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Caribbean Islands

$145+ Cheap flights from Pensacola (PNS) to Caribbean Islands

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 12/1. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — SJU
Nov 22 — Nov 291
Sat 11/22
Sat 11/29
1 adult, Economy
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Find flight deals from Pensacola to Caribbean Islands

Cheapest flights from Pensacola to Caribbean Islands
Explore the most affordable flight options available from Pensacola to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 23, 2025.

This Mytrip deal was found by Cheapflights users on 10/22. 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.
Tue 11/258:16 pmPNS - STT
1 stop14h 39mSpirit Airlines
Fri 12/51:01 pmSTT - PNS
1 stop7h 13mSpirit Airlines
Deal found 10/22$293
This Mytrip deal was found by Cheapflights users on 10/22. 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 11/298:16 pmPNS - STT
1 stop14h 39mSpirit Airlines
Sat 12/61:01 pmSTT - PNS
1 stop7h 13mSpirit Airlines
Deal found 10/22$342
This Trip.com deal was found by Cheapflights users on 10/21. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/208:16 pmPNS - STT
1 stop14h 39mSpirit Airlines
Thu 11/273:25 pmSTT - PNS
1 stop27h 34mSpirit Airlines
Deal found 10/21$344
This Delta deal was found by Cheapflights users on 10/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/73:44 pmPNS - SJU
1 stop5h 36mDelta
Tue 12/167:00 amSJU - PNS
1 stop9h 45mDelta
Deal found 10/23$345
This Cheapflightsfares deal was found by Cheapflights users on 10/22. 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 10/22$348
This Southwest deal was found by Cheapflights users on 10/23. 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.
Tue 12/99:55 amPNS - SJU
2 stops9h 35mSouthwest
Tue 12/166:40 amSJU - PNS
2 stops13h 55mSouthwest
Deal found 10/23$351
This KAYAK deal was found by Cheapflights users on 10/22. 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.
Sat 11/228:16 pmPNS - STT
1 stop14h 39mSpirit Airlines
Mon 12/12:00 pmSTT - PNS
1 stop7h 11mSpirit Airlines
Deal found 10/22$356
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 12/314:44 pmPNS - SJU
2 stops31h 50mMultiple Airlines
Sat 1/103:55 amSJU - PNS
1 stop15h 59mMultiple Airlines
Deal found 10/21$368
This Delta deal was found by Cheapflights users on 10/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/711:46 amPNS - SJU
1 stop9h 34mDelta
Thu 12/187:00 amSJU - PNS
1 stop9h 45mDelta
Deal found 10/23$370
This Kiwi.com deal was found by Cheapflights users on 10/23. 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.
Wed 12/311:58 pmPNS - SJU
2 stops32h 31mMultiple Airlines
Sat 1/105:20 pmSJU - PNS
1 stop24h 16mMultiple Airlines
Deal found 10/23$374
This Mytrip deal was found by Cheapflights users on 10/21. 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 12/47:09 pmPNS - SJU
1 stop15h 23mSpirit Airlines
Mon 12/83:59 amSJU - PNS
1 stop11h 04mSpirit Airlines
Deal found 10/21$382
This American Airlines deal was found by Cheapflights users on 10/23. 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.
Tue 12/96:00 amPNS - SJU
1 stop5h 30mAmerican Airlines
Tue 12/1612:49 pmSJU - PNS
1 stop13h 00mAmerican Airlines
Deal found 10/23$385

Cheap flight deals from Pensacola to Caribbean Islands

Keep the following information in mind while searching for Pensacola to Caribbean Islands flight deals. Data was last updated October 23, 2025.

Round-trip from

$293
(Mytrip)

One-way from

$145
(Expedia)

Popular in

September

Cheapest in

February

Average price

$419
From Pensacola to Caribbean Islands
Search Deals
One-way flight from Pensacola to Caribbean Islands
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 Islands 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 23, 2025.
Use the filters below to find and compare flights from Pensacola to Caribbean Islands that are best for you.

Fly from

Pensacola

Fly to

Caribbean Islands

Route

Depart

Return

Price

PensacolaSaint Thomas Island

PNS - STT

PNSSTT

Pensacola

Tue 11/25

8:16 pm-12:55 pm

1 stop14h 39m

Saint Thomas Island Cyril E King

Fri 12/5

1:01 pm-6:14 pm

1 stop7h 13m

$293

PensacolaSaint Thomas Island

PNS - STT

PNSSTT

Pensacola

Thu 11/20

8:16 pm-12:55 pm

1 stop14h 39m

Saint Thomas Island Cyril E King

Thu 11/27

3:25 pm-4:59 pm

1 stop27h 34m

$344

PensacolaSan Juan

PNS - SJU

PNSSJU

Pensacola

Mon 12/8

3:44 pm-11:20 pm

1 stop5h 36m

San Juan Luis Munoz Marin Intl

Tue 12/16

7:00 am-12:41 pm

1 stop7h 41m

$345

PensacolaSan Juan

PNS - SJU

PNSSJU

Pensacola

Sun 1/11

11:59 am-11:49 pm

1 stop9h 50m

San Juan Luis Munoz Marin Intl

Tue 1/20

6:24 pm-11:07 pm

1 stop6h 43m

$345

PensacolaSan Juan

PNS - SJU

PNSSJU

Pensacola

Wed 1/21

1:59 pm-11:49 pm

1 stop7h 50m

San Juan Luis Munoz Marin Intl

Wed 2/4

7:30 am-2:26 pm

1 stop8h 56m

$345

PensacolaSan Juan

PNS - SJU

PNSSJU

Pensacola

Thu 11/20

1:44 pm-12:24 am

1 stop8h 40m

San Juan Luis Munoz Marin Intl

Mon 11/24

11:55 am-7:11 pm

1 stop9h 16m

$348

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

Mon 12/8

3:44 pm-11:20 pm

1 stop5h 36m

San Juan Luis Munoz Marin Intl

Thu 12/18

7:00 am-2:45 pm

1 stop9h 45m

$370

PensacolaMontego Bay

PNS - MBJ

PNSMBJ

Pensacola

Wed 11/19

8:16 pm-12:02 pm

2 stops14h 46m

Montego Bay Sangster Intl

Sun 11/23

1:07 pm-7:11 pm

1 stop7h 04m

$394

PensacolaSan Juan

PNS - SJU

PNSSJU

Pensacola

Tue 11/4

7:20 am-6:35 pm

2 stops9h 15m

San Juan Luis Munoz Marin Intl

Tue 11/11

5:45 am-3:35 pm

2 stops11h 50m

$395

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/21

Showing 1-10 of 60 results
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Best time to book a flight from Pensacola to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands 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 Islands

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

Currently, May is the cheapest month in which you can book a flight from Pensacola to Caribbean Islands (average of $112). Flying from Pensacola to Caribbean Islands 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 EPX?

Find hourly flight availability from Pensacola to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 23, 2025.

It’s optimal to fly from Pensacola to Caribbean Islands in the afternoon. By choosing this option you can save up to 30% on the cost of your flight, compared to a flight in the morning.

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

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

Travelers seeking maximum savings on their Pensacola to Caribbean Islands 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 Islands

Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated October 23, 2025.
Read reviews from past customers who have flown Delta, American Airlines, and Spirit Airlines from Pensacola to Caribbean Islands. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
7,981 reviews

Entertainment

7.9

Boarding

8.2

Overall

7.9

Comfort

7.9

Food

7.3

Crew

8.5

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
Delta
7.9
Good
7,981 reviews
Delta
7.9
Good
7,981 reviews

Entertainment

7.9

Boarding

8.2

Overall

7.9

Comfort

7.9

Food

7.3

Crew

8.5

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
American Airlines
7.2
Good
11,028 reviews
Delta
7.9
Good
7,981 reviews

Entertainment

7.9

Boarding

8.2

Overall

7.9

Comfort

7.9

Food

7.3

Crew

8.5

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
Spirit Airlines
6.3
Okay
8,098 reviews
Delta
7.9
Good
7,981 reviews

Entertainment

7.9

Boarding

8.2

Overall

7.9

Comfort

7.9

Food

7.3

Crew

8.5

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.

Related info for your journey

Find useful and relevant information for your journey from Pensacola to Caribbean Islands. 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 Islands?

    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 Islands.

  • How long is the flight from Pensacola to Caribbean Islands?

    Airlines like Spirit Airlines, Delta, and American Airlines fly from Pensacola to Caribbean Islands in about 5h 36m. The time it takes to get you to your destination can typically vary by up to 14h 15m. There are 1565 mi between Pensacola and Caribbean Islands. 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 Islands one-way?

    The cheapest airline one-way is Spirit Airlines, with whom users have recently found tickets for as low as $164. However, be on the lookout for offers from Southwest and American Airlines, as they are both options that can get you from Pensacola to Caribbean Islands for a low price.

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

    When deciding which route to take from Pensacola to Caribbean Islands consider Pensacola - San Juan Luis Munoz Marin Intl, Pensacola - Punta Cana or Pensacola - Saint Thomas Island Cyril E King as they are the most popular.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Pensacola to Caribbean Islands 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 Islands?

    Currently, May is the cheapest month in which you can book a flight from Pensacola to Caribbean Islands (average of $112). Flying from Pensacola to Caribbean Islands 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.

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Top 5 airlines flying from Pensacola to Caribbean Islands

Discover the top 5 airlines that operate flights from Pensacola to Caribbean Islands. 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 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$115Average$385FlexibilityNo cancel feeOn-time65%
DeltaCheapest$300Average$523FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$335Average$634FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$380Average$689FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$381Average$539FlexibilityNo cancel feeOn-time63%

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