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Find cheap flights from Pensacola to Caribbean from $89

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 8/20. 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 7/11
Thu 7/18

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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$286
Montego Bay
Montego Bay1 stop$300
Santo Domingo
Santo Domingo1 stop$250
Oranjestad
Oranjestad1 stop$294
Nassau
Nassau1 stop$398
Kingston
Kingston1 stop$401
Simpson Bay
Simpson Bay2 stops$389
Providenciales
Providenciales1 stop$448
George Town
George Town1 stop$470
St. John's
St. John's1 stop$645

Good to know

Low season

November

High season

December

Cheapest flight

$89
Best time to beat the crowds but there is an average 24% increase in price.
Most popular time to fly with an average 8% 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 66% 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 10277 reviews
7.4Food
7.9Comfort
8.6Crew
8.2Boarding
8.0Entertainment
Airline reviews

If I can, I always fly Delta. I’ve found their service to always be reliable and pleasant.

8.0 ExcellentNikki, Jun 2024DAB - ATL
Read more about Delta reviews

If I can, I always fly Delta. I’ve found their service to always be reliable and pleasant.

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

The 1st class male crew member was very pleasant - the short female with round glasses , maybe in 50’s had no personality- never spoke when delivering my food, drink, & never smiled the whole trip! In fact looked annoyed when the boarding proses was happening- I would never hire this woman - unfriendly . Have never dealt with a crew member like her-

Best airline! Always friendly and welcoming. Skyclub was great and loved the fast free wifi on board. I also love that you can pre-order your meal on the app!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

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.

My window shade didn’t work. So I missed coming into my city. ☹️

Flight was delayed in the gate by 5 hours and ultimately cancelled- rebooking service by United agents was terrible

Well....let's start from the point that I had to stay in airport for 12 hours instead of 2 that was scheduled. Poor company and even worst customer service. Never again....

The Wi-Fi was unavailable on this flight for some reason.

The flight was delayed almost 2 hours. Bad customer service etc. I will never fly Luthansa. Ever!!!

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.

Information when booking said the flight would be with American Airlines but the flight was actualy with British Airways. Check in from Orlando was nice and quick. I agreed to put my cabin case in the checked luggage as it was a full flight. Case came back damaged (unable to put the handle down) so will have to dispose of it. Seats were quite cramped with very little leg room, even for economy. This was the experience of both the outgoing and return flight. Cabin crew were ok and flight time was punctual.

Was lucky to have a employee at the AA checkin counter that had compassion and understood they ordeal that we went through with our original flight being diverted, needing to stay in the aircraft and then flying to the original destination; adding hours to the trip and forcing us to miss our connection and our rebooked connection. She was able to get up on standby on the highest priority on the next flight to the closest airport we need to be at and it all worked out despite being many hours late.

Delayed so that missed connecting flight. Connecting flight was also delayed on the tarmac but they closed the gate before the rescheduled time.

Took off over an hour late with multiple mechanical issues. Gate agent in Dallas was lazy and was slow as molasses. Had a line 10 people long. Spirit bad..

They gave my seat away although it was a connecting flight with them and the flight was a bit delayed.

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

Not enough help at airport during boarding process. Flight was delayed. Overall WORST flying experience I’ve ever had. Will NEVER FLT SPIRIT AGAIN

This was the smoothest flight I have had in awhile. I was also offered an exit row seat for a great upgrade cost and was able to sleep almost thr whole flight due to comfort and a smooth flight. We left on time and arrived on time.

No food not even water offered unless you buy it and no usb in the seat but other than that everything was good

Because our flight from marsh Harbor to Fort Lauderdale was over three hours delayed it caused us to miss our flight in Fort Lauderdale. Because we missed that flight, it cost us nearly $100 apiece for four different travelers which totaled nearly $400. We are seeking a reimbursement for the flight that we missed in Fort Lauderdale Florida.

Flight was cancelled just 6 days before. No more flights that day, and the following date was sold out. Had to obtain a refund and buy more expensive flights on another airline.

The whole day was a nightmare. Flight extremely late. Boarding was a mess of a nightmare.

Never been on this flight as i had missed it due to delayed connecting flight

Missed our departing flight due to poor baggage drop staff. At the airport with 2 & 1/2 hours to spare and waited in bag check in until 15 minutes prior to gates closing before baggage staff asked us to move to the front of the line. We weren’t the only passengers that missed the flight. Poor organizational operations by Spirit staff. Otherwise , the return trip was fine.

Worst airline experience ever. Lost my IPad going thru security. Charged for my dog carriage at the gate not at ticket counter. Gave away my seat 6D. Expressed I wanted my seat back after charging me 99 for dog carriage. Should have thrown it out. Had a 16 yr old Yorkie heading to Boston after being a snowbird. Seats small. Very bad experience. Still don’t have my IPad. Horrible

The boarding gate was moved so many times that I missed my flight. No attendants would help me. The wrong gate was even on my boarding pass. I had to repurchase everything. I’ll never fly again. Really a terrible day as I had planned to see a former student who is dying in Louisville Never ever will I forget that day. Your airline is totally uncaring.

Book cheap flights from Pensacola to Caribbean

Recent round-trip flight deals

9/4Wed
1 stopSpirit Airlines
9h 08mPNS-SJU
9/9Mon
1 stopSpirit Airlines
13h 22mSJU-PNS
$165
7/5Fri
1 stopSpirit Airlines
16h 15mPNS-SJU
7/9Tue
1 stopSpirit Airlines
14h 26mSJU-PNS
$172
7/13Sat
2 stops
18h 01mPNS-SJU
7/16Tue
1 stop
8h 26mSJU-PNS
$253
7/12Fri
3 stops
13h 29mPNS-SJU
7/17Wed
2 stops
27h 17mSJU-PNS
$310
7/19Fri
2 stopsAmerican Airlines
20h 59mPNS-STX
7/24Wed
1 stopAmerican Airlines
7h 29mSTX-PNS
$326
8/2Fri
2 stopsAmerican Airlines
23h 43mPNS-SJU
8/7Wed
2 stopsAmerican Airlines
15h 46mSJU-PNS
$362
8/10Sat
1 stopDelta
6h 47mPNS-STX
8/17Sat
1 stopDelta
9h 00mSTX-PNS
$372
9/15Sun
2 stopsDelta
26h 22mPNS-AUA
9/24Tue
2 stopsDelta
29h 11mAUA-PNS
$443
9/4Wed
3 stopsUnited Airlines
22h 33mPNS-SJU
9/8Sun
2 stopsUnited Airlines
19h 45mSJU-PNS
$535
8/23Fri
1 stopUnited Airlines
7h 42mPNS-SJU
8/25Sun
2 stopsUnited Airlines
19h 45mSJU-PNS
$604

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Recent one-way flight deals

8/20Tue
1 stopSpirit Airlines
7h 34mPNS-SJU
$89
8/20Tue
1 stopSpirit Airlines
5h 41mPNS-STT
$103
7/2Tue
1 stopSpirit Airlines
13h 11mPNS-SJU
$110
6/19Wed
1 stopSpirit Airlines
7h 24mPNS-SJU
$114
10/26Sat
1 stopAmerican Airlines
15h 03mPNS-SJU
$132
7/3Wed
2 stopsFrontier
16h 35mPNS-SJU
$134
8/3Sat
1 stopSilver Airways
3h 55mPNS-MHH
$167
10/26Sat
2 stopsAmerican Airlines
26h 31mPNS-SJU
$187
8/3Sat
2 stopsSilver Airways
5h 50mPNS-MHH
$192
7/2Tue
3 stopsUnited Airlines
15h 12mPNS-SJU
$611

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Last minute flights from Pensacola to Caribbean

Last minute flight, train and bus deals

6/15Sat
multi-stopSpirit Airlines
16h 04mPNS-SJU
6/18Tue
multi-stopSpirit Airlines
13h 10mSJU-PNS
$259
6/15Sat
multi-stopSpirit Airlines
7h 44mPNS-SJU
6/18Tue
multi-stopSpirit Airlines
12h 10mSJU-PNS
$276
6/15Sat
multi-stopSpirit Airlines
21h 39mPNS-SJU
7/2Tue
multi-stopSpirit Airlines
13h 10mSJU-PNS
$281
6/14Fri
multi-stop
16h 15mPNS-SJU
6/16Sun
multi-stop
13h 59mSJU-PNS
$297
6/14Fri
multi-stop
16h 15mPNS-SJU
6/16Sun
multi-stop
13h 59mSJU-PNS
$317
6/15Sat
multi-stopAmerican Airlines
18h 09mPNS-SJU
6/18Tue
multi-stopAmerican Airlines
21h 54mSJU-PNS
$508
6/15Sat
multi-stopAmerican Airlines
10h 50mPNS-SJU
6/18Tue
multi-stopAmerican Airlines
11h 03mSJU-PNS
$528
6/14Fri
multi-stopDelta
6h 52mPNS-STT
6/16Sun
multi-stopDelta
7h 50mSTT-PNS
$1,046
6/13Thu
multi-stopUnited Airlines
21h 10mPNS-SJU
6/15Sat
multi-stopUnited Airlines
21h 37mSJU-PNS
$1,133
6/13Thu
multi-stopUnited Airlines
31h 25mPNS-MHH
6/23Sun
multi-stopUnited Airlines
48h 54mMHH-PNS
$1,142

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