$131 Find Cheap Flights from Caribbean Islands 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 3/12. 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 Caribbean Islands to Pensacola

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

ons, apr 8 - fre, apr 17
Frontier Logo
3:16 am - 2:51 pm
SJU
-
PNS
12h 35m
1 stop
Frontier Logo
3:20 pm - 2:01 am
PNS
-
SJU
9h 41m
1 stop
$192Frontier
fre, apr 3 - fre, apr 17
Frontier Logo
3:16 am - 2:51 pm
SJU
-
PNS
12h 35m
1 stop
Frontier Logo
3:20 pm - 2:01 am
PNS
-
SJU
9h 41m
1 stop
$234Frontier
ons, mar 18 - sön, mar 22
Multiple Airlines Logo
7:00 am - 8:55 am
SJU
-
PNS
26h 55m
1 stop
Multiple Airlines Logo
9:40 am - 2:13 am
PNS
-
SJU
15h 33m
1 stop
$275Multiple Airlines
tors, maj 14 - tors, maj 21
Multiple Airlines Logo
6:30 am - 1:59 pm
SJU
-
PNS
8h 29m
1 stop
Multiple Airlines Logo
2:46 pm - 12:47 am
PNS
-
SJU
9h 01m
1 stop
$279Multiple Airlines
tis, mar 17 - ons, mar 25
Spirit Airlines Logo
2:46 am - 1:16 pm
STI
-
PNS
11h 30m
1 stop
Spirit Airlines Logo
2:15 pm - 1:49 am
PNS
-
STI
10h 34m
1 stop
$345Spirit Airlines
tis, mar 17 - ons, mar 25
Spirit Airlines Logo
2:46 am - 1:16 pm
STI
-
PNS
11h 30m
1 stop
Spirit Airlines Logo
2:15 pm - 1:49 am
PNS
-
STI
10h 34m
1 stop
$347Spirit Airlines
mån, maj 25 - tis, sep 1
American Airlines Logo
12:41 pm - 6:54 pm
KIN
-
PNS
6h 13m
1 stop
American Airlines Logo
8:59 am - 7:55 pm
PNS
-
KIN
10h 56m
1 stop
$664American Airlines
sön, mar 15 - sön, mar 29
Delta Logo
3:55 pm - 11:13 pm
POP
-
PNS
8h 18m
1 stop
Delta Logo
6:00 am - 2:38 pm
PNS
-
POP
7h 38m
1 stop
$800Delta
sön, mar 15 - sön, mar 29
American Airlines Logo
3:35 pm - 11:59 pm
POP
-
PNS
9h 24m
1 stop
American Airlines Logo
6:00 am - 2:35 pm
PNS
-
POP
7h 35m
1 stop
$818American Airlines
lör, mar 14 - sön, mar 29
Delta Logo
3:55 pm - 11:13 pm
POP
-
PNS
8h 18m
1 stop
Delta Logo
6:00 am - 2:38 pm
PNS
-
POP
7h 38m
1 stop
$824Delta
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$131
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly with an average 4% increase in price.
Flight from San Juan to Pensacola

FAQs for booking flights from Caribbean Islands to Pensacola

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

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Pensacola from Caribbean Islands 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 Islands 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 Islands with another airline.

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

 
Need help choosing which airline to fly with from Caribbean Islands 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 8244 reviews
7.2Food
8.5Crew
8.1Boarding
7.8Entertainment
7.9Comfort
Airline reviews

We waited an hour on the runway to get a gate in Orlando

2.0 MediocreJason, Feb 2026
ATL - MCO
Read more Delta reviews

We waited an hour on the runway to get a gate in Orlando

Flight was delayed by 3-hours and their fix was… complimentary pretzels.

The staff on board and gate was nice - a welcome change from the usual. We also arrived early, which was a great benefit, given that it takes 30 minutes plus to get bags at SRQ.

They took all carry-on luggage from Groups 6 -9 - I was group 5 and waiting in line to board - they made me check my luggage too. That then went to baggage claim and delayed departure from the airport. There was overhead room in my seating area - Delta over reacted. Also, had a gentleman next to me that took up 1/2 my seat.

Sorry I didn't realize I was writing a review for each leg. Please see my previous review - it applies to the entire flight, not just a single leg.

boarded at 5:30 pm, pushed away from gate at 6pm ... takeoff was not until ~6:45pm; disappointing

Paid for wifi that didn't work. No plug in seat to work. No entertainment.

I've flown several other airlines, and Delta is really on top on things.

The flight was delayed and oversold. I volunteered to give up my seat for compensation. Thinking I could get a good night's sleep instead of arriving home at 2 am. It took over an hour to get the new reservation confirmed, three different gate attendants, and two red coats. It took even longer to confirm the overnight hotel, and when I arrived, the line was 45 minutes long, with two people checking in, and at least 15 people slowly, very slowly—no food except frozen convenience food, no coupon for food from airlines. Slept, headed back to the airport, and that flight had an equipment change and a gate change just as they were about to board. It took an additional hour to board as they cleaned the plane from storage.

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.

It was a train wreck but on an airplane. First off, flight was delayed then we board only to hear two announcements, First weather delays in Orlando and second backup battery warning on emergency lights. After sitting on the plane for almost 2 hours they have us deplane due to the maintenance issue. We were told they were getting another plane. In the mean time, I notice another American- Orlando flight and ask the gate agent if I can switch. He says he cant help me and I'd have to walk to A13 from A37. Really!? I get down there and get a seat only to get an announcement my original flight was RE-boarding. The Then inflight there's no communication and I notice on flightaware were circling over the Gulf of America. I call the flight attendant and of course she has no clue and apparently 5m later the pilot finally tells us about another delay. Why does American always have these service and delay issues? They are my LAST choice in flights now!

Flight boarded, departed and landed on time. Excellent service from flight attendant in FIRST

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

We were delayed and due to lateness we were traveling from 11pm we were rerouted to FLL and couldnt deplane but stayed on the plane with no extra Service given (extra good options etc$ there Were so many things that could go wrong and did. This was not an enjoyable experience at all thoroughly exhausting

We missed our flight and got stranded in Miami where we had to rent a hotel we could not afford. they would not work with us because they said it was weather related even though the gate attendant said it was not. I could go on but trying to get satisfaction has wore me down, which I believe is the intent. My only solution is to never fly AA again.

The flight was really crowded. Flight attendants were just ok.

Didn't get a seat assignment until the last minute even though i picked a seat.

Flight was on time and the meal and service were good.

Old equipment, needs upgrade and seat comfort. Internet didn't work 75% or the time.

No gates avail at DFW so our incoming had to wait 30 mins for a plane to push back because they Had mechanical. We boarded 90 mins delayed and then we had a mechanical. Come on American…do better. Also at my seat the tray table had not been cleaned. Floor had not been cleaned. But captain and flight Att were very picture and apologetic.

bought basic spirit fares, add checked bags - like the up front info on website about this. bring your own snacks, buy a soda after TSA security to bring with you, or buy on the plane (limited selection) all in all, a good experience

4 hour delay, 2 hours in the airport and then 2 hours on the tarmac. With a flight full of kids it would have been better to leave us in the airport for the delay, it was crying kids chaos on the flight. Miserable. And no apology or airline credit for the significant delay.

Flight was on time with no issues. Price is very competitive. Flight schedule works well for me

Seats were more spacious than other airlines. Crew kept us well informed as soon Ias we stepped into the plane.

I needed a cheaper option than Southwest who are almost as bad as Spirit...did the check in the morning of the flight and assigned the last row, middle seat. Paid 20.00 at the airport for an exit row window in 19 and all 8 rows behind me which sold occupied on their seat map were empty....so they force to you to pay for a better seat....I was alone in row 19 and shortly after take off two huge fat people came and grabbed the other seats, I rang the call button for the attendant and said I paid 20.00 for this seat and they just moved in here...I either want to be reseated, or have them take their original seats or a refund of what I paid, the attendant made them move back to their original seats. Worst, worst worst airline in the air....never again, never again, never again.

It was cancelled a few hours before take off. Spirit has yet to confirm I will be refunded for the trip

gate agents with the different rules at the different airports. made me pay for my bag as a carry on instead of a personal item, yet it fit under the seat on the way from Indy to Ft Laud

charging $3 for really bad and cold coffee on airplane flight is ridiculous.

Checking in and getting to gate fast and leasy at Laguardia airport. There is no entertainment on the plane and food was for purchase. Great experience flying with spirit

Flight was delayed for 12 h. They should stop overlooking flights.

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