$118+ Cheap flights from Fort Myers (RSW) to Caribbean
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/27. Fares are subject to change and may not be available on all flights or dates of travel.
RSW — SJU
Oct 10 — Oct 171
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 September 10, 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 September 10, 2026.
This Trip.com deal was found by Cheapflights users on 9/8. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/245:40 pm -
1 stop16h 33m
Wed 9/305:27 pm -
1 stop18h 24m
Deal found 9/8![Frontier logo]()
$241
This Travelocity deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/205:40 pm -
1 stop16h 33m
Thu 9/246:55 pm -
1 stop16h 56m
Deal found 9/5![Frontier logo]()
$276
This Frontier deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2110:06 am -
1 stop8h 33m
Thu 9/2412:59 am -
1 stop10h 52m
Deal found 9/6![Frontier logo]()
$306
This Priceline deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1412:46 pm -
1 stop21h 27m
Sat 9/1912:59 am -
1 stop15h 46m
Deal found 9/7![Frontier logo]()
$308
This Southwest deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/237:15 am -
1 stop4h 40m
Wed 10/2812:40 pm -
1 stop9h 25m
Deal found 9/7![Southwest logo]()
$310
This American Airlines deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/288:00 am -
2 stops14h 09m
Sat 11/77:05 am -
1 stop15h 56m
Deal found 9/7![American Airlines logo]()
$315
This American Airlines deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/294:14 pm -
2 stops18h 46m
Sat 10/106:00 am -
1 stop16h 22m
Deal found 9/7![American Airlines logo]()
$316
This American Airlines deal was found by Cheapflights users on 9/9. 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.
Tue 11/36:24 pm -
2 stops15h 21m
Tue 11/107:30 am -
2 stops15h 21m
Deal found 9/9![American Airlines logo]()
$321
This Priceline deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/912:45 pm -
1 stop11h 09m
Sun 10/1112:59 am -
1 stop10h 51m
Deal found 9/7![Frontier logo]()
$326
This Kiwi.com deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/77:00 am -
2 stops40h 59m
Sat 11/147:15 am -
1 stop29h 39m
Deal found 9/6![Multiple Airlines logo]()
$329
This Priceline deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/127:44 pm -
1 stop18h 17m
Sun 12/202:13 pm -
1 stop23h 02m
Deal found 9/7![Frontier logo]()
$330
This Expedia deal was found by Cheapflights users on 9/9. 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 9/1712:46 pm -
1 stop21h 27m
Sun 9/202:51 pm -
1 stop18h 30m
Deal found 9/9![Frontier logo]()
$336
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 September 10, 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 September 10, 2026.
This Southwest deal was found by Cheapflights users on 9/9. 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.
Wed 10/75:40 pm -
1 stop6h 10m
Wed 10/145:50 am -
1 stop11h 15m
Deal found 9/9![Southwest logo]()
$310
This American Airlines deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/76:50 pm -
2 stops18h 27m
Mon 2/156:36 pm -
2 stops17h 50m
Deal found 9/7![American Airlines logo]()
$405
This Air Canada deal was found by Cheapflights users on 9/9. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/46:25 pm -
2 stops18h 50m
Sun 12/62:05 pm -
1 stop23h 29m
Deal found 9/9![Air Canada logo]()
$454
This Delta deal was found by Cheapflights users on 9/9. 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.
Sun 2/75:35 am -
1 stop6h 05m
Mon 2/154:15 pm -
1 stop9h 20m
Deal found 9/9![Delta logo]()
$469
This Expedia deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/248:20 pm -
1 stop15h 30m
Sat 10/314:25 pm -
1 stop20h 35m
Deal found 9/7![Multiple Airlines logo]()
$548
This FlightHub deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/133:53 pm -
2 stops21h 15m
Sat 12/192:21 pm -
1 stop28h 28m
Deal found 9/5![Frontier logo]()
$613
This United Airlines deal was found by Cheapflights users on 9/8. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/186:50 am -
1 stop8h 40m
Mon 10/2611:16 am -
1 stop24h 13m
Deal found 9/8![United Airlines logo]()
$621
This Southwest deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/267:20 am -
1 stop9h 20m
Tue 9/296:00 am -
1 stop11h 00m
Deal found 9/5![Southwest logo]()
$386
This Southwest deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/67:20 am -
1 stop4h 30m
Tue 10/135:50 am -
1 stop11h 15m
Deal found 9/6![Southwest logo]()
$386
This Air Canada deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/216:25 pm -
2 stops18h 50m
Fri 11/272:05 pm -
1 stop23h 29m
Deal found 9/6![Air Canada logo]()
$462
This American Airlines deal was found by Cheapflights users on 9/8. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/17:46 am -
1 stop8h 07m
Mon 2/85:43 pm -
1 stop17h 40m
Deal found 9/8![American Airlines logo]()
$464
This Southwest deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/67:20 am -
1 stop6h 15m
Mon 10/126:30 am -
1 stop5h 15m
Deal found 9/6![Southwest logo]()
$386
This Southwest deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/77:05 am -
2 stops11h 10m
Mon 11/97:30 am -
1 stop5h 15m
Deal found 9/6![Southwest logo]()
$386
This American Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/174:56 pm -
2 stops20h 58m
Sun 1/243:51 pm -
2 stops19h 46m
Deal found 9/6![American Airlines logo]()
$468
This Air Canada deal was found by Cheapflights users on 9/8. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/156:25 pm -
1 stop20h 20m
Thu 11/193:45 pm -
2 stops26h 45m
Deal found 9/8![Air Canada logo]()
$485
This American Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/54:47 pm -
2 stops18h 30m
Mon 12/143:15 pm -
2 stops20h 02m
Deal found 9/5![American Airlines logo]()
$469
This Delta deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/45:35 am -
1 stop6h 05m
Sun 2/74:15 pm -
1 stop7h 53m
Deal found 9/6![Delta logo]()
$573
This Southwest deal was found by Cheapflights users on 9/8. 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.
Thu 10/82:50 pm -
2 stops9h 35m
Thu 10/1510:10 am -
2 stops10h 05m
Deal found 9/8![Southwest logo]()
$396
This Kiwi.com deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/299:30 pm -
1 stop31h 45m
Thu 11/58:00 pm -
1 stop15h 36m
Deal found 9/5![Multiple Airlines logo]()
$604
This Orbitz deal was found by Cheapflights users on 9/8. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/86:25 pm -
1 stop21h 00m
Wed 11/185:25 pm -
1 stop19h 35m
Deal found 9/8![Air Canada logo]()
$504
This Southwest deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/86:20 am -
2 stops10h 30m
Sat 11/148:45 am -
2 stops11h 35m
Deal found 9/5![Southwest logo]()
$411
This United Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/127:00 am -
1 stop7h 39m
Sun 12/133:45 pm -
1 stop7h 41m
Deal found 9/5![United Airlines logo]()
$662
This Delta deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/107:00 am -
1 stop5h 51m
Wed 11/183:28 pm -
1 stop6h 09m
Deal found 9/5![Delta logo]()
$610
This Air Canada deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/39:45 pm -
2 stops20h 00m
Wed 12/97:45 pm -
2 stops22h 45m
Deal found 9/6![Air Canada logo]()
$506
This United Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/58:50 pm -
1 stop18h 35m
Wed 12/95:35 pm -
1 stop18h 58m
Deal found 9/5![United Airlines logo]()
$669
This Delta deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/118:10 am -
1 stop8h 47m
Tue 11/172:16 pm -
1 stop10h 24m
Deal found 9/5![Delta logo]()
$610
This American Airlines deal was found by Cheapflights users on 9/8. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/87:28 pm -
1 stop17h 49m
Wed 11/185:59 pm -
2 stops17h 49m
Deal found 9/8![American Airlines logo]()
$560
This Southwest deal was found by Cheapflights users on 9/9. 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.
Wed 11/1810:35 am -
2 stops10h 15m
Fri 11/205:35 am -
1 stop7h 10m
Deal found 9/9![Southwest logo]()
$423
This Air Canada deal was found by Cheapflights users on 9/9. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/262:30 pm -
1 stop32h 05m
Thu 10/299:40 pm -
1 stop19h 50m
Deal found 9/9![Air Canada logo]()
$521
This American Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/207:00 am -
1 stop8h 12m
Fri 10/234:12 pm -
1 stop23h 43m
Deal found 9/6![American Airlines logo]()
$575
Last-minute flights from Fort Myers to CaribbeanDiscover last-minute flight deals from Fort Myers to Caribbean. Data last updated September 10, 2026 and is based on user searches.
Discover last-minute flight deals from Fort Myers to Caribbean. Data last updated September 10, 2026 and is based on user searches.
This Priceline deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1412:46 pm -
1 stop21h 27m
Sat 9/1912:59 am -
1 stop15h 46m
Deal found 9/7![Frontier logo]()
$308
This Expedia deal was found by Cheapflights users on 9/9. 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 9/1712:46 pm -
1 stop21h 27m
Sun 9/202:51 pm -
1 stop18h 30m
Deal found 9/9![Frontier logo]()
$336
This Travelocity deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/205:40 pm -
1 stop16h 33m
Thu 9/246:55 pm -
1 stop16h 56m
Deal found 9/5![Frontier logo]()
$276
This Frontier deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2110:06 am -
1 stop8h 33m
Thu 9/2412:59 am -
1 stop10h 52m
Deal found 9/6![Frontier logo]()
$306
This Trip.com deal was found by Cheapflights users on 9/8. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/245:40 pm -
1 stop16h 33m
Wed 9/305:27 pm -
1 stop18h 24m
Deal found 9/8![Frontier logo]()
$241
This Frontier deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2512:46 pm -
1 stop11h 15m
Sun 9/2712:59 am -
1 stop10h 52m
Deal found 9/6![Frontier logo]()
$347
This American Airlines deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/294:14 pm -
2 stops18h 46m
Sat 10/106:00 am -
1 stop16h 22m
Deal found 9/7![American Airlines logo]()
$316
This Priceline deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/512:46 pm -
1 stop21h 27m
Sun 10/1112:59 am -
1 stop10h 51m
Deal found 9/5![Frontier logo]()
$346
This Priceline deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/912:45 pm -
1 stop11h 09m
Sun 10/1112:59 am -
1 stop10h 51m
Deal found 9/7![Frontier logo]()
$326
This Southwest deal was found by Cheapflights users on 9/9. 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.
Tue 10/135:40 pm -
1 stop6h 10m
Sun 10/185:00 am -
1 stop6h 50m
Deal found 9/9![Southwest logo]()
$348
This Southwest deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/237:15 am -
1 stop4h 40m
Wed 10/2812:40 pm -
1 stop9h 25m
Deal found 9/7![Southwest logo]()
$310
This American Airlines deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/288:00 am -
2 stops14h 09m
Sat 11/77:05 am -
1 stop15h 56m
Deal found 9/7![American Airlines logo]()
$315
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 September 10, 2026.
Search for one-way flight options from Fort Myers to Caribbean. Find affordable one-way fares based on user searches. Data last updated September 10, 2026.
This Priceline deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/275:40 pm -
1 stop16h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Frontier logo]()
$118
This Priceline deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1312:45 pm -
1 stop10h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Frontier logo]()
$138
This American Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/167:45 pm -
1 stop19h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![American Airlines logo]()
$155
This Priceline deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1212:45 pm -
1 stop10h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Frontier logo]()
$158
This American Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/26:24 pm -
2 stops14h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![American Airlines logo]()
$160
This American Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/257:51 pm -
2 stops15h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![American Airlines logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/277:00 am -
2 stops32h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Multiple Airlines logo]()
$176
This Southwest deal was found by Cheapflights users on 9/9. 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.
Fri 11/137:25 am -
1 stop4h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Southwest logo]()
$186
This United Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1412:35 pm -
1 stop8h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![United Airlines logo]()
$193
This Kiwi.com deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/137:00 am -
3 stops32h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Multiple Airlines logo]()
$198
This Southwest deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/267:10 am -
1 stop7h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Southwest logo]()
$214
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 11/137:54 pm -
3 stops37h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$217
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 September 10, 2026.
Round-trip from | $241 (Trip.com) |
|---|---|
One-way from | $118 (Priceline) |
Popular in | July |
Cheapest in | January |
Average price | $363 |
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 7,457,451 searches. Data last updated September 10, 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 Fort Myers SW Florida Intl - SJU San Juan Luis Munoz Marin Intl
RSWSJU
Fort Myers SW Florida Intl
Sun 9/27
5:40 pm-10:13 am
1 stop16h 33m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$118
Fort MyersSan Juan
RSW Fort Myers SW Florida Intl - SJU San Juan Luis Munoz Marin Intl
RSWSJU
Fort Myers SW Florida Intl
Wed 10/7
12:15 pm-11:10 pm
2 stops10h 55m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$155
Fort MyersSan Juan
RSW Fort Myers SW Florida Intl - SJU San Juan Luis Munoz Marin Intl
RSWSJU
Fort Myers SW Florida Intl
Sun 11/15
7:00 am-12:16 am
1 stop16h 16m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$155
Fort MyersSan Juan
RSW Fort Myers SW Florida Intl - SJU San Juan Luis Munoz Marin Intl
RSWSJU
Fort Myers SW Florida Intl
Fri 11/13
7:28 pm-9:42 am
2 stops13h 14m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$155
Fort MyersSan Juan
RSW Fort Myers SW Florida Intl - SJU San Juan Luis Munoz Marin Intl
RSWSJU
Fort Myers SW Florida Intl
Mon 11/16
6:24 pm-10:45 am
2 stops15h 21m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$155
Fort MyersSan Juan
RSW Fort Myers SW Florida Intl - SJU San Juan Luis Munoz Marin Intl
RSWSJU
Fort Myers SW Florida Intl
Thu 11/12
12:45 pm-12:04 am
1 stop10h 19m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$158
Fort MyersSan Juan
RSW Fort Myers SW Florida Intl - SJU San Juan Luis Munoz Marin Intl
RSWSJU
Fort Myers SW Florida Intl
Sun 9/27
7:00 am-3:22 pm
2 stops32h 22m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$176
Quickest round-trip
Fort MyersNassau
RSW Fort Myers SW Florida Intl - NAS Nassau Intl
RSWNAS
Fort Myers SW Florida Intl
Fri 11/13
7:25 am-12:15 pm
1 stop4h 50m
Nassau Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$186
Fort MyersSan Juan
RSW Fort Myers SW Florida Intl - SJU San Juan Luis Munoz Marin Intl
RSWSJU
Fort Myers SW Florida Intl
Sat 11/14
12:35 pm-10:22 pm
1 stop8h 47m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$193
Fort MyersSan Juan
RSW Fort Myers SW Florida Intl - SJU San Juan Luis Munoz Marin Intl
RSWSJU
Fort Myers SW Florida Intl
Wed 12/2
1:35 pm-11:20 pm
1 stop8h 45m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$193
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-NAS
RSW-AUA
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-SJU
RSW-STT
RSW-NAS
RSW-AUA
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 $399). Flying from Fort Myers to Caribbean in July is currently the most expensive (average of $705). 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 September 10, 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.
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
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 September 10, 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 3 airlines flying from Fort Myers to Caribbean
Discover the top 3 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 7,457,451 searches. Data last updated September 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$245 | Average$566 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$333 | Average$593 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$445 | Average$632 | FlexibilityNo cancel fee | On-time71% |