$96 Find Cheap Flights from Pensacola to Caribbean

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 2/27. 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
1 adult, Economy, 0 bags

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Cheap Flights from Pensacola to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana2 stops$399
Santo Domingo
Santo Domingo1 stop$288
Montego Bay
Montego Bay1 stop$421
Oranjestad
Oranjestad1 stop$405
Nassau
Nassau1 stop$427
Kingston
Kingston1 stop$466
Simpson Bay
Simpson Bay1 stop$410
George Town
George Town1 stop$503
St. John's
St. John's2 stops$628
Puerto Plata
Puerto Plata1 stop$616
Aguadilla
Aguadilla1 stop$360
Punta Cana
Punta Cana2 stops$399
Santo Domingo
Santo Domingo1 stop$288
Montego Bay
Montego Bay1 stop$421
Oranjestad
Oranjestad1 stop$405
Nassau
Nassau1 stop$427
Kingston
Kingston1 stop$466
Simpson Bay
Simpson Bay1 stop$410
George Town
George Town1 stop$503
St. John's
St. John's2 stops$628
Puerto Plata
Puerto Plata1 stop$616
Aguadilla
Aguadilla1 stop$360

Book Cheap Pensacola to Caribbean Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Pensacola to Caribbean that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Pensacola to Caribbean

Fri, Apr 24 - Sat, May 2
Frontier Logo
3:13 pm - 10:48 pm
PNS
-
SJU
6h 35m
1 stop
Frontier Logo
3:08 am - 2:15 pm
SJU
-
PNS
12h 07m
1 stop
$192Frontier
Sun, May 10 - Sun, May 17
Frontier Logo
3:13 pm - 2:01 am
PNS
-
SJU
9h 48m
1 stop
Frontier Logo
6:30 am - 2:15 pm
SJU
-
PNS
8h 45m
1 stop
$193Frontier
Sun, May 10 - Sat, May 16
Frontier Logo
3:13 pm - 2:01 am
PNS
-
SJU
9h 48m
1 stop
Frontier Logo
3:08 am - 2:15 pm
SJU
-
PNS
12h 07m
1 stop
$194Frontier
Wed, May 20 - Wed, May 27
Spirit Airlines Logo
6:00 am - 1:31 pm
PNS
-
STT
6h 31m
1 stop
Spirit Airlines Logo
2:36 pm - 9:15 pm
STT
-
PNS
7h 39m
1 stop
$229Spirit Airlines
Tue, Mar 10 - Tue, Mar 17
Spirit Airlines Logo
6:37 pm - 1:31 pm
PNS
-
STT
17h 54m
1 stop
Spirit Airlines Logo
2:36 pm - 9:14 pm
STT
-
PNS
7h 38m
1 stop
$247Spirit Airlines
Tue, Jul 7 - Mon, Jul 13
American Airlines Logo
4:40 pm - 9:40 am
PNS
-
MHH
16h 00m
2 stops
American Airlines Logo
3:45 pm - 10:21 am
MHH
-
PNS
19h 36m
2 stops
$460American Airlines
Wed, May 13 - Mon, May 18
United Airlines Logo
6:30 am - 1:47 pm
PNS
-
NAS
6h 17m
1 stop
United Airlines Logo
2:53 pm - 7:49 pm
NAS
-
PNS
5h 56m
1 stop
$478United Airlines
Wed, Apr 15 - Mon, Apr 20
American Airlines Logo
6:57 pm - 1:20 pm
PNS
-
MHH
17h 23m
2 stops
American Airlines Logo
2:00 pm - 10:30 am
MHH
-
PNS
21h 30m
2 stops
$492American Airlines
Mon, Jun 1 - Mon, Jun 8
Delta Logo
6:00 am - 4:35 pm
PNS
-
NAS
9h 35m
1 stop
Delta Logo
3:10 pm - 10:02 pm
NAS
-
PNS
7h 52m
1 stop
$493Delta
Thu, Mar 5 - Thu, Mar 12
Delta Logo
6:00 am - 2:49 pm
PNS
-
ANU
6h 49m
1 stop
Delta Logo
3:03 pm - 10:04 pm
ANU
-
PNS
8h 01m
1 stop
$705Delta
Booking Insights

KAYAK's insights & trends for Pensacola to Caribbean flights

Get data-powered insights and trends into flights from Pensacola to Caribbean to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Pensacola to Caribbean?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Pensacola to Caribbean, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Pensacola to Caribbean is April, when tickets cost $399 (return) on average. On the other hand, the most expensive months are December and September, when the average cost of round-trip tickets is $669 and $607 respectively.

How far in advance should I book a flight from Pensacola to Caribbean?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Pensacola to Caribbean, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Pensacola to Caribbean, you should book around 2 weeks before departure, which saves you about 20% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 15 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$96
Best time to beat the crowds but there is an average 1% increase in price.
Most popular time to fly with an average 21% 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 from Pensacola to Caribbean 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 from Pensacola to Caribbean with an airline and back 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 from Pensacola to Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 5 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
SouthwestOverall score based on 4280 reviews
8.0Comfort
8.6Crew
7.0Food
7.5Entertainment
8.1Boarding
Airline reviews

Only downside was the legroom and seat width, which is always a problem unless I spend more for a premium seat.

10.0 ExcellentAnonymous, Feb 2026
STL - DAL
Read more Southwest reviews

Only downside was the legroom and seat width, which is always a problem unless I spend more for a premium seat.

My flight from Denver to Minneapolis was excellent. My flight from Minneapolis to Denver was one of the worst I flights I have ever experienced. I had a window seat, the gentleman in the middle seat was morbidly obese and SW should have made him purchase two seats. His elbow dug into my arm most of the way even after I asked to please be careful. I was literally squashed between the him and the window with no wiggle room. The plane was full so it was not possible to ask for a different seat. I realize I should have complained to the flight attendant but I didn't feel anything could be done to rectify the situation. I fly SW often, I will continue to do so as this was my first negative experience.

I appreciate the staff who allowed me to board though I arrived a little late! Regarding the assigned seating, I had booked my flight before this change and wasn't aware of the change at the time, and so I didn't select a seat at booking as I didn't realize it was relevant. Better communication about the change would have been helpful for preparing.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

Flight was on time. Wi-fi was a little spotty/slow. Boarding and exit were efficient.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

If we are going to have to pay for luggage, make it easier to do. Put something on the app during check-in so I don't need to do it at the kiosk. I've done it twice recently and I ended up having to pay at the desk because something went wrong at the kiosk in Tampa.

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

The flight was great as well as the airline staff

Comfort seating was on the tight side. Maybe it was a smaller plane(?)

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Connection through Atlanta was difficult. Mechanical issue on plane caused a two hour delay. New gate was a mile away.

No WiFi. Comfort plus should have alcohol provided, crew only offered water or tea. Who the heck wants tea?

I have diamond medallion status and usually we are in comfort plus . We were in main this time ( which was fine ) and my husband wanted wine . I have at least 10 vouchers for drinks that are good for this year and next! The attendant would not take the picture of the voucher as proof and never came back to check as She asked me to pull it up on delta Wi-Fi. Instead my husband just used his Amex to buy the wine . Disappointing!!!

Food is basically Sun Chips, cookies or Cheezits. I had an exit row seat so I had plenty of room. The crew was very nice and efficient. Pilot kept us informed. Pretty good flight.

The only thing nice I can say is the flight crew was really nice and apologetic about the situation. They shared as much information as they had and advised us on what we could do about missing connecting flights. The boarding process was so slow. The gate agent was working by herself and should have had someone working with her. It took almost an hour to board because she was trying to board a full flight of people and provide customer service to everyone who was flying standby and/or had questions. It was really chaotic. This didn't help the fact that we were delayed and folks were missing connections the longer it took.

The food is terrible. The staff is wonderful. Comfort is good.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

Check-in and in-flight staff were better than average. The seat was a fair size but too hard and not enough padding. The cushion/pillow provided is poor (thin and seems to be disposable ,it provides no effective cushioning or support). Food was OK-ish but no choice of inflight snacks and no easy place to get drinks other than water (I could ask for juice by intruding into the staff area at the back of the plane) Entertainment was very good actually. Overall better than I expected from a US-based airline (sorry!) but compared to ANA or Singapore it was so-so. (I live in Japan so they are my comparative airlines)

Everything was on time Will use united again for sure

Plane outlets in my row not working to charge phone. Staff response was, well it should be. Plug into seed for volume not working well. Had to find the sweet spot for plug in or it would shut off and on.

Wifi took a while to kick in and we had a maintenance issue that took over 40 mins at the gate in Washington before pulling back

Fine not above and beyond as I had a connection that was delayed due to maintenance

The power at the seat didn't work and the seat itself was difficult to adjust - this was a business class seat. Flight attendant gave me miles to compensate. The attendant was very professional and on top of his game the entire flight.

Terrible. Our first time back on United for 10 years, the seats in Polaris class are small and uncomfortable. They have squished too many people in to get more $$$. The staff are not friendly and not wanting to accommodate. I asked for two salads rather than a main meal and was advised no we wont do that. Then asked what I would like for breakfast and given something else anyway. I will not be flying United International anytime soon.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

Very turbulent trip made it pretty bearable, plus the lack of refreshments served and the lack of any air conditioning before takeoff which took an hour or more.

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

Awful. Original flight was delayed 5 hours. Had to to take a connecting flight instead of direct. Had a 4 hour layover. I missed all of my morning meetings getting in 5 hours later than I was supposed to and had to change to take a later flight the next day to get them back in which cia time another $150.

On time on a day with lots of weather cancellations on other flights. Thank you for getting me home during a winter storm!

Don't change gate multiple times make people run across the airport. Announce delays in a timely manner. Have maintenance crew ready. Don't delay and keep passengers on the plane for 3 hrs. on tarmac.

The attendants were kind and helpful. A sugar-free drink would have been very welcome.

Little warm on the plane and delayed for an hour

UGH I HAD TO MISS MY FIRST FLIGHT TO TAMPA CAUSE OF THE 10 MINUTE DELAY OF THE ORLANDO TO MIAMI ONE SO THEY HAD ME GET ANOTHER TICKET. I AM NOT HAPPY AT ALL BECAUSE IT MADE ME MISS MY CONNECTING FLIGHT FROM TAMPA TO LONDON AND FORCED ME TO MISS A DAY AT MY ROOM IN THE UK.

Wish they didnt delay off-boarding for 10 minutes so i could connect to my flight from miami to tampa

It was fine. My connection in Charlotte to go to WPB was too late and I had to spend the night in the Charlotte Airport in the mini suites.

Boarding was organized and timely. Food was mediocre, especially for first class travel.

We were 4+ hours delayed. AA is absolutely obnoxious. They just kept pushing back the time to the point where we did not get into Vegas until after midnight when we were supposed to arrive like 845pm.

Delay at the gate without any communication such as announcement, sign, monitor, email or text. Found out later we were boarded with the knowledge of a significant delay, awaiting communication from Europe. Pilot was the only source of information regarding the delay after a long gate delay and sitting for more than 30 minutes after boarding. More than 2 hour delay, landing at 2 AM. Offered to deplane and reboard, but probably should have just waited rather than repeat the process. Not the first time experiencing the lack of communication with Spirit airlines. This morning was not as bad as showing up to a terminal without an agent (or aircraft) without any sort of communication. Much later an email was sent that stated our flight was rescheduled for a week later. Situations do arise, but simple communication can alleviate a lot of the frustration. Hard to believe a corporation doesn't understand that. But, you get what you pay for...

No complaints with pricing so don’t expect a lot of extras.

Flight out was great but this flight was canceled and nothing was available for 2 days after this so I had to purchase an expensive ticket from another airline so I could go home. The flight cancellation was said to be a crew issue, it wasn’t weather or maintenance.

Flight got cancelled 1.5 hours prior to gate open and logistics of travel got delayed.

the fligh was delay form 9am to 10, delayed again from 10 to 11, than delay and gate change to 12 and delay another gate change to 3;25 pm

Missed flight cause tsa took so long, overbooked flight, left terminal earlier than posted departure ridiculous upcharges stayed at airport additional 6 hours to catch next available flight. Had to make other arrangements to be picked up for later flight. Terrible experience!

Cancelled my flight, said next flight was 30hrs later. Had to come out of pocket $500 to get on a SW flight

Everything was good. On time, boarding fast, flight attendants friendly.

Spirit has always and will always stink. Absolute worst airline around.

I know it's a low-cost airline. However, the seats are very basic, so after two hours of travel, they feel very uncomfortable and cannot be reclined. The two flights from Bogota to Orlando and the return flight were very punctual. The check-in process on the app works very well. I really liked the self-check-in process for luggage at the Orlando airport; it was quick, easy, and very convenient.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports