6/6

1:59 am-4:03 pm

2 stops14h 04m

$441

Fort MyersMontego Bay

RSW - MBJ

RSWMBJ

Fort Myers SW Florida Intl

Sun 5/25

8:30 am-2:35 pm

1 stop7h 05m

Montego Bay Sangster Intl

Thu 6/5

11:20 am-8:20 pm

1 stop8h 00m

$443

Fort MyersSaint Thomas Island

RSW - STT

RSWSTT

Fort Myers SW Florida Intl

Wed 10/8

5:43 pm-12:50 pm

2 stops19h 07m

Saint Thomas Island Cyril E King

Wed 10/15

1:45 pm-10:50 am

2 stops21h 05m

$459

Fort MyersSan Juan

RSW - SJU

RSWSJU

Fort Myers SW Florida Intl

Tue 7/22

1:40 pm-11:55 pm

2 stops10h 15m

San Juan Luis Munoz Marin Intl

Tue 7/29

6:30 am-3:20 pm

1 stop8h 50m

$459

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 47 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 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 May 1, 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 May 1, 2025.
Southwest
8.0
Very good
4,294 reviews

Crew

8.6

Food

7.1

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,294 reviews
Southwest
8.0
Very good
4,294 reviews

Crew

8.6

Food

7.1

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,934 reviews
Southwest
8.0
Very good
4,294 reviews

Crew

8.6

Food

7.1

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,696 reviews
Southwest
8.0
Very good
4,294 reviews

Crew

8.6

Food

7.1

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
JetBlue
7.3
Good
2,924 reviews
Southwest
8.0
Very good
4,294 reviews

Crew

8.6

Food

7.1

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,294 reviews

Crew

8.6

Food

7.1

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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. Delta flights start at $213 while deals on JetBlue start at $229 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 - Nassau Intl 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

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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 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$107Average$170FlexibilityNo cancel feeOn-time65%
FrontierCheapest$122Average$201FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$224Average$580FlexibilityNo cancel feeOn-time71%
DeltaCheapest$224Average$601FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$324Average$583FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$346Average$593FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$418Average$664FlexibilityNo cancel feeOn-time62%

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