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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

Sun, Oct 4 - Fri, Oct 9
Frontier Logo
2:57 am - 1:14 pmSJU  San Juan Luis Munoz Marin Intl-PNS Pensacola
11h 17m1 stop Orlando
Frontier Logo
8:15 pm - 2:36 pmPNS  Pensacola-SJU San Juan Luis Munoz Marin Intl
17h 21m1 stop Orlando
$241Frontier
Thu, Nov 5 - Mon, Nov 9
Frontier Logo
7:26 pm - 7:11 pmSJU  San Juan Luis Munoz Marin Intl-PNS Pensacola
25h 45m1 stop Orlando
Frontier Logo
8:06 pm - 10:15 amPNS  Pensacola-SJU San Juan Luis Munoz Marin Intl
12h 09m1 stop Orlando
$241Frontier
Fri, Oct 30 - Mon, Nov 2
Frontier Logo
10:20 am - 7:11 pmSJU  San Juan Luis Munoz Marin Intl-PNS Pensacola
9h 51m1 stop Orlando
Frontier Logo
8:06 pm - 10:15 amPNS  Pensacola-SJU San Juan Luis Munoz Marin Intl
12h 09m1 stop Orlando
$265Frontier
Thu, Nov 5 - Mon, Nov 9
American Airlines Logo
1:40 pm - 11:49 pmSJU  San Juan Luis Munoz Marin Intl-PNS Pensacola
12h 09m2 stops Miami Charlotte Douglas
American Airlines Logo
8:20 am - 10:39 pmPNS  Pensacola-SJU San Juan Luis Munoz Marin Intl
12h 19m2 stops Charlotte Douglas Miami
$466American Airlines
Fri, Oct 30 - Mon, Nov 2
American Airlines Logo
6:30 am - 2:30 pmSJU  San Juan Luis Munoz Marin Intl-PNS Pensacola
9h 00m1 stop Miami
American Airlines Logo
8:20 am - 9:38 pmPNS  Pensacola-SJU San Juan Luis Munoz Marin Intl
11h 18m2 stops Charlotte Douglas Miami
$466American Airlines
Tue, Nov 24 - Wed, Dec 2
American Airlines Logo
6:55 pm - 8:28 amSJU  San Juan Luis Munoz Marin Intl-PNS Pensacola
15h 33m1 stop Miami
American Airlines Logo
8:20 am - 10:39 pmPNS  Pensacola-SJU San Juan Luis Munoz Marin Intl
12h 19m2 stops Charlotte Douglas Miami
$471American Airlines
Thu, Dec 24 - Sun, Jan 3
Delta Logo
7:30 am - 12:43 pmSJU  San Juan Luis Munoz Marin Intl-PNS Pensacola
7h 13m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:00 am - 2:15 pmPNS  Pensacola-SJU San Juan Luis Munoz Marin Intl
6h 15m1 stop Atlanta Hartsfield-Jackson
$521Delta
Thu, Nov 12 - Tue, Nov 17
Delta Logo
3:28 pm - 10:04 pmMBJ  Montego Bay Sangster Intl-PNS Pensacola
7h 36m1 stop Atlanta Hartsfield-Jackson
Delta Logo
8:03 am - 2:03 pmPNS  Pensacola-MBJ Montego Bay Sangster Intl
5h 00m1 stop Atlanta Hartsfield-Jackson
$603Delta
Sat, Oct 31 - Sun, Nov 1
United Airlines Logo
2:46 pm - 9:50 pmSJU  San Juan Luis Munoz Marin Intl-PNS Pensacola
8h 04m1 stop Houston George Bush Intcntl
United Airlines Logo
6:35 am - 4:36 pmPNS  Pensacola-SJU San Juan Luis Munoz Marin Intl
8h 01m1 stop Houston George Bush Intcntl
$618United Airlines
Sat, Nov 14 - Sat, Nov 28
United Airlines Logo
3:45 pm - 9:50 pmMBJ  Montego Bay Sangster Intl-PNS Pensacola
7h 05m1 stop Houston George Bush Intcntl
United Airlines Logo
6:30 am - 2:39 pmPNS  Pensacola-MBJ Montego Bay Sangster Intl
7h 09m1 stop Houston George Bush Intcntl
$626United Airlines
Useful Info

Good to know

Low season

August

Cheapest flight

$148
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly and prices are also 5% 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 8557 reviews
7.8Comfort
7.8Entertainment
7.2Food
8.5Crew
8.1Boarding
Airline reviews

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?

6.0 GoodPaula, Sep 2026
Read more Delta reviews

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.

We were skipped when the snack cart passed and then the attendant said we weren’t . I am disabled and was in a row toward the back of the plane which was very difficult for me to navigate. Disabled people should not be forced to walk the plank.

Flight was delayed and then "they did not have time to load food". No snack or drink at all for 1.5 how flight. Somebody wasn't prepared.

It is usually very pleasant. Good service for the price, international flights are even better

New high end luggage ruined/zippers broken, items missing. All happened on return flight from msp to mso. Do better! Not store bought luggage but high end personalized ogio custom embroidered luggage. Total slap in the face ontop of an extra luggage fee that took me 3 hrs on chat to resolve.

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.

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.

Nothing was good about this flight. Although the flight actually departed more than 3 hours late, due to “air traffic control management” we pushed back from gate 2 hours and 20 minutes late and proceeded to sit 100 yards from gate for and then n tarmac for another 1/2 hour additional 20 minutes

Both the gate agent and flight crew did a horrible job of expediting the boarding process. It was simply miss managed. The airplane was late to Tampa. Therefore, they should have expedited the de-boarding process and also boarding process. This did not happen and caused me to miss my connection. I ended up with a 7 hour hour layover just to get home. The overall flying experience on American has simply been degraded. On-time performance is a real problem every single week. This has caused me to consider moving my loyalty to an airline that has better performance metrics.

Delayed flight led to missed connection which led to new flight with 3 hours of delay so our family of 5 went from a 7pm arrival time to 1am Absolutely terrible yet again.

Wheelchair folks are great. Food not to my liking. Crew more interested in their lives than the passengers. Got the job done but just the minimum.

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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