$96 Find Cheap Flights from Pensacola to Caribbean

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Pensacola to Caribbean departing on 4/17. 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 Pensacola to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$421
Santo Domingo
Santo Domingo1 stop$342
Montego Bay
Montego Bay1 stop$312
Oranjestad
Oranjestad1 stop$451
Nassau
Nassau1 stop$442
Kingston
Kingston1 stop$526
Simpson Bay
Simpson Bay1 stop$442
George Town
George Town1 stop$475
St. John's
St. John's1 stop$656
Puerto Plata
Puerto Plata1 stop$599
Aguadilla
Aguadilla1 stop$336
Punta Cana
Punta Cana1 stop$421
Santo Domingo
Santo Domingo1 stop$342
Montego Bay
Montego Bay1 stop$312
Oranjestad
Oranjestad1 stop$451
Nassau
Nassau1 stop$442
Kingston
Kingston1 stop$526
Simpson Bay
Simpson Bay1 stop$442
George Town
George Town1 stop$475
St. John's
St. John's1 stop$656
Puerto Plata
Puerto Plata1 stop$599
Aguadilla
Aguadilla1 stop$336

Book Cheap Pensacola to Caribbean Plane Tickets

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

Sun, Apr 12 - Sat, Apr 18
Frontier Logo
3:36 pm - 1:26 pm
PNS
-
SJU
20h 50m
1 stop
Frontier Logo
8:00 am - 9:17 am
SJU
-
PNS
26h 17m
1 stop
$213Frontier
Sun, May 10 - Sun, May 17
Frontier Logo
3:13 pm - 2:01 am
PNS
-
SJU
9h 48m
1 stop
Frontier Logo
6:30 am - 2:15 pm
SJU
-
PNS
8h 45m
1 stop
$214Frontier
Sun, Apr 12 - Sat, Apr 18
Frontier Logo
3:36 pm - 2:01 am
PNS
-
SJU
9h 25m
1 stop
Frontier Logo
8:00 am - 9:17 am
SJU
-
PNS
26h 17m
1 stop
$231Frontier
Thu, Mar 12 - Tue, Mar 17
Spirit Airlines Logo
7:00 am - 1:26 pm
PNS
-
STT
5h 26m
1 stop
Spirit Airlines Logo
2:36 pm - 9:14 pm
STT
-
PNS
7h 38m
1 stop
$262Spirit Airlines
Sun, Apr 19 - Sun, Apr 26
Spirit Airlines Logo
6:00 am - 12:28 pm
PNS
-
STT
5h 28m
1 stop
Spirit Airlines Logo
1:23 pm - 9:15 pm
STT
-
PNS
8h 52m
1 stop
$263Spirit Airlines
Sat, May 2 - Wed, May 6
American Airlines Logo
6:57 pm - 9:13 am
PNS
-
MBJ
14h 16m
1 stop
American Airlines Logo
12:56 pm - 6:37 pm
MBJ
-
PNS
5h 41m
1 stop
$312American Airlines
Sat, May 2 - Wed, May 6
American Airlines Logo
6:57 pm - 11:51 am
PNS
-
MBJ
16h 54m
2 stops
American Airlines Logo
12:56 pm - 6:37 pm
MBJ
-
PNS
5h 41m
1 stop
$317American Airlines
Tue, Apr 14 - Tue, Apr 21
Southwest Logo
3:30 pm - 1:15 pm
PNS
-
NAS
20h 45m
2 stops
Southwest Logo
8:45 am - 7:00 pm
NAS
-
PNS
11h 15m
2 stops
$452Southwest
Mon, May 25 - Fri, May 29
United Airlines Logo
7:00 am - 3:20 pm
PNS
-
AUA
7h 20m
1 stop
United Airlines Logo
3:10 pm - 10:01 pm
AUA
-
PNS
7h 51m
1 stop
$545United Airlines
Thu, Apr 16 - Thu, Apr 23
United Airlines Logo
6:15 am - 12:30 pm
PNS
-
GCM
6h 15m
1 stop
United Airlines Logo
1:35 pm - 8:00 pm
GCM
-
PNS
6h 25m
1 stop
$589United Airlines
Booking Insights

KAYAK's insights & trends for Pensacola to Caribbean flights

Get data-powered insights and trends into flights from Pensacola to Caribbean to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Pensacola to Caribbean?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Pensacola to Caribbean, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Pensacola to Caribbean is April, when tickets cost $396 (return) on average. On the other hand, the most expensive months are December and September, when the average cost of round-trip tickets is $669 and $607 respectively.

How far in advance should I book a flight from Pensacola to Caribbean?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Pensacola to Caribbean, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Pensacola to Caribbean, you should book around 2 weeks before departure, which saves you about 20% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 15 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$96
Best time to beat the crowds but there is an average 1% increase in price.
Most popular time to fly with an average 15% increase in price.
Flight from Pensacola to San Juan

FAQs - booking Caribbean flights

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

    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 Pensacola to Caribbean.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Pensacola to 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 Pensacola to Caribbean?

    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 from Pensacola to Caribbean with an airline and back with another airline.

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

    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 from Pensacola to Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 5 airlines serving from Pensacola to Caribbean

 
Need help choosing which airline to fly with from Pensacola to Caribbean? 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.
8.0
SouthwestOverall score based on 4303 reviews
8.1Boarding
8.6Crew
7.5Entertainment
8.0Comfort
7.0Food
Airline reviews

It was canceled. Supposedly weather. But there was no snow in Baltimore. At least we found out before driving to airport

2.0 MediocreAnonymous, Feb 2026
BWI - PBI
Read more Southwest reviews

It was canceled. Supposedly weather. But there was no snow in Baltimore. At least we found out before driving to airport

An entire day of delays. Cost lots of money. Meals and a hotel.

I appreciate the staff who allowed me to board though I arrived a little late! Regarding the assigned seating, I had booked my flight before this change and wasn't aware of the change at the time, and so I didn't select a seat at booking as I didn't realize it was relevant. Better communication about the change would have been helpful for preparing.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

Flight was on time. Wi-fi was a little spotty/slow. Boarding and exit were efficient.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

If we are going to have to pay for luggage, make it easier to do. Put something on the app during check-in so I don't need to do it at the kiosk. I've done it twice recently and I ended up having to pay at the desk because something went wrong at the kiosk in Tampa.

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

An awesome flight crew. FC seat cushion just doesn’t cut it for a 3+ hour flight.

Delta continues to set the benchmark for traveler-friendly service with minimal disruption and clear communication within the mainland US (coast to coast). I am consistently pleased to be a Delta customer, and this experience once again met my expectations. There was a brief delay departing from MIA due to a technical issue that required the aircraft to return to the gate. However, the situation was handled professionally and transparently. Fortunately, my planned layover allowed ample buffer time, so the adjustment caused no stress. Overall, another smooth and reassuring experience.

Totally worth the miles to upgrade to Delta Comfort. Plenty of legroom.

This was my first time flying Delta ever and I had a great experience!

The flight was great as well as the airline staff

Comfort seating was on the tight side. Maybe it was a smaller plane(?)

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Connection through Atlanta was difficult. Mechanical issue on plane caused a two hour delay. New gate was a mile away.

No WiFi. Comfort plus should have alcohol provided, crew only offered water or tea. Who the heck wants tea?

I have diamond medallion status and usually we are in comfort plus . We were in main this time ( which was fine ) and my husband wanted wine . I have at least 10 vouchers for drinks that are good for this year and next! The attendant would not take the picture of the voucher as proof and never came back to check as She asked me to pull it up on delta Wi-Fi. Instead my husband just used his Amex to buy the wine . Disappointing!!!

There was no WiFi available, there were mechanical problems with the plane and we landed at C 124, then the gate was switched to A 26, then all the way back to C126! For a 75 yo woman traveling alone, this was a difficult journey, indeed!

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

Staff were good. My seat was in need of repair, but for a short flight was not problematic. Usual basic snack and drink setup that you'll find on any US carrier. Over, a decent, basic flight.

Complimentary light meal would be appreciated. But great flight crew service on all legs

Terrible because it was cancelled due to volcanic ash clouds in Guatemala while all other airlines kept flying. Had to pay for a hotel to stay overnight in Houston and try to fly next day.

Plane outlets in my row not working to charge phone. Staff response was, well it should be. Plug into seed for volume not working well. Had to find the sweet spot for plug in or it would shut off and on.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

Very turbulent trip made it pretty bearable, plus the lack of refreshments served and the lack of any air conditioning before takeoff which took an hour or more.

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

They charged a fee for 1st bag checked. Others in same party were free.

For my arriving destination, we were delayed multiple times to the point that we arrived 6 hours after we were originally scheduled. On my flight home, they overbooked and involuntarily removed passengers (including me) from the plane. It was not a good experience.

Boarding is always an ordeal. Less dogs on flights. I am highly allergic to dogs and cats. Why are there so many animals these days?

Horrible. Got delayed many hours because their pilot wasn't trained for night landing at the airport and a rain delay made it a night landing. We have to wait hours for a qualified crew. They give us 12 dollar meal vouchers but most everything in the airport was closed and definitely more expensive than the vouchers.

I am an AA flyer for a very long time... AA has yet to disappoint.

Everything was good. Flight was very full so crew was busy. After we boarded and plane pulled away from the gate, we were delayed about 40 minutes- sitting on the runway - due to weather en route or at the destination. While weather is not the fault of the airline- it’s terrible to sit on a plane and not moving.

The smell from the bathroom kept wafting through the cabin. It made people sick.

Waited for oxygen tanks for 30 minutes after boarding was complete.

Awful. Original flight was delayed 5 hours. Had to to take a connecting flight instead of direct. Had a 4 hour layover. I missed all of my morning meetings getting in 5 hours later than I was supposed to and had to change to take a later flight the next day to get them back in which cia time another $150.

On time on a day with lots of weather cancellations on other flights. Thank you for getting me home during a winter storm!

Don't change gate multiple times make people run across the airport. Announce delays in a timely manner. Have maintenance crew ready. Don't delay and keep passengers on the plane for 3 hrs. on tarmac.

They charged late fees for selecting seats (no $0 options). They also changed my gate within the last half hour and are refusing to reimburse my costs to drive across the country with two small children in a rental car.

I was waiting in line for the restroom onboard, the flight attendant told me to step back two rows and stay on the carpet. She was rude and I expected a tik tok experience with me getting thrown off the plane. She was rude and frankly there was no where else to stand.

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

We flew Spirit because it was cheaper but the seats were so uncomfortable. I don;t need to be fed snacks on a plane but when it's a 3-4 hour trip then at least a drink is nice. The flight attendants had nothing to do the whole flight except for gossip loudly to each other right behind our seats, and they talked so much my husband couldn't even rest! I was fine with no tv or entertainment but the seats were so uncomfortable with no recline, no padding, and I am short but even for me to leg room was tough for a 3-4 hour trip. We probably would fly spirit again if we had to, but it's definitely not our favorite!

There was absolutely nothing good about this fight. They delayed us for over 2 hours to give our plane to a flight going to Tampa. By the time we got to norfolk conditions were too bad to land so they took us to Charlotte to refuel so they could fly back to Fort lauderdale. There was almost no communication from the pilot, no wifi, no chargers, and they wouldn't even give us free water when we were stuck in Charlotte refueling.

The flight itself and the crew were great. Sitting on the tarmac for over an hour until our gate opened up was really frustrating. Missed our scheduled bus and got home two hours later

This flight cancelled. I am in the airport right now and my kids sleep on the floor. We are waiting for information in the line 4 hours and rude woman from spirit airline offers us flight to Austin on 23 February. No water no food offer. The offer to book hotel and they will refund 150$. The nearest hotel 450$ per night. So I got flight to San Antonio 02/22 at 7am. I hate this company, they are rude and no empathy. So many people with kids were there. And I don’t sleep and it is cold here. I don’t have warm clothes for me and my kids. And I don’t have money for transport from San Antonio to my Austin.

It was the most turbulent terrifying flight I’ve ever been on. I will never fly spirit again.

We sat on the tarmac for an hour and a half after landing.

Horrible experience!! In the meantime we were in Philadelphia they didn’t give us some water and the information about the fly on the plane was without empathy!!! Plus the fly started with delay!! So very unhappy moment!!!

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports