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Caribbean Islands

$137+ 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 6/8. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — SJU
May 6 — May 131
Tue 5/6
Tue 5/13
1 adult, Economy
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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 May 1, 2025.

Round-trip from

$268
(Cheapflightsfares)

One-way from

$137
(Cheapflightsfares)

Popular in

December

Cheapest in

September

Average price

$427
From Pensacola to Caribbean Islands
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One-way flight from Pensacola to Caribbean Islands
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Highest demand for flights based on searches. 8% potential increase in price ($38 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in May 2025
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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 May 1, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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 6/66:14 pmPNS - SJU
1 stop5h 40mSpirit Airlines
Thu 6/121:27 amSJU - PNS
1 stop8h 01mSpirit Airlines
Deal found 4/30$268
This Priceline deal was found by Cheapflights users on 4/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/166:00 amPNS - STT
1 stop5h 29mSpirit Airlines
Thu 6/191:24 pmSTT - PNS
1 stop10h 13mSpirit Airlines
Deal found 4/30$273
This Priceline deal was found by Cheapflights users on 4/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/126:00 amPNS - PUJ
1 stop4h 39mSpirit Airlines
Thu 6/1912:34 pmPUJ - PNS
1 stop11h 03mSpirit Airlines
Deal found 4/29$307
This Booking.com deal was found by Cheapflights users on 4/30. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/146:00 amPNS - MBJ
1 stop7h 08mSpirit Airlines
Sat 6/2112:07 pmMBJ - PNS
1 stop7h 24mSpirit Airlines
Deal found 4/30$340
This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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.
Mon 6/169:28 amPNS - SDQ
1 stop5h 01mSpirit Airlines
Thu 6/267:15 amSDQ - PNS
1 stop16h 22mSpirit Airlines
Deal found 4/30$342
This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/306:00 amPNS - SJU
1 stop9h 33mDelta
Wed 6/45:43 pmSJU - PNS
1 stop6h 24mDelta
Deal found 4/29$350
This American Airlines deal was found by Cheapflights users on 4/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/216:37 amPNS - SJU
1 stop12h 33mAmerican Airlines
Sat 9/273:58 pmSJU - PNS
1 stop8h 26mAmerican Airlines
Deal found 4/29$370
This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/126:00 amPNS - NAS
1 stop4h 54mDelta
Tue 9/161:19 pmNAS - PNS
1 stop8h 22mDelta
Deal found 4/29$395
This Southwest deal was found by Cheapflights users on 5/1. 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.
Wed 11/59:55 amPNS - SJU
2 stops10h 10mSouthwest
Mon 11/105:40 amSJU - PNS
2 stops13h 10mSouthwest
Deal found 5/1$395
This Mytrip deal was found by Cheapflights users on 4/30. 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 6/44:35 pmPNS - SDQ
2 stops20h 24mMultiple Airlines
Mon 6/94:50 pmSDQ - PNS
1 stop23h 40mMultiple Airlines
Deal found 4/30$398
This Kiwi.com deal was found by Cheapflights users on 5/1. 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 5/274:35 pmPNS - PUJ
2 stops18h 12mMultiple Airlines
Sat 5/3112:00 pmPUJ - PNS
1 stop6h 09mMultiple Airlines
Deal found 5/1$403
This American Airlines deal was found by Cheapflights users on 4/30. 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.
Wed 5/287:00 amPNS - NAS
2 stops11h 15mAmerican Airlines
Wed 6/47:45 amNAS - PNS
2 stops7h 20mAmerican Airlines
Deal found 4/30$440

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 May 1, 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

PensacolaSan Juan

PNS - SJU

PNSSJU

Pensacola

Fri 6/6

6:14 pm-12:54 am

1 stop5h 40m

San Juan Luis Munoz Marin Intl

Thu 6/12

1:27 am-8:28 am

1 stop8h 01m

$268

PensacolaSaint Thomas Island

PNS - STT

PNSSTT

Pensacola

Mon 6/16

6:00 am-12:29 pm

1 stop5h 29m

Saint Thomas Island Cyril E King

Thu 6/19

1:24 pm-10:37 pm

1 stop10h 13m

$273

PensacolaPunta Cana

PNS - PUJ

PNSPUJ

Pensacola

Thu 6/12

6:00 am-11:39 am

1 stop4h 39m

Punta Cana

Thu 6/19

12:34 pm-10:37 pm

1 stop11h 03m

$307

PensacolaMontego Bay

PNS - MBJ

PNSMBJ

Pensacola

Sat 6/14

6:00 am-1:08 pm

1 stop7h 08m

Montego Bay Sangster Intl

Sat 6/21

12:07 pm-7:31 pm

1 stop7h 24m

$340

PensacolaSanto Domingo

PNS - SDQ

PNSSDQ

Pensacola

Mon 6/16

9:28 am-3:29 pm

1 stop5h 01m

Santo Domingo Las Americas

Thu 6/26

7:15 am-10:37 pm

1 stop16h 22m

$342

PensacolaSan Juan

PNS - SJU

PNSSJU

Pensacola

Wed 10/8

6:00 am-4:18 pm

1 stop9h 18m

San Juan Luis Munoz Marin Intl

Tue 10/14

5:30 pm-11:07 pm

1 stop6h 37m

$345

PensacolaSan Juan

PNS - SJU

PNSSJU

Pensacola

Sun 9/21

6:37 am-8:10 pm

1 stop12h 33m

San Juan Luis Munoz Marin Intl

Sat 9/27

3:58 pm-11:24 pm

1 stop8h 26m

$370

PensacolaNassau

PNS - NAS

PNSNAS

Pensacola

Fri 9/12

6:00 am-11:54 am

1 stop4h 54m

Nassau Intl

Tue 9/16

1:19 pm-8:41 pm

1 stop8h 22m

$395

PensacolaSanto Domingo

PNS - SDQ

PNSSDQ

Pensacola

Wed 6/4

4:35 pm-1:59 pm

2 stops20h 24m

Santo Domingo Las Americas

Mon 6/9

4:50 pm-3:30 pm

1 stop23h 40m

$398

PensacolaPunta Cana

PNS - PUJ

PNSPUJ

Pensacola

Tue 5/27

4:35 pm-11:47 am

2 stops18h 12m

Punta Cana

Sat 5/31

12:00 pm-5:09 pm

1 stop6h 09m

$403

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 51 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, 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 December is currently the most expensive (average of $336). 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 May 1, 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.

Rainfall in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean Islands ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean Islands when rainfall is around 2.2 in.

Temperature in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean Islands, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

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 May 1, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and LATAM Airlines from Pensacola to Caribbean Islands to help guide your decision. 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
4,293 reviews

Crew

8.6

Boarding

8.2

Entertainment

7.6

Food

7.1

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,293 reviews
Southwest
8.0
Very good
4,293 reviews

Crew

8.6

Boarding

8.2

Entertainment

7.6

Food

7.1

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,934 reviews
Southwest
8.0
Very good
4,293 reviews

Crew

8.6

Boarding

8.2

Entertainment

7.6

Food

7.1

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
LATAM Airlines
7.5
Good
1,767 reviews
Southwest
8.0
Very good
4,293 reviews

Crew

8.6

Boarding

8.2

Entertainment

7.6

Food

7.1

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,696 reviews
Southwest
8.0
Very good
4,293 reviews

Crew

8.6

Boarding

8.2

Entertainment

7.6

Food

7.1

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,293 reviews

Crew

8.6

Boarding

8.2

Entertainment

7.6

Food

7.1

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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 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 $137. However, be on the lookout for offers from Southwest and Delta, 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 - Montego Bay Sangster Intl 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 December is currently the most expensive (average of $336). 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 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$163Average$414FlexibilityNo cancel feeOn-time65%
DeltaCheapest$264Average$649FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$316Average$634FlexibilityNo cancel feeOn-time71%
Silver AirwaysCheapest$387Average$473FlexibilityNo cancel feeOn-timeN/A

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