$141 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 2/12. 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 Cana1 stop$379
Santo Domingo
Santo Domingo2 stops$387
Montego Bay
Montego Bay1 stop$481
Oranjestad
Oranjestad1 stop$535
Nassau
Nassau1 stop$454
Kingston
Kingston2 stops$551
Simpson Bay
Simpson Bay1 stop$539
George Town
George Town2 stops$376
Puerto Plata
Puerto Plata2 stops$582
Aguadilla
Aguadilla2 stops$723
Punta Cana
Punta Cana1 stop$379
Santo Domingo
Santo Domingo2 stops$387
Montego Bay
Montego Bay1 stop$481
Oranjestad
Oranjestad1 stop$535
Nassau
Nassau1 stop$454
Kingston
Kingston2 stops$551
Simpson Bay
Simpson Bay1 stop$539
George Town
George Town2 stops$376
Puerto Plata
Puerto Plata2 stops$582
Aguadilla
Aguadilla2 stops$723

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

Sat, Feb 21 - Wed, Feb 25
Multiple Airlines Logo
11:18 am - 2:50 am
PNS
-
SJU
37h 32m2 stops
Multiple Airlines Logo
4:36 pm - 3:56 pm
SJU
-
PNS
25h 20m1 stop
$275Multiple Airlines
Wed, Feb 25 - Sun, Mar 1
Multiple Airlines Logo
5:50 pm - 9:47 am
PNS
-
SJU
13h 57m1 stop
Multiple Airlines Logo
9:37 pm - 3:40 pm
SJU
-
PNS
20h 03m1 stop
$286Multiple Airlines
Fri, Jan 30 - Sun, Feb 1
Spirit Airlines Logo
5:33 pm - 9:47 am
PNS
-
SJU
14h 14m1 stop
Spirit Airlines Logo
6:00 am - 4:37 pm
SJU
-
PNS
12h 37m1 stop
$298Spirit Airlines
Sun, Feb 1 - Sat, Feb 7
Spirit Airlines Logo
5:33 pm - 2:52 pm
PNS
-
STT
19h 19m1 stop
Spirit Airlines Logo
5:42 pm - 3:08 pm
STT
-
PNS
23h 26m1 stop
$345Spirit Airlines
Mon, Jan 12 - Thu, Jan 15
Delta Logo
8:00 am - 1:09 pm
PNS
-
MHH
4h 09m1 stop
Delta Logo
2:05 pm - 7:58 pm
MHH
-
PNS
6h 53m1 stop
$444Delta
Sat, Jan 31 - Fri, Feb 6
American Airlines Logo
5:24 pm - 11:54 am
PNS
-
PUJ
16h 30m2 stops
American Airlines Logo
6:02 pm - 11:46 pm
PUJ
-
PNS
7h 44m1 stop
$465American Airlines
Sat, Jan 17 - Sat, Jan 24
American Airlines Logo
7:05 pm - 12:21 pm
PNS
-
SDQ
15h 16m1 stop
American Airlines Logo
1:23 pm - 11:46 pm
SDQ
-
PNS
12h 23m1 stop
$478American Airlines
Tue, Mar 10 - Tue, Mar 17
Delta Logo
6:15 am - 11:35 am
PNS
-
GCM
5h 20m1 stop
Delta Logo
1:00 pm - 8:28 pm
GCM
-
PNS
7h 28m1 stop
$480Delta
Sat, Jan 24 - Sat, Jan 31
United Airlines Logo
6:35 am - 2:00 pm
PNS
-
MBJ
6h 25m1 stop
United Airlines Logo
3:20 pm - 9:40 am
MBJ
-
PNS
19h 20m1 stop
$511United Airlines
Fri, Apr 24 - Thu, Apr 30
United Airlines Logo
1:56 pm - 12:49 pm
PNS
-
MBJ
22h 53m1 stop
United Airlines Logo
2:40 pm - 9:56 pm
MBJ
-
PNS
7h 16m1 stop
$512United Airlines
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 February, 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 $578 respectively.

What’s the cheapest day of the week to fly from Pensacola to Caribbean?

The average price of all round-trip flights from Pensacola to Caribbean clicked on KAYAK for each day over the last 12 months.

For Pensacola to Caribbean, Wednesday is the cheapest day to fly on average and Friday is the most expensive. Flying from Caribbean back to Pensacola, the best deals are generally found on Saturday, with Monday being the most expensive.

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 21% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 26 weeks before departure.

Good to know

Low seasonAugust
Cheapest flight$141
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 3% 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.

  • What is the cheapest time of day to fly to Caribbean?

    The cheapest time of day to fly to Caribbean is generally at night, when round-trip flights cost $306 on average. Morning departures are around 23% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $456.

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.
7.9
SouthwestOverall score based on 4252 reviews
7.5Entertainment
8.1Boarding
8.6Crew
8.0Comfort
7.0Food
Airline reviews

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

8.0 ExcellentRussell, Dec 2025
SAN - OAK
Read more Southwest reviews

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

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.

WiFi on the flight was not working. Thus, entertainment options were limited.

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

Crew was great flight was great baggage claim was a failure. It took over 1 hour for bags to arrive. Poor communication poor effort when I spoke to the supervisor about the delay

Planes are aged. The wifi is unreliable and on many fights, no-existent. The flight attendants were very good.

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!!!!

Getting to the flight was arduous and lengthy. The flight itself was good but the food option wasn’t a good selection. I need to do a Kosher option on my return. Flight crew were nice

We had a lot of really rough weather but that was not Delta's fault. Pilot was amazing.

This flight was straightforward and without difficulty. Service was OK, but I continue to be underwhelmed by level of attention given to Sky Priority passengers.

The ticket agents in West Palm Beach on Friday afternoon Nov. 7th were incredible in getting us on an earlier plane to Atlanta during the government shutdown. Had the taken our original flight we would have missed our connection. She did this on her own, We didn't even have to ask, and she did it all with a smile and showing genuine concern that we would be taken care of. We are very grateful and thankful. We fly often, and now we will be sure to fly Delta.

Non stop on long haul is the way to go. Great experience

The boarding process needs to be refined. Sometimes the gate crew call out the boarding zone, and then flip to the monitor to show which zones are boarding. So unless everyone is gathered around to see the monitor there is usually confusion as wi which zones are boarding.

Passengers need to check in big baggage instead of bringing on the plane. That cause inconvenience for everyone. Otherwise flight was good.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

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

Not great experience - we were super late boarding due to issues with aircraft. Then when we finally all got onboard and seated and they started taxiing out to the runway they just stopped then turned around and went back to the airport. Apparently the crew “ran out of time” to legally fly us. They mentioned that they were about 2 minutes away from taking off. I understand the rules and safety but kinda wonder why they would have bothered boarding us in the first place? Had to go all the way back and de plane and then wait in a HUGE line to get a hotel (this is somewhere around 2:30am) finally got to hotel by Uber (no shuttle after 20min so gave up) and they ended up putting us all back on the same aircraft at 10am next morning so got about 2.5 hours sleep. They did give us. $250 credit, but it was a São Paulo Brazil flight out of Dulles. The flight and everything was fine.

They charged a fee for 1st bag checked. Others in same party were free.

Flight team stood out for perzonal attention, kindness at bright cheery attitudes at 8am. Very helpful.

The worst landing I have ever had on a domestic flight. Thought we would lose the landing gear on landing in Newark. Then we spent 40 minutes trying to position the plane in the right place to be able to get the jet way to the plane. The plane arrived stopped. The announcer was that we were there. Everybody got up, then we were told to sit back down because they had to have us towed to a different position. We got towed and then everyone stood up and they told us we were in the wrong position to sit back down again, and then we got towed to a different position This did not happen immediately. It was 30 minutes while we wandered around a small section of the tarmac in Newark close to the gate, but apparently not close enough. Horrifying experience The CAB should be investigating that flight

Boarding was organized. Plane seats comfortable and service was attentive. Food options were good.

It is clear that someone knew, and competent, is in charge of food at United Airlines at least for the international flights. I was flying in coach, but the choices of the dinner were excellent. Tasty, and appropriate size. I had the beef, which was a little bit like a shepherds pie, and it was good. Nothing comparable has been served on a United flight in years. It will not be confused with three star food, but it is very good for airline food. Even better was the breakfast choice between a cinnamon roll and a breakfast sandwich. I chose the breakfast sandwich which was absolutely delicious and which I would happily order again at my local Starbucks or Panera. It is clear that someone knew indifferent is in charge of the food and it’s about time.

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

This is for UA2274 from Houston to Sacramento. The flight was delayed arriving due to mechanical issues so we left about 3 hours later than scheduled. When boarding the plane the temperature inside was excessive - likely close to 100. Pilot apologized and said it was going to improve at altitude, which it did. But before that I honestly thought there might have been more delays removing passengers made ill from the heat. We were delayed leaving due to another mechanical issue. There was not water on the plane due to a panel that was not secured. They did that quickly, but the combination of mechanical issues was rather disturbing and did not reflect well on United.

Staff members were not helpful they ignored all calls for an attendant.

I appreciated that it was on time, safe and professional. I didn’t like that I wasn’t in a place where I had a window at my window seat. It would have been nice to know that in advance. If it was mentioned in the ticketing, I didn’t notice it.

I like that the crew kept us informed but we moved back and forth from gate to gate before the aircraft arrived.

The experience with American Airlines was good, although the Philippines Airlines flight was much better (better seats, better food, better entertainment options, overall better). Again, the MIA to LAX flight was fine, but nothing in comparison to the comfort and accommodations of the Philippines Airlines flight from LAX to MNL.

I have a gluten allergy so didn't have any food

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

My flight was delayed for 17hs because the pilot forgot his passport!!! What a joke. AA used to be a great airline, now I have to think twice before flying with them again.

We had 3 flights. 1 & 2 were on the same plane but we had to de-board just to re-board 30 mins later. That may have been due to a crew change though. Our 3rd flight had a couple “maintenance” issues that held us up. They were quickly resolved but it took forever for someone to bring the paperwork needed so we could leave. Apparently there was a computer glitch so a driver had to bring a physical copy. It delayed us about 1 1/2 hrs. The flights themselves were smooth & no problems. For boarding, I don’t know why they don’t start with the back of the plane & move forward. It would eliminate the back up from people trying to find their seats & put their bags in the overhead bins. Unless you’re on an overseas flight, there is no food, you get a beverage & either a small bag of pretzels or a biscuit cookie. Take your own food or snacks of you want something more.

Lost bag and 2 days no word leaving for cruise no clothes or stuff

We will be writing a long, detailed letter to corporate about our awful experience with American airlines.

Internet was a bit expensive and did not work ask that week otherwise a good flight

Everything was smoothly and convenient! Just stay in this way!

Flight was on time. Friendly crew. Gate agents in the other hand were very unfriendly.

Speaker airport didn't work well, so we couldn't hear the boarding call but the plane was on time leaving and on time arriving took a while for them to open the door and there was a non-disruptive guy who was inebriated a few rows ahead of us. Overall the flight was good and we appreciate the on-time-ness

Bought round trip tickets. Ended up upgrading to first class. Both flights were new planes but hadn’t been equipped with WiFi and there were no charging ports at my seat despite it being new and first class accommodations.

Very uncomfortable seat. Hard bar under cushion. Flight had no solution except to walk a around at times

Endless, trip oof my life, we still are in in plane waiting for getting off.after 3 hours delay. Not even a glass of water.

To be Honest they canceled my flight and didn't have other options. Until 4 says later and I have a 2yr old very disappointed.

Flight was delayed. (To be excepted because of TSA shortage) I’m super short and still struggled with leg room, there was no screen, and the seat didn’t recline at all.

Boarding was easy. I loved that they sat our family together even though we didn't pay for specific seats. I thought $5+ was a lot for pretzels and wish they had a small free snack.

Prices for bags are extremely expensive and if you go higher on weight, the charge is ridiculous.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports