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$144+ 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 12/28. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — SJU
Dec 20 — Dec 271
Sat 12/20
Sat 12/27
1 adult, Economy
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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 November 20, 2025.

This Mytrip deal was found by Cheapflights users on 11/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/38:16 pmPNS - SJU
1 stop14h 16mSpirit Airlines
Sat 12/64:10 amSJU - PNS
1 stop16h 04mSpirit Airlines
Deal found 11/18$300
This Super.com deal was found by Cheapflights users on 11/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/197:09 pmPNS - STT
1 stop14h 22mSpirit Airlines
Fri 12/2612:31 pmSTT - PNS
1 stop7h 43mSpirit Airlines
Deal found 11/18$309
This Kiwi.com deal was found by Cheapflights users on 11/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/47:09 pmPNS - SJU
1 stop27h 36mMultiple Airlines
Thu 12/1110:42 amSJU - PNS
2 stops55h 22mMultiple Airlines
Deal found 11/18$310
This Cheapflightsfares deal was found by Cheapflights users on 11/17. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/201:44 pmPNS - SJU
1 stop8h 40mSpirit Airlines
Mon 11/2411:55 amSJU - PNS
1 stop9h 16mSpirit Airlines
Deal found 11/17$339
This KAYAK deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/57:09 pmPNS - SJU
1 stop15h 23mSpirit Airlines
Sun 12/74:10 amSJU - PNS
1 stop16h 04mSpirit Airlines
Deal found 11/20$363
This Kiwi.com deal was found by Cheapflights users on 11/17. 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.
Wed 11/265:44 pmPNS - SJU
1 stop18h 18mMultiple Airlines
Sun 12/77:00 amSJU - PNS
2 stops37h 14mMultiple Airlines
Deal found 11/17$366
This Kiwi.com deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/162:08 pmPNS - SJU
2 stops32h 08mMultiple Airlines
Tue 12/236:00 amSJU - PNS
1 stop9h 03mMultiple Airlines
Deal found 11/19$381
This Kiwi.com deal was found by Cheapflights users on 11/17. 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.
Sun 11/238:16 pmPNS - SJU
1 stop25h 28mMultiple Airlines
Sun 12/77:00 amSJU - PNS
2 stops37h 14mMultiple Airlines
Deal found 11/17$383
This Mytrip deal was found by Cheapflights users on 11/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/57:09 pmPNS - STT
1 stop14h 47mSpirit Airlines
Mon 12/81:01 pmSTT - PNS
1 stop7h 13mSpirit Airlines
Deal found 11/18$394
This Kiwi.com deal was found by Cheapflights users on 11/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/201:44 pmPNS - SJU
2 stops27h 54mSpirit Airlines
Fri 12/56:14 pmSJU - PNS
1 stop26h 00mSpirit Airlines
Deal found 11/18$394
This Kiwi.com deal was found by Cheapflights users on 11/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/102:08 pmPNS - KIN
1 stop21h 06mSpirit Airlines
Thu 12/181:19 pmKIN - PNS
1 stop5h 55mSpirit Airlines
Deal found 11/18$402
This Kiwi.com deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/117:09 pmPNS - KIN
1 stop16h 05mSpirit Airlines
Fri 12/191:19 pmKIN - PNS
1 stop5h 55mSpirit Airlines
Deal found 11/19$409

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 November 20, 2025.

Round-trip from

$277
(Spirit Airlines)

One-way from

$144
(Priceline)

Popular in

November

Cheapest in

February

Average price

$600
From Pensacola to Caribbean
Search Deals
One-way flight from Pensacola to Caribbean
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($57 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

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 November 20, 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

PensacolaSan Juan

PNS - SJU

PNSSJU

Pensacola

Sun 1/25

5:33 pm-9:47 am

1 stop14h 14m

San Juan Luis Munoz Marin Intl

Thu 1/29

6:00 am-4:37 pm

1 stop12h 37m

$277

PensacolaSan Juan

PNS - SJU

PNSSJU

Pensacola

Mon 1/19

4:03 pm-11:32 pm

2 stops29h 29m

San Juan Luis Munoz Marin Intl

Fri 1/23

6:00 am-4:37 pm

1 stop12h 37m

$308

PensacolaSan Juan

PNS - SJU

PNSSJU

Pensacola

Thu 2/26

5:35 pm-2:50 am

1 stop7h 15m

San Juan Luis Munoz Marin Intl

Mon 3/2

9:37 pm-4:39 pm

1 stop21h 02m

$316

PensacolaSan Juan

PNS - SJU

PNSSJU

Pensacola

Tue 2/3

5:33 pm-9:47 am

1 stop14h 14m

San Juan Luis Munoz Marin Intl

Fri 2/13

5:20 am-4:39 pm

1 stop13h 19m

$350

PensacolaSan Juan

PNS - SJU

PNSSJU

Pensacola

Thu 1/1

7:09 pm-12:19 pm

1 stop15h 10m

San Juan Luis Munoz Marin Intl

Thu 1/8

7:05 pm-10:38 am

2 stops41h 33m

$356

PensacolaSan Juan

PNS - SJU

PNSSJU

Pensacola

Fri 1/9

4:03 pm-9:47 am

2 stops15h 44m

San Juan Luis Munoz Marin Intl

Tue 1/13

6:00 am-4:37 pm

1 stop12h 37m

$358

PensacolaSan Juan

PNS - SJU

PNSSJU

Pensacola

Fri 12/5

7:09 pm-12:32 pm

1 stop15h 23m

San Juan Luis Munoz Marin Intl

Sun 12/7

4:10 am-6:14 pm

1 stop16h 04m

$363

PensacolaSaint Thomas Island

PNS - STT

PNSSTT

Pensacola

Sun 1/25

4:03 pm-2:52 pm

2 stops20h 49m

Saint Thomas Island Cyril E King

Thu 1/29

3:57 pm-3:08 pm

2 stops25h 11m

$366

PensacolaSan Juan

PNS - SJU

PNSSJU

Pensacola

Sat 1/3

7:09 pm-1:59 pm

1 stop16h 50m

San Juan Luis Munoz Marin Intl

Wed 1/7

1:55 am-3:08 pm

2 stops15h 13m

$369

PensacolaSan Juan

PNS - SJU

PNSSJU

Pensacola

Fri 1/2

7:09 pm-11:58 am

1 stop14h 49m

San Juan Luis Munoz Marin Intl

Thu 1/8

7:04 pm-2:32 pm

1 stop21h 28m

$374

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/18

Showing 1-10 of 47 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, May is the cheapest month in which you can book a flight from Pensacola to Caribbean (average of $112). Flying from Pensacola to Caribbean in September is currently the most expensive (average of $335). 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 November 20, 2025.

One of the essential ways to save on airfare from Pensacola to Caribbean is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight at noon could potentially save you up to 32% on airfare.

What is the cheapest day to fly from Pensacola to Caribbean?

Use this chart to determine the cheapest time to fly round-trip from Pensacola to Caribbean. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Pensacola to Caribbean flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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 November 20, 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
4,251 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Food

7.0

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
4,251 reviews
Southwest
8.0
Very good
4,251 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Food

7.0

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
7.9
Good
8,002 reviews
Southwest
8.0
Very good
4,251 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Food

7.0

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
9,028 reviews
Southwest
8.0
Very good
4,251 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Food

7.0

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
11,047 reviews
Southwest
8.0
Very good
4,251 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Food

7.0

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
8,159 reviews
Southwest
8.0
Very good
4,251 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Food

7.0

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 05m. Spirit Airlines provides one of the quickest options available for as low as $444. The distance from Pensacola to Caribbean is about 671 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 - Punta Cana or Pensacola - Marsh Harbour, 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, May is the cheapest month in which you can book a flight from Pensacola to Caribbean (average of $112). Flying from Pensacola to Caribbean in September is currently the most expensive (average of $335). 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

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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.
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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 November 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$115Average$384FlexibilityNo cancel feeOn-time65%
DeltaCheapest$300Average$525FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$338Average$624FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$380Average$689FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$381Average$539FlexibilityNo cancel feeOn-time63%

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