$141 Find Cheap Flights from Caribbean to Pensacola - Compare and Save

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Cheap Flights from Caribbean to Pensacola

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Caribbean to Pensacola

Fri, Nov 13 - Sun, Nov 15
Frontier Logo
11:20 am - 7:19 pmSJU  San Juan Luis Munoz Marin Intl-PNS Pensacola
9h 59m1 stop Orlando
Frontier Logo
8:14 pm - 10:15 amPNS  Pensacola-SJU San Juan Luis Munoz Marin Intl
12h 01m1 stop Orlando
$276Frontier
Tue, Nov 3 - Tue, Nov 10
Multiple Airlines Logo
8:45 am - 6:30 pmSJU  San Juan Luis Munoz Marin Intl-PNS Pensacola
11h 45m1 stop Fort Lauderdale
Multiple Airlines Logo
7:10 pm - 3:19 pmPNS  Pensacola-SJU San Juan Luis Munoz Marin Intl
18h 09m1 stop Fort Lauderdale
$287Multiple Airlines
Wed, Nov 4 - Tue, Nov 10
Multiple Airlines Logo
8:45 am - 7:05 pmSJU  San Juan Luis Munoz Marin Intl-PNS Pensacola
12h 20m1 stop Fort Lauderdale
Multiple Airlines Logo
7:10 pm - 3:19 pmPNS  Pensacola-SJU San Juan Luis Munoz Marin Intl
18h 09m1 stop Fort Lauderdale
$289Multiple Airlines
Tue, Apr 6 - Tue, Apr 13
Delta Logo
1:00 pm - 10:00 pmSJU  San Juan Luis Munoz Marin Intl-PNS Pensacola
10h 00m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:00 am - 4:20 pmPNS  Pensacola-SJU San Juan Luis Munoz Marin Intl
9h 20m1 stop Atlanta Hartsfield-Jackson
$426Delta
Wed, Nov 4 - Wed, Nov 18
American Airlines Logo
4:33 pm - 10:49 pmSTT  Saint Thomas Island Cyril E King-PNS Pensacola
8h 16m1 stop Charlotte Douglas
American Airlines Logo
3:04 pm - 12:15 pmPNS  Pensacola-STT Saint Thomas Island Cyril E King
19h 11m2 stops Charlotte Douglas Miami
$498American Airlines
Wed, Nov 4 - Wed, Nov 18
American Airlines Logo
1:07 pm - 10:49 pmSTT  Saint Thomas Island Cyril E King-PNS Pensacola
11h 42m2 stops Miami Charlotte Douglas
American Airlines Logo
3:04 pm - 12:15 pmPNS  Pensacola-STT Saint Thomas Island Cyril E King
19h 11m2 stops Charlotte Douglas Miami
$498American Airlines
Wed, Oct 28 - Tue, Dec 8
Delta Logo
2:59 pm - 11:30 pmSJU  San Juan Luis Munoz Marin Intl-PNS Pensacola
9h 31m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:00 am - 2:20 pmPNS  Pensacola-SJU San Juan Luis Munoz Marin Intl
6h 20m1 stop Atlanta Hartsfield-Jackson
$506Delta
Thu, Nov 19 - Thu, Nov 26
Delta Logo
6:55 pm - 11:41 pmSJU  San Juan Luis Munoz Marin Intl-PNS Pensacola
6h 46m1 stop Atlanta Hartsfield-Jackson
Delta Logo
9:27 am - 5:43 pmPNS  Pensacola-SJU San Juan Luis Munoz Marin Intl
6h 16m1 stop Atlanta Hartsfield-Jackson
$536Delta
Thu, Dec 24 - Sat, Jan 2
United Airlines Logo
3:45 pm - 8:03 pmMBJ  Montego Bay Sangster Intl-PNS Pensacola
29h 18m1 stop Houston George Bush Intcntl
United Airlines Logo
6:45 am - 2:39 pmPNS  Pensacola-MBJ Montego Bay Sangster Intl
6h 54m1 stop Houston George Bush Intcntl
$619United Airlines
Mon, Oct 26 - Mon, Nov 16
United Airlines Logo
2:01 pm - 1:26 pmMBJ  Montego Bay Sangster Intl-PNS Pensacola
23h 25m1 stop Chicago O'Hare Intl
United Airlines Logo
2:22 pm - 1:48 pmPNS  Pensacola-MBJ Montego Bay Sangster Intl
22h 26m1 stop Chicago O'Hare Intl
$644United Airlines
Useful Info

Good to know

Low season

August

Cheapest flight

$141
Best time to beat the crowds but there is an average 3% increase in price.
Most popular time to fly and prices are also 3% lower on average.
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.
7.8
DeltaOverall score based on 8636 reviews
8.1Boarding
7.2Food
7.8Entertainment
8.5Crew
7.8Comfort
Airline reviews

Late flight, screens not working and still had to pay for a drink

4.0 OkayAnonymous, Sep 2026
Read more Delta reviews

Late flight, screens not working and still had to pay for a drink

They changed my seat assignment from window to middle. I have a physical need to sit by the window because of spinal issues. I unboarded in pain, I also was placed between 2 very large men. I am very disappointed and now dealing with the physical aftermath.

The crew were awesome and ready to help as much as possible. The gate agent in Atlanta was tremendously helpful. The delays were ridiculous. Getting home at 4am when I could have driven home faster was unimpressive. Being delayed for countless hours through the night wasn't a great travel experience.

We sat at the gate for over 30 minutes, with no indication as to why

Flight Staff: Always great! Checking back vs carry-on: I typically check my bag since so much time is spent stowing the bag, it's heavy, maybe not enough room. Delta is charging $45 to check bags. Yet, the people who have multiple carry-on bags are then asked to check their bags and are offered this service for free. This does not seem fair to a person who is trying to be proactive in improving the process . Boarding: Boarding is always slow and exhausting. With the exception of First Class, Economy, why not board the zone in the back of the plane first??? Seats: Why cross the seat belts? I get that it looks nice, but people waste so much time moving them or sitting on them and then having to move. Seats: On both my flights the seat did not recline. Not a big deal. Smell: There was a horrific smell like the restrooms on my first flight. I thought I was going to be sick. Most flights do not smell great. Does Delta use air purifiers or anything?

DL482 did not wait for about 10 of us including a mother and 3 children when we were in the same terminal on DL486, where we were switching from waiting for a jet bridge fix, to moving to a neighboring gate. I understand taxiing delays are ok either but man. We only needed 5 more minutes. DL482 did not adjust from their times at all. This was my first time with Delta.

The actual flight was smooth and we arrived earlier than expected which was great. The flight attendants gave unclear instructions and were rude. They seemed overwhelmed or flustered for the flight. Inflight service was delayed and unsure why.

There needs to be better accommodations for waiting passengers. A a designated standing space that is separated and away from concourse traffic.

overall the crew onboarding and providing service during our flight was great; they were friendly and helpful. I said ok to the entertainment because there was none, but the crew explained why which was very helpful. I am a diabetic and the type of snacks are not diabetic friendly (full of carbs and sugar). However, I am always prepared because I know the catering is for the larger population.

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

We couldn’t take the direct flight back home in Florida because the flight in Palermo was delayed flor long time and keep us inside the cabin without moving the plane. The plane from Munich to Orlando was still there when we arrived to the gate but they said it was late for us to board the plane. We rushed the most to get there. It was a bad experience and got back exhausted and with pain in all muy body. We are seniors 72 and for us was very bad

The experience with United Airlines was excellent; however, the experience with Houston Intercontinental Airport (IAH) was horrible. Although our flight departed from Terminal B, we had to go through security in Terminal C and then get on a train for travel to Terminal B. Additionally, there was significant walking required to get to the boarding location.

Flight was delayed 5 hours. Updates kept changing. Sears were extremely cramped. Very little leg room. Flight attendant was rushing through with drinks and hit me in the knee either the cart and didn’t apologize. They gave a 15 dollar voucher in airport which doesn’t buy. Much and it was so late that choices were limited.

Always pretty good as far as I see it. Staff was friendly and process was quick to get on and off.

The flight was delayed because they closed several flight ways because of air shows, fire works, etc.

Lost one piece of luggage even though I checked in 2.5 hours before the flight

Horrifying Almost 2 million miles. Bring your own food and drink. One coffee or drink every three hours. Have to order meals on app more than 24 hours ahead Tiny and dirty bathrooms

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

I've been flying American mostly, and it's been very frustrating. This united flight makes me realize maybe the issue isn't flying, but the airline. United was a significantly better experience. The plane was more comfortable, with a normal amount of leg room (vs the ridiculous reductions AA has made), more comfortable seats, screens to watch movies. It was a much better experience!

Always wish for more healthy, gluten free options. We have to bring our own.

When we landed, there was only one gate agent to handle three planes, including retrieval of carry on luggage. I was stuck in the jet way waiting on my carry on for almost 20-30 minutes. NOT GOOD

Might want to rethink the snacks you offer in first class they were pretty pathetic

The staff and flight were great! The inflight enteretaintment did not work from EZE to MIA. They attempted to troubleshoot but exhausted all options.

The flight from American side was good, my main issue this was a part of a partner flight with gol, preventing me to use digital boarding passes and doing checking previous of the arrival to the airport.

5 hours delay - minimum communication, no compensation, no support from Airline. Terrible customer experience

Flying under Economy Class shouldn’t mean having to deal with such uncomfortable seats. For an overnight flight, it is expected that the seat would recline a decent amount. The food portion could have been more generous. There was an incident with someone by my side. They got sick and vomited. I hit the button for the crew but no one showed up. So I went to the back of the plane and explained what happened. They only brought clean tissues and coffee ground bags. There wasn’t any kind of disinfecting wipes nor any type of sprays. She cleaned as best as she could and poured the coffee ground around. The crew did not seem to care how she was doing. The coffee helped with the smell, but it should have been cleaned in a more efficient manner.

The big challenge here was that the inbound flight was delayed, THEN, the aircraft was deemed in need of service, so we had to deplane after being a few minutes away from departure, THEN we had to switch terminals, where another plane in our gate had maintenance issues so we had to change gates again. I am a regular flyer (not on American) so I understand these things happen. The crew was great. The pilot in particular was gracious and understanding and stayed with the passengers the whole time to answer questions and give updates - that was impressive. But the flight was massively delayed as a result, and today I really wanted to be home in time. Sigh The flight was otherwise great.

I am Plstinum Pro snd was standby on earlier flight. They gave seats to people that asked rather than follow standby order. When realized what was happening was too late to get on as no seats left. My scheduled flight was late. Then filled the seat beside me Ruth rude person that they had to move from her original seat

I have yet to come across an AA agent or flight attendant that is friendly. They really inhibit a good experience.

Fine. On time, cabin service was fine, bag arrived. All good. Flying into DCA so did not collide with any helicopters, which is also good. Horrid incident that could have and should have been prevented.

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