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Find cheap flights from Pensacola to Caribbean Islands from $94

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Pensacola to Caribbean Islands departing on 5/28. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Thu 5/23
Thu 5/30

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Best Caribbean Islands Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Punta Cana
Punta Cana2 stops$374
Montego Bay
Montego Bay2 stops$323
Santo Domingo
Santo Domingo1 stop$234
Oranjestad
Oranjestad1 stop$387
Nassau
Nassau1 stop$403
Kingston
Kingston1 stop$343
Simpson Bay
Simpson Bay1 stop$501
Providenciales
Providenciales1 stop$438
George Town
George Town1 stop$518
Aguadilla
Aguadilla2 stops$911
St. John's
St. John's1 stop$687

Good to know

Low season

October

High season

June

Cheapest flight

$94
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly with an average 24% increase in price.
Flight from Pensacola to Saint Thomas Island

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from Pensacola to Caribbean Islands?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Pensacola to Caribbean Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Pensacola to Caribbean Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Caribbean Islands from Pensacola is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Pensacola to Caribbean Islands?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Caribbean Islands with an airline and back to Pensacola with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Pensacola to Caribbean Islands?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Caribbean Islands from Pensacola up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top 4 airlines serving from Pensacola to Caribbean Islands

 
Need help choosing which airline to fly with from Pensacola to Caribbean Islands? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
DeltaOverall score based on 11028 reviews
7.5food
8.2boarding
8.6crew
7.9comfort
8.0entertainment
Airline reviews

The main person that was coordinating everything was a short white/light skin Spanish man and he was very rude. It honestly made me feel like it was everyone’s First day at work. His announcements were very not reasonable and they did not make sense. The stewardess on the flight that made the announcements she didn’t even know what she was talking about she sounded inebriated. There were no snacks or drinks on our flight there wasn’t even much turbulence. This flight was not enjoyable nor was it what a Delta flight should be and just this past week I flew with Delta 3 times.

2.0 MediocreLizette, Mar 2024MIA - JFK
Read more about Delta reviews

The main person that was coordinating everything was a short white/light skin Spanish man and he was very rude. It honestly made me feel like it was everyone’s First day at work. His announcements were very not reasonable and they did not make sense. The stewardess on the flight that made the announcements she didn’t even know what she was talking about she sounded inebriated. There were no snacks or drinks on our flight there wasn’t even much turbulence. This flight was not enjoyable nor was it what a Delta flight should be and just this past week I flew with Delta 3 times.

nothing Delta could do... the person sitting next to me was huge and overflowing into my seat

Crew was great! I need wheelchair assistance and they knew who I was and updated me that my chair was on its way and to just hang tight. There was some turbulence but the captain announced we would be going thru it and he handled the plane well. Landing was soft and his.

Aircraft very cramped. Check-in was great with an agent helping us. Food was almost non-existent. Pre-flight went well once I got the app reloaded on my phone since we don’t fly much anymore.

I like that it got us where we were going. Everything else needed work. It was 1/2 hour late and we took off an hour late. The plane had to be cleaned and the disabled loaded on board before we could take off which took forever and then we sat at the terminal FOREVER before we took off. The ride was so bumpy that they couldn’t serve drinks and snack but to about 1/2 the plane. Seriously we should have flown out of Fort Lauderdale. We probably would’ve gotten home several hours earlier.

Flight was on time, the staff was personable & professional, & the plane arrived on time.

Flight was great. DELTA did a fantastic job! FLL airport was chaotic!

You lost my luggage!!! How frustrating!!! Now they can’t find one of our bags!!!! I really don’t have time for this!!!

Fast boarding and exit. Different snacks other than almonds and sun chips.

The boarding agents appeared to do the minimum customer service. They did not appear to try to find solutions to problems.

the flight from Tampa departed with a delay. The food on board was poor, usually on international airlines alcoholic beverages are offered free of charge , but here it was for a fee, the cutlery was wooden, there were no hot drinks (tea, coffee). Unfortunately, I didn't take pictures of the portions of food, but it wouldn't have been enough for a child either.And in the future, I will try not to use the services of this airline

That flight was smooth, and staff we courteous. it was a full flight so very tight. The boarding through security was not properly controlled. it was rushed and the scanning process for our bags, etc. was pilling up at the other end with no time to empty our belonging my personal items almost toppled over on the floor if i hadn't caught it rapidly. Was it just that time, or always like this - cant say. other than that all else was fine.

Boarding was friendly and quick. While the plane model was older with no live tv, the entertainment was full of movies and tv shows. All food was available. Pilots were very communicative with status of the flight. Flight landed on time.

It was terrible because the flight was delayed for 3 hours.

Crowded flight, but upbeat and kind crew. Pilot greeted us at door, flight attendant thanked a number of “special” passengers for their business, another addressed an eight-year old boy as “young man.” United obviously trying to up their game, but though all of that is nice and notable, flying still feels like moving along a human assembly line, being herded into one small space after another (boarding areas with too few seats, planes with limited personal space, shuttles (IAD) packed too full.

Did not like the seat spacing. The seat was very narrow and tight.

United domestic flight was better than international flight. There was no switch to control Ac In international united flight. Food was also average, Air canada food was much better than united.

Seat didn't recline all the way back. Very uncomfortable flight for 8 hours. The turbulence eliminated snack and food stops

Nothing exceptional but all good. Business class seats are like the domestic Mint class on Jet Blue. Comfortable but not exceptional. Food is good but not superb. Flight attendants were better than US carriers but that is to be expected. However, not the caliber of Asian or Middle Eastern airlines. Very Lufthansa like but Lufthansa has slightly better seats, even though they are hardly best in class

The flight was clean and on time, the crew were all very nice and we got the seats we booked. Plenty of food and beverages. The seats are too close so it’s very difficult to try and sleep comfortably.

The Flight attendant had an attitude and didn't allow anyone any time to prepare for landing despite being absent throughout the entire trip

Ac was broken so we deplaned, waited 2 hours, taxiing for takeoff they said the plane would not fly so we went back to the gate and got a new plane which took another hour. In all a 4 hour delay for an 80 min flight.

Horrible people at the gate, they force me to check in my carry on, even thought no one behind me has to do it. I had to get out of the airport in NY to get my bag and go thru security again on my way to Honk Kong. The worst part is the employee threatened me with loosing the flights if don’t comply.

Delayed flight, few announcements with information, no comps, cluster f boarding because zones weren’t spread out and announced loud and repeatedly, staff did their job -nothing more nothing less, annoying kids were speaking and kicking the heck out of the back of my seat and parents weren’t willing to parent… so another typical day of air travel in the US.,

Flight was delayed until Next day as crew timed out

The flight was great until towards the end when the flight attendant read an excessively long commercial for purchasing an american airlines credit card. The worst part is that we are doing a lot of traveling this year so i was actually interested in getting the credit card, but I was so annoyed with the long commercial that I completely dismissed the flight attendant bringing around the information. Next time, keep the sales pitch to 10 seconds and then pass around the brochures!!

I was able to get on standby with relative ease

Terrible, oxygen masks were deployed mid-flight. We returned to airport. Took additional 12 hours to get home.

6 plus hour delay with no explanation. No wheelchairs to transport us on arrival. Very disappointed.

Me and my husband experienced very bad in American Airlines. We missed our flight going to Doha. The American Airlines was delayed we arrived already 10:27pm. Supposed to be 9:40 pm. So what they did they rebooked our flight and they gave us a hotel. When we arrived at the hotel the front desk said it was fully booked already. Oh my gosh! I said why did you accept the booking if it's fully booked. The guy said that's American Airlines they just book even it's already full. That's 2am already, we have nothing to do so, we decided to go another hotel. We pay the room, food and taxi. Pls give an action on this matter. Refund our expenses and give us more compensation. Not only our room, food, taxi but also our efforts, tiredness looking for a room that can accommodate us.

I paid just under 200 for flight and luggage, then paid 200 to change the flight, then paid 100 for a carry on. Then the cancelled the flight. Of the 500 I spent they refunded 250. I bought a delta flight for 270 never flew with spirit, but spirit kept 250, not even refunding the 100 for the carry on though they cancelled the flight (for weather on a day with only a slight rain ).

Flight attendants heavily pushed their affinity credit card. Very annoying

On time and fast. Overall it was a pleasant experience.

The seat are terrible. Don’t even think of sleeping on a Spirit flight. The kids that run the plane aka flight attendants are pretty rude and straight forward. They get the job done but without class.

I had a death in my family and booked my flight on Spirit. My flight was cancelled the morning of my flight, no explanation, no help to rebook, nobody to talk to. The next available flight was 2days later !!!! Terrible airline, will NEVER fly with them again!

Flight was canceled. Knew there was weather, and were notified of 20 min delayed, and then suddenly canceled. Next reschedule was for 2 days. No help other than to refund. Thankfully full refund and appreciate that. I appreciate discounted airline but felt they could've done more for customer inconvenience.

They seemingly have no respect for their customers, on any level. Avoid flying spirit, they will bump you to another flight without thinking twice so they can sell your seat, no joke.

Flying on Spirit Airline is a penny-pinching beat down.

Bag self drop off was terrible! No staff there to help. Almost missed my flight. Would never check a bag in with Spirit again.

They took a horrible route with a lot of turbulence and I eneded up getting sick. Even if the flight takes longer. Don't put people life at risk just to get to the airport on time.

Book cheap flights from Pensacola to Caribbean Islands

Recent round-trip flight deals

5/14Tue
1 stopSpirit Airlines
16h 11mPNS-SJU
5/15Wed
1 stopSpirit Airlines
11h 55mSJU-PNS
$191
5/8Wed
1 stopSpirit Airlines
23h 26mPNS-SJU
5/10Fri
1 stopSpirit Airlines
21h 31mSJU-PNS
$196
5/31Fri
1 stop
8h 36mPNS-SJU
6/13Thu
1 stop
7h 06mSJU-PNS
$294
5/8Wed
2 stopsAmerican Airlines
13h 13mPNS-SJU
5/9Thu
1 stopAmerican Airlines
10h 47mSJU-PNS
$299
5/31Fri
1 stop
8h 36mPNS-SJU
6/14Fri
1 stop
22h 25mSJU-PNS
$308
5/11Sat
2 stopsAmerican Airlines
19h 49mPNS-SJU
5/18Sat
1 stopAmerican Airlines
10h 08mSJU-PNS
$314
5/11Sat
1 stopDelta
25h 26mPNS-AUA
5/15Wed
2 stopsDelta
19h 07mAUA-PNS
$490
5/6Mon
1 stopUnited Airlines
5h 53mPNS-NAS
5/13Mon
1 stopUnited Airlines
5h 45mNAS-PNS
$493
5/11Sat
2 stopsDelta
29h 23mPNS-AUA
5/15Wed
2 stopsDelta
19h 07mAUA-PNS
$497
8/25Sun
1 stopUnited Airlines
7h 42mPNS-SJU
8/31Sat
2 stopsUnited Airlines
21h 40mSJU-PNS
$655

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Recent one-way flight deals

5/28Tue
1 stopSpirit Airlines
14h 13mPNS-STT
$94
5/11Sat
1 stopSpirit Airlines
16h 11mPNS-SJU
$97
5/20Mon
1 stopSpirit Airlines
16h 20mPNS-MBJ
$124
5/27Mon
1 stopSpirit Airlines
19h 42mPNS-STT
$124
8/20Tue
1 stopDelta
5h 29mPNS-SJU
$132
5/22Wed
1 stopSpirit Airlines
17h 19mPNS-SJU
$133
5/28Tue
2 stops
23h 14mPNS-SJU
$155
5/28Tue
2 stops
23h 14mPNS-SJU
$156
5/11Sat
2 stopsAmerican Airlines
19h 49mPNS-SJU
$157
8/7Wed
2 stopsAmerican Airlines
17h 23mPNS-SJU
$161

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Last minute flights from Pensacola to Caribbean Islands

Last minute flight, train and bus deals

4/27Sat
multi-stopSpirit Airlines
13h 00mPNS-SJU
5/6Mon
multi-stopSpirit Airlines
14h 04mSJU-PNS
$256
4/27Sat
multi-stopSpirit Airlines
13h 00mPNS-SJU
5/5Sun
multi-stopSpirit Airlines
14h 37mSJU-PNS
$321
4/23Tue
multi-stopSpirit Airlines
10h 41mPNS-SJU
4/30Tue
multi-stopSpirit Airlines
14h 12mSJU-PNS
$323
4/27Sat
multi-stop
13h 00mPNS-SJU
5/6Mon
multi-stop
17h 21mSJU-PNS
$352
4/25Thu
multi-stop
8h 35mPNS-SJU
4/27Sat
multi-stop
13h 15mSJU-PNS
$382
4/28Sun
multi-stopAmerican Airlines
15h 20mPNS-STT
4/30Tue
multi-stopAmerican Airlines
16h 15mSTT-PNS
$396
4/26Fri
multi-stopSilver Airways
13h 55mPNS-NAS
4/29Mon
multi-stopSilver Airways
8h 05mNAS-PNS
$597
4/26Fri
multi-stopSilver Airways
17h 15mPNS-NAS
4/29Mon
multi-stopSilver Airways
8h 05mNAS-PNS
$609
4/27Sat
multi-stopDelta
6h 50mPNS-PUJ
5/1Wed
multi-stopDelta
9h 11mPUJ-PNS
$741
4/26Fri
multi-stopAmerican Airlines
9h 10mPNS-NAS
4/29Mon
multi-stopAmerican Airlines
7h 20mNAS-PNS
$761

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Pensacola - Caribbean Islands Flights

Departure:

Pensacola (PNS)United States

Return flight deals:

Caribbean Islands - Pensacola

Cabin classes:

$479
$546
$291
$34