$150 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 12/5. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

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$524
Santo Domingo
Santo Domingo1 stop$377
Montego Bay
Montego Bay1 stop$479
Oranjestad
Oranjestad1 stop$560
Nassau
Nassau1 stop$472
Kingston
Kingston1 stop$462
George Town
George Town1 stop$347
St. John's
St. John's2 stops$590
Puerto Plata
Puerto Plata1 stop$518
Aguadilla
Aguadilla2 stops$714
Punta Cana
Punta Cana1 stop$524
Santo Domingo
Santo Domingo1 stop$377
Montego Bay
Montego Bay1 stop$479
Oranjestad
Oranjestad1 stop$560
Nassau
Nassau1 stop$472
Kingston
Kingston1 stop$462
George Town
George Town1 stop$347
St. John's
St. John's2 stops$590
Puerto Plata
Puerto Plata1 stop$518
Aguadilla
Aguadilla2 stops$714

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

Wed, Dec 3 - Mon, Dec 8
Spirit Airlines Logo
8:16 pm - 12:32 pmPNS-SJU
14h 16m1 stop
Spirit Airlines Logo
6:14 pm - 1:13 pmSJU-PNS
20h 59m1 stop
$273Spirit Airlines
Find Deal
Wed, Dec 3 - Mon, Dec 8
Spirit Airlines Logo
8:16 pm - 12:32 pmPNS-SJU
14h 16m1 stop
Spirit Airlines Logo
6:14 pm - 1:13 pmSJU-PNS
20h 59m1 stop
$274Spirit Airlines
Find Deal
Thu, Dec 4 - Mon, Dec 8
Spirit Airlines Logo
7:09 pm - 12:45 amPNS-SJU
27h 36m1 stop
Spirit Airlines Logo
6:14 pm - 1:13 pmSJU-PNS
20h 59m1 stop
$279Spirit Airlines
Find Deal
Sat, Dec 6 - Mon, Dec 8
Spirit Airlines Logo
7:09 pm - 12:32 pmPNS-SJU
15h 23m1 stop
Spirit Airlines Logo
6:14 pm - 1:13 pmSJU-PNS
20h 59m1 stop
$296Spirit Airlines
Find Deal
Fri, Dec 5 - Mon, Dec 8
Multiple Airlines Logo
3:35 pm - 9:55 amPNS-SJU
16h 20m2 stops
Multiple Airlines Logo
6:14 pm - 1:13 pmSJU-PNS
20h 59m1 stop
$311Multiple Airlines
Find Deal
Sun, Jan 4 - Thu, Jan 15
Multiple Airlines Logo
7:09 pm - 3:23 pmPNS-SDQ
18h 14m1 stop
Multiple Airlines Logo
4:45 pm - 3:08 pmSDQ-PNS
24h 23m2 stops
$419Multiple Airlines
Find Deal
Sat, Jan 31 - Sat, Feb 7
American Airlines Logo
5:24 pm - 1:45 pmPNS-MHH
19h 21m2 stops
American Airlines Logo
11:57 am - 6:34 pmMHH-PNS
7h 37m1 stop
$432American Airlines
Find Deal
Sat, Jan 31 - Sat, Feb 7
American Airlines Logo
5:24 pm - 12:47 pmPNS-MHH
18h 23m1 stop
American Airlines Logo
2:26 pm - 6:34 pmMHH-PNS
5h 08m1 stop
$437American Airlines
Find Deal
Fri, Feb 20 - Wed, Feb 25
Delta Logo
6:00 am - 4:45 pmPNS-NAS
9h 45m1 stop
Delta Logo
2:55 pm - 11:13 pmNAS-PNS
9h 18m1 stop
$472Delta
Find Deal
Tue, Mar 31 - Wed, Apr 1
Delta Logo
7:00 am - 1:30 pmPNS-NAS
5h 30m1 stop
Delta Logo
2:55 pm - 8:42 pmNAS-PNS
6h 47m1 stop
$475Delta
Find Deal
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 February, when tickets cost $390 (return) on average. On the other hand, the most expensive months are November and September, when the average cost of round-trip tickets is $610 and $578 respectively.

What’s the cheapest day of the week to fly from Pensacola to Caribbean?

The average price of all round-trip flights from Pensacola to Caribbean clicked on KAYAK for each day over the last 12 months.

For Pensacola to Caribbean, Wednesday is the cheapest day to fly on average and Friday is the most expensive. Flying from Caribbean back to Pensacola, the best deals are generally found on Saturday, with Monday being the most expensive.

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 25% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 26 weeks before departure.

Good to know

Low seasonAugust
Cheapest flight$150
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 4% increase in price.
Flight from Pensacola to Saint Thomas Island

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.

  • What is the cheapest time of day to fly to Caribbean?

    The cheapest time of day to fly to Caribbean is generally at night, when round-trip flights cost $306 on average. Morning departures are around 23% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $456.

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 4235 reviews
7.5Entertainment
7.0Food
8.0Comfort
8.6Crew
8.1Boarding
Airline reviews

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

10.0 ExcellentMichael, Nov 2025LAX - BWI
Read more Southwest reviews

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

Everything a cheap airline should be at normal airline rates.

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.

WiFi on the flight was not working. Thus, entertainment options were limited.

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

Non stop on long haul is the way to go. Great experience

The boarding process needs to be refined. Sometimes the gate crew call out the boarding zone, and then flip to the monitor to show which zones are boarding. So unless everyone is gathered around to see the monitor there is usually confusion as wi which zones are boarding.

Passengers need to check in big baggage instead of bringing on the plane. That cause inconvenience for everyone. Otherwise flight was good.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

Quick check in. Everything went smooth. I don't know what can be done about airline food.

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

Flight was an hour late, who knows why. It was OK, nothing outstanding.

Excellent check-in. Crew was good. Excellent communication from flight deck.

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Older aircraft, no meal, only food was for purchase. Not impressed United.

United needs to step up their game. Delayed flight leaving Seattle, San Francisco. Older aircraft, not very comfortable.

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

Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.

Other than a way way too cold cabinets for the entire flight, all was great

One bag is incorrect and not acceptable for an international flight. The food was not just good. I won't fly with them again.

Not pleasant trip cross country when the entertainment and WiFi system not working. No entertainment for entirety of route. Staff was rather nonchalant in that they dismissed the problem due to age of plane. It would have been nice to know this up front so I could have come prepared to read or download movies before boarding Coincidentally or not, there was a similar issue with the entertainment system on my previous flight I took on my fist leg of the trip. There are no seat TVs, so you must rely on the app when it works. United can do better. Also, what use it it to pay for boarding group 2 when half of the passengers are in the same line as you?

Plane boarded early a quickly, was mostly full. We left close to on time. And landed early.

My experience on this United Airlines flight was highly uncomfortable, primarily due to two issues: Cabin Temperature: The temperature on the Boeing 737 MAX 8 was unacceptably high, feeling consistently around 80 degrees throughout the flight. This made sleeping impossible and significantly detracted from the experience. Seating Arrangement: Being stuck in a middle seat for a six-and-a-half-hour overnight flight compounded the discomfort. Moving forward, I will always purchase a seat assignment to avoid this situation.

The worst landing I have ever had on a domestic flight. Thought we would lose the landing gear on landing in Newark. Then we spent 40 minutes trying to position the plane in the right place to be able to get the jet way to the plane. The plane arrived stopped. The announcer was that we were there. Everybody got up, then we were told to sit back down because they had to have us towed to a different position. We got towed and then everyone stood up and they told us we were in the wrong position to sit back down again, and then we got towed to a different position This did not happen immediately. It was 30 minutes while we wandered around a small section of the tarmac in Newark close to the gate, but apparently not close enough. Horrifying experience The CAB should be investigating that flight

I have a gluten allergy so didn't have any food

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

My flight was delayed for 17hs because the pilot forgot his passport!!! What a joke. AA used to be a great airline, now I have to think twice before flying with them again.

We had 3 flights. 1 & 2 were on the same plane but we had to de-board just to re-board 30 mins later. That may have been due to a crew change though. Our 3rd flight had a couple “maintenance” issues that held us up. They were quickly resolved but it took forever for someone to bring the paperwork needed so we could leave. Apparently there was a computer glitch so a driver had to bring a physical copy. It delayed us about 1 1/2 hrs. The flights themselves were smooth & no problems. For boarding, I don’t know why they don’t start with the back of the plane & move forward. It would eliminate the back up from people trying to find their seats & put their bags in the overhead bins. Unless you’re on an overseas flight, there is no food, you get a beverage & either a small bag of pretzels or a biscuit cookie. Take your own food or snacks of you want something more.

Lost bag and 2 days no word leaving for cruise no clothes or stuff

We will be writing a long, detailed letter to corporate about our awful experience with American airlines.

Internet was a bit expensive and did not work ask that week otherwise a good flight

Food was ok, but not as good as I have had before on AA.

Pretty good. The food was just mediocre, the boarding and crew were good.

It was very difficult to stretch my knee out and I am very short. I also had a torn tendon in my knee which made it extra uncomfortable anyways. My husband is 6'2" and I can't imagine him flying in that plane.

To be Honest they canceled my flight and didn't have other options. Until 4 says later and I have a 2yr old very disappointed.

Flight was delayed. (To be excepted because of TSA shortage) I’m super short and still struggled with leg room, there was no screen, and the seat didn’t recline at all.

Boarding was easy. I loved that they sat our family together even though we didn't pay for specific seats. I thought $5+ was a lot for pretzels and wish they had a small free snack.

Prices for bags are extremely expensive and if you go higher on weight, the charge is ridiculous.

Excellent experience when I am looking for a budget airline where the main expectation is getting me from point A to point B with no frills.

Very sad about what Spirit has become, because the flights I had with them were delayed between an hour and a half and two, terrible service

Terrible seat, no in flight entertainment. No complimentary food or drinks. Seats really hurt my back after flying spirit for the day.

Plastic seat really hurt my back. Cannot even recline on the flight. Very hard to sleep on the plane due to terrible seats . Food and drinks were expensive and not very good. There were like 2 open exit rows behind me. My isle was full so I asked flight attendants if I could sit there. They told me it was a safety issue??? I think it more unsafe to have no one sitting there. In case of emergency, you’d want someone there to help.

Had to deplane for undisclosed mechanical issue. Landed in Chicago 3 hours late. Food voucher at FLL came just as we were recording. Crew and agents were troopers--better than Spirit last night.

It was delayed, and the airport had cockroaches jumping on our bags. The flight crew was great, the seats were pretty comfortable.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports