$94+ 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 3/25. Fares are subject to change and may not be available on all flights or dates of travel.
RSW — SJU
Apr 13 — Apr 201
Round-trip
1 adult, Economy
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Cheapest flights from Fort Myers to CaribbeanExplore 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 March 14, 2026.
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 March 14, 2026.
This Priceline deal was found by Cheapflights users on 3/10. 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 4/2511:40 am
RSW
- SJU
1 stop12h 49m
Frontier
Wed 4/291:59 am
SJU
- RSW
1 stop8h 46m
Frontier
Deal found 3/10![Frontier logo]()
$223
This Orbitz deal was found by Cheapflights users on 3/9. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/2511:40 am
RSW
- SJU
1 stop12h 49m
Multiple Airlines
Thu 4/304:34 pm
SJU
- RSW
1 stop17h 43m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$225
This CheapOair deal was found by Cheapflights users on 3/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/127:35 am
RSW
- SJU
1 stop18h 54m
Spirit Airlines
Mon 3/1611:14 am
SJU
- RSW
1 stop12h 10m
Spirit Airlines
Deal found 3/11![Spirit Airlines logo]()
$271
This CheapOair deal was found by Cheapflights users on 3/9. 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 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
Tue 4/1410:00 am
SJU
- RSW
1 stop8h 19m
Spirit Airlines
Deal found 3/9![Spirit Airlines logo]()
$290
This Expedia deal was found by Cheapflights users on 3/9. 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.
Thu 3/127:35 am
RSW
- SJU
1 stop18h 54m
Multiple Airlines
Mon 3/161:59 am
SJU
- RSW
1 stop8h 53m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$294
This Southwest deal was found by Cheapflights users on 3/13. 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 5/116:00 pm
RSW
- SJU
1 stop5h 55m
Southwest
Fri 5/156:50 am
SJU
- RSW
2 stops9h 25m
Southwest
Deal found 3/13![Southwest logo]()
$296
This Southwest deal was found by Cheapflights users on 3/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/46:35 am
RSW
- SJU
1 stop8h 20m
Southwest
Fri 5/85:05 am
SJU
- RSW
2 stops11h 10m
Southwest
Deal found 3/8![Southwest logo]()
$298
This Southwest deal was found by Cheapflights users on 3/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/76:10 am
RSW
- SJU
1 stop4h 35m
Southwest
Tue 6/96:00 am
SJU
- RSW
2 stops10h 40m
Southwest
Deal found 3/8![Southwest logo]()
$303
This Southwest deal was found by Cheapflights users on 3/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/2510:30 am
RSW
- SJU
2 stops10h 55m
Southwest
Thu 4/305:35 am
SJU
- RSW
1 stop11h 45m
Southwest
Deal found 3/9![Southwest logo]()
$306
This Delta deal was found by Cheapflights users on 3/9. 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.
Mon 4/275:30 am
RSW
- MBJ
1 stop8h 24m
Delta
Fri 5/14:32 pm
MBJ
- RSW
1 stop7h 16m
Delta
Deal found 3/9![Delta logo]()
$332
This Delta deal was found by Cheapflights users on 3/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:50 am
RSW
- MBJ
1 stop9h 44m
Delta
Thu 8/271:14 pm
MBJ
- RSW
1 stop10h 22m
Delta
Deal found 3/10![Delta logo]()
$352
This Frontier deal was found by Cheapflights users on 3/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/246:20 am
RSW
- PUJ
1 stop10h 09m
Frontier
Thu 3/262:14 pm
PUJ
- RSW
1 stop10h 29m
Frontier
Deal found 3/10![Frontier logo]()
$394
Best flights from Fort Myers to CaribbeanDiscover carefully curated flight deals from Fort Myers to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 14, 2026.
Discover carefully curated flight deals from Fort Myers to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 14, 2026.
This Southwest deal was found by Cheapflights users on 3/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/46:35 am
RSW
- SJU
1 stop8h 20m
Southwest
Fri 5/82:00 pm
SJU
- RSW
1 stop7h 50m
Southwest
Deal found 3/8![Southwest logo]()
$298
This United Airlines deal was found by Cheapflights users on 3/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/163:28 pm
RSW
- SJU
1 stop8h 22m
United Airlines
Mon 5/181:00 am
SJU
- RSW
1 stop10h 06m
United Airlines
Deal found 3/11![United Airlines logo]()
$412
This American Airlines deal was found by Cheapflights users on 3/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/87:41 pm
RSW
- STT
1 stop15h 06m
American Airlines
Tue 5/121:15 pm
STT
- RSW
1 stop9h 53m
American Airlines
Deal found 3/11![American Airlines logo]()
$422
This Kiwi.com deal was found by Cheapflights users on 3/12. 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 4/97:24 pm
RSW
- SDQ
1 stop21h 06m
Multiple Airlines
Thu 4/162:35 pm
SDQ
- RSW
2 stops20h 18m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$474
This Mytrip deal was found by Cheapflights users on 3/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/17:24 pm
RSW
- STT
2 stops20h 04m
Spirit Airlines
Wed 4/82:36 pm
STT
- RSW
3 stops24h 29m
Spirit Airlines
Deal found 3/10![Spirit Airlines logo]()
$510
This Delta deal was found by Cheapflights users on 3/14. 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 6/26:45 am
RSW
- MBJ
1 stop6h 08m
Delta
Fri 6/51:18 pm
MBJ
- RSW
1 stop8h 07m
Delta
Deal found 3/14![Delta logo]()
$513
This FlightHub deal was found by Cheapflights users on 3/11. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/279:43 pm
RSW
- STT
1 stop15h 58m
JetBlue
Sun 4/53:00 pm
STT
- RSW
2 stops9h 54m
JetBlue
Deal found 3/11![JetBlue logo]()
$597
This Southwest deal was found by Cheapflights users on 3/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/16:00 pm
RSW
- SJU
1 stop5h 55m
Southwest
Thu 5/76:50 am
SJU
- RSW
2 stops12h 55m
Southwest
Deal found 3/10![Southwest logo]()
$346
This Southwest deal was found by Cheapflights users on 3/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/76:30 am
RSW
- SJU
2 stops9h 55m
Southwest
Tue 6/96:00 am
SJU
- RSW
2 stops10h 40m
Southwest
Deal found 3/8![Southwest logo]()
$366
This Southwest deal was found by Cheapflights users on 3/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/1511:50 am
RSW
- SJU
2 stops11h 35m
Southwest
Sun 5/175:35 am
SJU
- RSW
2 stops12h 50m
Southwest
Deal found 3/11![Southwest logo]()
$368
This United Airlines deal was found by Cheapflights users on 3/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/67:00 am
RSW
- MBJ
1 stop9h 26m
United Airlines
Wed 6/104:12 pm
MBJ
- RSW
1 stop17h 41m
United Airlines
Deal found 3/10![United Airlines logo]()
$477
This Kiwi.com deal was found by Cheapflights users on 3/12. 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 4/107:24 pm
RSW
- SDQ
1 stop31h 16m
Multiple Airlines
Fri 4/172:35 pm
SDQ
- RSW
2 stops22h 21m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$495
This Delta deal was found by Cheapflights users on 3/12. 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 4/16:32 am
RSW
- STT
1 stop8h 16m
Delta
Wed 4/81:55 pm
STT
- RSW
1 stop10h 41m
Delta
Deal found 3/12![Delta logo]()
$513
This Mytrip deal was found by Cheapflights users on 3/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/89:20 pm
RSW
- STT
3 stops36h 34m
Spirit Airlines
Tue 5/122:04 pm
STT
- RSW
2 stops19h 32m
Spirit Airlines
Deal found 3/11![Spirit Airlines logo]()
$541
This Southwest deal was found by Cheapflights users on 3/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/256:35 am
RSW
- SJU
1 stop8h 20m
Southwest
Sun 5/315:35 am
SJU
- RSW
2 stops12h 50m
Southwest
Deal found 3/11![Southwest logo]()
$417
This American Airlines deal was found by Cheapflights users on 3/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/37:41 pm
RSW
- PUJ
2 stops19h 37m
American Airlines
Fri 7/104:50 pm
PUJ
- RSW
1 stop16h 18m
American Airlines
Deal found 3/9![American Airlines logo]()
$574
This Delta deal was found by Cheapflights users on 3/9. 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.
Tue 3/245:30 am
RSW
- STT
1 stop9h 15m
Delta
Sat 3/2812:49 pm
STT
- RSW
1 stop8h 19m
Delta
Deal found 3/9![Delta logo]()
$541
This FlightHub deal was found by Cheapflights users on 3/9. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/218:00 am
RSW
- MBJ
1 stop27h 15m
JetBlue
Sun 4/268:41 am
MBJ
- RSW
2 stops32h 44m
JetBlue
Deal found 3/9![JetBlue logo]()
$611
This Southwest deal was found by Cheapflights users on 3/12. 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.
Fri 5/18:50 pm
RSW
- SJU
1 stop13h 35m
Southwest
Mon 5/45:05 am
SJU
- RSW
2 stops11h 10m
Southwest
Deal found 3/12![Southwest logo]()
$431
This American Airlines deal was found by Cheapflights users on 3/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/17:00 am
RSW
- STT
1 stop9h 02m
American Airlines
Wed 4/82:05 pm
STT
- RSW
2 stops19h 31m
American Airlines
Deal found 3/10![American Airlines logo]()
$575
This United Airlines deal was found by Cheapflights users on 3/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/187:07 pm
RSW
- AUA
1 stop20h 13m
United Airlines
Sat 4/254:30 pm
AUA
- RSW
1 stop19h 16m
United Airlines
Deal found 3/10![United Airlines logo]()
$585
This Delta deal was found by Cheapflights users on 3/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1312:26 pm
RSW
- SDQ
1 stop12h 12m
Delta
Tue 5/192:49 pm
SDQ
- RSW
1 stop9h 38m
Delta
Deal found 3/10![Delta logo]()
$550
This FlightHub deal was found by Cheapflights users on 3/14. 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.
Tue 6/24:35 pm
RSW
- MBJ
2 stops23h 33m
JetBlue
Fri 6/54:13 pm
MBJ
- RSW
2 stops22h 18m
JetBlue
Deal found 3/14![JetBlue logo]()
$629
This American Airlines deal was found by Cheapflights users on 3/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/236:00 am
RSW
- SDQ
2 stops10h 55m
American Airlines
Thu 4/302:25 pm
SDQ
- RSW
2 stops19h 11m
American Airlines
Deal found 3/9![American Airlines logo]()
$583
This United Airlines deal was found by Cheapflights users on 3/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/15:00 pm
RSW
- AUA
1 stop22h 20m
United Airlines
Sat 8/83:10 pm
AUA
- RSW
1 stop30h 49m
United Airlines
Deal found 3/9![United Airlines logo]()
$585
This Southwest deal was found by Cheapflights users on 3/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/209:10 am
RSW
- SJU
2 stops10h 50m
Southwest
Fri 4/245:05 am
SJU
- RSW
2 stops11h 10m
Southwest
Deal found 3/9![Southwest logo]()
$451
This Mytrip deal was found by Cheapflights users on 3/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/77:24 pm
RSW
- KIN
2 stops18h 11m
Multiple Airlines
Thu 4/912:32 pm
KIN
- RSW
3 stops25h 33m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$664
This Delta deal was found by Cheapflights users on 3/9. 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.
Thu 4/235:30 am
RSW
- SDQ
2 stops13h 04m
Delta
Thu 4/307:59 pm
SDQ
- RSW
1 stop14h 19m
Delta
Deal found 3/9![Delta logo]()
$553
This American Airlines deal was found by Cheapflights users on 3/14. 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 7/206:26 am
RSW
- SDQ
2 stops16h 33m
American Airlines
Fri 7/317:45 pm
SDQ
- RSW
2 stops23h 06m
American Airlines
Deal found 3/14![American Airlines logo]()
$583
This United Airlines deal was found by Cheapflights users on 3/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/155:00 pm
RSW
- AUA
1 stop22h 20m
United Airlines
Tue 7/214:30 pm
AUA
- RSW
1 stop18h 23m
United Airlines
Deal found 3/11![United Airlines logo]()
$595
Last-minute flights from Fort Myers to CaribbeanDiscover last-minute flight deals from Fort Myers to Caribbean. Data last updated March 14, 2026 and is based on user searches.
Discover last-minute flight deals from Fort Myers to Caribbean. Data last updated March 14, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 3/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/196:30 am
RSW
- PUJ
1 stop9h 59m
Frontier
Tue 3/242:14 pm
PUJ
- RSW
1 stop10h 29m
Frontier
Deal found 3/10![Frontier logo]()
$439
This CheapOair deal was found by Cheapflights users on 3/13. 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 3/247:35 am
RSW
- SJU
1 stop18h 54m
Multiple Airlines
Mon 3/309:12 pm
SJU
- RSW
1 stop13h 40m
Multiple Airlines
Deal found 3/13![Multiple Airlines logo]()
$322
This Frontier deal was found by Cheapflights users on 3/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/246:20 am
RSW
- PUJ
1 stop10h 09m
Frontier
Thu 3/262:14 pm
PUJ
- RSW
1 stop10h 29m
Frontier
Deal found 3/10![Frontier logo]()
$394
This Kiwi.com deal was found by Cheapflights users on 3/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/66:46 pm
RSW
- SJU
2 stops31h 15m
Multiple Airlines
Sun 4/192:09 am
SJU
- RSW
1 stop8h 36m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$333
This CheapOair deal was found by Cheapflights users on 3/9. 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 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
Tue 4/1410:00 am
SJU
- RSW
1 stop8h 19m
Spirit Airlines
Deal found 3/9![Spirit Airlines logo]()
$290
This CheapOair deal was found by Cheapflights users on 3/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/107:24 pm
RSW
- SJU
1 stop23h 55m
Spirit Airlines
Sat 4/184:34 pm
SJU
- RSW
1 stop17h 43m
Spirit Airlines
Deal found 3/10![Spirit Airlines logo]()
$336
This American Airlines deal was found by Cheapflights users on 3/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/247:41 pm
RSW
- SJU
1 stop15h 07m
American Airlines
Wed 4/297:25 am
SJU
- RSW
1 stop11h 26m
American Airlines
Deal found 3/9![American Airlines logo]()
$320
This Priceline deal was found by Cheapflights users on 3/10. 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 4/2511:40 am
RSW
- SJU
1 stop12h 49m
Frontier
Wed 4/291:59 am
SJU
- RSW
1 stop8h 46m
Frontier
Deal found 3/10![Frontier logo]()
$223
This Orbitz deal was found by Cheapflights users on 3/9. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/2511:40 am
RSW
- SJU
1 stop12h 49m
Multiple Airlines
Thu 4/304:34 pm
SJU
- RSW
1 stop17h 43m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$225
This Southwest deal was found by Cheapflights users on 3/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/2510:30 am
RSW
- SJU
2 stops10h 55m
Southwest
Thu 4/305:35 am
SJU
- RSW
1 stop11h 45m
Southwest
Deal found 3/9![Southwest logo]()
$306
This Delta deal was found by Cheapflights users on 3/9. 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.
Mon 4/275:30 am
RSW
- MBJ
1 stop8h 24m
Delta
Fri 5/14:32 pm
MBJ
- RSW
1 stop7h 16m
Delta
Deal found 3/9![Delta logo]()
$332
This Priceline deal was found by Cheapflights users on 3/10. 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.
Thu 4/3011:40 am
RSW
- SJU
1 stop12h 49m
Frontier
Fri 5/89:12 pm
SJU
- RSW
1 stop13h 33m
Frontier
Deal found 3/10![Frontier logo]()
$310
One-way flights from Fort Myers to CaribbeanSearch for one-way flight options from Fort Myers to Caribbean. Find affordable one-way fares based on user searches. Data last updated March 14, 2026.
Search for one-way flight options from Fort Myers to Caribbean. Find affordable one-way fares based on user searches. Data last updated March 14, 2026.
This Travelocity deal was found by Cheapflights users on 3/13. 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.
Wed 3/257:35 am
RSW
- SJU
1 stop18h 54m
Spirit Airlines
Deal found 3/13![Spirit Airlines logo]()
$94
This Delta deal was found by Cheapflights users on 3/11. 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.
Mon 4/205:30 am
RSW
- SJU
1 stop10h 53m
Delta
Deal found 3/11![Delta logo]()
$143
This Kiwi.com deal was found by Cheapflights users on 3/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1711:47 am
RSW
- SJU
2 stops37h 32m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 3/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/127:41 pm
RSW
- SJU
1 stop24h 09m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$145
This Southwest deal was found by Cheapflights users on 3/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/186:00 pm
RSW
- SJU
1 stop5h 55m
Southwest
Deal found 3/11![Southwest logo]()
$148
This eDestinos deal was found by Cheapflights users on 3/11. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/177:35 am
RSW
- SJU
1 stop18h 54m
Spirit Airlines
Deal found 3/11![Spirit Airlines logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 3/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/127:41 pm
RSW
- SJU
2 stops15h 37m
Frontier
Deal found 3/10![Frontier logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 3/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/181:51 pm
RSW
- SJU
2 stops52h 08m
Frontier
Deal found 3/10![Frontier logo]()
$162
This Southwest deal was found by Cheapflights users on 3/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/276:35 am
RSW
- NAS
1 stop6h 40m
Southwest
Deal found 3/9![Southwest logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 3/9. 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.
Fri 5/111:12 am
RSW
- SJU
2 stops49h 11m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$167
This Travelocity deal was found by Cheapflights users on 3/10. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/97:36 pm
RSW
- SDQ
1 stop19h 17m
Frontier
Deal found 3/10![Frontier logo]()
$170
This American Airlines deal was found by Cheapflights users on 3/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/162:13 pm
RSW
- SJU
1 stop6h 42m
American Airlines
Deal found 3/11![American Airlines logo]()
$170
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 March 14, 2026.
Round-trip from | $223 (Priceline) |
|---|---|
One-way from | $94 (Travelocity) |
Popular in | July |
Cheapest in | June |
Average price | $465 |
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 March 14, 2026.
Use the filters below to find and compare flights from Fort Myers to Caribbean that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Fort MyersSan Juan
RSW - SJU
RSWSJU
Fort Myers SW Florida Intl
Mon 5/4
6:35 am-2:55 pm
1 stop8h 20m
San Juan Luis Munoz Marin Intl
Fri 5/8
2:00 pm-9:50 pm
1 stop7h 50m
$298
Fort MyersSan Juan
RSW - SJU
RSWSJU
Fort Myers SW Florida Intl
Fri 5/1
6:00 pm-11:55 pm
1 stop5h 55m
San Juan Luis Munoz Marin Intl
Thu 5/7
6:50 am-7:45 pm
2 stops12h 55m
$346
Fort MyersSan Juan
RSW - SJU
RSWSJU
Fort Myers SW Florida Intl
Sun 6/7
6:30 am-4:25 pm
2 stops9h 55m
San Juan Luis Munoz Marin Intl
Tue 6/9
6:00 am-4:40 pm
2 stops10h 40m
$366
Fort MyersSan Juan
RSW - SJU
RSWSJU
Fort Myers SW Florida Intl
Fri 5/15
11:50 am-11:25 pm
2 stops11h 35m
San Juan Luis Munoz Marin Intl
Sun 5/17
5:35 am-6:25 pm
2 stops12h 50m
$368
Fort MyersSan Juan
RSW - SJU
RSWSJU
Fort Myers SW Florida Intl
Sat 5/16
3:28 pm-11:50 pm
1 stop8h 22m
San Juan Luis Munoz Marin Intl
Mon 5/18
1:00 am-11:06 am
1 stop10h 06m
$412
Fort MyersSan Juan
RSW - SJU
RSWSJU
Fort Myers SW Florida Intl
Mon 5/25
6:35 am-2:55 pm
1 stop8h 20m
San Juan Luis Munoz Marin Intl
Sun 5/31
5:35 am-6:25 pm
2 stops12h 50m
$417
Fort MyersSaint Thomas Island
RSW - STT
RSWSTT
Fort Myers SW Florida Intl
Fri 5/8
7:41 pm-10:47 am
1 stop15h 06m
Saint Thomas Island Cyril E King
Tue 5/12
1:15 pm-11:08 pm
1 stop9h 53m
$422
Fort MyersSan Juan
RSW - SJU
RSWSJU
Fort Myers SW Florida Intl
Fri 5/1
8:50 pm-10:25 am
1 stop13h 35m
San Juan Luis Munoz Marin Intl
Mon 5/4
5:05 am-4:15 pm
2 stops11h 10m
$431
Fort MyersSan Juan
RSW - SJU
RSWSJU
Fort Myers SW Florida Intl
Mon 4/20
9:10 am-8:00 pm
2 stops10h 50m
San Juan Luis Munoz Marin Intl
Fri 4/24
5:05 am-4:15 pm
2 stops11h 10m
$451
Fort MyersSanto Domingo
RSW - SDQ
RSWSDQ
Fort Myers SW Florida Intl
Thu 4/9
7:24 pm-4:30 pm
1 stop21h 06m
Santo Domingo Las Americas
Thu 4/16
2:35 pm-10:53 am
2 stops20h 18m
$474
Showing 1-10 of 60 resultsSorted by cheapest first
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.
RSW-SJU
RSW-STT
RSW-SDQ
RSW-MBJ
RSW-PUJ
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
RSW-0CB
RSW-SJU
RSW-STT
RSW-SDQ
RSW-MBJ
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 March 14, 2026.
It’s typically best to fly out from Fort Myers to Caribbean 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
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 March 14, 2026.
See what other customers who have flown with Southwest,Delta, andJetBlue 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.
Boarding
8.1
Overall
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Boarding
8.1
Overall
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Boarding
8.1
Overall
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Boarding
8.1
Overall
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Boarding
8.1
Overall
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Boarding
8.1
Overall
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
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.
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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.
Complete your trip
Complete your trip to Caribbean by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Fort Myers to Caribbean by cabin class
Find flights from Fort Myers to Caribbean, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Fort Myers and Caribbean flights
Browse other Fort Myers and Caribbean flight options. Last updated on March 14, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Fly to Caribbean countries
Consider these flights traveling to countries located in Caribbean.
Fort Myers to Caribbean flights
Consider these flights traveling from Fort Myers to Caribbean.
Top 5 airlines flying from Fort Myers to Caribbean
Discover the top 5 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 March 14, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$138 | Average$259 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$204 | Average$505 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$254 | Average$627 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$333 | Average$586 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$365 | Average$571 | FlexibilityNo cancel fee | On-time71% |