HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean Islands

$114+ 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 9/15. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — SJU
Aug 16 — Aug 231
Sat 8/16
Sat 8/23
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Pensacola to Caribbean Islands with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 August 11, 2025.

Round-trip from

$278
(FlightHub)

One-way from

$114
(Mytrip)

Popular in

December

Cheapest in

October

Average price

$417
From Pensacola to Caribbean Islands
Search Deals
One-way flight from Pensacola to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 1% potential increase in price ($6 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2025
Search Deals

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 August 11, 2025.

This FlightHub deal was found by Cheapflights users on 8/10. 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.
Sat 9/274:44 pmPNS - STT
1 stop16h 00mSpirit Airlines
Sat 10/410:49 amSTT - PNS
1 stop5h 50mSpirit Airlines
Deal found 8/10$278
This Mytrip deal was found by Cheapflights users on 8/10. 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.
Mon 9/154:44 pmPNS - SJU
2 stops20h 27mSpirit Airlines
Mon 9/226:44 amSJU - PNS
1 stop12h 26mSpirit Airlines
Deal found 8/10$285
This Kiwi.com deal was found by Cheapflights users on 8/10. 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 8/256:25 pmPNS - SJU
1 stop28h 32mSpirit Airlines
Fri 8/295:42 pmSJU - PNS
1 stop15h 26mSpirit Airlines
Deal found 8/10$290
This FlightHub deal was found by Cheapflights users on 8/10. 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 9/304:44 pmPNS - SJU
2 stops20h 27mSpirit Airlines
Sat 10/43:19 pmSJU - PNS
2 stops25h 20mSpirit Airlines
Deal found 8/10$291
This FlightHub deal was found by Cheapflights users on 8/10. 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 - SJU
1 stop17h 20mSpirit Airlines
Wed 9/246:44 amSJU - PNS
1 stop12h 26mSpirit Airlines
Deal found 8/10$295
This FlightHub deal was found by Cheapflights users on 8/10. 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 9/244:44 pmPNS - STT
1 stop16h 00mSpirit Airlines
Mon 9/2910:49 amSTT - PNS
1 stop5h 50mSpirit Airlines
Deal found 8/10$296
This Kiwi.com deal was found by Cheapflights users on 8/10. 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 8/2511:05 amPNS - SJU
2 stops9h 43mMultiple Airlines
Fri 8/295:42 pmSJU - PNS
1 stop15h 26mMultiple Airlines
Deal found 8/10$296
This FlightHub deal was found by Cheapflights users on 8/11. 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 9/74:44 pmPNS - STT
1 stop16h 00mSpirit Airlines
Sun 9/1410:49 amSTT - PNS
1 stop5h 50mSpirit Airlines
Deal found 8/11$297
This FlightHub deal was found by Cheapflights users on 8/10. 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 11/34:44 pmPNS - STT
1 stop16h 05mSpirit Airlines
Mon 11/101:33 pmSTT - PNS
1 stop28h 03mSpirit Airlines
Deal found 8/10$301
This FlightHub deal was found by Cheapflights users on 8/10. 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 8/10$303
This FlightHub deal was found by Cheapflights users on 8/10. 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.
Sat 9/204:44 pmPNS - SJU
1 stop17h 20mSpirit Airlines
Sat 9/273:19 pmSJU - PNS
2 stops25h 20mSpirit Airlines
Deal found 8/10$303
This FlightHub deal was found by Cheapflights users on 8/11. 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 9/184:44 pmPNS - STT
1 stop16h 00mSpirit Airlines
Fri 9/2610:49 amSTT - PNS
1 stop5h 50mSpirit Airlines
Deal found 8/11$306

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 August 11, 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

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

$278

PensacolaSan Juan

PNS - SJU

PNSSJU

Pensacola

Mon 9/15

4:44 pm-2:11 pm

2 stops20h 27m

San Juan Luis Munoz Marin Intl

Mon 9/22

6:44 am-6:10 pm

1 stop12h 26m

$285

PensacolaSan Juan

PNS - SJU

PNSSJU

Pensacola

Mon 8/25

6:25 pm-11:57 pm

1 stop28h 32m

San Juan Luis Munoz Marin Intl

Fri 8/29

5:42 pm-8:08 am

1 stop15h 26m

$290

PensacolaSan Juan

PNS - SJU

PNSSJU

Pensacola

Tue 9/30

4:44 pm-2:11 pm

2 stops20h 27m

San Juan Luis Munoz Marin Intl

Sat 10/4

3:19 pm-3:39 pm

2 stops25h 20m

$291

PensacolaSan Juan

PNS - SJU

PNSSJU

Pensacola

Sun 9/21

4:44 pm-11:04 am

1 stop17h 20m

San Juan Luis Munoz Marin Intl

Wed 9/24

6:44 am-6:10 pm

1 stop12h 26m

$295

PensacolaSan Juan

PNS - SJU

PNSSJU

Pensacola

Mon 8/25

11:05 am-9:48 pm

2 stops9h 43m

San Juan Luis Munoz Marin Intl

Fri 8/29

5:42 pm-8:08 am

1 stop15h 26m

$296

PensacolaSaint Thomas Island

PNS - STT

PNSSTT

Pensacola

Wed 9/24

4:44 pm-9:44 am

1 stop16h 00m

Saint Thomas Island Cyril E King

Mon 9/29

10:49 am-3:39 pm

1 stop5h 50m

$296

PensacolaSaint Thomas Island

PNS - STT

PNSSTT

Pensacola

Sun 9/7

4:44 pm-9:44 am

1 stop16h 00m

Saint Thomas Island Cyril E King

Sun 9/14

10:49 am-3:39 pm

1 stop5h 50m

$297

PensacolaSaint Thomas Island

PNS - STT

PNSSTT

Pensacola

Mon 11/3

4:44 pm-10:49 am

1 stop16h 05m

Saint Thomas Island Cyril E King

Mon 11/10

1:33 pm-3:36 pm

1 stop28h 03m

$301

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

$303

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/10

Showing 1-10 of 43 results
1
2
3
...
5

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, September is the cheapest month in which you can book a flight from Pensacola to Caribbean Islands (average of $254). Flying from Pensacola to Caribbean Islands 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 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 August 11, 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 Islands as you normally would.

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 August 11, 2025.
Read reviews from past customers who have flown Southwest, Delta, and LATAM 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.
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,978 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
LATAM Airlines
7.5
Good
1,837 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
WestJet
7.2
Good
3,007 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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.

  • 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 - Basseterre Robert Bradshaw Intl or Pensacola - Punta Cana 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, September is the cheapest month in which you can book a flight from Pensacola to Caribbean Islands (average of $254). Flying from Pensacola to Caribbean Islands 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Pensacola to Caribbean Islands

See prices for flight routes from nearby airports that may be better suited for you.
Fort Lauderdale to Newark flights
Miami to John F Kennedy Intl flights
Orlando to John F Kennedy Intl flights
Fort Lauderdale to LaGuardia flights
Fort Lauderdale to John F Kennedy Intl flights
Fort Lauderdale to Las Vegas flights
Miami to Newark flights
Orlando to Las Vegas flights
Miami to LaGuardia flights
Orlando to Newark flights
Tampa to John F Kennedy Intl flights
Orlando to LaGuardia flights
Tampa to LaGuardia flights
Tampa to Boston flights
Tampa to Newark flights
Orlando to Seattle flights
Orlando to Dallas/Fort Worth flights
Tampa to Seattle flights
West Palm Beach to John F Kennedy Intl flights
Tampa to Las Vegas flights
Orlando to Denver flights
Miami to Las Vegas flights
Miami to Los Angeles flights
Orlando to O'Hare Intl flights
Tampa to Denver flights
Orlando to Los Angeles flights
Fort Lauderdale to Atlanta flights
Miami to Mexico City flights
Miami to Cancún flights
Fort Lauderdale to Los Angeles flights
Fort Lauderdale to Dallas/Fort Worth flights
Orlando to Reagan-National flights
West Palm Beach to LaGuardia flights
Fort Lauderdale to Boston flights
Miami to Boston flights
Miami to Denver flights
Orlando to Cancún flights
Jacksonville to John F Kennedy Intl flights
Jacksonville to Newark flights
Tampa to Sky Harbor Intl flights
Miami to Atlanta flights
Tampa to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Miami to Reagan-National flights
Miami to O'Hare Intl flights
Orlando to Midway flights
Fort Lauderdale to Denver flights
Orlando to Boston flights
Tampa to Dulles Intl flights
Fort Lauderdale to Cancún flights

Top 4 airlines flying from Pensacola to Caribbean Islands

Discover the top 4 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 August 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$157Average$375FlexibilityNo cancel feeOn-time65%
DeltaCheapest$292Average$578FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$334Average$641FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$381Average$510FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.