$111 Find Cheap Flights from Caribbean to Pensacola

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Pensacola departing on 5/19. 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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Everything you should know

Cheapest round-trip
$209
Overall average: $505
Frontier
Thu 2/19Mon 2/23
SJU - PNS • 1 stop
Cheapest one-way
$111
Typical prices: $218-$319
Spirit Airlines
Tue 5/19
SJU - PNS • 1 stop
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Flight Deals
Useful Info
Flight Deals

Cheap Flights from Caribbean to Pensacola

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Caribbean to Pensacola 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 Caribbean to Pensacola

Thu, Feb 19 - Mon, Feb 23
Frontier Logo
3:53 am - 8:50 am
SJU
-
PNS
6h 57m1 stop
Frontier Logo
2:23 pm - 2:53 am
PNS
-
SJU
10h 30m1 stop
$209Frontier
Sat, Jan 31 - Mon, Feb 2
Spirit Airlines Logo
6:00 am - 4:37 pm
SJU
-
PNS
12h 37m1 stop
Spirit Airlines Logo
5:33 pm - 9:47 am
PNS
-
SJU
14h 14m1 stop
$241Spirit Airlines
Mon, Feb 9 - Mon, Feb 23
Multiple Airlines Logo
3:53 am - 4:37 pm
SJU
-
PNS
14h 44m1 stop
Multiple Airlines Logo
6:37 pm - 4:25 pm
PNS
-
SJU
19h 48m2 stops
$257Multiple Airlines
Wed, Feb 11 - Mon, Feb 23
Multiple Airlines Logo
5:25 pm - 5:42 pm
SJU
-
PNS
26h 17m1 stop
Multiple Airlines Logo
6:37 pm - 4:25 pm
PNS
-
SJU
19h 48m2 stops
$261Multiple Airlines
Sun, Mar 1 - Wed, Apr 1
American Airlines Logo
2:33 pm - 10:21 am
MBJ
-
PNS
20h 48m2 stops
American Airlines Logo
6:00 am - 12:27 pm
PNS
-
MBJ
6h 27m1 stop
$531American Airlines
Wed, May 20 - Thu, May 28
American Airlines Logo
7:00 am - 3:54 pm
KIN
-
PNS
8h 54m1 stop
American Airlines Logo
6:00 am - 11:26 am
PNS
-
KIN
5h 26m1 stop
$549American Airlines
Mon, May 25 - Tue, Sep 1
Delta Logo
9:00 am - 11:06 pm
KIN
-
PNS
14h 06m1 stop
Delta Logo
8:00 am - 8:04 pm
PNS
-
KIN
12h 04m1 stop
$555Delta
Wed, May 20 - Thu, May 28
Delta Logo
9:00 am - 6:02 pm
KIN
-
PNS
9h 02m1 stop
Delta Logo
7:00 am - 8:05 pm
PNS
-
KIN
13h 05m1 stop
$565Delta
Thu, Jan 29 - Mon, Feb 2
WestJet Logo
5:30 pm - 11:13 pm
POP
-
PNS
31h 43m2 stops
WestJet Logo
6:07 pm - 4:27 pm
PNS
-
POP
20h 20m2 stops
$2,164WestJet
Thu, Jan 29 - Mon, Feb 2
WestJet Logo
5:30 pm - 11:13 pm
POP
-
PNS
31h 43m2 stops
WestJet Logo
11:25 am - 4:27 pm
PNS
-
POP
27h 02m2 stops
$2,542WestJet
Useful Info

Good to know

Low seasonOctober
Cheapest flight$111
Best time to beat the crowds but there is an average 26% increase in price.
Most popular time to fly with an average 8% increase in price.
Flight from San Juan to Pensacola

FAQs for booking flights from Caribbean to Pensacola

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

    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 Caribbean to Pensacola.

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

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

    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 Pensacola with an airline and back to Caribbean with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Caribbean to Pensacola?

    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 Pensacola from Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 3 airlines serving from Caribbean to Pensacola

 
Need help choosing which airline to fly with from Caribbean to Pensacola? 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
DeltaOverall score based on 8037 reviews
8.1Boarding
7.8Entertainment
7.2Food
7.9Comfort
8.5Crew
Airline reviews

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.

8.0 ExcellentG, Jan 2026
FLL - ATL
Read more Delta reviews

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.

Air travel sucks. It continues to be awful for all airlines. No shame on delta alone.

Comfort Plus seat 11E seemed smaller than prior flights. The movie selection is good. Watched most of the most recent Tron movie. I'll watch the remaining part later as my movie is saved in the Delta Seatback Experience.

Delta is a good airline. I've never had an issue with Delta. I'll continue to fly with them until they show me that I shouldn't.

Flight was operated by Virgin Atlantic and it was up to their usual high standard. Minor grips about some issues, but they are really first world issues and as a whole, was an excellent flight.

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

First, Delta needs more flights to/from Miami. Second, a 1000pm leaving at 1230pm is unacceptable from their biggest airport world hub. Another aircraft could have been used such as the aircraft scheduled to be used in the morning for that exact same route. Yes, I did get me there but the lack of sleep the next day didn't help me enjoy my entire trip since I was busy with activities during the weekend. This can be and is expected from Spirit (going bankrupt) and Frontier (despite they're nickel and dimers). But from Delta's World Hub? That's totally unacceptable!

Service in business class was not impressive. I ordered coffee with dinner and then watched other people get 2 refills before I got my 1 cup of coffee, and only after I pressed the attendant button overhead. Furthermore, the seats in the forward cabin need maintenance on this 737-800: the upholstery is detaching from the seat frame, at least on the backs of seats 1C, 1D.

I truly love flying with Delta. They have always treated me with the upmost respect

Our flight attendant in FIRST CLASS was one of the worst I’ve ever had. She was not at all pleasant, nor particularly good at her service.

I was originally scheduled on AA 1763. When I landed in Miami, I went to the counter for flight AA 2115 to try to move my flight to this one. I was in a first class seat on AA 1763. While they moved to me this flight, I was told that there were no other 1st class seats available and they assigned me into coach. However, when I was getting off the plane I noticed that one of the pilots who was also in line to go jump seat - somehow miraculously got a 1st class seat on this flight. It is actually infuriating that I had a paid 1st class seat yet somehow they would move an AA employee ahead of that. At a bare minimum, they should have compensated me for the fare difference and I really think paying customers should ALWAYs get the premiere seats.

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

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

Original flight was canceled and rescheduled for the next day. Cancelation notice was sent in the middle of the night (only saw it in the morning), leaving no room to find other options. No offers to reimburse for the extra expenses or compensations. My flight to Rio on 12/12 was also delayed for 16 hours. This seems to be the new normal for AA.

I got sick nothing contagious but distressing and the care I received by Kayla? Keighly the flight attendant will be memorable for ever. Thank You

Waaay too small plane. They also need to up the size of the overhead bins. I would love to keep me 3k with of camera equipment in my hard case baggahe instead of it being thrown into the belly of the plane

Attendants were pleasant and the flight was smooth and relaxed.

It was fine. No drinks nor snacks offered though. I thought that was unusual.

I like how the crew and pilot kept us updated Even though our flight was slightly delayed. We made up time for it in the air. I really did enjoy my seat and amenities and my trip and value overall.

I've flown two Spirit flights recently - boarding for one was somewhat chaotic, with the board listing the wrong flight and causing much confusion; boarding for the other was very smooth and easy. My seat (for which I did not pay extra) was a bit narrow and without great legroom, but it was fine for a NY-Florida trip and was more than worth the low price I paid. The crew was friendly and one flight landed early and the other was only very slightly delayed. All in all a very good experience.

Spirit sucks. Horrible employees in Medellín. Never again. I hope this company goes out of business completely.

Your flight crew and boarding area crew need to have microphone use training. They all hold the microphone right up to their mouths, way to close making understanding them almost impossible. The microphone should be held about 3 to 4 inches away from their mouths. This would provide for much better clarity through the PA system. ‘Eating the mic’ DOES NOT work.

It was the first time I flew on that airline and had a very positive experience. Nearly identical to Jetblue which consider the standard of airlines excellence.

A bottled or canned drink, whether water or soda would have been appreciated upon settling in and flying, without being charged for it.

Horrible. I never will travel again with Spirit. Delays and cancellations. Not more words .

COMMUNICATION!!!! The issue was a crew shortage, which means you knew in advance the issue. Instead of notifying people in advance, we're finding out an hour before the flight it's canceled. You rebooked people to more flights you knew wouldn't get out. You ended by taking part of my party to a completely different state and leaving them there. The next morning, you still have no way to get them to the original destination and they ended up missing an important event. We came out of so much money to check bags multiple times. And on top of all that, the staff in the building seemed to not care and were fairly rude. Overall, just go on and fold and quit making promises to people to get them places when you know you can't. Shoutout to Delta for doing a great job at making it less painful (for those of us who made it).

The flight was cancelled without prior notice. I was inform as I was checking in. No hotel accommodation nor any simple explanation as why it was cancelled.

Terrible. I never made my trip to Puerto Rico and my layover flight from IAH to MCO was delayed over 3 hours and made me miss my connecting flight. I spend 2 days in an airport just to have to go back to Houston. This was a trip for my birthday and I lost money on this trip. I understand the situation with Venezuela affected flights but it’s always something with Spirit.

Bad experience with gate agent. I asked what group she was boarding. She gave me a face and said, with attitude, group 1. I stood back and waited for my group, group 2 to be called. After an awful lot of people boarded she took the mic and announced, now boarding group 5. The lack of professionalism amongst spirit staff is astounding.

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