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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

Wed, Oct 21 - Mon, Oct 26
Multiple Airlines Logo
8:45 am - 6:55 pmSJU  San Juan Luis Munoz Marin Intl-PNS Pensacola
11h 10m1 stop Fort Lauderdale
Multiple Airlines Logo
8:54 pm - 9:15 amPNS  Pensacola-SJU San Juan Luis Munoz Marin Intl
11h 21m1 stop Orlando
$257Multiple Airlines
Wed, Sep 16 - Wed, Sep 23
Multiple Airlines Logo
8:45 am - 6:55 pmSJU  San Juan Luis Munoz Marin Intl-PNS Pensacola
11h 10m1 stop Fort Lauderdale
Multiple Airlines Logo
7:35 pm - 1:34 pmPNS  Pensacola-SJU San Juan Luis Munoz Marin Intl
16h 59m1 stop Fort Lauderdale
$262Multiple Airlines
Fri, Sep 18 - Wed, Sep 23
Multiple Airlines Logo
7:00 am - 6:45 pmSJU  San Juan Luis Munoz Marin Intl-PNS Pensacola
12h 45m1 stop Fort Lauderdale
Multiple Airlines Logo
7:35 pm - 1:34 pmPNS  Pensacola-SJU San Juan Luis Munoz Marin Intl
16h 59m1 stop Fort Lauderdale
$262Multiple 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, Feb 23 - Sat, Feb 27
American Airlines Logo
2:31 pm - 6:50 pmSJU  San Juan Luis Munoz Marin Intl-PNS Pensacola
6h 19m1 stop Miami
American Airlines Logo
7:26 pm - 10:38 amPNS  Pensacola-SJU San Juan Luis Munoz Marin Intl
13h 12m1 stop Miami
$466American Airlines
Tue, Feb 23 - Sat, Feb 27
American Airlines Logo
7:00 pm - 7:59 amSJU  San Juan Luis Munoz Marin Intl-PNS Pensacola
14h 59m1 stop Miami
American Airlines Logo
7:26 pm - 10:38 amPNS  Pensacola-SJU San Juan Luis Munoz Marin Intl
13h 12m1 stop Miami
$466American Airlines
Thu, Nov 19 - Thu, Nov 26
Delta Logo
4:10 pm - 11:41 pmSJU  San Juan Luis Munoz Marin Intl-PNS Pensacola
9h 31m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:00 am - 2:55 pmPNS  Pensacola-SJU San Juan Luis Munoz Marin Intl
6h 55m1 stop Atlanta Hartsfield-Jackson
$511Delta
Tue, Dec 1 - Thu, Dec 31
United Airlines Logo
2:54 pm - 12:54 pmMBJ  Montego Bay Sangster Intl-PNS Pensacola
23h 00m1 stop Chicago O'Hare Intl
United Airlines Logo
3:05 pm - 2:39 pmPNS  Pensacola-MBJ Montego Bay Sangster Intl
22h 34m1 stop Houston George Bush Intcntl
$575United Airlines
Thu, Oct 22 - Thu, Oct 29
Delta Logo
9:15 am - 11:30 pmKIN  Kingston Norman Manley-PNS Pensacola
14h 15m1 stop Atlanta Hartsfield-Jackson
Delta Logo
11:58 am - 8:15 pmPNS  Pensacola-KIN Kingston Norman Manley
8h 17m1 stop Atlanta Hartsfield-Jackson
$676Delta
Fri, Nov 13 - Sun, Nov 22
United Airlines Logo
5:50 pm - 1:26 pmSJU  San Juan Luis Munoz Marin Intl-PNS Pensacola
21h 36m3 stops Washington, D.C. Dulles Intl Hartford Bradley Intl Chicago O'Hare Intl
United Airlines Logo
10:30 am - 9:24 pmPNS  Pensacola-SJU San Juan Luis Munoz Marin Intl
8h 54m1 stop Houston George Bush Intcntl
$707United Airlines
Useful Info

Good to know

Low season

August

Cheapest flight

$142
Best time to beat the crowds but there is an average 3% increase in price.
Most popular time to fly and prices are also 4% 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 8538 reviews
8.5Crew
7.8Entertainment
7.2Food
8.1Boarding
7.8Comfort
Airline reviews

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.

6.0 GoodCynthia, Aug 2026
Read more Delta reviews

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.

Third flight in two months where the crew was not there. Comfort seating does not guarantee overhead bin space. Passengers with children are allowed on the plane first - if you are flying to and from Orlando, this means half the plane has boarded before you get on. And somehow all the bin space is taken up. 3 out of 5 flights have had issues with equipment or procedure. Some of these instances caused the flight to be delayed because of a "nuisance" light. One time it was a bag that had been brought on board but did not belong to anyone so we had to return to the gate. Last night we were told the "AC" on the plane doesn't work well and we're 10th for take off- because the crew was late - and that it will get cool when we're in the air. Not sure if this is usual, but I didn't think flight crew could jump seat in first class. Movie and TV selection has not been refreshed for several months- flying one to two round trips each month easily exhausts the list of content.

Definitely a southern flavor. Cordiality was evident even though no drinks or snacks were served.

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.

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.

I don’t know why you’re sending me this. I never booked my flight through kayak. I booked it directly through American Airlines so please do not send me any information or any inquiries unless I book with kayak.

Flight was very delayed. That made me lose the next flight. Rebooked for 23 hours later without any compensation and using a worse airline. I did not expect that from AA. Disappointing.

It was ok because it’s a short flight. The attendants weren’t friendly and didn’t serve any beverages even through they announced that they would. Also. The attendants looked messy, not presentable

The flight had a 6 hours delay. This should not happen to anyone. Airlines should provide an alternative with no additional costs.

Paid for wifi but it didn't work once. Seats were incredibly cramped and passengers sitting in front was reclined the entire time and staff did nothing

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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