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$128+ 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 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — SJU
Feb 5 — Feb 121
Thu 2/5
Thu 2/12
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 January 6, 2026.

Round-trip from

$229
(Priceline)

One-way from

$128
(Cheapflightsfares)

Popular in

December

Cheapest in

February

Average price

$425
From Pensacola to Caribbean
Search Deals
One-way flight from Pensacola to Caribbean
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Highest demand for flights based on searches. 9% potential increase in price ($50 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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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 January 6, 2026.

This Priceline deal was found by Cheapflights users on 1/4. 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.
Wed 2/186:37 pmPNS - SJU
1 stop13h 40mMultiple Airlines
Thu 2/265:25 pmSJU - PNS
1 stop17h 25mMultiple Airlines
Deal found 1/4$229
This Priceline deal was found by Cheapflights users on 1/6. 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 3/22:23 pmPNS - SJU
1 stop10h 30mFrontier
Sun 3/86:30 amSJU - PNS
1 stop8h 28mFrontier
Deal found 1/6$251
This Trip.com deal was found by Cheapflights users on 1/6. 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.
Sun 2/226:37 pmPNS - SJU
1 stop6h 16mMultiple Airlines
Tue 2/243:53 amSJU - PNS
1 stop15h 49mMultiple Airlines
Deal found 1/6$255
This Cheapflightsfares deal was found by Cheapflights users on 1/6. 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 2/55:33 pmPNS - SJU
1 stop14h 14mSpirit Airlines
Thu 2/1211:52 amSJU - PNS
1 stop7h 50mSpirit Airlines
Deal found 1/6$261
This Kiwi.com deal was found by Cheapflights users on 1/6. 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 2/95:33 pmPNS - SJU
1 stop14h 14mMultiple Airlines
Sun 2/156:00 amSJU - PNS
1 stop13h 42mMultiple Airlines
Deal found 1/6$274
This Kiwi.com deal was found by Cheapflights users on 1/5. 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 1/305:33 pmPNS - SJU
1 stop14h 14mSpirit Airlines
Tue 2/35:50 pmSJU - PNS
2 stops24h 47mSpirit Airlines
Deal found 1/5$280
This Priceline deal was found by Cheapflights users on 1/4. 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.
Fri 4/1011:24 amPNS - SJU
1 stop5h 37mFrontier
Sun 4/123:55 amSJU - PNS
1 stop7h 34mFrontier
Deal found 1/4$282
This Trip.com deal was found by Cheapflights users on 1/5. 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.
Sat 2/146:37 pmPNS - SJU
1 stop13h 40mMultiple Airlines
Sat 2/213:53 amSJU - PNS
1 stop15h 49mMultiple Airlines
Deal found 1/5$283
This Priceline deal was found by Cheapflights users on 1/5. 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.
Fri 2/279:35 amPNS - SJU
1 stop13h 08mFrontier
Sat 3/73:08 amSJU - PNS
1 stop11h 50mFrontier
Deal found 1/5$286
This Kiwi.com deal was found by Cheapflights users on 1/5. 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 1/305:33 pmPNS - SJU
2 stops21h 27mMultiple Airlines
Mon 2/28:05 pmSJU - PNS
1 stop22h 32mMultiple Airlines
Deal found 1/5$287
This Kiwi.com deal was found by Cheapflights users on 1/5. 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 2/185:20 pmPNS - GCM
1 stop19h 23mSpirit Airlines
Thu 2/262:49 pmGCM - PNS
1 stop26h 05mSpirit Airlines
Deal found 1/5$321
This Kiwi.com deal was found by Cheapflights users on 1/4. 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 2/94:03 pmPNS - STT
1 stop22h 34mSpirit Airlines
Wed 2/185:40 pmSTT - PNS
1 stop24h 14mSpirit Airlines
Deal found 1/4$323

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 January 6, 2026.
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

Mon 2/2

5:33 pm-9:47 am

1 stop14h 14m

San Juan Luis Munoz Marin Intl

Mon 2/9

6:00 am-4:37 pm

1 stop12h 37m

$280

PensacolaSan Juan

PNS - SJU

PNSSJU

Pensacola

Tue 2/17

6:37 pm-9:54 am

1 stop13h 17m

San Juan Luis Munoz Marin Intl

Sat 2/21

5:20 am-5:42 pm

1 stop14h 22m

$292

PensacolaSan Juan

PNS - SJU

PNSSJU

Pensacola

Sat 2/14

11:18 am-2:29 am

2 stops37h 11m

San Juan Luis Munoz Marin Intl

Sun 2/22

5:20 am-5:42 pm

1 stop14h 22m

$297

PensacolaSan Juan

PNS - SJU

PNSSJU

Pensacola

Mon 3/2

6:37 pm-9:54 am

1 stop13h 17m

San Juan Luis Munoz Marin Intl

Sun 3/8

6:00 am-5:42 pm

2 stops36h 42m

$310

PensacolaSan Juan

PNS - SJU

PNSSJU

Pensacola

Thu 2/26

6:37 pm-2:53 am

1 stop6h 16m

San Juan Luis Munoz Marin Intl

Mon 3/9

4:29 pm-5:42 pm

2 stops26h 13m

$315

PensacolaSaint Thomas Island

PNS - STT

PNSSTT

Pensacola

Wed 5/20

6:00 am-1:31 pm

1 stop6h 31m

Saint Thomas Island Cyril E King

Wed 5/27

2:36 pm-9:21 pm

1 stop7h 45m

$332

PensacolaSaint Thomas Island

PNS - STT

PNSSTT

Pensacola

Tue 2/3

5:33 pm-2:52 pm

1 stop19h 19m

Saint Thomas Island Cyril E King

Tue 2/10

3:57 pm-4:37 pm

1 stop26h 40m

$335

PensacolaPunta Cana

PNS - PUJ

PNSPUJ

Pensacola

Mon 2/16

5:20 pm-4:36 pm

1 stop21h 16m

Punta Cana

Tue 2/24

5:47 pm-3:54 pm

1 stop24h 07m

$345

PensacolaSan Juan

PNS - SJU

PNSSJU

Pensacola

Sat 1/31

5:33 pm-3:35 pm

2 stops20h 02m

San Juan Luis Munoz Marin Intl

Sat 2/7

2:59 am-3:08 pm

2 stops14h 09m

$347

PensacolaMontego Bay

PNS - MBJ

PNSMBJ

Pensacola

Tue 2/17

5:20 pm-12:02 pm

1 stop17h 42m

Montego Bay Sangster Intl

Fri 2/27

1:00 pm-3:54 pm

1 stop27h 54m

$356

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/5

Showing 1-10 of 52 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, January is the cheapest month in which you can book a flight from Pensacola to Caribbean (average of $115). 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.

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 January 6, 2026.
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
4,248 reviews

Boarding

8.1

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,018 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,132 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,084 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Spirit Airlines
6.3
Okay
8,271 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 8h 40m. Spirit Airlines provides one of the quickest options available for as low as $448. 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?

    $75 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 Southwest and American Airlines, with prices starting from $162 and $201, respectively.

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

    While some choose either Pensacola - Saint Thomas Island Cyril E King or Pensacola - Puerto Plata La Union, 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, January is the cheapest month in which you can book a flight from Pensacola to Caribbean (average of $115). 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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Alternative routes for Pensacola to Caribbean

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 January 6, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$115Average$347FlexibilityNo cancel feeOn-time65%
DeltaCheapest$276Average$516FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$374Average$595FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$380Average$650FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$381Average$539FlexibilityNo cancel feeOn-time63%

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