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$145+ 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 11/20. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — SJU
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
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 October 30, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/29. 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 11/245:54 pmPNS - SJU
1 stop7h 00mMultiple Airlines
Tue 11/255:19 pmSJU - PNS
1 stop27h 52mMultiple Airlines
Deal found 10/29$247
This Kiwi.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/218:16 pmPNS - SJU
2 stops28h 38mMultiple Airlines
Tue 11/255:19 pmSJU - PNS
1 stop27h 52mMultiple Airlines
Deal found 10/29$286
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 11/198:16 pmPNS - SJU
1 stop11h 40mMultiple Airlines
Tue 11/255:19 pmSJU - PNS
1 stop27h 52mMultiple Airlines
Deal found 10/29$290
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 11/198:16 pmPNS - SJU
1 stop11h 40mMultiple Airlines
Thu 11/203:59 amSJU - PNS
1 stop15h 00mMultiple Airlines
Deal found 10/29$293
This Kiwi.com deal was found by Cheapflights users on 10/29. 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
1 stop11h 10mMultiple Airlines
Fri 11/217:15 amSJU - PNS
1 stop11h 44mMultiple Airlines
Deal found 10/29$294
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 11/198:16 pmPNS - SJU
1 stop16h 22mMultiple Airlines
Sat 11/223:59 amSJU - PNS
1 stop10h 50mMultiple Airlines
Deal found 10/29$296
This Kiwi.com deal was found by Cheapflights users on 10/29. 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
1 stop11h 10mMultiple Airlines
Sat 11/223:59 amSJU - PNS
1 stop10h 50mMultiple Airlines
Deal found 10/29$297
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 11/231:44 pmPNS - SJU
1 stop11h 10mMultiple Airlines
Tue 11/255:19 pmSJU - PNS
1 stop27h 52mMultiple Airlines
Deal found 10/29$310
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 12/57:09 pmPNS - STT
1 stop14h 47mSpirit Airlines
Sat 12/131:01 pmSTT - PNS
1 stop7h 13mSpirit Airlines
Deal found 10/29$320
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 12/28:16 pmPNS - STT
1 stop14h 39mSpirit Airlines
Sat 12/131:01 pmSTT - PNS
1 stop7h 13mSpirit Airlines
Deal found 10/29$322
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 - STT
1 stop14h 47mSpirit Airlines
Sat 12/131:01 pmSTT - PNS
1 stop7h 13mSpirit Airlines
Deal found 10/29$334
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 12/18:16 pmPNS - STT
1 stop14h 39mSpirit Airlines
Sat 12/131:01 pmSTT - PNS
1 stop7h 13mSpirit Airlines
Deal found 10/29$337

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 October 30, 2025.

Round-trip from

$247
(Kiwi.com)

One-way from

$145
(Expedia)

Popular in

September

Cheapest in

February

Average price

$419
From Pensacola to Caribbean
Search Deals
One-way flight from Pensacola to Caribbean
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($18 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 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 October 30, 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

Wed 11/19

8:16 pm-9:56 am

1 stop11h 40m

San Juan Luis Munoz Marin Intl

Tue 11/25

5:19 pm-4:59 pm

2 stops25h 40m

$325

PensacolaSan Juan

PNS - SJU

PNSSJU

Pensacola

Sun 1/11

2:58 pm-11:44 pm

1 stop6h 46m

San Juan Luis Munoz Marin Intl

Tue 1/20

6:27 pm-11:12 pm

1 stop6h 45m

$345

PensacolaSan Juan

PNS - SJU

PNSSJU

Pensacola

Mon 11/10

4:45 pm-11:19 am

2 stops16h 34m

San Juan Luis Munoz Marin Intl

Fri 11/14

2:11 am-3:23 pm

2 stops15h 12m

$355

PensacolaSaint Thomas Island

PNS - STT

PNSSTT

Pensacola

Sat 11/22

8:16 pm-12:55 pm

1 stop14h 39m

Saint Thomas Island Cyril E King

Mon 12/1

2:00 pm-7:11 pm

1 stop7h 11m

$356

PensacolaSan Juan

PNS - SJU

PNSSJU

Pensacola

Thu 11/20

1:44 pm-12:24 am

1 stop8h 40m

San Juan Luis Munoz Marin Intl

Sat 12/6

4:10 am-6:14 pm

1 stop16h 04m

$363

PensacolaSan Juan

PNS - SJU

PNSSJU

Pensacola

Tue 11/18

7:20 am-9:30 pm

2 stops12h 10m

San Juan Luis Munoz Marin Intl

Sat 12/6

6:15 am-5:00 pm

2 stops12h 45m

$370

PensacolaSan Juan

PNS - SJU

PNSSJU

Pensacola

Thu 11/20

8:16 pm-11:44 pm

1 stop25h 28m

San Juan Luis Munoz Marin Intl

Sun 12/7

7:00 am-7:14 pm

2 stops38h 14m

$380

PensacolaSan Juan

PNS - SJU

PNSSJU

Pensacola

Mon 1/19

6:49 pm-9:55 am

1 stop13h 06m

San Juan Luis Munoz Marin Intl

Thu 1/29

3:55 am-5:54 pm

1 stop15h 59m

$387

PensacolaSan Juan

PNS - SJU

PNSSJU

Pensacola

Tue 11/18

7:20 am-9:30 pm

2 stops12h 10m

San Juan Luis Munoz Marin Intl

Thu 12/4

5:45 am-6:35 pm

2 stops14h 50m

$394

PensacolaSan Juan

PNS - SJU

PNSSJU

Pensacola

Sat 11/22

8:16 pm-8:27 pm

1 stop22h 11m

San Juan Luis Munoz Marin Intl

Mon 11/24

7:10 am-7:11 pm

2 stops14h 01m

$396

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

Showing 1-10 of 46 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 October 30, 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 31% 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 October 30, 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
4,243 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.5

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
4,243 reviews
Southwest
8.0
Very good
4,243 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.5

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
7,998 reviews
Southwest
8.0
Very good
4,243 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.5

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
8,998 reviews
Southwest
8.0
Very good
4,243 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.5

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
11,035 reviews
Southwest
8.0
Very good
4,243 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.5

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
8,116 reviews
Southwest
8.0
Very good
4,243 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.5

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 46m. Delta provides one of the quickest options available for as low as $345. 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 cheapest airlines to fly from Pensacola to Caribbean one-way?

    $145 is the cheapest one-way deal found within the past few days, from Spirit Airlines. You may also be able to find cheap deals on United Airlines and American Airlines, with prices starting from $231 and $239, respectively.

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

    While some choose either Pensacola - Marsh Harbour or Pensacola - Saint Thomas Island Cyril E King, 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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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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$115Average$384FlexibilityNo cancel feeOn-time65%
DeltaCheapest$300Average$524FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$335Average$623FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$380Average$689FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$381Average$539FlexibilityNo cancel feeOn-time63%

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