$153+ Cheap flights from Pensacola (PNS) 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 5/28. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — SJU
May 28 — Jun 41
Round-trip
1 adult, Economy
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Find cheap flights from Pensacola to Caribbean with Cheapflights
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Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Pensacola to CaribbeanExplore the most affordable flight options available from Pensacola to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 28, 2026.
Explore the most affordable flight options available from Pensacola to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 28, 2026.
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.
Thu 5/141:26 pm
PNS
- SJU
1 stop11h 42m
Frontier
Sat 5/163:03 am
SJU
- PNS
1 stop10h 54m
Frontier
Deal found 4/23![Frontier logo]()
$194
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.
Sun 5/101:42 pm
PNS
- SJU
1 stop11h 26m
Frontier
Sat 5/163:03 am
SJU
- PNS
1 stop10h 54m
Frontier
Deal found 4/23![Frontier logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 5/225:58 pm
PNS
- SJU
2 stops33h 03m
Multiple Airlines
Fri 5/296:00 am
SJU
- PNS
1 stop12h 03m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$280
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.
Sat 5/94:48 pm
PNS
- SJU
1 stop8h 20m
Multiple Airlines
Wed 5/137:30 am
SJU
- PNS
2 stops33h 23m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$282
This Kiwi.com deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 5/210:00 am
PNS
- SJU
1 stop21h 49m
Multiple Airlines
Sat 5/95:15 pm
SJU
- PNS
2 stops23h 38m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$286
This Kiwi.com deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 5/14:31 pm
PNS
- SJU
1 stop15h 18m
Multiple Airlines
Fri 5/83:33 pm
SJU
- PNS
1 stop25h 20m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$289
This Kiwi.com deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 5/210:00 am
PNS
- SJU
1 stop21h 49m
Spirit Airlines
Sat 5/98:04 pm
SJU
- PNS
1 stop21h 59m
Spirit Airlines
Deal found 4/24![Spirit Airlines logo]()
$294
This Kiwi.com deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 6/42:46 pm
PNS
- SJU
1 stop27h 13m
Multiple Airlines
Sat 6/68:13 pm
SJU
- PNS
1 stop20h 40m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$295
This Kiwi.com deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 5/184:48 pm
PNS
- SJU
1 stop8h 20m
Multiple Airlines
Fri 5/228:04 pm
SJU
- PNS
1 stop17h 42m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$301
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.
Thu 5/217:38 pm
PNS
- SJU
1 stop27h 41m
Multiple Airlines
Sun 6/78:04 pm
SJU
- PNS
1 stop21h 59m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$306
This Delta deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/169:25 am
PNS
- MBJ
1 stop6h 09m
Delta
Fri 8/214:59 pm
MBJ
- PNS
1 stop6h 27m
Delta
Deal found 4/24![Delta logo]()
$352
This Kiwi.com deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 5/161:46 pm
PNS
- PUJ
1 stop22h 44m
Multiple Airlines
Sat 5/2312:07 pm
PUJ
- PNS
2 stops28h 46m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$355
Best flights from Pensacola to CaribbeanDiscover carefully curated flight deals from Pensacola to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 28, 2026.
Discover carefully curated flight deals from Pensacola to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 28, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 5/287:38 pm
PNS
- STT
1 stop17h 38m
Multiple Airlines
Mon 6/13:21 pm
STT
- PNS
1 stop25h 37m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$383
This American Airlines deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 7/126:00 am
PNS
- MBJ
1 stop7h 09m
American Airlines
Mon 7/202:23 pm
MBJ
- PNS
1 stop24h 10m
American Airlines
Deal found 4/25![American Airlines logo]()
$395
This Delta deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/87:00 am
PNS
- SJU
1 stop8h 35m
Delta
Wed 9/167:30 am
SJU
- PNS
1 stop7h 52m
Delta
Deal found 4/25![Delta logo]()
$416
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/144:48 pm
PNS
- SJU
3 stops25h 11m
Spirit Airlines
Sat 5/162:59 am
SJU
- PNS
1 stop13h 54m
Spirit Airlines
Deal found 4/23![Spirit Airlines logo]()
$424
This Southwest deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 8/271:45 pm
PNS
- SJU
2 stops9h 05m
Southwest
Sun 8/306:35 am
SJU
- PNS
2 stops9h 50m
Southwest
Deal found 4/26![Southwest logo]()
$446
This United Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 6/147:00 am
PNS
- MBJ
1 stop8h 26m
United Airlines
Sun 6/214:33 pm
MBJ
- PNS
1 stop17h 10m
United Airlines
Deal found 4/27![United Airlines logo]()
$454
This Delta deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 9/36:00 am
PNS
- SJU
1 stop6h 30m
Delta
Wed 9/167:30 am
SJU
- PNS
1 stop7h 52m
Delta
Deal found 4/25![Delta logo]()
$436
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.
Sat 10/311:45 am
PNS
- SJU
2 stops11h 05m
Southwest
Sat 10/105:30 am
SJU
- PNS
2 stops10h 25m
Southwest
Deal found 4/23![Southwest logo]()
$461
This Kiwi.com deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 7/233:33 pm
PNS
- STT
1 stop20h 54m
Spirit Airlines
Thu 7/302:32 pm
STT
- PNS
1 stop25h 06m
Spirit Airlines
Deal found 4/26![Spirit Airlines logo]()
$464
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/37:03 pm
PNS
- SJU
1 stop15h 07m
American Airlines
Sat 10/107:00 pm
SJU
- PNS
1 stop15h 23m
American Airlines
Deal found 4/23![American Airlines logo]()
$471
This Delta deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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.
Sat 9/196:00 am
PNS
- SJU
1 stop9h 31m
Delta
Thu 9/247:30 am
SJU
- PNS
1 stop7h 52m
Delta
Deal found 4/26![Delta logo]()
$436
This Kiwi.com deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 7/237:38 pm
PNS
- STT
2 stops16h 49m
Multiple Airlines
Thu 7/302:32 pm
STT
- PNS
1 stop25h 06m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$500
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/214:48 pm
PNS
- SJU
2 stops25h 11m
Spirit Airlines
Sun 6/77:00 am
SJU
- PNS
3 stops33h 58m
Spirit Airlines
Deal found 4/23![Spirit Airlines logo]()
$468
This Southwest deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 10/2212:40 pm
PNS
- SJU
2 stops10h 55m
Southwest
Sun 10/2510:50 pm
SJU
- PNS
2 stops11h 35m
Southwest
Deal found 4/26![Southwest logo]()
$471
This American Airlines deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/17:31 pm
PNS
- MBJ
1 stop17h 39m
American Airlines
Tue 5/512:56 pm
MBJ
- PNS
2 stops21h 23m
American Airlines
Deal found 4/24![American Airlines logo]()
$486
This Delta deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 6/96:00 am
PNS
- MBJ
1 stop9h 34m
Delta
Tue 6/162:37 pm
MBJ
- PNS
1 stop6h 23m
Delta
Deal found 4/27![Delta logo]()
$449
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 6/224:56 pm
PNS
- STT
1 stop21h 48m
Spirit Airlines
Sun 6/282:32 pm
STT
- PNS
2 stops26h 19m
Spirit Airlines
Deal found 4/28![Spirit Airlines logo]()
$470
This American Airlines deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 5/199:44 am
PNS
- STT
1 stop5h 31m
American Airlines
Wed 5/274:48 pm
STT
- PNS
2 stops19h 33m
American Airlines
Deal found 4/24![American Airlines logo]()
$487
This Kiwi.com deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 5/85:58 pm
PNS
- NAS
1 stop18h 52m
Multiple Airlines
Sun 5/1011:00 am
NAS
- PNS
1 stop7h 03m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$540
This Delta deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 5/247:05 am
PNS
- AUA
1 stop6h 05m
Delta
Fri 5/291:15 pm
AUA
- PNS
1 stop11h 15m
Delta
Deal found 4/26![Delta logo]()
$461
This CheapOair deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/154:48 pm
PNS
- MBJ
2 stops43h 43m
Spirit Airlines
Thu 5/211:36 pm
MBJ
- PNS
2 stops26h 17m
Spirit Airlines
Deal found 4/27![Spirit Airlines logo]()
$493
This Southwest deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 7/3111:55 am
PNS
- SJU
1 stop11h 30m
Southwest
Fri 8/75:00 am
SJU
- PNS
2 stops9h 05m
Southwest
Deal found 4/27![Southwest logo]()
$546
This Delta deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 7/76:00 am
PNS
- AUA
1 stop7h 10m
Delta
Sat 7/111:31 pm
AUA
- PNS
1 stop8h 20m
Delta
Deal found 4/26![Delta logo]()
$461
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 6/34:53 pm
PNS
- STT
1 stop20h 23m
Multiple Airlines
Wed 6/104:45 pm
STT
- PNS
2 stops49h 24m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$564
This American Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/287:24 pm
PNS
- SDQ
1 stop13h 00m
American Airlines
Fri 6/57:35 pm
SDQ
- PNS
1 stop14h 53m
American Airlines
Deal found 4/28![American Airlines logo]()
$540
This United Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/176:15 am
PNS
- STT
1 stop8h 28m
United Airlines
Thu 5/211:22 pm
STT
- PNS
1 stop9h 39m
United Airlines
Deal found 4/27![United Airlines logo]()
$720
This Delta deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 6/307:00 am
PNS
- AUA
1 stop6h 10m
Delta
Fri 7/103:25 pm
AUA
- PNS
1 stop9h 18m
Delta
Deal found 4/26![Delta logo]()
$461
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 6/233:31 pm
PNS
- STT
1 stop20h 56m
Spirit Airlines
Sun 6/282:32 pm
STT
- PNS
1 stop25h 04m
Spirit Airlines
Deal found 4/28![Spirit Airlines logo]()
$510
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 7/177:32 pm
PNS
- GGT
2 stops34h 58m
Multiple Airlines
Fri 7/2411:30 am
GGT
- PNS
1 stop22h 16m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$577
This American Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/264:41 pm
PNS
- SDQ
1 stop5h 14m
American Airlines
Tue 6/27:35 pm
SDQ
- PNS
1 stop21h 36m
American Airlines
Deal found 4/27![American Airlines logo]()
$553
Last-minute flights from Pensacola to CaribbeanDiscover last-minute flight deals from Pensacola to Caribbean. Data last updated April 28, 2026 and is based on user searches.
Discover last-minute flight deals from Pensacola to Caribbean. Data last updated April 28, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 5/14:31 pm
PNS
- SJU
1 stop15h 18m
Multiple Airlines
Fri 5/83:33 pm
SJU
- PNS
1 stop25h 20m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$289
This Kiwi.com deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 5/210:00 am
PNS
- SJU
1 stop21h 49m
Multiple Airlines
Sat 5/95:15 pm
SJU
- PNS
2 stops23h 38m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$286
This Kiwi.com deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 5/210:00 am
PNS
- SJU
1 stop21h 49m
Spirit Airlines
Sat 5/98:04 pm
SJU
- PNS
1 stop21h 59m
Spirit Airlines
Deal found 4/24![Spirit Airlines logo]()
$294
This Frontier deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/71:42 pm
PNS
- SJU
1 stop11h 26m
Frontier
Thu 5/146:00 am
SJU
- PNS
1 stop7h 41m
Frontier
Deal found 4/27![Frontier logo]()
$308
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.
Sat 5/94:48 pm
PNS
- SJU
1 stop8h 20m
Multiple Airlines
Wed 5/137:30 am
SJU
- PNS
2 stops33h 23m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$282
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.
Sun 5/101:42 pm
PNS
- SJU
1 stop11h 26m
Frontier
Sat 5/163:03 am
SJU
- PNS
1 stop10h 54m
Frontier
Deal found 4/23![Frontier logo]()
$212
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.
Thu 5/141:26 pm
PNS
- SJU
1 stop11h 42m
Frontier
Sat 5/163:03 am
SJU
- PNS
1 stop10h 54m
Frontier
Deal found 4/23![Frontier logo]()
$194
This Kiwi.com deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 5/161:46 pm
PNS
- PUJ
1 stop22h 44m
Multiple Airlines
Sat 5/2312:07 pm
PUJ
- PNS
2 stops28h 46m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$355
This Kiwi.com deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 5/161:46 pm
PNS
- PUJ
1 stop22h 44m
Multiple Airlines
Tue 5/2611:45 am
PUJ
- PNS
2 stops29h 08m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$373
This Kiwi.com deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 5/184:48 pm
PNS
- SJU
1 stop8h 20m
Multiple Airlines
Fri 5/228:04 pm
SJU
- PNS
1 stop17h 42m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$301
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.
Thu 5/217:38 pm
PNS
- SJU
1 stop27h 41m
Multiple Airlines
Sun 6/78:04 pm
SJU
- PNS
1 stop21h 59m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$306
This Kiwi.com deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 5/225:58 pm
PNS
- SJU
2 stops33h 03m
Multiple Airlines
Fri 5/296:00 am
SJU
- PNS
1 stop12h 03m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$280
One-way flights from Pensacola to CaribbeanSearch for one-way flight options from Pensacola to Caribbean. Find affordable one-way fares based on user searches. Data last updated April 28, 2026.
Search for one-way flight options from Pensacola to Caribbean. Find affordable one-way fares based on user searches. Data last updated April 28, 2026.
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.
Thu 5/285:58 pm
PNS
- SJU
1 stop24h 01m
Spirit Airlines
Deal found 4/23![Spirit Airlines logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 7/19:26 am
PNS
- SJU
1 stop29h 32m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 5/175:58 pm
PNS
- MBJ
2 stops18h 13m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$164
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.
Thu 5/285:58 pm
PNS
- SJU
2 stops22h 16m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$164
This Kiwi.com deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 5/204:48 pm
PNS
- STT
1 stop20h 28m
Spirit Airlines
Deal found 4/24![Spirit Airlines logo]()
$173
This Mytrip deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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.
Sat 5/304:48 pm
PNS
- SJU
1 stop6h 31m
Spirit Airlines
Deal found 4/28![Spirit Airlines logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 5/224:48 pm
PNS
- STT
1 stop20h 28m
Spirit Airlines
Deal found 4/24![Spirit Airlines logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 5/115:58 pm
PNS
- NAS
1 stop18h 52m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 6/146:05 pm
PNS
- SJU
1 stop23h 54m
Spirit Airlines
Deal found 4/24![Spirit Airlines logo]()
$180
This Delta deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 5/176:00 am
PNS
- MBJ
1 stop5h 53m
Delta
Deal found 4/24![Delta logo]()
$181
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.
Tue 9/298:48 am
PNS
- SJU
1 stop11h 46m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$188
This Kiwi.com deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 6/147:38 pm
PNS
- SJU
2 stops20h 55m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$190
Find flight deals from Pensacola to Caribbean
Keep the following information in mind while searching for Pensacola to Caribbean flight deals. Data was last updated April 28, 2026.
Round-trip from | $194 (Priceline) |
|---|---|
One-way from | $153 (Kiwi.com) |
Popular in | December |
Cheapest in | January |
Average price | $584 |
Cheapflights Fare Finder
Customize your flight search to find flights from Pensacola 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 28, 2026.
Use the filters below to find and compare flights from Pensacola to Caribbean that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PensacolaSaint Thomas Island
PNS - STT
PNSSTT
Pensacola
Thu 5/28
7:38 pm-2:16 pm
1 stop17h 38m
Saint Thomas Island Cyril E King
Mon 6/1
3:21 pm-3:58 pm
1 stop25h 37m
$383
PensacolaMontego Bay
PNS - MBJ
PNSMBJ
Pensacola
Sun 7/12
6:00 am-1:09 pm
1 stop7h 09m
Montego Bay Sangster Intl
Mon 7/20
2:23 pm-2:33 pm
1 stop24h 10m
$395
PensacolaSan Juan
PNS - SJU
PNSSJU
Pensacola
Tue 9/8
7:00 am-4:35 pm
1 stop8h 35m
San Juan Luis Munoz Marin Intl
Wed 9/16
7:30 am-2:22 pm
1 stop7h 52m
$416
PensacolaSan Juan
PNS - SJU
PNSSJU
Pensacola
Thu 5/14
4:48 pm-6:59 pm
3 stops25h 11m
San Juan Luis Munoz Marin Intl
Sat 5/16
2:59 am-3:53 pm
1 stop13h 54m
$424
Quickest round-trip
PensacolaSan Juan
PNS - SJU
PNSSJU
Pensacola
Thu 9/3
6:00 am-1:30 pm
1 stop6h 30m
San Juan Luis Munoz Marin Intl
Wed 9/16
7:30 am-2:22 pm
1 stop7h 52m
$436
PensacolaSan Juan
PNS - SJU
PNSSJU
Pensacola
Sat 9/19
6:00 am-4:31 pm
1 stop9h 31m
San Juan Luis Munoz Marin Intl
Thu 9/24
7:30 am-2:22 pm
1 stop7h 52m
$436
PensacolaSan Juan
PNS - SJU
PNSSJU
Pensacola
Thu 8/27
1:45 pm-11:50 pm
2 stops9h 05m
San Juan Luis Munoz Marin Intl
Sun 8/30
6:35 am-3:25 pm
2 stops9h 50m
$446
PensacolaMontego Bay
PNS - MBJ
PNSMBJ
Pensacola
Tue 6/9
6:00 am-3:34 pm
1 stop9h 34m
Montego Bay Sangster Intl
Tue 6/16
2:37 pm-9:00 pm
1 stop6h 23m
$449
PensacolaMontego Bay
PNS - MBJ
PNSMBJ
Pensacola
Sun 6/14
7:00 am-3:26 pm
1 stop8h 26m
Montego Bay Sangster Intl
Sun 6/21
4:33 pm-9:43 am
1 stop17h 10m
$454
PensacolaSan Juan
PNS - SJU
PNSSJU
Pensacola
Sat 10/3
11:45 am-11:50 pm
2 stops11h 05m
San Juan Luis Munoz Marin Intl
Sat 10/10
5:30 am-2:55 pm
2 stops10h 25m
$461
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Pensacola to Caribbean
Have a flexible travel schedule? Discover the best time to fly to Caribbean from Pensacola with our price prediction graph.
PNS-SJU
PNS-MBJ
PNS-PUJ
PNS-STT
PNS-NAS
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Pensacola to Caribbean
PNS-0CB
PNS-SJU
PNS-MBJ
PNS-PUJ
PNS-STT
How far ahead should I book a flight from Pensacola to Caribbean?
The price you pay for your flight from Pensacola to Caribbean may vary depending on when you book. For the best chance of a lower fare, look to book 13 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest month to book a flight from Pensacola to Caribbean?
Currently, April is the cheapest month in which you can book a flight from Pensacola to Caribbean (average of $114). Flying from Pensacola to Caribbean in March is currently the most expensive (average of $365). 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 28, 2026.
See what other customers who have flown with Delta,United Airlines, andAmerican Airlines from Pensacola 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
Entertainment
7.8
Crew
8.5
Food
7.2
Overall
7.9
Comfort
7.9
Reviews
1 / 20
6.0
Goodpilar,May 2025
RSW - ATL
Boarding
8.1
Entertainment
7.8
Crew
8.5
Food
7.2
Overall
7.9
Comfort
7.9
Reviews
1 / 20
6.0
Goodpilar,May 2025
RSW - ATL
Boarding
8.1
Entertainment
7.8
Crew
8.5
Food
7.2
Overall
7.9
Comfort
7.9
Reviews
1 / 20
6.0
Goodpilar,May 2025
RSW - ATL
Boarding
8.1
Entertainment
7.8
Crew
8.5
Food
7.2
Overall
7.9
Comfort
7.9
Reviews
1 / 20
6.0
Goodpilar,May 2025
RSW - ATL
Boarding
8.1
Entertainment
7.8
Crew
8.5
Food
7.2
Overall
7.9
Comfort
7.9
Reviews
1 / 20
6.0
Goodpilar,May 2025
RSW - ATL
Related info for your journey
Find useful and relevant information for your journey from Pensacola 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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Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for Pensacola 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 Pensacola to Caribbean by cabin class
Find flights from Pensacola to Caribbean, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Pensacola and Caribbean flights
Browse other Pensacola and Caribbean flight options. Last updated on April 28, 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.
Pensacola to Caribbean flights
Consider these flights traveling from Pensacola to Caribbean.
Top 4 airlines flying from Pensacola to Caribbean
Discover the top 4 airlines that operate flights from Pensacola 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 28, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$276 | Average$587 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$289 | Average$347 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$380 | Average$706 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$390 | Average$630 | FlexibilityNo cancel fee | On-time71% |