$166 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 7/8. 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

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Best Caribbean Flight Deals from Pensacola

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$381
Santo Domingo
Santo Domingo1 stop$388
Montego Bay
Montego Bay1 stop$375
Oranjestad
Oranjestad1 stop$463
Nassau
Nassau1 stop$471
Kingston
Kingston1 stop$415
Simpson Bay
Simpson Bay2 stops$457
George Town
George Town1 stop$496
St. John's
St. John's1 stop$599
Puerto Plata
Puerto Plata2 stops$519
Aguadilla
Aguadilla1 stop$566
Punta Cana
Punta Cana1 stop$381
Santo Domingo
Santo Domingo1 stop$388
Montego Bay
Montego Bay1 stop$375
Oranjestad
Oranjestad1 stop$463
Nassau
Nassau1 stop$471
Kingston
Kingston1 stop$415
Simpson Bay
Simpson Bay2 stops$457
George Town
George Town1 stop$496
St. John's
St. John's1 stop$599
Puerto Plata
Puerto Plata2 stops$519
Aguadilla
Aguadilla1 stop$566

Cheap Flights from Pensacola to Caribbean

 
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

Fri, Jul 25 - Wed, Jul 30
Spirit Airlines Logo
6:00 am - 3:10 pmPNS-STT
8h 10m1 stop
Spirit Airlines Logo
1:25 pm - 10:41 pmSTT-PNS
10h 16m1 stop
$286Spirit Airlines
Find Deal
Fri, Aug 15 - Fri, Aug 22
Spirit Airlines Logo
4:52 pm - 3:10 pmPNS-SJU
21h 18m2 stops
Spirit Airlines Logo
5:42 pm - 8:08 amSJU-PNS
15h 26m1 stop
$292Spirit Airlines
Find Deal
Mon, Aug 4 - Fri, Aug 8
Spirit Airlines Logo
6:00 am - 12:02 pmPNS-SJU
5h 02m1 stop
Spirit Airlines Logo
1:37 am - 10:57 amSJU-PNS
10h 20m1 stop
$297Spirit Airlines
Find Deal
Mon, Aug 11 - Thu, Aug 21
Delta Logo
6:00 am - 1:30 pmPNS-SJU
6h 30m1 stop
Delta Logo
5:46 pm - 11:12 pmSJU-PNS
6h 26m1 stop
$345Delta
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Wed, Nov 5 - Mon, Nov 10
Southwest Logo
7:20 am - 6:35 pmPNS-SJU
9h 15m2 stops
Southwest Logo
5:40 am - 3:50 pmSJU-PNS
12h 10m2 stops
$370Southwest
Find Deal
Tue, Oct 21 - Wed, Oct 29
Delta Logo
6:00 am - 11:48 amPNS-MBJ
5h 48m1 stop
Delta Logo
1:13 pm - 9:48 pmMBJ-PNS
8h 35m1 stop
$453Delta
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Wed, Jul 30 - Wed, Aug 6
United Airlines Logo
7:00 am - 3:20 pmPNS-AUA
7h 20m1 stop
United Airlines Logo
3:10 pm - 10:14 pmAUA-PNS
8h 04m1 stop
$469United Airlines
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Mon, Aug 18 - Fri, Aug 22
American Airlines Logo
6:10 am - 12:05 pmPNS-NAS
4h 55m1 stop
American Airlines Logo
7:50 am - 5:11 pmNAS-PNS
10h 21m1 stop
$471American Airlines
Find Deal
Mon, Dec 8 - Fri, Dec 12
American Airlines Logo
7:05 pm - 12:00 pmPNS-PUJ
14h 55m2 stops
American Airlines Logo
6:20 pm - 10:07 amPUJ-PNS
17h 47m1 stop
$475American Airlines
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Thu, Aug 14 - Sat, Aug 23
United Airlines Logo
11:05 am - 3:20 pmPNS-AUA
27h 15m1 stop
United Airlines Logo
3:00 pm - 4:13 pmAUA-PNS
26h 13m1 stop
$543United Airlines
Find Deal
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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 September, when tickets cost $294 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $558 and $490 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. For the absolute cheapest price, our data suggests you should book 19 weeks before departure.


Good to know

Low seasonSeptember
High seasonDecember
Cheapest flight$166
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 24% 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.

  • 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 4270 reviews
8.0Comfort
8.2Boarding
7.6Entertainment
8.6Crew
7.0Food
Airline reviews

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

4.0 OkayTraci, Jun 2025OAK - SEA
Read more Southwest reviews

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

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.

Crew was great flight was great baggage claim was a failure. It took over 1 hour for bags to arrive. Poor communication poor effort when I spoke to the supervisor about the delay

Planes are aged. The wifi is unreliable and on many fights, no-existent. The flight attendants were very good.

I had a wonderful flight, but the only thing that annoyed me was how crowded TSA was. I still believe airports and all planes work together to bunch everyone together to drive up cost.

Easy to book and to get check in and get on and off.

Everything worked well. Crew was as entertaining as is possible on a plane flight. Southwest still has good legroom:

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.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

Friendly flight attendants, smooth 8-9 hours flight. Economy seats are small and uncomfortable as usual.

The young man who was our flight attendant in first class was lazy and did not do his job well at all. Never offered drinks upon boarding - actually I take that back... said "are you okay with water" as if I do not want to get you anything else, only passed the snacks around once, got my drink order wrong and then never offered a second round of drinks. He was the worst I have ever seen on Delta and we fly a lot.

Flight left early and arrived early. the whole trip was excellent.

Newer plane, relatively easy boarding, not a full flight and was told that we could not be moved up because of weight and balance issues. Otherwise, a very good experience.

We love united ! We would like to acknowledge Aimee in the lounge near gate 130

Boarded plane and then delayed 1.5 hours while on the plane

Although the flight was delayed the crew and the flight itself were very good. Couldn't fault anything and after the disappointment of being abandoned in the US by BA it was a welcome relief to travel with United

Survey sent before we actually left. Delay after delay. Now a crew problem.

I love flying with United. Unfortunately, I flew on an older plane with minimal upgraded technology (no Bluetooth functionality or handy charging ports). Otherwise, the flight was great and even arrived early.

They changed my seats after I checked in and I was stressed from the time I saw that information until just before boarding, when the gate attendant fixed it, but it shouldn't have happened. And if it couldn't be prevented, then the people on the phone I spoke with should have done something to help, which they did not, nor did they offer me compensation, just meaningless apologies.

online check in was not available so i had to get to airport extra early. The flight was delayed and my luggage was lost. I had an argument with the person behind me who wanted to keep her bag on the floor and not allow my seat to recline on a 9hr plus flight. So overall, lots and lots of areas for improvement.

My flight was delayed a very short period of time but they did not hold my connecting flight to San Diego, also through United. So they closed the doors before we got off our plane. They would only have to help the door open for another five to ten minutes. So I missed a court deadline for a manditory mediation settlement conference for my client. I had to get an associate to be there in person and be on the phone with him relaying what he needs to do the entire time. The court was very upset with me and so was my client. United cannot be trusted.

Multiple delays and not straight answer from the United team

Food and flight attendents with positive dispositions and friendly behavior, more professional attitudes

Food was terrible, all served at once, poor quality . Wine and bread offered only once.

It was one of my worst flight ever. First they were changing the gate for at least 4 times, changing from gate D7 to D12 to D44. Considering the size of the Miami Airport, we are talking about long distance and the train at the airport was not working. Then the flight was delayed around one hour. Then finally we boarded into the plane and when everybody was seated, there was an announcement that there is an issue with one of the tire of the plane, so we all had to get out of the plane with our belongings, to replace the tire. So we had around 2.5-hour delay

No entertainment yatem in flight at seat 51H. Would not shut down either leaving a self moving and openin and changing menus with changes in colors,images brightness levels sort of the type when you get sleep deprivation and image overload when being tortured during an interrogation. 8 hours worth of it. Unable to place backpack underneath seat on that chair. One female stewardess was excellent as she gave up her carryon's space for my backpack but the rest of the iberia crew were very sharp an chtting during the whole flight. The plane did not have hot water so nobody had coffee nor tea. The plane was not up to par to be flying.

I was late from Jacksonville, FL but the limited interaction I had with the Philly crew was great.

The delays and cancellations kept me stuck in Miami for an additional 24 hours, and the whole thing seemed extremely disorganized

The chicken adobo was a little too spicy but good otherwise. My personal opinion. Movie selection could be improved, too many horror movies. Could add a few more chick flicks! The flight was bumpy at times. We arrived a little early too! Flight attendants friendly.

really bad they refused to check in luggages that I had purchased, even showing them the transaction receipt from british airways app the staff in miami was MEDIOCRE

The flight to Tokyo AA61 took off about two hours late, but then had to turn back. By that time the crew had to be replaced. Then they kept promising to take off in an hour, then in 3, then switch to the next day.

Uncomfortable seats and flight attendant was rude as she insisted on waking up my husband to ask him if he wanted a drink. When he said that he was sleeping, she replied “without an attitude “. He was seated at 8c

No food/snack served during the flight. Crew wasn’t interested at all. Flew American First but flying low cost with Ryanair is even better

Flight was on time and was not crowded. Flight attendants were very understanding of my wife’s back problems.

The flight was canceled and was bounced around time wise with my elderly parents. That being said the gentleman in custody service was amazingly helpful

It amaze me how other airlines leave on time and Spirit always have some type of delay. I’ve flown with Spirit many times, but it reached a point I’d rather pay twice the amount and not deal with this corporation they never do nothing to reimburse people for their time or headaches.

Easy boarding and good flight. Need to work on the beverage and snack situation

Spirit charges you to breathe in their presence. They have you pick and buy your seat in advance and then I got bumped from the seat I paid for because THEY overbooked the flight by a dozen people. they do not provide any entertainment, they do not provide even a small cup of water - you have to pay for everything. I will never fly Spirit again.

While on the flight we had a delay and had to sit on the plane while maintenance fixed it. It’s ended up taking an hour and a half longer to leave than expected. I had an unruly passenger sitting behind me that vaped during the flight and was rude and loud for the majority of the flight.

I feel like Spirit Airlines is a trash airline. They canceled my flight and could not Even help me book a new flight for the same date

The seats! Do not nickel and dime! Be transparent about all your fees!

Not great. Overpriced and charge you for everything. All but breathing was an extra charge. Never again! Oh if you didn’t check a carry on, you couldn’t use the overhead bins. Crew said those spaces were not available. Personal items MUST go on floor. Yet, there was only 50% capacity at best! So ridiculous.

why's KAYAK involved? why'd Spirit charge me $19.72 on Apr 28 and $4.49 on May 1 ? And ironically my credit card had to be cancelled after trip due to a bogus charge, wonder if using it on the plane enabled a scammer to get it.

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