$116 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 2/20. 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
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$385
Santo Domingo
Santo Domingo1 stop$324
Montego Bay
Montego Bay1 stop$391
Oranjestad
Oranjestad1 stop$481
Nassau
Nassau1 stop$475
Kingston
Kingston1 stop$641
Simpson Bay
Simpson Bay1 stop$410
George Town
George Town3 stops$520
St. John's
St. John's2 stops$606
Puerto Plata
Puerto Plata2 stops$603
Aguadilla
Aguadilla1 stop$381
Punta Cana
Punta Cana2 stops$385
Santo Domingo
Santo Domingo1 stop$324
Montego Bay
Montego Bay1 stop$391
Oranjestad
Oranjestad1 stop$481
Nassau
Nassau1 stop$475
Kingston
Kingston1 stop$641
Simpson Bay
Simpson Bay1 stop$410
George Town
George Town3 stops$520
St. John's
St. John's2 stops$606
Puerto Plata
Puerto Plata2 stops$603
Aguadilla
Aguadilla1 stop$381

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
Spirit Airlines Logo
6:37 pm - 10:17 am
PNS
-
SJU
13h 40m
1 stop
Spirit Airlines Logo
6:00 am - 5:42 pm
SJU
-
PNS
13h 42m
1 stop
$215Spirit Airlines
Sat, May 2 - Wed, May 6
Spirit Airlines Logo
6:00 am - 10:09 pm
PNS
-
SJU
15h 09m
1 stop
Spirit Airlines Logo
3:43 pm - 9:21 pm
SJU
-
PNS
6h 38m
1 stop
$221Spirit Airlines
Mon, Mar 2 - Sun, Mar 8
Spirit Airlines Logo
6:37 pm - 10:17 am
PNS
-
SJU
13h 40m
1 stop
Spirit Airlines Logo
5:00 am - 5:42 pm
SJU
-
PNS
13h 42m
1 stop
$226Spirit Airlines
Sat, Feb 21 - Thu, Feb 26
Multiple Airlines Logo
6:37 pm - 10:17 am
PNS
-
SJU
13h 40m
1 stop
Multiple Airlines Logo
5:25 pm - 8:50 am
SJU
-
PNS
17h 25m
1 stop
$232Multiple Airlines
Tue, Feb 24 - Tue, Mar 3
Multiple Airlines Logo
5:20 pm - 2:20 pm
PNS
-
SDQ
19h 00m
1 stop
Multiple Airlines Logo
1:11 pm - 5:42 pm
SDQ
-
PNS
6h 31m
1 stop
$329Multiple Airlines
Fri, Feb 27 - Sat, Mar 7
Frontier Logo
9:35 am - 11:02 am
PNS
-
PUJ
47h 27m
2 stops
Frontier Logo
2:16 pm - 1:08 pm
PUJ
-
PNS
24h 52m
1 stop
$385Frontier
Tue, Feb 24 - Tue, Mar 3
American Airlines Logo
6:00 am - 5:50 pm
PNS
-
SDQ
9h 50m
1 stop
American Airlines Logo
7:00 am - 4:34 pm
SDQ
-
PNS
11h 34m
1 stop
$489American Airlines
Tue, Feb 24 - Tue, Mar 3
Delta Logo
6:00 am - 7:14 pm
PNS
-
SDQ
11h 14m
2 stops
Delta Logo
7:30 am - 6:42 pm
SDQ
-
PNS
13h 12m
2 stops
$493Delta
Sun, Apr 12 - Fri, Apr 17
Delta Logo
6:00 am - 4:45 pm
PNS
-
NAS
9h 45m
1 stop
Delta Logo
5:58 pm - 11:23 pm
NAS
-
PNS
6h 25m
1 stop
$496Delta
Thu, Apr 30 - Wed, May 6
American Airlines Logo
4:24 pm - 10:52 pm
PNS
-
SDQ
5h 28m
1 stop
American Airlines Logo
5:55 pm - 9:12 am
SDQ
-
PNS
16h 17m
1 stop
$499American 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 $396 (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.

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 26% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 11 weeks before departure.

Good to know

Low seasonNovember
Cheapest flight$116
Best time to beat the crowds but there is an average 3% increase in price.
Most popular time to fly with an average 6% 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 4268 reviews
8.1Boarding
8.6Crew
7.5Entertainment
8.0Comfort
7.0Food
Airline reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

10.0 ExcellentAnonymous, Jan 2026
PHX - MDW
Read more Southwest reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Everything went smoothly and we even arrived a little bit early.

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.

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

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!!!!

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.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

The food was terrible this time. Otherwise pleasant, quiet, on-time.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

Flight arrived 30 min early and bag was waiting at the baggage pickup. United Club HNL was one of the nicest in the system

Unfortunately weather delayed our flight waiting for our plane to arrive and due to a little snow time was needed to deice the plane so departure was very delayed and I missed the connecting flight

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

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 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.

My last flight on 25 Dec, it’s Christmas Day, everyone happy and very good mood. I really enjoy traveling with Americans Airlines from Miami to Minneapolis my home town after long flight from lhe to Doha then Miami. Thank you again to make my travels comfortable and relaxed. Best regards

I don’t know who decides what food to serve on these flights but I would be so embarrassed if I served this to anyone and call it food…

For whatever reason, the flight was not catered -we were told it would be a 45 minute delay waiting for catering - so no food. There were opened candy and peanuts in the seatback pocket. Flight landed early in DFW but due to the assigned gate not being available, we sat on the ground for 30 minutes waiting for the gate to open - making the flight actually arrive at the gate late.

For the cost you can't e too critical, but the inablitiy to recline the seat and minimal cushioning in the seats made for a less than comfortable flight. Other than that we had an ealry departure and arrival, boarding was smooth.

Nothing everything cost money a bottle of water is 5 dollars and there wasn't even an outlet to plug 🔌 in my 📱 phone

Extra legroom with my upgrade bundle. Clean aircraft, on-time departure, early arrival. Good value for the price.

Even though the plane was delayed from the previous airport, the staff recognized this and kept us informed. The flight crew was absolutely awesome from on my flight from Ft. Meyers to AC. Great experience all around!

Not seat assigned because overbooking. We could go because some people decided to give their seats.

Spirit loves to pick and choose when to harass you about your personal item. I’ve flown numerous times with the same bag with no problem yet flying out of Orlando they forced me to pay $99 for a carry on and then ran out of overhead space. Do better!

didn't order food on board. there's no way to hold a water botton on the way. otherwise it was a pleasant flight, thanks to the crew.

Even though there was a delay the crew was exceptional.

Flight was not on time and it was very annoying flight. Keep changing gates.

The flights were very uncomfortable the seats don't have much leg room at all and they are pretty hard as well.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports