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$148+ 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 10/26. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — SJU
oct. 17 — oct. 241
vie. 10/17
vie. 10/24
1 adult, Economy
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Cheap flight deals from Pensacola to Caribbean

Keep the following information in mind while searching for Pensacola to Caribbean flight deals. Data was last updated septiembre 17, 2025.

Round-trip from

$311
(Travelocity)

One-way from

$148
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$488
From Pensacola to Caribbean
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One-way flight from Pensacola to Caribbean
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Highest demand for flights based on searches. 2% potential increase in price ($10 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Pensacola to Caribbean

Cheapest flights from Pensacola to Caribbean
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 septiembre 17, 2025.

This Travelocity deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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.
vie. 10/174:36 pmPNS - STT
1 stop16h 20mSpirit Airlines
dom. 10/192:04 pmSTT - PNS
1 stop5h 11mSpirit Airlines
Deal found 9/16$311
This Cheapflightsfares deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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.
jue. 11/136:49 pmPNS - SJU
1 stop13h 03mSpirit Airlines
lun. 11/1712:10 pmSJU - PNS
1 stop7h 44mSpirit Airlines
Deal found 9/16$313
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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.
jue. 10/164:36 pmPNS - SJU
1 stop21h 40mMultiple Airlines
sáb. 10/187:58 pmSJU - PNS
1 stop12h 33mMultiple Airlines
Deal found 9/15$333
This Kiwi.com deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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.
jue. 11/66:49 pmPNS - STT
1 stop18h 22mSpirit Airlines
dom. 11/94:06 pmSTT - PNS
1 stop27h 48mSpirit Airlines
Deal found 9/17$341
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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.
mié. 11/121:25 pmPNS - SJU
2 stops9h 10mSouthwest
mar. 11/186:40 amSJU - PNS
2 stops13h 55mSouthwest
Deal found 9/15$345
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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.
jue. 10/164:36 pmPNS - SJU
1 stop21h 40mMultiple Airlines
mar. 10/212:49 amSJU - PNS
1 stop15h 12mMultiple Airlines
Deal found 9/15$355
This Kiwi.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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.
mar. 9/307:10 pmPNS - SJU
1 stop24h 46mMultiple Airlines
mar. 10/76:22 amSJU - PNS
2 stops35h 39mMultiple Airlines
Deal found 9/16$364
This American Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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.
mié. 11/58:30 amPNS - SJU
1 stop7h 22mAmerican Airlines
lun. 11/106:42 pmSJU - PNS
1 stop15h 18mAmerican Airlines
Deal found 9/15$365
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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.
sáb. 9/275:44 pmPNS - SJU
2 stops19h 27mMultiple Airlines
sáb. 10/43:19 pmSJU - PNS
1 stop18h 55mMultiple Airlines
Deal found 9/15$384
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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.
vie. 10/316:25 pmPNS - PUJ
1 stop16h 03mSpirit Airlines
vie. 11/71:21 pmPUJ - PNS
1 stop21h 36mSpirit Airlines
Deal found 9/15$386
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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.
vie. 10/244:36 pmPNS - PUJ
1 stop21h 13mSpirit Airlines
mié. 10/293:57 pmPUJ - PNS
1 stop24h 34mSpirit Airlines
Deal found 9/15$388
This Mytrip deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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.
vie. 10/246:25 pmPNS - PUJ
1 stop16h 03mSpirit Airlines
sáb. 10/251:30 pmPUJ - PNS
2 stops20h 44mSpirit Airlines
Deal found 9/15$401

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 septiembre 17, 2025.
Use the filters below to find and compare flights from Pensacola to Caribbean that are best for you.

Fly from

Pensacola

Fly to

Caribbean

Route

Depart

Return

Price

PensacolaSaint Thomas Island

PNS - STT

PNSSTT

Pensacola

vie. 10/17

4:36 pm-9:56 am

1 stop16h 20m

Saint Thomas Island Cyril E King

dom. 10/19

2:04 pm-6:15 pm

1 stop5h 11m

$311

PensacolaSaint Thomas Island

PNS - STT

PNSSTT

Pensacola

jue. 11/6

6:49 pm-3:11 pm

1 stop18h 22m

Saint Thomas Island Cyril E King

dom. 11/9

4:06 pm-5:54 pm

1 stop27h 48m

$341

PensacolaSan Juan

PNS - SJU

PNSSJU

Pensacola

mié. 11/12

1:25 pm-12:35 am

2 stops9h 10m

San Juan Luis Munoz Marin Intl

mar. 11/18

6:40 am-6:35 pm

2 stops13h 55m

$345

PensacolaSan Juan

PNS - SJU

PNSSJU

Pensacola

vie. 1/9

8:35 am-5:15 pm

1 stop6h 40m

San Juan Luis Munoz Marin Intl

lun. 1/12

7:15 am-8:30 pm

1 stop15h 15m

$365

PensacolaSan Juan

PNS - SJU

PNSSJU

Pensacola

mié. 11/12

5:24 am-5:52 pm

2 stops10h 28m

San Juan Luis Munoz Marin Intl

mar. 11/18

7:15 am-6:52 pm

1 stop13h 37m

$365

PensacolaSan Juan

PNS - SJU

PNSSJU

Pensacola

jue. 11/13

4:41 pm-7:21 pm

3 stops24h 40m

San Juan Luis Munoz Marin Intl

lun. 11/17

10:57 am-5:54 pm

1 stop8h 57m

$380

PensacolaSan Juan

PNS - SJU

PNSSJU

Pensacola

jue. 10/16

7:10 pm-3:16 pm

2 stops19h 06m

San Juan Luis Munoz Marin Intl

sáb. 10/18

7:58 pm-7:31 am

1 stop12h 33m

$381

PensacolaSan Juan

PNS - SJU

PNSSJU

Pensacola

jue. 10/16

4:36 pm-1:44 am

3 stops32h 08m

San Juan Luis Munoz Marin Intl

mar. 10/21

2:49 am-5:01 pm

1 stop15h 12m

$386

PensacolaPunta Cana

PNS - PUJ

PNSPUJ

Pensacola

vie. 10/24

4:36 pm-2:49 pm

1 stop21h 13m

Punta Cana

mié. 10/29

3:57 pm-3:31 pm

1 stop24h 34m

$388

PensacolaPunta Cana

PNS - PUJ

PNSPUJ

Pensacola

vie. 10/31

4:36 pm-11:28 am

2 stops17h 52m

Punta Cana

vie. 11/7

1:21 pm-8:57 am

1 stop21h 36m

$390

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 55 results
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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.
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

What is the cheapest month to book a flight from Pensacola to Caribbean?

Currently, September is the cheapest month in which you can book a flight from Pensacola to Caribbean (average of $254). Flying from Pensacola to Caribbean in June is currently the most expensive (average of $339). 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.

What is the cheapest time of day to fly from PNS to CB?

Find hourly flight availability from Pensacola to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated septiembre 17, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Pensacola to Caribbean as you normally would.

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 septiembre 17, 2025.
See what other customers who have flown with Southwest, Delta, and United 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.
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,961 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,926 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,023 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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.

  • What airport do you fly from for flights from Pensacola to Caribbean?

    Pensacola (PNS), located 4.0 mi from the city center, is the airport you fly out of when you book flights from Pensacola to Caribbean.

  • How long is the flight from Pensacola to Caribbean?

    A quick flight from Pensacola to Caribbean can take about 6h 40m. Spirit Airlines provides one of the quickest options available for as low as $365. The distance from Pensacola to Caribbean is about 1565 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the most popular routes from Pensacola to Caribbean?

    While some choose either Pensacola - Saint Thomas Island Cyril E King or Pensacola - Punta Cana, Pensacola - San Juan Luis Munoz Marin Intl is the most popular route from Pensacola to Caribbean.

  • Can I find deals for flights from Pensacola to Caribbean that include hotel bookings?

    Yes. In addition to deals on Pensacola to Caribbean flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Pensacola to Caribbean?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Pensacola to Caribbean.

  • Can I find deals for business class flights from Pensacola to Caribbean?

    Yes. Cheapflights offers flight deals from Pensacola to Caribbean by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Pensacola to Caribbean?

    Currently, September is the cheapest month in which you can book a flight from Pensacola to Caribbean (average of $254). Flying from Pensacola to Caribbean in June is currently the most expensive (average of $339). 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Pensacola to Caribbean

Discover the top 5 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 septiembre 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$157Average$384FlexibilityNo cancel feeOn-time65%
DeltaCheapest$292Average$538FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$335Average$627FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$380Average$523FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$381Average$510FlexibilityNo cancel feeOn-time63%

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