$64+ Cheap flights from Caribbean Islands
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/15. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MCO
Apr 14 — Apr 211
Round-trip
1 adult, Economy
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Cheapest flights from Caribbean IslandsExplore the most affordable flight options available from Caribbean Islands. Find the lowest fares based on data from user searches, with prices last updated on March 15, 2026.
Explore the most affordable flight options available from Caribbean Islands. Find the lowest fares based on data from user searches, with prices last updated on March 15, 2026.
This eDestinos deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/36:07 pm
SJU
- MIA
Nonstop3h 03m
Frontier
Mon 4/139:10 pm
MIA
- SJU
Nonstop2h 43m
Frontier
Deal found 3/13![Frontier logo]()
$124
This eDestinos deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/96:00 am
SJU
- MIA
Nonstop3h 00m
Frontier
Tue 4/143:24 pm
MIA
- SJU
Nonstop2h 35m
Frontier
Deal found 3/14![Frontier logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/96:07 pm
SJU
- MIA
Nonstop3h 03m
Frontier
Mon 4/139:10 pm
MIA
- SJU
Nonstop2h 43m
Frontier
Deal found 3/10![Frontier logo]()
$127
This Frontier deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/96:00 am
SJU
- MIA
Nonstop3h 00m
Frontier
Sun 4/1210:36 pm
MIA
- SJU
Nonstop2h 41m
Frontier
Deal found 3/11![Frontier logo]()
$128
This Expedia deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1011:03 am
SJU
- MIA
Nonstop2h 52m
Multiple Airlines
Sun 4/123:04 pm
MIA
- SJU
Nonstop2h 35m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$129
This eDestinos deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/266:46 pm
SJU
- MIA
Nonstop3h 01m
Frontier
Mon 3/3010:42 pm
MIA
- SJU
Nonstop2h 39m
Frontier
Deal found 3/13![Frontier logo]()
$131
This Cheapflightsfares deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/311:03 am
SJU
- MIA
Nonstop2h 52m
Spirit Airlines
Tue 4/79:25 pm
MIA
- SJU
Nonstop2h 33m
Spirit Airlines
Deal found 3/14![Spirit Airlines logo]()
$132
This Frontier deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/36:00 am
SJU
- MIA
Nonstop3h 00m
Frontier
Fri 4/1010:20 pm
MIA
- SJU
Nonstop2h 41m
Frontier
Deal found 3/10![Frontier logo]()
$133
This Mytrip deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/811:03 am
SJU
- MIA
Nonstop2h 52m
Multiple Airlines
Tue 4/143:24 pm
MIA
- SJU
Nonstop2h 35m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/36:00 am
SJU
- MIA
Nonstop3h 00m
Multiple Airlines
Fri 4/109:25 pm
MIA
- SJU
Nonstop2h 33m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/911:03 am
SJU
- MIA
Nonstop2h 52m
Multiple Airlines
Sun 4/1210:36 pm
MIA
- SJU
Nonstop2h 41m
Multiple Airlines
Deal found 3/14![Multiple Airlines logo]()
$136
This Kiwi.com deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/36:00 am
SJU
- MIA
Nonstop3h 00m
Frontier
Fri 4/310:20 pm
MIA
- SJU
Nonstop2h 41m
Frontier
Deal found 3/10![Frontier logo]()
$137
Best flights from Caribbean IslandsDiscover carefully curated flight deals from Caribbean Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 15, 2026.
Discover carefully curated flight deals from Caribbean Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 15, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/177:00 am
SJU
- MIA
Nonstop2h 46m
Multiple Airlines
Mon 4/2012:53 pm
MIA
- SJU
2 stops13h 08m
Multiple Airlines
Deal found 3/14![Multiple Airlines logo]()
$228
This Copa Airlines deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/246:12 pm
SJU
- MDE
1 stop15h 03m
Copa Airlines
Wed 4/2910:35 am
MDE
- SJU
1 stop10h 49m
Copa Airlines
Deal found 3/10![Copa Airlines logo]()
$249
This Spirit deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/2612:05 pm
SJU
- MIA
1 stop8h 02m
Spirit Airlines
Tue 3/318:35 pm
MIA
- SJU
1 stop14h 32m
Spirit Airlines
Deal found 3/10![Spirit Airlines logo]()
$264
This Southwest deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/710:00 am
SJU
- MIA
2 stops13h 00m
Southwest
Fri 5/85:45 pm
MIA
- SJU
1 stop6h 10m
Southwest
Deal found 3/14![Southwest logo]()
$284
This JetBlue deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/134:50 pm
SJU
- EWR
Nonstop4h 10m
JetBlue
Sat 5/167:30 pm
EWR
- SJU
Nonstop4h 03m
JetBlue
Deal found 3/10![JetBlue logo]()
$307
This Delta deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/97:00 am
SJU
- JFK
Nonstop4h 15m
Delta
Thu 6/117:30 pm
JFK
- SJU
Nonstop4h 05m
Delta
Deal found 3/11![Delta logo]()
$307
This United Airlines deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/131:00 am
SJU
- EWR
Nonstop4h 04m
United Airlines
Fri 8/219:47 am
EWR
- SJU
Nonstop3h 58m
United Airlines
Deal found 3/12![United Airlines logo]()
$386
This WorldTicket deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WorldTicket is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/256:10 am
SDQ
- EWR
Nonstop4h 20m
WorldTicket
Mon 4/2712:59 am
EWR
- SDQ
Nonstop4h 30m
WorldTicket
Deal found 3/14![WorldTicket logo]()
$468
This Copa Airlines deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/243:11 pm
SJU
- MDE
1 stop6h 24m
Copa Airlines
Fri 7/315:00 am
MDE
- SJU
1 stop6h 47m
Copa Airlines
Deal found 3/14![Copa Airlines logo]()
$277
This Southwest deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/145:05 am
SJU
- MIA
2 stops10h 15m
Southwest
Sun 5/176:30 am
MIA
- SJU
1 stop10h 00m
Southwest
Deal found 3/14![Southwest logo]()
$293
This Arajet deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/87:10 pm
SDQ
- EWR
Nonstop4h 20m
Multiple Airlines
Sun 5/1712:00 pm
EWR
- SDQ
1 stop10h 15m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$296
This Copa Airlines deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:12 pm
SJU
- MDE
1 stop15h 03m
Copa Airlines
Tue 6/25:00 am
MDE
- SJU
1 stop6h 47m
Copa Airlines
Deal found 3/12![Copa Airlines logo]()
$277
This Delta deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/107:00 am
SJU
- JFK
Nonstop4h 04m
Delta
Sun 9/137:29 pm
JFK
- SJU
Nonstop4h 15m
Delta
Deal found 3/12![Delta logo]()
$307
This Copa Airlines deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/66:17 pm
SJU
- MDE
1 stop14h 58m
Copa Airlines
Sat 6/135:00 am
MDE
- SJU
1 stop6h 47m
Copa Airlines
Deal found 3/14![Copa Airlines logo]()
$277
This Southwest deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/95:15 am
SJU
- MIA
2 stops11h 45m
Southwest
Sat 5/169:30 am
MIA
- SJU
1 stop9h 35m
Southwest
Deal found 3/14![Southwest logo]()
$305
This JetBlue deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/145:01 am
SJU
- JFK
1 stop7h 54m
JetBlue
Sat 5/169:59 pm
JFK
- SJU
Nonstop4h 08m
JetBlue
Deal found 3/10![JetBlue logo]()
$351
This Arajet deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/91:40 pm
SDQ
- EWR
1 stop9h 50m
Multiple Airlines
Tue 5/1912:59 am
EWR
- SDQ
Nonstop4h 30m
Multiple Airlines
Deal found 3/14![Multiple Airlines logo]()
$326
This Copa Airlines deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/186:17 pm
SJU
- MDE
1 stop14h 58m
Copa Airlines
Fri 7/246:25 am
MDE
- SJU
1 stop5h 22m
Copa Airlines
Deal found 3/14![Copa Airlines logo]()
$277
This Delta deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/67:00 am
SJU
- JFK
Nonstop4h 15m
Delta
Sat 8/87:30 pm
JFK
- SJU
Nonstop4h 05m
Delta
Deal found 3/14![Delta logo]()
$337
This Southwest deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/1110:20 pm
SJU
- MCO
Nonstop2h 55m
Southwest
Tue 6/239:20 pm
MCO
- SJU
Nonstop2h 55m
Southwest
Deal found 3/10![Southwest logo]()
$325
This JetBlue deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/217:58 pm
SJU
- JFK
Nonstop4h 01m
JetBlue
Sat 4/259:59 pm
JFK
- SJU
Nonstop4h 08m
JetBlue
Deal found 3/12![JetBlue logo]()
$366
This United Airlines deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/291:00 am
SJU
- EWR
Nonstop4h 10m
United Airlines
Sat 8/157:47 pm
EWR
- SJU
Nonstop4h 03m
United Airlines
Deal found 3/12![United Airlines logo]()
$407
This Copa Airlines deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/76:12 pm
SJU
- MDE
1 stop15h 03m
Copa Airlines
Tue 5/1210:35 am
MDE
- SJU
1 stop10h 49m
Copa Airlines
Deal found 3/12![Copa Airlines logo]()
$287
This Southwest deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/86:50 am
SJU
- MCO
2 stops9h 55m
Southwest
Sun 5/102:40 pm
MCO
- SJU
2 stops9h 25m
Southwest
Deal found 3/12![Southwest logo]()
$330
This United Airlines deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/51:00 am
SJU
- EWR
Nonstop4h 10m
United Airlines
Sun 8/97:45 pm
EWR
- SJU
Nonstop4h 05m
United Airlines
Deal found 3/12![United Airlines logo]()
$407
This Delta deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/37:00 am
SJU
- JFK
Nonstop4h 06m
Delta
Fri 9/117:29 pm
JFK
- SJU
Nonstop4h 15m
Delta
Deal found 3/12![Delta logo]()
$376
This JetBlue deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/14:30 pm
SJU
- JFK
1 stop7h 26m
JetBlue
Tue 5/510:00 am
JFK
- SJU
1 stop10h 30m
JetBlue
Deal found 3/10![JetBlue logo]()
$377
This Copa Airlines deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/105:27 am
SJU
- MDE
1 stop16h 08m
Copa Airlines
Thu 5/149:15 am
MDE
- SJU
1 stop12h 09m
Copa Airlines
Deal found 3/12![Copa Airlines logo]()
$287
This Southwest deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/116:00 am
SJU
- MCO
2 stops9h 30m
Southwest
Mon 6/159:05 pm
MCO
- SJU
Nonstop3h 00m
Southwest
Deal found 3/14![Southwest logo]()
$330
This Copa Airlines deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/36:17 pm
SJU
- MDE
1 stop14h 58m
Copa Airlines
Tue 6/95:00 am
MDE
- SJU
1 stop6h 47m
Copa Airlines
Deal found 3/10![Copa Airlines logo]()
$287
Last-minute flights from Caribbean IslandsDiscover last-minute flight deals departing from Caribbean Islands. Data last updated March 15, 2026 and is based on user searches.
Discover last-minute flight deals departing from Caribbean Islands. Data last updated March 15, 2026 and is based on user searches.
This eDestinos deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/231:39 am
SJU
- MIA
1 stop11h 08m
Spirit Airlines
Sat 3/289:25 pm
MIA
- SJU
Nonstop2h 33m
Spirit Airlines
Deal found 3/12![Spirit Airlines logo]()
$141
This Kiwi.com deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/231:39 am
SJU
- MIA
1 stop11h 08m
Multiple Airlines
Sun 4/1210:36 pm
MIA
- SJU
Nonstop2h 41m
Multiple Airlines
Deal found 3/13![Multiple Airlines logo]()
$154
This eDestinos deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/231:39 am
SJU
- MIA
1 stop11h 08m
Spirit Airlines
Thu 4/29:25 pm
MIA
- SJU
Nonstop2h 33m
Spirit Airlines
Deal found 3/11![Spirit Airlines logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/239:58 pm
SJU
- MIA
Nonstop3h 01m
Frontier
Tue 3/2410:40 pm
MIA
- SJU
Nonstop2h 39m
Frontier
Deal found 3/10![Frontier logo]()
$160
This Expedia deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/231:39 am
SJU
- MIA
1 stop11h 08m
Multiple Airlines
Wed 3/2510:40 pm
MIA
- SJU
Nonstop2h 39m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$165
This Kiwi.com deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/246:39 pm
SJU
- MIA
Nonstop3h 01m
Frontier
Wed 3/2510:40 pm
MIA
- SJU
Nonstop2h 39m
Frontier
Deal found 3/12![Frontier logo]()
$138
This eDestinos deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/246:39 pm
SJU
- MIA
Nonstop3h 01m
Frontier
Sat 3/2811:34 am
MIA
- SJU
Nonstop2h 40m
Frontier
Deal found 3/12![Frontier logo]()
$163
This Expedia deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/2412:05 pm
SJU
- MIA
1 stop8h 02m
Spirit Airlines
Fri 3/279:25 pm
MIA
- SJU
Nonstop2h 33m
Spirit Airlines
Deal found 3/10![Spirit Airlines logo]()
$171
This Cheapflightsfares deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/81:45 am
SJU
- MCO
Nonstop3h 15m
Spirit Airlines
Sun 4/126:10 am
MCO
- SJU
Nonstop2h 43m
Spirit Airlines
Deal found 3/13![Spirit Airlines logo]()
$176
This Cheapflightsfares deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/142:59 am
SJU
- MCO
Nonstop3h 03m
Spirit Airlines
Fri 4/179:03 am
MCO
- SJU
Nonstop2h 49m
Spirit Airlines
Deal found 3/13![Spirit Airlines logo]()
$174
This CheapOair deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/228:27 pm
SJU
- MCO
Nonstop3h 02m
Spirit Airlines
Wed 5/66:00 am
MCO
- SJU
Nonstop2h 49m
Spirit Airlines
Deal found 3/13![Spirit Airlines logo]()
$177
This Expedia deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/298:27 pm
SJU
- MCO
Nonstop3h 02m
Spirit Airlines
Mon 5/46:00 am
MCO
- SJU
Nonstop2h 49m
Spirit Airlines
Deal found 3/12![Spirit Airlines logo]()
$175
One-way flights from Caribbean IslandsSearch for one-way flight options from Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated March 15, 2026.
Search for one-way flight options from Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated March 15, 2026.
This CheapOair deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/1511:30 am
SJU
- MIA
Nonstop2h 59m
Frontier
Deal found 3/10![Frontier logo]()
$64
This Kiwi.com deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/106:07 pm
SJU
- MIA
Nonstop3h 03m
Frontier
Deal found 3/13![Frontier logo]()
$66
This Cheapflightsfares deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/173:21 am
SJU
- MIA
Nonstop2h 45m
Spirit Airlines
Deal found 3/11![Spirit Airlines logo]()
$67
This Super.com deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/410:28 pm
SJU
- MIA
Nonstop3h 00m
Frontier
Deal found 3/13![Frontier logo]()
$68
This Cheapflightsfares deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/143:21 am
SJU
- MIA
Nonstop2h 45m
Spirit Airlines
Deal found 3/10![Spirit Airlines logo]()
$69
This CheapOair deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/311:03 am
SJU
- MIA
Nonstop2h 52m
Spirit Airlines
Deal found 3/13![Spirit Airlines logo]()
$70
This Frontier deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/510:58 am
SJU
- MIA
Nonstop3h 01m
Frontier
Deal found 3/12![Frontier logo]()
$73
This eDestinos deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/276:41 pm
SJU
- MIA
Nonstop2h 58m
Frontier
Deal found 3/11![Frontier logo]()
$74
This Kiwi.com deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/811:03 am
SJU
- MIA
Nonstop2h 52m
Spirit Airlines
Deal found 3/10![Spirit Airlines logo]()
$75
This Expedia deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/812:55 pm
SJU
- MCO
1 stop6h 26m
Spirit Airlines
Deal found 3/12![Spirit Airlines logo]()
$75
This Cheapflightsfares deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/93:21 am
SJU
- MIA
Nonstop2h 45m
Spirit Airlines
Deal found 3/10![Spirit Airlines logo]()
$77
This FlightHub deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/289:35 am
SJU
- MDE
1 stop5h 10m
Arajet
Deal found 3/14![Arajet logo]()
$77
Find flights from Caribbean Islands within your budget
Find flights departing from Caribbean Islands that match your specified budget. Filter results by price range, allowing you to narrow down options and find flights that fit within your financial constraints. Please note that the search results are based on data from user searches, with fares last updated on March 15, 2026. In the last 7 days, Cheapflights users made a total of 2,558,603 searches
Fly to
Route
Depart
Return
Cheapest round-trip
San JuanMiami
SJU - MIA
SJUMIA
San Juan Luis Munoz Marin Intl
Fri 4/17
7:00 am-9:46 am
Nonstop2h 46m
Miami
Mon 4/20
12:53 pm-2:01 am
2 stops13h 08m
$228
San JuanMedellín
SJU - MDE
SJUMDE
San Juan Luis Munoz Marin Intl
Fri 4/24
6:12 pm-8:15 am
1 stop15h 03m
Medellín Jose Maria Cordova Intl
Wed 4/29
10:35 am-10:24 pm
1 stop10h 49m
$249
San JuanMiami
SJU - MIA
SJUMIA
San Juan Luis Munoz Marin Intl
Thu 3/26
12:05 pm-8:07 pm
1 stop8h 02m
Miami
Tue 3/31
8:35 pm-11:07 am
1 stop14h 32m
$264
San JuanMedellín
SJU - MDE
SJUMDE
San Juan Luis Munoz Marin Intl
Fri 7/24
3:11 pm-8:35 pm
1 stop6h 24m
Medellín Jose Maria Cordova Intl
Fri 7/31
5:00 am-12:47 pm
1 stop6h 47m
$277
San JuanMedellín
SJU - MDE
SJUMDE
San Juan Luis Munoz Marin Intl
Thu 5/28
6:12 pm-8:15 am
1 stop15h 03m
Medellín Jose Maria Cordova Intl
Tue 6/2
5:00 am-12:47 pm
1 stop6h 47m
$277
San JuanMedellín
SJU - MDE
SJUMDE
San Juan Luis Munoz Marin Intl
Sat 6/6
6:17 pm-8:15 am
1 stop14h 58m
Medellín Jose Maria Cordova Intl
Sat 6/13
5:00 am-12:47 pm
1 stop6h 47m
$277
San JuanMedellín
SJU - MDE
SJUMDE
San Juan Luis Munoz Marin Intl
Sat 7/18
6:17 pm-8:15 am
1 stop14h 58m
Medellín Jose Maria Cordova Intl
Fri 7/24
6:25 am-12:47 pm
1 stop5h 22m
$277
San JuanMiami
SJU - MIA
SJUMIA
San Juan Luis Munoz Marin Intl
Thu 5/7
10:00 am-11:00 pm
2 stops13h 00m
Miami
Fri 5/8
5:45 pm-11:55 pm
1 stop6h 10m
$284
San JuanMedellín
SJU - MDE
SJUMDE
San Juan Luis Munoz Marin Intl
Thu 5/7
6:12 pm-8:15 am
1 stop15h 03m
Medellín Jose Maria Cordova Intl
Tue 5/12
10:35 am-10:24 pm
1 stop10h 49m
$287
San JuanMedellín
SJU - MDE
SJUMDE
San Juan Luis Munoz Marin Intl
Sun 5/10
5:27 am-8:35 pm
1 stop16h 08m
Medellín Jose Maria Cordova Intl
Thu 5/14
9:15 am-10:24 pm
1 stop12h 09m
$287
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Caribbean Islands
Have a flexible travel schedule? Discover the best time to fly from Caribbean Islands with our price prediction graph.
SJU-MIA
SJU-MCO
SJU-MDE
SJU-EWR
SDQ-EWR
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.
Travel insights for flights from Caribbean Islands
Get recent, data-driven insights about flights from Caribbean Islands including ideal travel times, pricing trends, and more.
zzEPX-MCO
SJU-MIA
SJU-MCO
SJU-MDE
SJU-EWR
What is the cheapest month to book a flight from Caribbean Islands?
Currently, May is the cheapest month in which you can book a flight from Caribbean Islands (average of $99). Flying from Caribbean Islands in October will prove the most costly (average of $131). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.
When is the cheapest time to fly from Caribbean Islands?
Use this chart to determine the cheapest time to fly round-trip from Caribbean Islands to Orlando. Price data was last updated on March 12, 2026.
Those who are seeking the cheapest fare on flights departing from Caribbean Islands would be wise to consider leaving during Monday mornings when prices are typically at their lowest. When considering other options, price-conscious travelers should avoid Sunday mornings when fares are usually the most expensive.
Which airlines fly from Caribbean Islands?
For flights departing from Caribbean Islands check dates and pricing for the following: Frontier, JetBlue, Spirit Airlines, Bahamasair, Southwest. These airlines depart to the following popular destinations: Orlando.
Airline reviews for flights from Caribbean Islands
Read reviews and ratings of airlines operating flights from Caribbean Islands. Gain insights into the quality of service, in-flight amenities, customer experiences, and overall satisfaction to choose the best airline for your Caribbean Islands travel. Please note that the reviews are sourced from user searches and were last updated on March 15, 2026. In the last 7 days, Cheapflights users made a total of 2,558,603 searches.
Peruse reviews from past customers who have flown JetBlue,American Airlines, andSpirit Airlines from Caribbean Islands to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.0
Overall
7.2
Comfort
7.5
Food
6.6
Boarding
7.4
Entertainment
7.2
Reviews
1 / 20
6.0
GoodAnonymous,Mar 2026
FLL - ORH
Crew
8.0
Overall
7.2
Comfort
7.5
Food
6.6
Boarding
7.4
Entertainment
7.2
Reviews
1 / 20
6.0
GoodAnonymous,Mar 2026
FLL - ORH
Crew
8.0
Overall
7.2
Comfort
7.5
Food
6.6
Boarding
7.4
Entertainment
7.2
Reviews
1 / 20
6.0
GoodAnonymous,Mar 2026
FLL - ORH
Crew
8.0
Overall
7.2
Comfort
7.5
Food
6.6
Boarding
7.4
Entertainment
7.2
Reviews
1 / 20
6.0
GoodAnonymous,Mar 2026
FLL - ORH
Crew
8.0
Overall
7.2
Comfort
7.5
Food
6.6
Boarding
7.4
Entertainment
7.2
Reviews
1 / 20
6.0
GoodAnonymous,Mar 2026
FLL - ORH
Crew
8.0
Overall
7.2
Comfort
7.5
Food
6.6
Boarding
7.4
Entertainment
7.2
Reviews
1 / 20
6.0
GoodAnonymous,Mar 2026
FLL - ORH
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