HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean

$90+ 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 1/24. Fares are subject to change and may not be available on all flights or dates of travel.
RSW — SJU
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
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

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 December 12, 2025.

This Expedia deal was found by Cheapflights users on 12/11. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/315:45 amRSW - SJU
1 stop18h 39mFrontier
Fri 1/92:29 amSJU - RSW
1 stop10h 51mFrontier
Deal found 12/11$227
This Expedia deal was found by Cheapflights users on 12/11. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/315:45 amRSW - SJU
1 stop18h 39mMultiple Airlines
Sat 1/106:00 amSJU - RSW
2 stops15h 00mMultiple Airlines
Deal found 12/11$296
This Expedia deal was found by Cheapflights users on 12/11. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/315:45 amRSW - SJU
1 stop18h 39mMultiple Airlines
Thu 1/81:22 pmSJU - RSW
1 stop11h 02mMultiple Airlines
Deal found 12/11$341
This Priceline deal was found by Cheapflights users on 12/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/2711:50 amRSW - SJU
1 stop12h 40mFrontier
Mon 12/292:44 pmSJU - RSW
1 stop10h 06mFrontier
Deal found 12/10$369
This Expedia deal was found by Cheapflights users on 12/9. 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.
Wed 12/319:55 pmRSW - SJU
1 stop13h 31mSpirit Airlines
Mon 1/58:08 pmSJU - RSW
1 stop18h 21mSpirit Airlines
Deal found 12/9$384
This Expedia deal was found by Cheapflights users on 12/11. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/319:55 pmRSW - SJU
2 stops23h 10mSpirit Airlines
Sat 1/106:00 amSJU - RSW
2 stops15h 00mSpirit Airlines
Deal found 12/11$386
This Expedia deal was found by Cheapflights users on 12/11. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/2612:31 pmRSW - SJU
1 stop11h 53mFrontier
Tue 12/309:06 pmSJU - RSW
1 stop20h 57mFrontier
Deal found 12/11$419
This Kiwi.com deal was found by Cheapflights users on 12/9. 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.
Wed 12/109:02 pmRSW - SJU
2 stops50h 43mMultiple Airlines
Wed 1/141:22 pmSJU - RSW
1 stop11h 02mMultiple Airlines
Deal found 12/9$433
This Delta deal was found by Cheapflights users on 12/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/101:37 pmRSW - SJU
1 stop8h 43mDelta
Wed 1/143:55 pmSJU - RSW
1 stop9h 18mDelta
Deal found 12/9$436
This Priceline deal was found by Cheapflights users on 12/11. 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.
Fri 12/1212:32 pmRSW - SJU
1 stop21h 15mMultiple Airlines
Mon 12/156:10 amSJU - RSW
1 stop16h 54mMultiple Airlines
Deal found 12/11$437
This Delta deal was found by Cheapflights users on 12/11. 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.
Thu 12/255:35 amRSW - STT
1 stop6h 03mDelta
Wed 12/313:06 pmSTT - RSW
1 stop10h 14mDelta
Deal found 12/11$449
This Kiwi.com deal was found by Cheapflights users on 12/9. 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.
Wed 12/109:02 pmRSW - SJU
2 stops50h 43mMultiple Airlines
Wed 12/247:30 amSJU - RSW
1 stop11h 48mMultiple Airlines
Deal found 12/9$449

Find 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 December 12, 2025.

Most accurate provider

Expedia
2 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$192
(Travelocity)

One-way from

$90
(Priceline)

Popular in

July

Cheapest in

June

Average price

$511
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
High demand for flights, 0% potential price rise
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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 December 12, 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 2/18

7:00 am-6:54 pm

1 stop10h 54m

San Juan Luis Munoz Marin Intl

Tue 2/24

1:22 pm-11:23 pm

1 stop11h 01m

$204

Fort MyersSan Juan

RSW - SJU

RSWSJU

Fort Myers SW Florida Intl

Fri 1/9

7:45 pm-8:54 am

2 stops36h 09m

San Juan Luis Munoz Marin Intl

Fri 1/16

8:15 pm-6:25 pm

1 stop23h 10m

$223

Fort MyersSan Juan

RSW - SJU

RSWSJU

Fort Myers SW Florida Intl

Mon 2/2

9:11 pm-12:45 pm

1 stop14h 34m

San Juan Luis Munoz Marin Intl

Mon 2/23

2:54 am-7:14 pm

1 stop17h 20m

$232

Fort MyersSan Juan

RSW - SJU

RSWSJU

Fort Myers SW Florida Intl

Mon 2/2

9:11 pm-12:45 pm

1 stop14h 34m

San Juan Luis Munoz Marin Intl

Tue 2/24

2:54 am-7:14 pm

1 stop17h 20m

$232

Fort MyersSan Juan

RSW - SJU

RSWSJU

Fort Myers SW Florida Intl

Mon 1/12

7:31 am-12:59 am

2 stops16h 28m

San Juan Luis Munoz Marin Intl

Fri 1/23

2:59 am-12:11 pm

1 stop10h 12m

$241

Fort MyersSan Juan

RSW - SJU

RSWSJU

Fort Myers SW Florida Intl

Sat 1/10

7:31 am-8:54 am

2 stops24h 23m

San Juan Luis Munoz Marin Intl

Fri 1/23

8:31 pm-12:11 pm

1 stop16h 40m

$244

Fort MyersSan Juan

RSW - SJU

RSWSJU

Fort Myers SW Florida Intl

Tue 2/3

6:35 am-2:31 pm

1 stop6h 56m

San Juan Luis Munoz Marin Intl

Thu 2/26

6:27 pm-12:33 am

1 stop7h 06m

$245

Fort MyersSan Juan

RSW - SJU

RSWSJU

Fort Myers SW Florida Intl

Wed 2/4

6:50 am-7:05 pm

2 stops11h 15m

San Juan Luis Munoz Marin Intl

Wed 2/25

5:40 am-11:35 am

1 stop6h 55m

$245

Fort MyersSan Juan

RSW - SJU

RSWSJU

Fort Myers SW Florida Intl

Tue 2/3

5:35 am-1:06 pm

1 stop6h 31m

San Juan Luis Munoz Marin Intl

Wed 2/25

7:30 am-3:37 pm

1 stop9h 07m

$245

Fort MyersSan Juan

RSW - SJU

RSWSJU

Fort Myers SW Florida Intl

Mon 2/2

9:11 pm-12:45 pm

1 stop14h 34m

San Juan Luis Munoz Marin Intl

Mon 2/23

6:00 am-4:32 pm

1 stop11h 32m

$250

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/11

Showing 1-10 of 60 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, 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 $274). 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 December 12, 2025.

It’s typically best to fly out from Fort Myers to Caribbean at noon. Doing so could potentially save you 39% on the flight price compared to flying in the evening, 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 December 12, 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
7.9
Good
4,252 reviews

Comfort

8.0

Crew

8.6

Overall

7.9

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
7.9
Good
4,252 reviews
Southwest
7.9
Good
4,252 reviews

Comfort

8.0

Crew

8.6

Overall

7.9

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,009 reviews
Southwest
7.9
Good
4,252 reviews

Comfort

8.0

Crew

8.6

Overall

7.9

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,049 reviews
Southwest
7.9
Good
4,252 reviews

Comfort

8.0

Crew

8.6

Overall

7.9

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
JetBlue
7.2
Good
2,898 reviews
Southwest
7.9
Good
4,252 reviews

Comfort

8.0

Crew

8.6

Overall

7.9

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Frontier
5.8
Fair
3,084 reviews
Southwest
7.9
Good
4,252 reviews

Comfort

8.0

Crew

8.6

Overall

7.9

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 7h 57m. Spirit Airlines provides one of the quickest options available for as low as $416. The distance between Fort Myers and Caribbean is about 1015 mi. This flight may include one or multiple stops.

  • 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 - 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, 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 $274). 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.
Miami to John F Kennedy Intl flights
Fort Lauderdale to John F Kennedy Intl flights
Miami to LaGuardia flights
Orlando to John F Kennedy Intl flights
Fort Lauderdale to Newark flights
Orlando to Newark flights
Fort Lauderdale to LaGuardia flights
West Palm Beach to Newark flights
Miami to Newark flights
Orlando to Luis Munoz Marin Intl flights
Orlando to Las Vegas flights
Orlando to LaGuardia flights
Fort Lauderdale to Dallas/Fort Worth flights
Orlando to Dallas/Fort Worth flights
Tampa to LaGuardia flights
Miami to Jose Maria Cordova Intl flights
Miami to Madrid flights
West Palm Beach to John F Kennedy Intl flights
Tampa to John F Kennedy Intl flights
Miami to Denver flights
Miami to Dallas/Fort Worth flights
Fort Lauderdale to Las Vegas flights
Orlando to Denver flights
Fort Lauderdale to Hobby flights
Miami to Mexico City flights
Miami to Hobby flights
Tampa to Luis Munoz Marin Intl flights
Tampa to Newark flights
Miami to Santo Domingo flights
Orlando to Punta Cana flights
Fort Lauderdale to Jose Maria Cordova Intl flights
Orlando to Los Angeles flights
Miami to Las Vegas flights
West Palm Beach to LaGuardia flights
Tampa to Las Vegas flights
Miami to Los Angeles flights
Fort Lauderdale to Luis Munoz Marin Intl flights
Miami to Cancún flights
Orlando to Cancún flights
Fort Lauderdale to Los Angeles flights
Miami to Punta Cana flights
Tampa to Denver flights
Fort Lauderdale to Santo Domingo flights
Fort Lauderdale to Atlanta flights
Fort Lauderdale to George Bush Intcntl flights
Miami to George Bush Intcntl flights
Fort Lauderdale to Denver flights
Orlando to Seattle flights
Miami to Bogotá flights
Jacksonville to LaGuardia flights

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 December 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$127Average$219FlexibilityNo cancel feeOn-time62%
DeltaCheapest$238Average$566FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$254Average$508FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$335Average$599FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$360Average$575FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$494Average$671FlexibilityNo cancel feeOn-time69%

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.