$91+ Cheap flights from Fort Myers (RSW) to Caribbean Islands
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 3/17. Fares are subject to change and may not be available on all flights or dates of travel.
RSW — SJU
Mar 10 — Mar 171
1 adult, Economy
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Find cheap flights from Fort Myers to Caribbean Islands 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
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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 Islands
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Cheapest flights from Fort Myers to Caribbean IslandsExplore the most affordable flight options available from Fort Myers to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 8, 2026.
Explore the most affordable flight options available from Fort Myers to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 8, 2026.
This Frontier deal was found by Cheapflights users on 2/6. 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.
Tue 3/1710:43 am
RSW
- SJU
1 stop13h 46m
Frontier
Mon 3/231:59 am
SJU
- RSW
1 stop8h 53m
Frontier
Deal found 2/6![Frontier logo]()
$182
This Frontier deal was found by Cheapflights users on 2/7. 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.
Tue 4/1411:40 am
RSW
- SJU
1 stop12h 49m
Frontier
Sun 4/191:59 am
SJU
- RSW
1 stop8h 46m
Frontier
Deal found 2/7![Frontier logo]()
$203
This Expedia deal was found by Cheapflights users on 2/6. 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.
Tue 3/36:00 am
RSW
- SJU
1 stop11h 49m
Multiple Airlines
Mon 3/91:59 am
SJU
- RSW
1 stop8h 53m
Multiple Airlines
Deal found 2/6![Multiple Airlines logo]()
$215
This Expedia deal was found by Cheapflights users on 2/7. 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 2/239:31 pm
RSW
- SJU
1 stop14h 14m
Frontier
Thu 2/262:54 am
SJU
- RSW
1 stop18h 42m
Frontier
Deal found 2/7![Frontier logo]()
$224
This Orbitz deal was found by Cheapflights users on 2/6. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/106:00 am
RSW
- SJU
1 stop9h 04m
Frontier
Fri 4/171:59 am
SJU
- RSW
1 stop8h 46m
Frontier
Deal found 2/6![Frontier logo]()
$237
This Frontier deal was found by Cheapflights users on 2/5. 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.
Tue 4/2111:40 am
RSW
- SJU
1 stop12h 49m
Frontier
Sat 4/251:59 am
SJU
- RSW
1 stop8h 46m
Frontier
Deal found 2/5![Frontier logo]()
$238
This Kiwi.com deal was found by Cheapflights users on 2/8. 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 2/1911:02 am
RSW
- SJU
1 stop11h 22m
Frontier
Fri 2/272:54 am
SJU
- RSW
1 stop32h 13m
Frontier
Deal found 2/8![Frontier logo]()
$239
This Kiwi.com deal was found by Cheapflights users on 2/4. 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 2/209:31 pm
RSW
- SJU
1 stop26h 53m
Frontier
Tue 2/244:11 pm
SJU
- RSW
1 stop20h 50m
Frontier
Deal found 2/4![Frontier logo]()
$247
This Expedia deal was found by Cheapflights users on 2/5. 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 3/96:00 am
RSW
- SJU
1 stop11h 54m
Spirit Airlines
Thu 3/1211:14 am
SJU
- RSW
1 stop12h 10m
Spirit Airlines
Deal found 2/5![Spirit Airlines logo]()
$248
This Orbitz deal was found by Cheapflights users on 2/6. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/38:00 am
RSW
- SJU
2 stops15h 59m
Multiple Airlines
Sun 3/81:59 am
SJU
- RSW
1 stop18h 45m
Multiple Airlines
Deal found 2/6![Multiple Airlines logo]()
$262
This Frontier deal was found by Cheapflights users on 2/7. 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 2/2811:02 am
RSW
- PUJ
1 stop23h 00m
Frontier
Sat 3/76:39 pm
PUJ
- RSW
1 stop17h 13m
Frontier
Deal found 2/7![Frontier logo]()
$303
This Orbitz deal was found by Cheapflights users on 2/6. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/1411:02 am
RSW
- SDQ
1 stop23h 18m
Frontier
Sat 2/212:25 pm
SDQ
- RSW
1 stop20h 42m
Frontier
Deal found 2/6![Frontier logo]()
$335
Best flights from Fort Myers to Caribbean IslandsDiscover carefully curated flight deals from Fort Myers to Caribbean Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 8, 2026.
Discover carefully curated flight deals from Fort Myers to Caribbean Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 8, 2026.
This Frontier deal was found by Cheapflights users on 2/6. 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.
Tue 3/1710:43 am
RSW
- SJU
1 stop13h 46m
Frontier
Mon 3/231:59 am
SJU
- RSW
1 stop8h 53m
Frontier
Deal found 2/6![Frontier logo]()
$182
This Travelocity deal was found by Cheapflights users on 2/7. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/137:50 am
RSW
- SJU
1 stop10h 10m
Multiple Airlines
Mon 4/201:59 am
SJU
- RSW
1 stop8h 46m
Multiple Airlines
Deal found 2/7![Multiple Airlines logo]()
$215
This CheapOair deal was found by Cheapflights users on 2/6. 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.
Mon 3/96:00 am
RSW
- SJU
1 stop11h 54m
Spirit Airlines
Thu 3/1211:14 am
SJU
- RSW
1 stop12h 10m
Spirit Airlines
Deal found 2/6![Spirit Airlines logo]()
$248
This Southwest deal was found by Cheapflights users on 2/7. 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.
Mon 5/46:40 am
RSW
- STT
1 stop6h 55m
Southwest
Thu 5/72:30 pm
STT
- RSW
2 stops19h 05m
Southwest
Deal found 2/7![Southwest logo]()
$363
This Expedia deal was found by Cheapflights users on 2/5. 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.
Tue 4/1411:40 am
RSW
- SJU
1 stop12h 49m
Frontier
Mon 4/201:59 am
SJU
- RSW
1 stop8h 46m
Frontier
Deal found 2/5![Frontier logo]()
$203
This Frontier deal was found by Cheapflights users on 2/7. 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.
Tue 4/1411:40 am
RSW
- SJU
1 stop12h 49m
Frontier
Sun 4/191:59 am
SJU
- RSW
1 stop8h 46m
Frontier
Deal found 2/7![Frontier logo]()
$203
This Orbitz deal was found by Cheapflights users on 2/7. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/155:55 pm
RSW
- MBJ
1 stop21h 31m
JetBlue
Fri 5/299:15 am
MBJ
- RSW
2 stops34h 22m
JetBlue
Deal found 2/7![JetBlue logo]()
$465
This Frontier deal was found by Cheapflights users on 2/5. 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 4/1611:40 am
RSW
- SJU
1 stop8h 27m
Frontier
Sun 4/191:59 am
SJU
- RSW
1 stop8h 46m
Frontier
Deal found 2/5![Frontier logo]()
$203
This Delta deal was found by Cheapflights users on 2/5. 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.
Sun 5/105:50 am
RSW
- SDQ
1 stop7h 31m
Delta
Mon 5/187:45 pm
SDQ
- RSW
1 stop15h 35m
Delta
Deal found 2/5![Delta logo]()
$499
This United Airlines deal was found by Cheapflights users on 2/5. 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 4/256:30 am
RSW
- AUA
1 stop9h 10m
United Airlines
Sat 5/23:10 pm
AUA
- RSW
1 stop24h 47m
United Airlines
Deal found 2/5![United Airlines logo]()
$520
This Priceline deal was found by Cheapflights users on 2/8. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/2411:40 am
RSW
- SJU
1 stop8h 27m
Frontier
Mon 4/279:12 pm
SJU
- RSW
1 stop13h 33m
Frontier
Deal found 2/8![Frontier logo]()
$203
This Kiwi.com deal was found by Cheapflights users on 2/5. 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.
Tue 4/1411:40 am
RSW
- SJU
1 stop12h 49m
Multiple Airlines
Tue 4/2111:07 am
SJU
- RSW
2 stops23h 39m
Multiple Airlines
Deal found 2/5![Multiple Airlines logo]()
$273
This CheapOair deal was found by Cheapflights users on 2/6. 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.
Tue 4/77:24 pm
RSW
- SJU
1 stop23h 55m
Spirit Airlines
Mon 4/1310:00 am
SJU
- RSW
1 stop8h 19m
Spirit Airlines
Deal found 2/6![Spirit Airlines logo]()
$278
This American Airlines deal was found by Cheapflights users on 2/6. 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 3/245:26 pm
RSW
- AUA
1 stop18h 07m
American Airlines
Tue 3/314:10 pm
AUA
- RSW
1 stop17h 20m
American Airlines
Deal found 2/6![American Airlines logo]()
$557
This Expedia deal was found by Cheapflights users on 2/7. 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 2/239:31 pm
RSW
- SJU
1 stop14h 14m
Frontier
Thu 2/262:54 am
SJU
- RSW
1 stop18h 42m
Frontier
Deal found 2/7![Frontier logo]()
$224
This Southwest deal was found by Cheapflights users on 2/7. 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 4/266:40 am
RSW
- STT
1 stop6h 30m
Southwest
Fri 5/12:30 pm
STT
- RSW
1 stop7h 15m
Southwest
Deal found 2/7![Southwest logo]()
$368
This Mytrip deal was found by Cheapflights users on 2/4. 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.
Mon 4/137:24 pm
RSW
- STT
2 stops20h 04m
Spirit Airlines
Thu 4/164:40 pm
STT
- RSW
2 stops17h 03m
Spirit Airlines
Deal found 2/4![Spirit Airlines logo]()
$366
This Kiwi.com deal was found by Cheapflights users on 2/7. 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.
Mon 3/97:35 pm
RSW
- SDQ
2 stops17h 45m
Multiple Airlines
Sun 3/153:55 am
SDQ
- RSW
1 stop14h 24m
Multiple Airlines
Deal found 2/7![Multiple Airlines logo]()
$371
This Southwest deal was found by Cheapflights users on 2/4. 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.
Wed 3/186:45 am
RSW
- STT
1 stop7h 35m
Southwest
Wed 3/251:50 pm
STT
- RSW
1 stop8h 20m
Southwest
Deal found 2/4![Southwest logo]()
$379
This Kiwi.com deal was found by Cheapflights users on 2/6. 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.
Sat 4/183:42 pm
RSW
- SDQ
1 stop11h 18m
Multiple Airlines
Sat 4/253:37 pm
SDQ
- RSW
2 stops19h 08m
Multiple Airlines
Deal found 2/6![Multiple Airlines logo]()
$390
This Mytrip deal was found by Cheapflights users on 2/4. 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.
Sun 4/127:24 pm
RSW
- STT
2 stops20h 04m
Spirit Airlines
Thu 4/164:40 pm
STT
- RSW
2 stops17h 03m
Spirit Airlines
Deal found 2/4![Spirit Airlines logo]()
$409
This KAYAK deal was found by Cheapflights users on 2/5. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/68:52 pm
RSW
- AUA
1 stop15h 33m
JetBlue
Mon 3/91:40 pm
AUA
- RSW
1 stop10h 12m
JetBlue
Deal found 2/5![JetBlue logo]()
$501
This Southwest deal was found by Cheapflights users on 2/7. 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 4/266:40 am
RSW
- STT
1 stop6h 30m
Southwest
Thu 4/302:30 pm
STT
- RSW
2 stops19h 05m
Southwest
Deal found 2/7![Southwest logo]()
$418
This Delta deal was found by Cheapflights users on 2/5. 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 5/156:50 am
RSW
- MBJ
1 stop9h 39m
Delta
Tue 5/194:55 pm
MBJ
- RSW
1 stop6h 32m
Delta
Deal found 2/5![Delta logo]()
$517
This United Airlines deal was found by Cheapflights users on 2/5. 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 4/116:30 am
RSW
- AUA
1 stop9h 10m
United Airlines
Sat 4/183:10 pm
AUA
- RSW
1 stop19h 37m
United Airlines
Deal found 2/5![United Airlines logo]()
$520
This Kiwi.com deal was found by Cheapflights users on 2/6. 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.
Mon 3/97:35 pm
RSW
- PUJ
2 stops22h 25m
Multiple Airlines
Sun 3/156:00 pm
PUJ
- RSW
1 stop29h 24m
Multiple Airlines
Deal found 2/6![Multiple Airlines logo]()
$394
This KAYAK deal was found by Cheapflights users on 2/7. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/910:46 am
RSW
- SDQ
1 stop16h 14m
Spirit Airlines
Sun 3/153:55 am
SDQ
- RSW
1 stop14h 24m
Spirit Airlines
Deal found 2/7![Spirit Airlines logo]()
$416
This American Airlines deal was found by Cheapflights users on 2/7. 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.
Mon 6/86:17 pm
RSW
- AUA
2 stops19h 13m
American Airlines
Thu 6/185:07 pm
AUA
- RSW
1 stop15h 59m
American Airlines
Deal found 2/7![American Airlines logo]()
$561
This Kiwi.com deal was found by Cheapflights users on 2/8. 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.
Sun 4/127:41 pm
RSW
- PUJ
2 stops15h 11m
Frontier
Sat 4/1811:47 am
PUJ
- RSW
1 stop22h 58m
Frontier
Deal found 2/8![Frontier logo]()
$349
This Delta deal was found by Cheapflights users on 2/8. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/196:50 am
RSW
- NAS
1 stop9h 05m
Delta
Sat 7/45:20 pm
NAS
- RSW
1 stop7h 16m
Delta
Deal found 2/8![Delta logo]()
$518
Last-minute flights from Fort Myers to Caribbean IslandsDiscover last-minute flight deals from Fort Myers to Caribbean Islands. Data last updated February 8, 2026 and is based on user searches.
Discover last-minute flight deals from Fort Myers to Caribbean Islands. Data last updated February 8, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 2/8. 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 2/1911:02 am
RSW
- SJU
1 stop11h 22m
Frontier
Fri 2/272:54 am
SJU
- RSW
1 stop32h 13m
Frontier
Deal found 2/8![Frontier logo]()
$239
This Kiwi.com deal was found by Cheapflights users on 2/4. 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 2/209:31 pm
RSW
- SJU
1 stop26h 53m
Frontier
Tue 2/244:11 pm
SJU
- RSW
1 stop20h 50m
Frontier
Deal found 2/4![Frontier logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 2/4. 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 2/202:41 pm
RSW
- SJU
1 stop24h 40m
Multiple Airlines
Tue 2/244:31 pm
SJU
- RSW
2 stops20h 30m
Multiple Airlines
Deal found 2/4![Multiple Airlines logo]()
$264
This Expedia deal was found by Cheapflights users on 2/7. 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 2/239:31 pm
RSW
- SJU
1 stop14h 14m
Frontier
Thu 2/262:54 am
SJU
- RSW
1 stop18h 42m
Frontier
Deal found 2/7![Frontier logo]()
$224
This Frontier deal was found by Cheapflights users on 2/7. 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 2/2811:02 am
RSW
- PUJ
1 stop23h 00m
Frontier
Sat 3/76:39 pm
PUJ
- RSW
1 stop17h 13m
Frontier
Deal found 2/7![Frontier logo]()
$303
This Expedia deal was found by Cheapflights users on 2/6. 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.
Tue 3/36:00 am
RSW
- SJU
1 stop11h 49m
Multiple Airlines
Mon 3/91:59 am
SJU
- RSW
1 stop8h 53m
Multiple Airlines
Deal found 2/6![Multiple Airlines logo]()
$215
This Orbitz deal was found by Cheapflights users on 2/6. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/38:00 am
RSW
- SJU
2 stops15h 59m
Multiple Airlines
Sun 3/81:59 am
SJU
- RSW
1 stop18h 45m
Multiple Airlines
Deal found 2/6![Multiple Airlines logo]()
$262
This Expedia deal was found by Cheapflights users on 2/5. 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 3/96:00 am
RSW
- SJU
1 stop11h 54m
Spirit Airlines
Thu 3/1211:14 am
SJU
- RSW
1 stop12h 10m
Spirit Airlines
Deal found 2/5![Spirit Airlines logo]()
$248
This Kiwi.com deal was found by Cheapflights users on 2/7. 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 3/1110:46 am
RSW
- SJU
1 stop8h 20m
Multiple Airlines
Tue 3/173:08 am
SJU
- RSW
2 stops15h 07m
Multiple Airlines
Deal found 2/7![Multiple Airlines logo]()
$278
This Kiwi.com deal was found by Cheapflights users on 2/8. 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.
Mon 3/167:35 pm
RSW
- SJU
2 stops29h 44m
Frontier
Tue 3/243:22 pm
SJU
- RSW
1 stop27h 10m
Frontier
Deal found 2/8![Frontier logo]()
$279
This Frontier deal was found by Cheapflights users on 2/6. 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.
Tue 3/1710:43 am
RSW
- SJU
1 stop13h 46m
Frontier
Mon 3/231:59 am
SJU
- RSW
1 stop8h 53m
Frontier
Deal found 2/6![Frontier logo]()
$182
This Frontier deal was found by Cheapflights users on 2/8. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1810:43 am
RSW
- SJU
1 stop13h 46m
Frontier
Mon 3/231:59 am
SJU
- RSW
1 stop8h 53m
Frontier
Deal found 2/8![Frontier logo]()
$203
One-way flights from Fort Myers to Caribbean IslandsSearch for one-way flight options from Fort Myers to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated February 8, 2026.
Search for one-way flight options from Fort Myers to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated February 8, 2026.
This Priceline deal was found by Cheapflights users on 2/7. 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.
Tue 3/1710:43 am
RSW
- SJU
1 stop13h 46m
Frontier
Deal found 2/7![Frontier logo]()
$91
This Kiwi.com deal was found by Cheapflights users on 2/5. 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 2/209:31 pm
RSW
- SJU
1 stop26h 53m
Frontier
Deal found 2/5![Frontier logo]()
$112
This Delta deal was found by Cheapflights users on 2/5. 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 5/63:00 pm
RSW
- SJU
1 stop8h 13m
Delta
Deal found 2/5![Delta logo]()
$123
This Southwest deal was found by Cheapflights users on 2/4. 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.
Mon 4/206:40 am
RSW
- STT
1 stop6h 55m
Southwest
Deal found 2/4![Southwest logo]()
$127
This Mytrip deal was found by Cheapflights users on 2/5. 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.
Fri 3/277:24 pm
RSW
- SJU
2 stops28h 34m
Spirit Airlines
Deal found 2/5![Spirit Airlines logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 2/7. 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.
Tue 3/177:35 am
RSW
- SJU
2 stops17h 44m
Multiple Airlines
Deal found 2/7![Multiple Airlines logo]()
$149
This Trip.com deal was found by Cheapflights users on 2/5. 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.
Mon 3/97:35 pm
RSW
- SXM
2 stops17h 40m
Multiple Airlines
Deal found 2/5![Multiple Airlines logo]()
$151
This Kiwi.com deal was found by Cheapflights users on 2/4. 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.
Sun 4/127:41 pm
RSW
- AUA
2 stops18h 54m
Multiple Airlines
Deal found 2/4![Multiple Airlines logo]()
$154
This Southwest deal was found by Cheapflights users on 2/6. 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.
Wed 3/116:45 am
RSW
- NAS
1 stop5h 45m
Southwest
Deal found 2/6![Southwest logo]()
$156
This Kiwi.com deal was found by Cheapflights users on 2/5. 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 2/202:41 pm
RSW
- SJU
2 stops28h 02m
Multiple Airlines
Deal found 2/5![Multiple Airlines logo]()
$162
This United Airlines deal was found by Cheapflights users on 2/7. 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.
Mon 4/201:15 pm
RSW
- SJU
1 stop8h 09m
United Airlines
Deal found 2/7![United Airlines logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 2/6. 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 3/184:10 pm
RSW
- SDQ
2 stops13h 15m
Multiple Airlines
Deal found 2/6![Multiple Airlines logo]()
$168
Find flight deals from Fort Myers to Caribbean Islands
Keep the following information in mind while searching for Fort Myers to Caribbean Islands flight deals. Data was last updated February 8, 2026.
Round-trip from | $182 (Frontier) |
|---|---|
One-way from | $91 (Priceline) |
Popular in | November |
Cheapest in | June |
Average price | $507 |
Cheapflights Fare Finder
Customize your flight search to find flights from Fort Myers to Caribbean Islands 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 February 8, 2026.
Use the filters below to find and compare flights from Fort Myers to Caribbean Islands that are best for you.
Fly from
Fort Myers
Fly to
Caribbean Islands
Route
Depart
Return
Price
Fort MyersSan Juan
RSW - SJU
RSWSJU
Fort Myers SW Florida Intl
Tue 3/17
10:43 am-12:29 am
1 stop13h 46m
San Juan Luis Munoz Marin Intl
Mon 3/23
1:59 am-10:52 am
1 stop8h 53m
$182
Fort MyersSan Juan
RSW - SJU
RSWSJU
Fort Myers SW Florida Intl
Tue 4/14
11:40 am-12:29 am
1 stop12h 49m
San Juan Luis Munoz Marin Intl
Mon 4/20
1:59 am-10:45 am
1 stop8h 46m
$203
Fort MyersSan Juan
RSW - SJU
RSWSJU
Fort Myers SW Florida Intl
Tue 4/14
11:40 am-12:29 am
1 stop12h 49m
San Juan Luis Munoz Marin Intl
Sun 4/19
1:59 am-10:45 am
1 stop8h 46m
$203
Fort MyersSan Juan
RSW - SJU
RSWSJU
Fort Myers SW Florida Intl
Thu 4/16
11:40 am-8:07 pm
1 stop8h 27m
San Juan Luis Munoz Marin Intl
Sun 4/19
1:59 am-10:45 am
1 stop8h 46m
$203
Fort MyersSan Juan
RSW - SJU
RSWSJU
Fort Myers SW Florida Intl
Fri 4/24
11:40 am-8:07 pm
1 stop8h 27m
San Juan Luis Munoz Marin Intl
Mon 4/27
9:12 pm-10:45 am
1 stop13h 33m
$203
Fort MyersSan Juan
RSW - SJU
RSWSJU
Fort Myers SW Florida Intl
Mon 4/13
7:50 am-6:00 pm
1 stop10h 10m
San Juan Luis Munoz Marin Intl
Mon 4/20
1:59 am-10:45 am
1 stop8h 46m
$215
Fort MyersSan Juan
RSW - SJU
RSWSJU
Fort Myers SW Florida Intl
Mon 2/23
9:31 pm-12:45 pm
1 stop14h 14m
San Juan Luis Munoz Marin Intl
Thu 2/26
2:54 am-8:36 pm
1 stop18h 42m
$224
Fort MyersSan Juan
RSW - SJU
RSWSJU
Fort Myers SW Florida Intl
Mon 3/9
6:00 am-5:54 pm
1 stop11h 54m
San Juan Luis Munoz Marin Intl
Thu 3/12
11:14 am-11:24 pm
1 stop12h 10m
$248
Fort MyersSan Juan
RSW - SJU
RSWSJU
Fort Myers SW Florida Intl
Tue 4/14
11:40 am-12:29 am
1 stop12h 49m
San Juan Luis Munoz Marin Intl
Tue 4/21
11:07 am-10:46 am
2 stops23h 39m
$273
Fort MyersSan Juan
RSW - SJU
RSWSJU
Fort Myers SW Florida Intl
Tue 4/7
7:24 pm-7:19 pm
1 stop23h 55m
San Juan Luis Munoz Marin Intl
Mon 4/13
10:00 am-6:19 pm
1 stop8h 19m
$278
Showing 1-10 of 60 results
Best time to book a flight from Fort Myers to Caribbean Islands
Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from Fort Myers with our price prediction graph.
RSW-SJU
RSW-STT
RSW-SXM
RSW-AUA
RSW-NAS
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 Islands
RSW-zzEPX
RSW-SJU
RSW-STT
RSW-SXM
RSW-AUA
What is the cheapest month to book a flight from Fort Myers to Caribbean Islands?
Currently, August is the cheapest month in which you can book a flight from Fort Myers to Caribbean Islands (average of $53). Flying from Fort Myers to Caribbean Islands 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 EPX?
Find hourly flight availability from Fort Myers to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 8, 2026.
It’s typically best to fly out from Fort Myers to Caribbean Islands in the evening. Doing so could potentially save you 65% on the flight price compared to flying in the afternoon, which is usually more expensive.
Reviews of airlines servicing Caribbean Islands
Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated February 8, 2026.
Read reviews from past customers who have flown Southwest, Delta, and American Airlines from Fort Myers to Caribbean Islands. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Related info for your journey
Find useful and relevant information for your journey from Fort Myers to Caribbean Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Fort Myers to Caribbean Islands
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Caribbean Islands by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Fort Myers to Caribbean Islands by cabin class
Find flights from Fort Myers to Caribbean Islands, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Fort Myers and Caribbean Islands flights
Browse other Fort Myers and Caribbean Islands flight options. Last updated on February 8, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Fort Myers to Caribbean Islands flights
Consider these flights traveling from Fort Myers to Caribbean Islands.
Top 5 airlines flying from Fort Myers to Caribbean Islands
Discover the top 5 airlines that operate flights from Fort Myers to Caribbean Islands. 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 February 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$138 | Average$244 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$204 | Average$559 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$254 | Average$627 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$333 | Average$573 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$365 | Average$577 | FlexibilityNo cancel fee | On-time71% |