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$143+ 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 9/17. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — SJU
Sep 2 — Sep 91
Tue 9/2
Tue 9/9
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 August 28, 2025.

Round-trip from

$296
(FlightHub)

One-way from

$143
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$458
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. 0% potential increase in price ($2 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in August 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 August 28, 2025.

This FlightHub deal was found by Cheapflights users on 8/28. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/174:36 pmPNS - STT
1 stop16h 20mSpirit Airlines
Sun 10/1911:01 amSTT - PNS
1 stop5h 30mSpirit Airlines
Deal found 8/28$296
This FlightHub deal was found by Cheapflights users on 8/28. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/214:44 pmPNS - STT
1 stop16h 00mSpirit Airlines
Sun 9/2810:49 amSTT - PNS
1 stop5h 50mSpirit Airlines
Deal found 8/28$308
This FlightHub deal was found by Cheapflights users on 8/28. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/34:36 pmPNS - STT
1 stop16h 15mSpirit Airlines
Mon 11/101:33 pmSTT - PNS
1 stop28h 03mSpirit Airlines
Deal found 8/28$311
This FlightHub deal was found by Cheapflights users on 8/27. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/66:49 pmPNS - STT
1 stop18h 22mSpirit Airlines
Wed 11/124:06 pmSTT - PNS
1 stop27h 48mSpirit Airlines
Deal found 8/27$335
This Cheapflightsfares deal was found by Cheapflights users on 8/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/176:25 pmPNS - SJU
1 stop6h 19mSpirit Airlines
Sat 10/182:49 amSJU - PNS
1 stop7h 25mSpirit Airlines
Deal found 8/28$335
This FlightHub deal was found by Cheapflights users on 8/28. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/85:56 pmPNS - SJU
1 stop6h 48mSpirit Airlines
Mon 10/132:49 amSJU - PNS
1 stop15h 12mSpirit Airlines
Deal found 8/28$339
This FlightHub deal was found by Cheapflights users on 8/27. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/45:56 pmPNS - STT
1 stop19h 15mSpirit Airlines
Tue 11/111:33 pmSTT - PNS
1 stop28h 03mSpirit Airlines
Deal found 8/27$340
This FlightHub deal was found by Cheapflights users on 8/25. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/215:56 pmPNS - SJU
1 stop6h 48mSpirit Airlines
Sat 10/252:49 amSJU - PNS
1 stop7h 25mSpirit Airlines
Deal found 8/25$341
This FlightHub deal was found by Cheapflights users on 8/26. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/910:28 amPNS - SJU
1 stop14h 16mSpirit Airlines
Mon 10/132:49 amSJU - PNS
1 stop15h 12mSpirit Airlines
Deal found 8/26$342
This Kiwi.com deal was found by Cheapflights users on 8/28. 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.
Fri 9/197:10 pmPNS - SJU
1 stop27h 49mMultiple Airlines
Mon 9/229:26 pmSJU - PNS
2 stops21h 44mMultiple Airlines
Deal found 8/28$343
This FlightHub deal was found by Cheapflights users on 8/27. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/264:44 pmPNS - SJU
2 stops20h 27mSpirit Airlines
Tue 9/306:44 amSJU - PNS
1 stop12h 26mSpirit Airlines
Deal found 8/27$346
This Kiwi.com deal was found by Cheapflights users on 8/28. 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 10/225:56 pmPNS - SJU
1 stop6h 48mMultiple Airlines
Mon 10/279:00 amSJU - PNS
1 stop7h 31mMultiple Airlines
Deal found 8/28$347

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 August 28, 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

Fri 10/17

4:36 pm-9:56 am

1 stop16h 20m

Saint Thomas Island Cyril E King

Sun 10/19

11:01 am-3:31 pm

1 stop5h 30m

$296

PensacolaSaint Thomas Island

PNS - STT

PNSSTT

Pensacola

Sun 9/21

4:44 pm-9:44 am

1 stop16h 00m

Saint Thomas Island Cyril E King

Sun 9/28

10:49 am-3:39 pm

1 stop5h 50m

$308

PensacolaSaint Thomas Island

PNS - STT

PNSSTT

Pensacola

Sat 9/27

4:44 pm-9:44 am

1 stop16h 00m

Saint Thomas Island Cyril E King

Sat 10/4

10:49 am-3:39 pm

1 stop5h 50m

$308

PensacolaSaint Thomas Island

PNS - STT

PNSSTT

Pensacola

Mon 11/3

4:36 pm-10:51 am

1 stop16h 15m

Saint Thomas Island Cyril E King

Mon 11/10

1:33 pm-3:36 pm

1 stop28h 03m

$311

PensacolaSaint Thomas Island

PNS - STT

PNSSTT

Pensacola

Thu 11/6

6:49 pm-3:11 pm

1 stop18h 22m

Saint Thomas Island Cyril E King

Wed 11/12

4:06 pm-5:54 pm

1 stop27h 48m

$335

PensacolaSan Juan

PNS - SJU

PNSSJU

Pensacola

Fri 10/17

6:25 pm-1:44 am

1 stop6h 19m

San Juan Luis Munoz Marin Intl

Sat 10/18

2:49 am-9:14 am

1 stop7h 25m

$335

PensacolaSan Juan

PNS - SJU

PNSSJU

Pensacola

Wed 10/8

5:56 pm-1:44 am

1 stop6h 48m

San Juan Luis Munoz Marin Intl

Mon 10/13

2:49 am-5:01 pm

1 stop15h 12m

$339

PensacolaSaint Thomas Island

PNS - STT

PNSSTT

Pensacola

Tue 11/4

5:56 pm-3:11 pm

1 stop19h 15m

Saint Thomas Island Cyril E King

Tue 11/11

1:33 pm-3:36 pm

1 stop28h 03m

$340

PensacolaSan Juan

PNS - SJU

PNSSJU

Pensacola

Sun 11/9

6:49 pm-9:52 am

1 stop13h 03m

San Juan Luis Munoz Marin Intl

Sun 11/16

10:57 am-5:54 pm

1 stop8h 57m

$341

PensacolaSan Juan

PNS - SJU

PNSSJU

Pensacola

Tue 10/21

5:56 pm-1:44 am

1 stop6h 48m

San Juan Luis Munoz Marin Intl

Sat 10/25

2:49 am-9:14 am

1 stop7h 25m

$341

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/27

Showing 1-10 of 58 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 August 28, 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 August 28, 2025.
See what other customers who have flown with Southwest, Delta, and American 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

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

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

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

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
7,977 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

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

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

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
8,028 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

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 5h 33m. Spirit Airlines provides one of the quickest options available for as low as $456. The distance from Pensacola to Caribbean is about 702 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?

    $163 is the cheapest one-way deal found within the past few days, from Southwest. You may also be able to find cheap deals on Spirit Airlines and United Airlines, with prices starting from $176 and $182, respectively.

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

    While some choose either Pensacola - Punta Cana or Pensacola - Montego Bay Sangster Intl, 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

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See prices for flight routes from nearby airports that may be better suited for you.
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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 August 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$157Average$383FlexibilityNo cancel feeOn-time65%
DeltaCheapest$292Average$572FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$335Average$640FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$381Average$510FlexibilityNo cancel feeOn-time63%

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