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Find cheap flights from Pensacola to Caribbean from $67

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 departing on 5/15. 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
Mon 5/27
Mon 6/3

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Best Caribbean Flight Deals

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

Punta Cana
Punta Cana1 stop$552
Montego Bay
Montego Bay1 stop$328
Santo Domingo
Santo Domingo1 stop$208
Oranjestad
Oranjestad1 stop$385
Nassau
Nassau1 stop$397
Kingston
Kingston1 stop$394
Simpson Bay
Simpson Bay1 stop$412
Providenciales
Providenciales1 stop$1,187
George Town
George Town1 stop$518
St. John's
St. John's1 stop$846

Good to know

Low season

October

High season

June

Cheapest flight

$67
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 San Juan

FAQs - booking Caribbean flights

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

    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.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Caribbean 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?

    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 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?

    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 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 tips for finding cheap flights to Caribbean

  • Morning departure is around 6% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

Top 4 airlines serving from Pensacola to Caribbean

 
Need help choosing which airline to fly with from Pensacola to Caribbean? 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 10966 reviews
7.9comfort
8.0entertainment
8.6crew
8.2boarding
7.4food
Airline reviews

I liked the ease of checking in, luggage check in, wheel chair assistance, boarding and flight.

10.0 ExcellentAnonymous, Apr 2024PNS - ATL
Read more about Delta reviews

I liked the ease of checking in, luggage check in, wheel chair assistance, boarding and flight.

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 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.

Spirit canceled the flight in March and never notified me!

Seats suck, not enough room, overcrowded planes, hectic situation all together.

I do not like the customer service, I had an emergency and needed to cancel a pet reservation right after I had booked it and they would not do anything but issue a credit. I haven't flown in years as I have 7 kids and don't have spare time. I want my $125 back on my card please

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.

Book cheap flights from Pensacola to Caribbean

Recent round-trip flight deals

5/8Wed
1 stopSpirit Airlines
16h 11mPNS-SJU
5/10Fri
1 stopSpirit Airlines
21h 31mSJU-PNS
$182
5/8Wed
1 stopSpirit Airlines
16h 11mPNS-SJU
5/9Thu
1 stopSpirit Airlines
7h 12mSJU-PNS
$187
5/20Mon
1 stop
15h 11mPNS-SJU
5/23Thu
1 stop
12h 19mSJU-PNS
$262
8/14Wed
1 stopAmerican Airlines
7h 22mPNS-STT
8/21Wed
2 stopsAmerican Airlines
19h 10mSTT-PNS
$350
6/1Sat
1 stop
20h 34mPNS-MHH
6/5Wed
1 stop
6h 44mMHH-PNS
$354
9/26Thu
2 stopsAmerican Airlines
21h 04mPNS-STT
10/2Wed
2 stopsAmerican Airlines
19h 10mSTT-PNS
$396
7/6Sat
1 stopDelta
11h 55mPNS-KIN
7/14Sun
1 stopDelta
12h 30mKIN-PNS
$480
7/11Thu
1 stopDelta
24h 19mPNS-KIN
7/14Sun
1 stopDelta
9h 23mKIN-PNS
$487
7/26Fri
1 stopUnited Airlines
6h 14mPNS-PLS
7/26Fri
2 stopsUnited Airlines
21h 07mPLS-PNS
$1,187
9/27Fri
3 stopsUnited Airlines
21h 46mPNS-STT
9/30Mon
2 stopsUnited Airlines
13h 46mSTT-PNS
$1,508

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Recent one-way flight deals

5/15Wed
1 stopSpirit Airlines
16h 11mPNS-SJU
$67
5/11Sat
1 stopSpirit Airlines
16h 11mPNS-SJU
$80
5/15Wed
3 stopsSpirit Airlines
16h 05mPNS-SJU
$95
5/15Wed
2 stopsSpirit Airlines
17h 40mPNS-SJU
$97
5/13Mon
3 stopsSpirit Airlines
26h 04mPNS-SJU
$103
5/13Mon
1 stopSpirit Airlines
20h 19mPNS-SJU
$104
5/13Mon
2 stopsSpirit Airlines
20h 27mPNS-SJU
$124
5/22Wed
1 stopFrontier
8h 39mPNS-SJU
$149
5/11Sat
2 stopsAmerican Airlines
17h 35mPNS-SJU
$161
7/26Fri
1 stopAmerican Airlines
14h 57mPNS-PLS
$346

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Last minute flights from Pensacola to Caribbean

Last minute flight, train and bus deals

5/2Thu
multi-stopSpirit Airlines
10h 14mPNS-SJU
5/5Sun
multi-stopSpirit Airlines
10h 13mSJU-PNS
$321
5/2Thu
multi-stopSpirit Airlines
11h 00mPNS-SJU
5/5Sun
multi-stopSpirit Airlines
19h 13mSJU-PNS
$340
5/2Thu
multi-stopSpirit Airlines
10h 14mPNS-SJU
5/5Sun
multi-stopSpirit Airlines
10h 13mSJU-PNS
$343
4/30Tue
multi-stopSpirit Airlines
10h 41mPNS-SJU
5/2Thu
multi-stopSpirit Airlines
10h 05mSJU-PNS
$363
4/29Mon
multi-stop
21h 07mPNS-STT
5/10Fri
multi-stop
24h 01mSTT-PNS
$614
4/30Tue
multi-stopDelta
4h 50mPNS-MBJ
5/4Sat
multi-stopDelta
6h 09mMBJ-PNS
$624
4/30Tue
multi-stop
12h 17mPNS-SJU
5/2Thu
multi-stop
26h 57mSJU-PNS
$649
4/30Tue
multi-stopAmerican Airlines
6h 20mPNS-MBJ
5/4Sat
multi-stopAmerican Airlines
10h 56mMBJ-PNS
$725
4/30Tue
multi-stopAmerican Airlines
6h 00mPNS-MHH
6/11Tue
multi-stopAmerican Airlines
10h 56mMHH-PNS
$798
4/30Tue
multi-stopUnited Airlines
20h 54mPNS-STT
5/2Thu
multi-stopUnited Airlines
25h 07mSTT-PNS
$1,635

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