$138 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 7/16. 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 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

Fri, Jul 10 - Thu, Jul 16
Frontier Logo
6:31 pm - 2:18 pm
SJU
-
PNS
20h 47m
1 stop
Frontier Logo
3:15 pm - 2:11 am
PNS
-
SJU
9h 56m
1 stop
$276Frontier
Thu, Nov 5 - Sun, Nov 8
Frontier Logo
7:05 am - 2:18 pm
SJU
-
PNS
9h 13m
1 stop
Frontier Logo
3:15 pm - 2:50 am
PNS
-
SJU
9h 35m
1 stop
$277Frontier
Wed, May 27 - Mon, Sep 14
Delta Logo
4:59 pm - 11:16 pm
MBJ
-
PNS
6h 17m
1 stop
Delta Logo
9:25 am - 3:34 pm
PNS
-
MBJ
6h 09m
1 stop
$307Delta
Wed, May 27 - Sun, Sep 6
Delta Logo
4:59 pm - 11:16 pm
MBJ
-
PNS
6h 17m
1 stop
Delta Logo
3:35 pm - 11:24 am
PNS
-
MBJ
19h 49m
2 stops
$312Delta
Wed, May 27 - Mon, Sep 14
American Airlines Logo
2:55 pm - 10:17 am
MBJ
-
PNS
19h 22m
1 stop
American Airlines Logo
6:05 pm - 12:45 pm
PNS
-
MBJ
18h 40m
2 stops
$328American Airlines
Thu, Jun 11 - Sat, Aug 15
American Airlines Logo
3:00 pm - 10:24 am
MBJ
-
PNS
19h 24m
1 stop
American Airlines Logo
7:12 pm - 11:42 am
PNS
-
MBJ
16h 30m
1 stop
$331American Airlines
Fri, Aug 28 - Sat, Sep 5
Multiple Airlines Logo
6:00 am - 6:52 pm
SJU
-
PNS
13h 52m
1 stop
Multiple Airlines Logo
10:26 am - 4:34 pm
PNS
-
SJU
29h 08m
1 stop
$331Multiple Airlines
Fri, Aug 28 - Sat, Sep 5
Multiple Airlines Logo
6:00 am - 6:52 pm
SJU
-
PNS
13h 52m
1 stop
Multiple Airlines Logo
10:26 am - 8:09 am
PNS
-
SJU
20h 43m
2 stops
$348Multiple Airlines
Mon, May 25 - Tue, Sep 1
United Airlines Logo
2:59 pm - 7:51 pm
KIN
-
PNS
52h 52m
2 stops
United Airlines Logo
2:26 pm - 1:54 pm
PNS
-
KIN
47h 28m
2 stops
$697United Airlines
Mon, May 25 - Tue, Sep 1
United Airlines Logo
2:59 pm - 10:01 pm
KIN
-
PNS
31h 02m
2 stops
United Airlines Logo
2:26 pm - 1:54 pm
PNS
-
KIN
47h 28m
2 stops
$709United Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$138
Best time to beat the crowds with an average 20% drop 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 4 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 8457 reviews
7.8Entertainment
7.9Comfort
8.5Crew
7.2Food
8.1Boarding
Airline reviews

Everything could and should be better. We are paying for, it's not a favor, it's a service and should involve quality, responsibility and respect.

2.0 MediocreIrmara, May 2026
GRU - MCO
Read more Delta reviews

Everything could and should be better. We are paying for, it's not a favor, it's a service and should involve quality, responsibility and respect.

Overall Good! The weather delayed our takeoff from Atlanta and our arrival in Miami! If Mother Nature can mess up a flight she will do it every time!

N Everything was perfect from boarding to assistance to baggage in Tampa

I lost my plane and spend 5 hours at the airport arriving at Buffalo at 1 am taxis are very expensive at that time.

Snacks and included beverages were appreciated. Boarding went smoothly. Plenty of overhead bin space. Seats get very uncomfortable after a couple of hours. After waiting 10 painful minutes for my walker, a very nice Delta guest agent pushed me in a wheelchair to the gate. It was finally delivered to me after another 15 minutes . Our checked bag was on the carousel long b4 I was able to retrieve it. Fortunately it was still there but somewhere along the way the straps we used to secure it were removed and and were not reattached. Wish I had made note of the agents name.

The whole experience was excellent. As it most often is with Delta

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.

It was good overall except from Omaha to Denver when flight a was a repeatedly delayed apparently due to some issue at Denver. Communications could have been handled better. I had to board then deboard with luggage and board again

Left an hour and a half after the listed time. Up side was it had TV screens on the seat.

No screens or meal options. Freezing cold. Dirty seats. Left late.

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

Seats very comfortable; service efficient and pleasant; flight was on-time; boarding organized.

Seats were not super comfortable and food was not good at all. If I had a chance I would definitely fly a different airline. Of course they are better than any budget airline, but not by much.

Overall a good experience, but no wifi available for free or for purchase and we got wet from condensation or other water source during descent.

Very friendly and helpful staff on board and United was excellent when I missed my onward flight due to the delay in London. Very well organised meant much less stress

Flew steerage class. Short on leg room unless you pay more. No window unless you pay more. Etc. United is trying to squeeze every cent from you. It doesn’t make for any loyalty.

Booked through Kayak Business, had a seat in middle and towards back due to booking rate, not comfortable.

Everything was fine except the end of the flight. We spent more than an hour circling around Miami due to weather conditions. That was not good.

They lost my bag. ... And I asked them 3 times to 3 different people if my checked bag will maKe it all the way - they all confirmed and at the end it was left at the connection... Bravo

Cancelled BOYH legs of our flight home 30 min before initial boarding

Poor... food was horrible, boarding very slow, service on board mediocre

Flight left early and arrived 30 MINUTES early at the destination. Smooth trip.

Departed late but made up the time en route. Uncrowded and clean aircraft.

I was able to get the AA customer Service desk to put me on an earlier flight without any issues.

Incredibly delayed. First delay was due to plane coming in being late. Resulted in 30 minute delay. Boarded and then had multiple mechanical issues. Was on plane for an hour until they told people they could get off if they wanted but couldn't come back. Then gate agent rushed in and said they had lost control of who went off and we would all have to deplane and then get back on. They said flight had not been cancelled. Then while sitting waiting to board again they announced it would take two hours to get new plane and to wait at new gate. New plane arrived, reboarded only to find out that pilots had timed out. Waited for new pilots. In that time one of the flight attendants timed out. Never received food or water while waiting. Was confusing mess as to what was happening. Even flight attendants and gate agents were getting frustrated. Almost 6 hours delayed. Called American to received flight credit but can't get anywhere as Kayak reservation and don't have a ticket number. Reached out to Kayak but never heard back.

Very disappointing. Flight was delayed by 1.5 hours and food options are very underwhelming even for first class seats (same food given to economy seats)

Was not able to do a online check-in because the American Airlines system doesn't store our visa or other passport information, allowing us to have a trouble-free check-in. We were forced to have to check-in at the counter which Changes are upgrade status given that we were not able to check in much earlier.

Flights were canceled due to airline shutting down and haven’t received a reimbursement. Had to book last minute new flights which were expensive

The company went out of business and now I'm stuck in Ft. Lauderdale. Would not recommend.

Spirit changed flight times by 12 hours with coming and going so I refunded tickets and drove

The agent cancel my flight without my consent. So the situation generate me a lot of troubles, specially because we were traveling with a baby

Wonderful! Very polite crew that was dedicated to excellent customer service

The flight was delayed for over an hour. No one at the gate said anything about the flight being delayed. I had to rely on my phone for updates. Absolutely no communication at the gate.

The boarding process was simple but the seats were very uncomfortable. The staff lady was also very hard to understand when she spoke over the intercom about procedures and updates. Other staff members seemed like they were just tired and didnt want to be on the plane. Im used to happy attendants and being able to understand what is said over the speakers.

The seats on this aircraft were so uncomfortable it was like sitting on high school gym bleachers. I’m not sure we will fly spirit again. I also paid for the so called shortcut security and ended up being told to get in the regular security line, don’t waste your money.

Flight was delayed 6plus hours Did not take flight Customer service was terrible Will never fly again and will spread how terrible you are You stink

I didnt have a flight. Kayak must be on drugs because I confirmed with spirit that I had no booked flight.

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