$132+ 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 9/11. Fares are subject to change and may not be available on all flights or dates of travel.
RSW — SJU
Aug 22 — Aug 291
Round-trip
1 adult, Economy
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Find cheap flights from Fort Myers to Caribbean with Cheapflights
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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 July 23, 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 July 23, 2026.
This Priceline deal was found by Cheapflights users on 7/19. 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 8/2010:52 am
RSW
- SJU
1 stop7h 57m
Frontier
Wed 8/265:50 pm
SJU
- RSW
1 stop16h 07m
Frontier
Deal found 7/19![Frontier logo]()
$270
This Frontier deal was found by Cheapflights users on 7/19. 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 9/1012:45 pm
RSW
- SJU
1 stop11h 05m
Frontier
Sun 9/131:59 am
SJU
- RSW
1 stop9h 51m
Frontier
Deal found 7/19![Frontier logo]()
$284
This Frontier deal was found by Cheapflights users on 7/19. 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 9/1012:45 pm
RSW
- SJU
1 stop11h 05m
Frontier
Thu 9/101:59 am
SJU
- RSW
1 stop9h 51m
Frontier
Deal found 7/19![Frontier logo]()
$285
This Frontier deal was found by Cheapflights users on 7/19. 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.
Sun 9/610:52 am
RSW
- SJU
1 stop7h 57m
Frontier
Wed 9/91:59 am
SJU
- RSW
1 stop9h 51m
Frontier
Deal found 7/19![Frontier logo]()
$290
This Frontier deal was found by Cheapflights users on 7/23. 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 9/1012:45 pm
RSW
- SJU
1 stop11h 05m
Frontier
Sun 9/201:59 am
SJU
- RSW
1 stop9h 51m
Frontier
Deal found 7/23![Frontier logo]()
$294
This Frontier deal was found by Cheapflights users on 7/19. 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.
Sun 9/610:52 am
RSW
- SJU
1 stop7h 57m
Frontier
Sat 9/121:59 am
SJU
- RSW
1 stop9h 51m
Frontier
Deal found 7/19![Frontier logo]()
$296
This Frontier deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1812:45 pm
RSW
- SJU
1 stop11h 05m
Frontier
Sun 9/201:59 am
SJU
- RSW
1 stop9h 51m
Frontier
Deal found 7/23![Frontier logo]()
$300
This Frontier deal was found by Cheapflights users on 7/19. 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.
Mon 9/712:50 pm
RSW
- SJU
1 stop14h 09m
Frontier
Wed 9/91:59 am
SJU
- RSW
1 stop9h 51m
Frontier
Deal found 7/19![Frontier logo]()
$310
This Frontier deal was found by Cheapflights users on 7/19. 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.
Mon 9/712:50 pm
RSW
- SJU
1 stop14h 09m
Frontier
Thu 9/101:59 am
SJU
- RSW
1 stop9h 51m
Frontier
Deal found 7/19![Frontier logo]()
$316
This Frontier deal was found by Cheapflights users on 7/22. 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.
Mon 11/212:45 pm
RSW
- SJU
1 stop11h 05m
Frontier
Thu 11/52:59 am
SJU
- RSW
1 stop9h 51m
Frontier
Deal found 7/22![Frontier logo]()
$320
This American Airlines deal was found by Cheapflights users on 7/19. 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 12/57:21 pm
RSW
- STT
2 stops17h 31m
American Airlines
Mon 12/144:16 pm
STT
- RSW
2 stops18h 18m
American Airlines
Deal found 7/19![American Airlines logo]()
$418
This American Airlines deal was found by Cheapflights users on 7/21. 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 12/27:21 pm
RSW
- STT
2 stops20h 37m
American Airlines
Mon 12/72:49 pm
STT
- RSW
2 stops19h 45m
American Airlines
Deal found 7/21![American Airlines logo]()
$439
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 July 23, 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 July 23, 2026.
This Southwest deal was found by Cheapflights users on 7/22. 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 9/98:45 am
RSW
- SJU
2 stops10h 15m
Southwest
Sat 9/126:25 am
SJU
- RSW
1 stop5h 25m
Southwest
Deal found 7/22![Southwest logo]()
$356
This Delta deal was found by Cheapflights users on 7/19. 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 9/87:00 am
RSW
- SJU
1 stop9h 49m
Delta
Thu 9/107:00 am
SJU
- RSW
1 stop8h 21m
Delta
Deal found 7/19![Delta logo]()
$396
This American Airlines deal was found by Cheapflights users on 7/19. 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 12/55:23 pm
RSW
- STT
2 stops19h 29m
American Airlines
Mon 12/1412:27 pm
STT
- RSW
1 stop9h 11m
American Airlines
Deal found 7/19![American Airlines logo]()
$418
This Expedia deal was found by Cheapflights users on 7/19. 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 11/256:25 pm
RSW
- NAS
1 stop26h 00m
Air Canada
Sun 11/292:05 pm
NAS
- RSW
1 stop23h 29m
Air Canada
Deal found 7/19![Air Canada logo]()
$442
This Priceline deal was found by Cheapflights users on 7/23. 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 8/2812:50 pm
RSW
- SDQ
1 stop22h 13m
Frontier
Sat 9/512:18 pm
SDQ
- RSW
1 stop21h 39m
Frontier
Deal found 7/23![Frontier logo]()
$451
This United Airlines deal was found by Cheapflights users on 7/22. 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 10/319:15 am
RSW
- SJU
1 stop10h 45m
United Airlines
Fri 11/62:35 pm
SJU
- RSW
1 stop10h 01m
United Airlines
Deal found 7/22![United Airlines logo]()
$456
This JetBlue deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/288:43 pm
RSW
- SXM
1 stop14h 50m
JetBlue
Wed 9/211:20 am
SXM
- RSW
1 stop12h 35m
JetBlue
Deal found 7/20![JetBlue logo]()
$592
This Travelocity deal was found by Cheapflights users on 7/18. 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.
Tue 9/86:05 am
RSW
- PUJ
1 stop9h 25m
Multiple Airlines
Sat 9/125:05 pm
PUJ
- RSW
2 stops17h 49m
Multiple Airlines
Deal found 7/18![Multiple Airlines logo]()
$593
This Southwest deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/227:30 am
RSW
- SJU
2 stops10h 40m
Southwest
Tue 9/298:20 am
SJU
- RSW
2 stops11h 30m
Southwest
Deal found 7/21![Southwest logo]()
$356
This Southwest deal was found by Cheapflights users on 7/20. 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 9/1811:55 am
RSW
- SJU
2 stops10h 15m
Southwest
Mon 9/2110:00 am
SJU
- RSW
2 stops10h 10m
Southwest
Deal found 7/20![Southwest logo]()
$356
This Delta deal was found by Cheapflights users on 7/22. 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 11/32:42 pm
RSW
- SJU
1 stop7h 17m
Delta
Mon 11/96:35 pm
SJU
- RSW
1 stop7h 00m
Delta
Deal found 7/22![Delta logo]()
$436
This Southwest deal was found by Cheapflights users on 7/20. 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.
Thu 10/82:25 pm
RSW
- SJU
2 stops9h 55m
Southwest
Sun 10/185:00 am
SJU
- RSW
1 stop6h 50m
Southwest
Deal found 7/20![Southwest logo]()
$376
This Delta deal was found by Cheapflights users on 7/19. 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 10/217:00 am
RSW
- SJU
1 stop9h 33m
Delta
Sat 10/245:43 pm
SJU
- RSW
1 stop6h 48m
Delta
Deal found 7/19![Delta logo]()
$438
This FlightHub deal was found by Cheapflights users on 7/19. 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.
Wed 7/298:09 pm
RSW
- PUJ
1 stop18h 16m
Frontier
Sun 8/211:50 am
PUJ
- RSW
1 stop22h 53m
Frontier
Deal found 7/19![Frontier logo]()
$497
This Southwest deal was found by Cheapflights users on 7/21. 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.
Thu 9/1011:55 am
RSW
- SJU
2 stops11h 10m
Southwest
Mon 9/2110:00 am
SJU
- RSW
2 stops10h 10m
Southwest
Deal found 7/21![Southwest logo]()
$378
This American Airlines deal was found by Cheapflights users on 7/19. 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 10/58:00 am
RSW
- AUA
1 stop7h 16m
American Airlines
Wed 10/142:30 pm
AUA
- RSW
2 stops20h 28m
American Airlines
Deal found 7/19![American Airlines logo]()
$550
This Delta deal was found by Cheapflights users on 7/20. 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 8/316:46 am
RSW
- MBJ
1 stop9h 48m
Delta
Fri 9/41:09 pm
MBJ
- RSW
1 stop10h 31m
Delta
Deal found 7/20![Delta logo]()
$482
This Air Canada deal was found by Cheapflights users on 7/18. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/72:30 pm
RSW
- GCM
2 stops45h 40m
Air Canada
Fri 12/111:10 pm
GCM
- RSW
2 stops24h 24m
Air Canada
Deal found 7/18![Air Canada logo]()
$589
This Southwest deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2011:35 am
RSW
- SJU
2 stops10h 15m
Southwest
Fri 10/236:30 am
SJU
- RSW
2 stops9h 40m
Southwest
Deal found 7/19![Southwest logo]()
$411
This United Airlines deal was found by Cheapflights users on 7/18. 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 9/79:00 am
RSW
- AUA
1 stop30h 20m
United Airlines
Wed 9/164:30 pm
AUA
- RSW
1 stop25h 37m
United Airlines
Deal found 7/18![United Airlines logo]()
$603
This Travelocity deal was found by Cheapflights users on 7/23. 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.
Sat 10/248:20 pm
RSW
- SXM
2 stops16h 15m
Multiple Airlines
Sat 10/312:40 pm
SXM
- RSW
2 stops51h 50m
Multiple Airlines
Deal found 7/23![Multiple Airlines logo]()
$622
This American Airlines deal was found by Cheapflights users on 7/20. 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 8/1812:50 pm
RSW
- AUA
1 stop24h 00m
American Airlines
Wed 8/264:50 pm
AUA
- RSW
2 stops21h 18m
American Airlines
Deal found 7/20![American Airlines logo]()
$579
This JetBlue deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/48:43 pm
RSW
- AUA
1 stop16h 32m
JetBlue
Fri 9/115:00 pm
AUA
- RSW
1 stop16h 53m
JetBlue
Deal found 7/21![JetBlue logo]()
$654
This United Airlines deal was found by Cheapflights users on 7/23. 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 9/217:00 am
RSW
- PUJ
1 stop8h 30m
United Airlines
Wed 9/234:40 pm
PUJ
- RSW
1 stop18h 21m
United Airlines
Deal found 7/23![United Airlines logo]()
$626
This Southwest deal was found by Cheapflights users on 7/20. 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 10/92:25 pm
RSW
- SJU
2 stops9h 55m
Southwest
Sun 10/185:00 am
SJU
- RSW
2 stops11h 45m
Southwest
Deal found 7/20![Southwest logo]()
$431
This American Airlines deal was found by Cheapflights users on 7/23. 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 8/286:34 pm
RSW
- SDQ
2 stops18h 48m
American Airlines
Sat 9/510:27 am
SDQ
- RSW
2 stops26h 43m
American Airlines
Deal found 7/23![American Airlines logo]()
$595
This United deal was found by Cheapflights users on 7/23. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/197:00 am
RSW
- STT
1 stop8h 43m
Multiple Airlines
Tue 9/2210:49 am
STT
- RSW
2 stops29h 06m
Multiple Airlines
Deal found 7/23![Multiple Airlines logo]()
$663
This Delta deal was found by Cheapflights users on 7/18. 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 9/85:30 am
RSW
- MBJ
1 stop8h 31m
Delta
Fri 9/112:26 pm
MBJ
- RSW
1 stop6h 08m
Delta
Deal found 7/18![Delta logo]()
$552
This JetBlue deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:04 am
RSW
- UVF
1 stop9h 08m
JetBlue
Mon 8/241:59 pm
UVF
- RSW
1 stop9h 56m
JetBlue
Deal found 7/20![JetBlue logo]()
$680
This FlightHub deal was found by Cheapflights users on 7/22. 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 9/1812:45 pm
RSW
- MBJ
2 stops25h 46m
Frontier
Sun 9/202:49 pm
MBJ
- RSW
2 stops42h 50m
Frontier
Deal found 7/22![Frontier logo]()
$696
Last-minute flights from Fort Myers to CaribbeanDiscover last-minute flight deals from Fort Myers to Caribbean. Data last updated July 23, 2026 and is based on user searches.
Discover last-minute flight deals from Fort Myers to Caribbean. Data last updated July 23, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 7/19. 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 8/165:35 am
RSW
- SJU
1 stop6h 11m
Delta
Sun 9/65:49 pm
SJU
- RSW
1 stop6h 51m
Delta
Deal found 7/19![Delta logo]()
$396
This Southwest deal was found by Cheapflights users on 7/22. 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 8/176:10 am
RSW
- SJU
2 stops10h 45m
Southwest
Tue 8/185:15 am
SJU
- RSW
2 stops11h 45m
Southwest
Deal found 7/22![Southwest logo]()
$391
This Priceline deal was found by Cheapflights users on 7/22. 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.
Wed 8/196:04 am
RSW
- SJU
1 stop18h 09m
Multiple Airlines
Wed 8/2610:39 am
SJU
- RSW
1 stop23h 18m
Multiple Airlines
Deal found 7/22![Multiple Airlines logo]()
$392
This Priceline deal was found by Cheapflights users on 7/19. 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 8/2010:52 am
RSW
- SJU
1 stop7h 57m
Frontier
Wed 8/265:50 pm
SJU
- RSW
1 stop16h 07m
Frontier
Deal found 7/19![Frontier logo]()
$270
This Southwest deal was found by Cheapflights users on 7/19. 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.
Thu 8/206:10 am
RSW
- SJU
2 stops10h 45m
Southwest
Wed 8/266:00 am
SJU
- RSW
1 stop11h 00m
Southwest
Deal found 7/19![Southwest logo]()
$376
This Southwest deal was found by Cheapflights users on 7/19. 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 8/226:25 am
RSW
- SJU
2 stops10h 15m
Southwest
Wed 8/266:00 am
SJU
- RSW
1 stop14h 10m
Southwest
Deal found 7/19![Southwest logo]()
$356
This Priceline deal was found by Cheapflights users on 7/21. 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 8/2710:52 am
RSW
- SJU
1 stop7h 57m
Frontier
Thu 9/37:55 pm
SJU
- RSW
1 stop16h 05m
Frontier
Deal found 7/21![Frontier logo]()
$290
This Kiwi.com deal was found by Cheapflights users on 7/19. 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 8/277:00 am
RSW
- SJU
1 stop16h 59m
Multiple Airlines
Sun 8/303:10 am
SJU
- RSW
2 stops19h 58m
Multiple Airlines
Deal found 7/19![Multiple Airlines logo]()
$375
This American Airlines deal was found by Cheapflights users on 7/19. 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 8/276:31 pm
RSW
- STT
2 stops21h 21m
American Airlines
Wed 9/21:49 pm
STT
- RSW
2 stops20h 25m
American Airlines
Deal found 7/19![American Airlines logo]()
$418
This American Airlines deal was found by Cheapflights users on 7/19. 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 8/276:31 pm
RSW
- STT
2 stops21h 21m
American Airlines
Sat 9/53:43 pm
STT
- RSW
1 stop7h 07m
American Airlines
Deal found 7/19![American Airlines logo]()
$478
This Priceline deal was found by Cheapflights users on 7/23. 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 8/2812:50 pm
RSW
- SDQ
1 stop22h 13m
Frontier
Sat 9/512:18 pm
SDQ
- RSW
1 stop21h 39m
Frontier
Deal found 7/23![Frontier logo]()
$451
This Delta deal was found by Cheapflights users on 7/20. 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 8/316:46 am
RSW
- MBJ
1 stop9h 48m
Delta
Fri 9/41:09 pm
MBJ
- RSW
1 stop10h 31m
Delta
Deal found 7/20![Delta logo]()
$482
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 July 23, 2026.
Search for one-way flight options from Fort Myers to Caribbean. Find affordable one-way fares based on user searches. Data last updated July 23, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/22. 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 9/1112:45 pm
RSW
- SJU
1 stop11h 05m
Frontier
Deal found 7/22![Frontier logo]()
$132
This Frontier deal was found by Cheapflights users on 7/19. 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.
Mon 10/1912:45 pm
RSW
- SJU
1 stop11h 05m
Frontier
Deal found 7/19![Frontier logo]()
$142
This Frontier deal was found by Cheapflights users on 7/19. 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.
Sun 10/1812:45 pm
RSW
- SJU
1 stop11h 05m
Frontier
Deal found 7/19![Frontier logo]()
$148
This Priceline deal was found by Cheapflights users on 7/22. 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 11/1312:45 pm
RSW
- SJU
1 stop22h 19m
Frontier
Deal found 7/22![Frontier logo]()
$159
This Kiwi.com deal was found by Cheapflights users on 7/19. 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 11/212:45 pm
RSW
- SJU
2 stops35h 12m
Multiple Airlines
Deal found 7/19![Multiple Airlines logo]()
$164
This Frontier deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/612:45 pm
RSW
- SJU
1 stop11h 05m
Frontier
Deal found 7/19![Frontier logo]()
$168
This Kiwi.com deal was found by Cheapflights users on 7/19. 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 10/217:00 am
RSW
- SJU
2 stops16h 38m
Multiple Airlines
Deal found 7/19![Multiple Airlines logo]()
$177
This Southwest deal was found by Cheapflights users on 7/20. 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 8/198:45 am
RSW
- SJU
2 stops9h 25m
Southwest
Deal found 7/20![Southwest logo]()
$178
This Kiwi.com deal was found by Cheapflights users on 7/19. 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 10/2312:45 pm
RSW
- SJU
2 stops35h 12m
Frontier
Deal found 7/19![Frontier logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 7/19. 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 11/311:34 am
RSW
- SJU
2 stops12h 23m
Frontier
Deal found 7/19![Frontier logo]()
$184
This Delta deal was found by Cheapflights users on 7/20. 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 1/55:35 am
RSW
- STT
1 stop6h 05m
Delta
Deal found 7/20![Delta logo]()
$192
This Southwest deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/157:10 am
RSW
- NAS
1 stop5h 05m
Southwest
Deal found 7/23![Southwest logo]()
$192
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 July 23, 2026.
Round-trip from | $270 (Priceline) |
|---|---|
One-way from | $132 (Kiwi.com) |
Popular in | July |
Cheapest in | September |
Average price | $629 |
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 July 23, 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
Wed 9/9
8:45 am-7:00 pm
2 stops10h 15m
San Juan Luis Munoz Marin Intl
Sat 9/12
6:25 am-11:50 am
1 stop5h 25m
$356
Fort MyersSan Juan
RSW - SJU
RSWSJU
Fort Myers SW Florida Intl
Tue 9/22
7:30 am-6:10 pm
2 stops10h 40m
San Juan Luis Munoz Marin Intl
Tue 9/29
8:20 am-7:50 pm
2 stops11h 30m
$356
Fort MyersSan Juan
RSW - SJU
RSWSJU
Fort Myers SW Florida Intl
Fri 9/18
11:55 am-10:10 pm
2 stops10h 15m
San Juan Luis Munoz Marin Intl
Mon 9/21
10:00 am-8:10 pm
2 stops10h 10m
$356
Fort MyersSan Juan
RSW - SJU
RSWSJU
Fort Myers SW Florida Intl
Thu 10/8
2:25 pm-12:20 am
2 stops9h 55m
San Juan Luis Munoz Marin Intl
Sun 10/18
5:00 am-11:50 am
1 stop6h 50m
$376
Fort MyersSan Juan
RSW - SJU
RSWSJU
Fort Myers SW Florida Intl
Thu 9/10
11:55 am-11:05 pm
2 stops11h 10m
San Juan Luis Munoz Marin Intl
Mon 9/21
10:00 am-8:10 pm
2 stops10h 10m
$378
Fort MyersSan Juan
RSW - SJU
RSWSJU
Fort Myers SW Florida Intl
Tue 9/8
7:00 am-4:49 pm
1 stop9h 49m
San Juan Luis Munoz Marin Intl
Thu 9/10
7:00 am-3:21 pm
1 stop8h 21m
$396
Fort MyersSan Juan
RSW - SJU
RSWSJU
Fort Myers SW Florida Intl
Tue 10/20
11:35 am-9:50 pm
2 stops10h 15m
San Juan Luis Munoz Marin Intl
Fri 10/23
6:30 am-4:10 pm
2 stops9h 40m
$411
Fort MyersSaint Thomas Island
RSW - STT
RSWSTT
Fort Myers SW Florida Intl
Sat 12/5
5:23 pm-1:52 pm
2 stops19h 29m
Saint Thomas Island Cyril E King
Mon 12/14
12:27 pm-8:38 pm
1 stop9h 11m
$418
Fort MyersSan Juan
RSW - SJU
RSWSJU
Fort Myers SW Florida Intl
Fri 10/9
2:25 pm-12:20 am
2 stops9h 55m
San Juan Luis Munoz Marin Intl
Sun 10/18
5:00 am-4:45 pm
2 stops11h 45m
$431
Quickest round-trip
Fort MyersSan Juan
RSW - SJU
RSWSJU
Fort Myers SW Florida Intl
Tue 11/3
2:42 pm-10:59 pm
1 stop7h 17m
San Juan Luis Munoz Marin Intl
Mon 11/9
6:35 pm-12:35 am
1 stop7h 00m
$436
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-AUA
RSW-PUJ
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
RSW-0CB
RSW-SJU
RSW-STT
RSW-AUA
RSW-PUJ
What is the cheapest month to book a flight from Fort Myers to Caribbean?
Currently, January is the cheapest month in which you can book a flight from Fort Myers to Caribbean (average of $430). Flying from Fort Myers to Caribbean in July is currently the most expensive (average of $670). 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.
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 July 23, 2026.
See what other customers who have flown with Southwest,Delta, andAmerican 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.
Crew
8.6
Comfort
8.0
Boarding
8.1
Food
7.0
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Comfort
8.0
Boarding
8.1
Food
7.0
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Comfort
8.0
Boarding
8.1
Food
7.0
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Comfort
8.0
Boarding
8.1
Food
7.0
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Comfort
8.0
Boarding
8.1
Food
7.0
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
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 July 23, 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 4 airlines flying from Fort Myers to Caribbean
Discover the top 4 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 July 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$138 | Average$259 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$245 | Average$572 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$325 | Average$594 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$365 | Average$600 | FlexibilityNo cancel fee | On-time71% |