$114+ 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 5/17. Fares are subject to change and may not be available on all flights or dates of travel.
RSW — SJU
May 23 — May 301
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 April 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 April 23, 2026.
This Frontier deal was found by Cheapflights users on 4/19. 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 6/48:01 pm
RSW
- SJU
1 stop8h 00m
Frontier
Sun 6/216:44 am
SJU
- RSW
1 stop12h 37m
Frontier
Deal found 4/19![Frontier logo]()
$239
This Priceline deal was found by Cheapflights users on 4/19. 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.
Fri 5/111:30 am
RSW
- SJU
1 stop22h 20m
Frontier
Tue 5/56:30 am
SJU
- RSW
1 stop12h 46m
Frontier
Deal found 4/19![Frontier logo]()
$244
This Frontier deal was found by Cheapflights users on 4/19. 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 6/78:01 pm
RSW
- SJU
1 stop8h 00m
Frontier
Sun 6/216:44 am
SJU
- RSW
1 stop12h 37m
Frontier
Deal found 4/19![Frontier logo]()
$260
This Frontier deal was found by Cheapflights users on 4/23. 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 5/111:30 am
RSW
- SJU
1 stop12h 59m
Frontier
Thu 5/76:30 am
SJU
- RSW
1 stop12h 46m
Frontier
Deal found 4/23![Frontier logo]()
$290
This Priceline deal was found by Cheapflights users on 4/20. 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 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
Mon 5/47:17 pm
SJU
- RSW
1 stop23h 59m
Frontier
Deal found 4/20![Frontier logo]()
$293
This Kiwi.com deal was found by Cheapflights users on 4/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/111:30 am
RSW
- SJU
1 stop12h 59m
Multiple Airlines
Sun 5/312:59 am
SJU
- RSW
1 stop10h 47m
Multiple Airlines
Deal found 4/20![Multiple Airlines logo]()
$303
This Frontier deal was found by Cheapflights users on 4/21. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/318:01 pm
RSW
- SJU
1 stop8h 00m
Frontier
Sun 6/146:44 am
SJU
- RSW
1 stop12h 37m
Frontier
Deal found 4/21![Frontier logo]()
$305
This Frontier deal was found by Cheapflights users on 4/19. 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 5/111:30 am
RSW
- SJU
1 stop12h 59m
Frontier
Sun 5/31:59 am
SJU
- RSW
1 stop8h 46m
Frontier
Deal found 4/19![Frontier logo]()
$314
This Southwest deal was found by Cheapflights users on 4/20. 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.
Mon 8/1710:15 am
RSW
- SJU
1 stop12h 35m
Southwest
Wed 8/2611:50 am
SJU
- RSW
1 stop8h 00m
Southwest
Deal found 4/20![Southwest logo]()
$316
This Frontier deal was found by Cheapflights users on 4/19. 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.
Tue 6/28:01 pm
RSW
- SJU
1 stop8h 00m
Frontier
Tue 6/166:44 am
SJU
- RSW
1 stop12h 37m
Frontier
Deal found 4/19![Frontier logo]()
$321
This Priceline deal was found by Cheapflights users on 4/23. 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.
Sat 4/2511:40 am
RSW
- SJU
1 stop12h 49m
Frontier
Fri 5/11:59 am
SJU
- RSW
1 stop8h 46m
Frontier
Deal found 4/23![Frontier logo]()
$325
This Southwest deal was found by Cheapflights users on 4/20. 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 8/205:05 pm
RSW
- SJU
1 stop5h 10m
Southwest
Tue 8/255:15 am
SJU
- RSW
1 stop6h 20m
Southwest
Deal found 4/20![Southwest logo]()
$326
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 April 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 April 23, 2026.
This Expedia deal was found by Cheapflights users on 4/18. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/201:19 pm
RSW
- PUJ
1 stop24h 58m
Frontier
Sat 5/2312:07 pm
PUJ
- RSW
1 stop30h 59m
Frontier
Deal found 4/18![Frontier logo]()
$340
This Delta deal was found by Cheapflights users on 4/18. 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.
Sun 5/35:30 am
RSW
- SJU
1 stop10h 53m
Delta
Thu 5/75:43 pm
SJU
- RSW
1 stop6h 44m
Delta
Deal found 4/18![Delta logo]()
$383
This Southwest deal was found by Cheapflights users on 4/21. 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.
Sat 7/47:15 am
RSW
- SJU
1 stop4h 40m
Southwest
Wed 7/86:00 am
SJU
- RSW
2 stops10h 40m
Southwest
Deal found 4/21![Southwest logo]()
$403
This United Airlines deal was found by Cheapflights users on 4/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/91:00 pm
RSW
- SJU
1 stop10h 50m
United Airlines
Wed 5/137:00 am
SJU
- RSW
1 stop8h 57m
United Airlines
Deal found 4/20![United Airlines logo]()
$426
This Expedia deal was found by Cheapflights users on 4/18. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/201:19 pm
RSW
- PUJ
1 stop24h 58m
Multiple Airlines
Sat 5/239:45 am
PUJ
- RSW
2 stops28h 43m
Multiple Airlines
Deal found 4/18![Multiple Airlines logo]()
$503
This American Airlines deal was found by Cheapflights users on 4/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/186:00 am
RSW
- STT
1 stop8h 49m
American Airlines
Mon 5/254:42 pm
STT
- RSW
1 stop16h 25m
American Airlines
Deal found 4/18![American Airlines logo]()
$529
This Expedia deal was found by Cheapflights users on 4/23. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1911:07 am
RSW
- NAS
1 stop25h 44m
JetBlue
Sat 5/232:49 pm
NAS
- RSW
1 stop21h 00m
JetBlue
Deal found 4/23![JetBlue logo]()
$624
This Delta deal was found by Cheapflights users on 4/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/145:35 am
RSW
- MBJ
1 stop10h 59m
Delta
Tue 8/184:59 pm
MBJ
- RSW
1 stop6h 37m
Delta
Deal found 4/23![Delta logo]()
$387
This FlightHub deal was found by Cheapflights users on 4/23. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/98:28 pm
RSW
- PUJ
1 stop15h 27m
Frontier
Mon 6/151:05 pm
PUJ
- RSW
1 stop30h 16m
Frontier
Deal found 4/23![Frontier logo]()
$403
This Southwest deal was found by Cheapflights users on 4/20. 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 5/112:55 pm
RSW
- SJU
2 stops10h 45m
Southwest
Tue 5/55:35 am
SJU
- RSW
2 stops11h 00m
Southwest
Deal found 4/20![Southwest logo]()
$418
This United Airlines deal was found by Cheapflights users on 4/18. 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.
Sun 5/36:45 am
RSW
- SJU
1 stop8h 57m
United Airlines
Wed 5/61:00 am
SJU
- RSW
1 stop8h 43m
United Airlines
Deal found 4/18![United Airlines logo]()
$426
This Delta deal was found by Cheapflights users on 4/22. 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.
Thu 8/275:35 am
RSW
- STT
1 stop8h 17m
Delta
Sat 9/54:10 pm
STT
- RSW
1 stop8h 26m
Delta
Deal found 4/22![Delta logo]()
$403
This Southwest deal was found by Cheapflights users on 4/19. 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 5/96:25 am
RSW
- SJU
1 stop8h 15m
Southwest
Wed 5/135:35 am
SJU
- RSW
1 stop5h 40m
Southwest
Deal found 4/19![Southwest logo]()
$419
This United Airlines deal was found by Cheapflights users on 4/18. 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.
Sat 5/211:49 am
RSW
- SJU
1 stop8h 49m
United Airlines
Wed 5/67:00 am
SJU
- RSW
1 stop8h 57m
United Airlines
Deal found 4/18![United Airlines logo]()
$426
This Southwest deal was found by Cheapflights users on 4/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/36:30 am
RSW
- SJU
2 stops10h 00m
Southwest
Thu 5/75:05 am
SJU
- RSW
2 stops11h 10m
Southwest
Deal found 4/18![Southwest logo]()
$440
This Justfly.com deal was found by Cheapflights users on 4/20. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/118:17 pm
RSW
- PUJ
1 stop18h 00m
Multiple Airlines
Mon 5/1812:30 pm
PUJ
- RSW
1 stop29h 23m
Multiple Airlines
Deal found 4/20![Multiple Airlines logo]()
$548
This Delta deal was found by Cheapflights users on 4/18. 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.
Fri 5/15:30 am
RSW
- SJU
1 stop7h 55m
Delta
Fri 5/86:15 am
SJU
- RSW
1 stop10h 35m
Delta
Deal found 4/18![Delta logo]()
$461
This United Airlines deal was found by Cheapflights users on 4/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/106:45 am
RSW
- STT
1 stop8h 58m
United Airlines
Thu 5/141:22 pm
STT
- RSW
1 stop9h 19m
United Airlines
Deal found 4/21![United Airlines logo]()
$464
This American Airlines deal was found by Cheapflights users on 4/21. 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.
Sun 8/167:39 pm
RSW
- PUJ
2 stops19h 40m
American Airlines
Fri 8/2112:10 pm
PUJ
- RSW
1 stop10h 33m
American Airlines
Deal found 4/21![American Airlines logo]()
$571
This Southwest deal was found by Cheapflights users on 4/23. 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.
Thu 5/712:55 pm
RSW
- SJU
2 stops10h 45m
Southwest
Wed 5/135:35 am
SJU
- RSW
2 stops12h 00m
Southwest
Deal found 4/23![Southwest logo]()
$440
This FlightHub deal was found by Cheapflights users on 4/19. 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.
Fri 5/158:17 pm
RSW
- MBJ
2 stops40h 54m
Frontier
Mon 5/181:16 pm
MBJ
- RSW
2 stops29h 00m
Frontier
Deal found 4/19![Frontier logo]()
$550
This United Airlines deal was found by Cheapflights users on 4/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/86:45 am
RSW
- SJU
1 stop8h 57m
United Airlines
Tue 5/127:40 am
SJU
- RSW
2 stops15h 01m
United Airlines
Deal found 4/20![United Airlines logo]()
$471
This American Airlines deal was found by Cheapflights users on 4/20. 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 10/205:44 pm
RSW
- STT
2 stops18h 56m
American Airlines
Sun 10/255:40 pm
STT
- RSW
2 stops19h 46m
American Airlines
Deal found 4/20![American Airlines logo]()
$576
This Delta deal was found by Cheapflights users on 4/20. 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.
Fri 7/35:37 am
RSW
- STT
1 stop8h 42m
Delta
Tue 7/71:21 pm
STT
- RSW
1 stop11h 34m
Delta
Deal found 4/20![Delta logo]()
$479
This FlightHub deal was found by Cheapflights users on 4/21. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/288:07 pm
RSW
- SXM
1 stop15h 26m
JetBlue
Wed 9/211:20 am
SXM
- RSW
2 stops27h 03m
JetBlue
Deal found 4/21![JetBlue logo]()
$655
This American Airlines deal was found by Cheapflights users on 4/21. 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.
Thu 6/47:35 pm
RSW
- STT
1 stop15h 28m
American Airlines
Thu 7/24:46 pm
STT
- RSW
1 stop16h 22m
American Airlines
Deal found 4/21![American Airlines logo]()
$580
This United Airlines deal was found by Cheapflights users on 4/18. 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.
Tue 5/126:45 am
RSW
- MBJ
1 stop7h 45m
United Airlines
Wed 5/132:40 pm
MBJ
- RSW
1 stop19h 07m
United Airlines
Deal found 4/18![United Airlines logo]()
$481
This Booking.com deal was found by Cheapflights users on 4/22. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/125:30 pm
RSW
- SXM
1 stop20h 50m
Multiple Airlines
Sat 9/196:00 pm
SXM
- RSW
1 stop16h 57m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$646
This Southwest deal was found by Cheapflights users on 4/23. 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.
Fri 8/147:20 am
RSW
- MBJ
1 stop6h 55m
Southwest
Tue 8/182:10 pm
MBJ
- RSW
1 stop4h 40m
Southwest
Deal found 4/23![Southwest logo]()
$504
This JetBlue deal was found by Cheapflights users on 4/22. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/116:00 am
RSW
- AUA
1 stop9h 40m
JetBlue
Fri 5/155:00 pm
AUA
- RSW
1 stop16h 33m
JetBlue
Deal found 4/22![JetBlue logo]()
$687
Last-minute flights from Fort Myers to CaribbeanDiscover last-minute flight deals from Fort Myers to Caribbean. Data last updated April 23, 2026 and is based on user searches.
Discover last-minute flight deals from Fort Myers to Caribbean. Data last updated April 23, 2026 and is based on user searches.
This Priceline deal was found by Cheapflights users on 4/23. 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.
Sat 4/2511:40 am
RSW
- SJU
1 stop12h 49m
Frontier
Fri 5/11:59 am
SJU
- RSW
1 stop8h 46m
Frontier
Deal found 4/23![Frontier logo]()
$325
This Priceline deal was found by Cheapflights users on 4/20. 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 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
Mon 5/47:17 pm
SJU
- RSW
1 stop23h 59m
Frontier
Deal found 4/20![Frontier logo]()
$293
This Priceline deal was found by Cheapflights users on 4/19. 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.
Fri 5/111:30 am
RSW
- SJU
1 stop22h 20m
Frontier
Tue 5/56:30 am
SJU
- RSW
1 stop12h 46m
Frontier
Deal found 4/19![Frontier logo]()
$244
This Frontier deal was found by Cheapflights users on 4/23. 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 5/111:30 am
RSW
- SJU
1 stop12h 59m
Frontier
Thu 5/76:30 am
SJU
- RSW
1 stop12h 46m
Frontier
Deal found 4/23![Frontier logo]()
$290
This Kiwi.com deal was found by Cheapflights users on 4/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/111:30 am
RSW
- SJU
1 stop12h 59m
Multiple Airlines
Sun 5/312:59 am
SJU
- RSW
1 stop10h 47m
Multiple Airlines
Deal found 4/20![Multiple Airlines logo]()
$303
This Frontier deal was found by Cheapflights users on 4/19. 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 5/111:30 am
RSW
- SJU
1 stop12h 59m
Frontier
Sun 5/31:59 am
SJU
- RSW
1 stop8h 46m
Frontier
Deal found 4/19![Frontier logo]()
$314
This Kiwi.com deal was found by Cheapflights users on 4/19. 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 5/111:30 am
RSW
- SJU
1 stop13h 24m
Multiple Airlines
Tue 5/56:00 am
SJU
- RSW
2 stops13h 16m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$316
This Delta deal was found by Cheapflights users on 4/22. 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.
Wed 5/65:30 am
RSW
- SJU
1 stop10h 53m
Delta
Sat 5/95:43 pm
SJU
- RSW
1 stop6h 44m
Delta
Deal found 4/22![Delta logo]()
$326
This Expedia deal was found by Cheapflights users on 4/18. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/201:19 pm
RSW
- PUJ
1 stop24h 58m
Frontier
Sat 5/2312:07 pm
PUJ
- RSW
1 stop30h 59m
Frontier
Deal found 4/18![Frontier logo]()
$340
This Delta deal was found by Cheapflights users on 4/22. 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 5/268:00 am
RSW
- MBJ
1 stop8h 34m
Delta
Mon 6/14:59 pm
MBJ
- RSW
1 stop6h 28m
Delta
Deal found 4/22![Delta logo]()
$387
This Travelocity deal was found by Cheapflights users on 4/19. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/288:01 pm
RSW
- PUJ
1 stop14h 56m
Frontier
Sun 5/3111:45 am
PUJ
- RSW
1 stop24h 39m
Frontier
Deal found 4/19![Frontier logo]()
$350
This Frontier deal was found by Cheapflights users on 4/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/318:01 pm
RSW
- SJU
1 stop8h 00m
Frontier
Sun 6/146:44 am
SJU
- RSW
1 stop12h 37m
Frontier
Deal found 4/20![Frontier logo]()
$239
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 April 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 April 23, 2026.
This Expedia deal was found by Cheapflights users on 4/19. 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.
Sun 5/178:01 pm
RSW
- PUJ
1 stop14h 56m
Frontier
Deal found 4/19![Frontier logo]()
$114
This Kiwi.com deal was found by Cheapflights users on 4/22. 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.
Tue 5/58:01 pm
RSW
- SJU
1 stop19h 49m
Frontier
Deal found 4/22![Frontier logo]()
$117
This Frontier deal was found by Cheapflights users on 4/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/288:01 pm
RSW
- SJU
1 stop8h 00m
Frontier
Deal found 4/20![Frontier logo]()
$122
This Priceline deal was found by Cheapflights users on 4/19. 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.
Sun 5/248:01 pm
RSW
- SJU
1 stop8h 00m
Frontier
Deal found 4/19![Frontier logo]()
$123
This Expedia deal was found by Cheapflights users on 4/21. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/258:16 pm
RSW
- SJU
1 stop7h 41m
Frontier
Deal found 4/21![Frontier logo]()
$130
This Delta deal was found by Cheapflights users on 4/18. 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.
Mon 5/185:35 am
RSW
- MBJ
1 stop10h 59m
Delta
Deal found 4/18![Delta logo]()
$152
This Southwest deal was found by Cheapflights users on 4/23. 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.
Wed 8/268:45 am
RSW
- SJU
2 stops10h 15m
Southwest
Deal found 4/23![Southwest logo]()
$158
This United Airlines deal was found by Cheapflights users on 4/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/81:05 pm
RSW
- SJU
1 stop8h 19m
United Airlines
Deal found 4/19![United Airlines logo]()
$163
This Delta deal was found by Cheapflights users on 4/22. 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 5/195:35 am
RSW
- STT
1 stop8h 16m
Delta
Deal found 4/22![Delta logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 4/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/17:06 pm
RSW
- SJU
2 stops37h 43m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$173
This Delta deal was found by Cheapflights users on 4/22. 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.
Wed 5/136:45 am
RSW
- MBJ
1 stop9h 49m
Delta
Deal found 4/22![Delta logo]()
$181
This Priceline deal was found by Cheapflights users on 4/20. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/218:01 pm
RSW
- SJU
1 stop8h 00m
Frontier
Deal found 4/20![Frontier logo]()
$183
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 April 23, 2026.
Round-trip from | $239 (Frontier) |
|---|---|
One-way from | $114 (Expedia) |
Popular in | July |
Cheapest in | June |
Average price | $496 |
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 April 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 MyersPunta Cana
RSW - PUJ
RSWPUJ
Fort Myers SW Florida Intl
Wed 5/20
1:19 pm-2:17 pm
1 stop24h 58m
Punta Cana
Sat 5/23
12:07 pm-7:06 pm
1 stop30h 59m
$340
Fort MyersSan Juan
RSW - SJU
RSWSJU
Fort Myers SW Florida Intl
Sun 5/3
5:30 am-4:23 pm
1 stop10h 53m
San Juan Luis Munoz Marin Intl
Thu 5/7
5:43 pm-12:27 am
1 stop6h 44m
$383
Fort MyersMontego Bay
RSW - MBJ
RSWMBJ
Fort Myers SW Florida Intl
Fri 8/14
5:35 am-3:34 pm
1 stop10h 59m
Montego Bay Sangster Intl
Tue 8/18
4:59 pm-12:36 am
1 stop6h 37m
$387
Fort MyersSan Juan
RSW - SJU
RSWSJU
Fort Myers SW Florida Intl
Sat 7/4
7:15 am-11:55 am
1 stop4h 40m
San Juan Luis Munoz Marin Intl
Wed 7/8
6:00 am-4:40 pm
2 stops10h 40m
$403
Fort MyersPunta Cana
RSW - PUJ
RSWPUJ
Fort Myers SW Florida Intl
Tue 6/9
8:28 pm-11:55 am
1 stop15h 27m
Punta Cana
Mon 6/15
1:05 pm-7:21 pm
1 stop30h 16m
$403
Fort MyersSaint Thomas Island
RSW - STT
RSWSTT
Fort Myers SW Florida Intl
Thu 8/27
5:35 am-1:52 pm
1 stop8h 17m
Saint Thomas Island Cyril E King
Sat 9/5
4:10 pm-12:36 am
1 stop8h 26m
$403
Fort MyersSan Juan
RSW - SJU
RSWSJU
Fort Myers SW Florida Intl
Fri 5/1
12:55 pm-11:40 pm
2 stops10h 45m
San Juan Luis Munoz Marin Intl
Tue 5/5
5:35 am-4:35 pm
2 stops11h 00m
$418
Fort MyersSan Juan
RSW - SJU
RSWSJU
Fort Myers SW Florida Intl
Sat 5/9
6:25 am-2:40 pm
1 stop8h 15m
San Juan Luis Munoz Marin Intl
Wed 5/13
5:35 am-11:15 am
1 stop5h 40m
$419
Fort MyersSan Juan
RSW - SJU
RSWSJU
Fort Myers SW Florida Intl
Sat 5/9
1:00 pm-11:50 pm
1 stop10h 50m
San Juan Luis Munoz Marin Intl
Wed 5/13
7:00 am-3:57 pm
1 stop8h 57m
$426
Fort MyersSan Juan
RSW - SJU
RSWSJU
Fort Myers SW Florida Intl
Sun 5/3
6:45 am-3:42 pm
1 stop8h 57m
San Juan Luis Munoz Marin Intl
Wed 5/6
1:00 am-9:43 am
1 stop8h 43m
$426
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-PUJ
RSW-SJU
RSW-STT
RSW-NAS
RSW-MBJ
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-PUJ
RSW-SJU
RSW-STT
RSW-NAS
What is the cheapest month to book a flight from Fort Myers to Caribbean?
Currently, February is the cheapest month in which you can book a flight from Fort Myers to Caribbean (average of $138). Flying from Fort Myers to Caribbean in December is currently the most expensive (average of $314). 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 April 23, 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
Crew
8.6
Food
7.0
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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 April 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 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 April 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$168 | Average$256 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$204 | Average$512 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$254 | Average$711 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$325 | Average$603 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$365 | Average$571 | FlexibilityNo cancel fee | On-time71% |