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$99+ 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 8/5. Fares are subject to change and may not be available on all flights or dates of travel.
RSW — SJU
ago. 3 — ago. 101
dom. 8/3
dom. 8/10
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 julio 29, 2025.

Round-trip from

$209
(Priceline)

One-way from

$99
(Frontier)

Popular in

August

Cheapest in

June

Average price

$341
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. 0% potential increase in price ($3 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in July 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 julio 29, 2025.

This Priceline deal was found by Cheapflights users on 7/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 8/135:37 pmRSW - SJU
1 stop22h 30mFrontier
sáb. 8/161:43 pmSJU - RSW
1 stop23h 29mFrontier
Deal found 7/28$209
This CheapOair deal was found by Cheapflights users on 7/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 9/87:00 amRSW - SJU
1 stop11h 34mMultiple Airlines
sáb. 9/1312:28 amSJU - RSW
1 stop8h 30mMultiple Airlines
Deal found 7/27$216
This Mytrip deal was found by Cheapflights users on 7/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 8/237:00 amRSW - SJU
1 stop11h 40mSpirit Airlines
sáb. 8/3010:10 amSJU - RSW
2 stops22h 28mSpirit Airlines
Deal found 7/29$283
This Trip.com deal was found by Cheapflights users on 7/29. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/2011:30 amRSW - SJU
1 stop9h 29mJetBlue
mar. 9/236:00 amSJU - RSW
1 stop11h 44mJetBlue
Deal found 7/29$310
This Southwest deal was found by Cheapflights users on 7/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/2011:25 amRSW - SJU
1 stop11h 15mSouthwest
mar. 9/235:00 amSJU - RSW
2 stops12h 35mSouthwest
Deal found 7/29$345
This American Airlines deal was found by Cheapflights users on 7/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/86:39 pmRSW - SJU
2 stops16h 27mAmerican Airlines
mié. 10/157:00 amSJU - RSW
2 stops15h 35mAmerican Airlines
Deal found 7/28$365
This FlightHub deal was found by Cheapflights users on 7/27. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 9/257:00 amRSW - STT
2 stops32h 17mSpirit Airlines
jue. 10/210:49 amSTT - RSW
2 stops21h 56mSpirit Airlines
Deal found 7/27$382
This Booking.com deal was found by Cheapflights users on 7/27. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 8/42:07 pmRSW - PUJ
1 stop26h 28mFrontier
jue. 8/71:44 pmPUJ - RSW
1 stop23h 28mFrontier
Deal found 7/27$405
This Delta deal was found by Cheapflights users on 7/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 9/287:00 amRSW - NAS
1 stop6h 49mDelta
mié. 10/11:15 pmNAS - RSW
1 stop4h 49mDelta
Deal found 7/27$426
This Expedia deal was found by Cheapflights users on 7/28. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/123:40 pmRSW - PUJ
1 stop18h 35mJetBlue
lun. 9/1511:30 amPUJ - RSW
1 stop23h 12mJetBlue
Deal found 7/28$437
This Delta deal was found by Cheapflights users on 7/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 11/175:35 amRSW - AUA
1 stop8h 40mDelta
lun. 11/244:30 pmAUA - RSW
1 stop9h 05mDelta
Deal found 7/29$444
This Expedia deal was found by Cheapflights users on 7/28. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 9/143:40 pmRSW - AUA
1 stop23h 30mJetBlue
jue. 9/185:21 pmAUA - RSW
1 stop17h 20mJetBlue
Deal found 7/28$446

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 julio 29, 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

mié. 8/13

5:37 pm-4:07 pm

1 stop22h 30m

San Juan Luis Munoz Marin Intl

sáb. 8/16

1:43 pm-1:12 pm

1 stop23h 29m

$209

Fort MyersSan Juan

RSW - SJU

RSWSJU

Fort Myers SW Florida Intl

lun. 9/8

7:00 am-6:34 pm

1 stop11h 34m

San Juan Luis Munoz Marin Intl

sáb. 9/13

12:28 am-8:58 am

1 stop8h 30m

$216

Fort MyersSan Juan

RSW - SJU

RSWSJU

Fort Myers SW Florida Intl

sáb. 8/23

7:00 am-6:40 pm

1 stop11h 40m

San Juan Luis Munoz Marin Intl

sáb. 8/30

10:10 am-8:38 am

2 stops22h 28m

$283

Fort MyersSan Juan

RSW - SJU

RSWSJU

Fort Myers SW Florida Intl

sáb. 9/20

11:30 am-8:59 pm

1 stop9h 29m

San Juan Luis Munoz Marin Intl

mar. 9/23

6:00 am-5:44 pm

1 stop11h 44m

$310

Fort MyersSan Juan

RSW - SJU

RSWSJU

Fort Myers SW Florida Intl

sáb. 9/20

11:25 am-10:40 pm

1 stop11h 15m

San Juan Luis Munoz Marin Intl

mar. 9/23

5:00 am-5:35 pm

2 stops12h 35m

$345

Fort MyersSan Juan

RSW - SJU

RSWSJU

Fort Myers SW Florida Intl

mié. 10/8

11:08 am-10:10 pm

1 stop11h 02m

San Juan Luis Munoz Marin Intl

mié. 10/15

7:45 am-10:35 pm

1 stop14h 50m

$365

Fort MyersSaint Thomas Island

RSW - STT

RSWSTT

Fort Myers SW Florida Intl

jue. 9/25

7:00 am-3:17 pm

2 stops32h 17m

Saint Thomas Island Cyril E King

jue. 10/2

10:49 am-8:45 am

2 stops21h 56m

$382

Fort MyersNassau

RSW - NAS

RSWNAS

Fort Myers SW Florida Intl

dom. 9/28

7:00 am-1:49 pm

1 stop6h 49m

Nassau Intl

mié. 10/1

1:15 pm-6:04 pm

1 stop4h 49m

$426

Fort MyersPunta Cana

RSW - PUJ

RSWPUJ

Fort Myers SW Florida Intl

vie. 9/12

3:40 pm-10:15 am

1 stop18h 35m

Punta Cana

lun. 9/15

11:30 am-10:42 am

1 stop23h 12m

$437

Fort MyersOranjestad

RSW - AUA

RSWAUA

Fort Myers SW Florida Intl

lun. 11/17

5:35 am-3:15 pm

1 stop8h 40m

Oranjestad Reina Beatrix

lun. 11/24

4:30 pm-12:35 am

1 stop9h 05m

$444

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

Showing 1-10 of 51 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 julio 29, 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 julio 29, 2025.
See what other customers who have flown with Southwest, Delta, and United 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
4,238 reviews

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,977 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,899 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
JetBlue
7.3
Good
2,913 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 $99. Southwest flights start at $157 while deals on JetBlue start at $167 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 - Nassau Intl or Fort Myers SW Florida Intl - Oranjestad Reina Beatrix 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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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 julio 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$122Average$193FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$262Average$530FlexibilityNo cancel feeOn-time62%
DeltaCheapest$301Average$563FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$335Average$565FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$340Average$574FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$346Average$577FlexibilityNo cancel feeOn-time69%

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