$144 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 9/15. 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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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$359
Santo Domingo
Santo Domingo1 stop$345
Montego Bay
Montego Bay2 stops$379
Oranjestad
Oranjestad1 stop$534
Nassau
Nassau1 stop$462
Simpson Bay
Simpson Bay2 stops$400
Kingston
Kingston1 stop$405
George Town
George Town1 stop$498
St. John's
St. John's1 stop$555
Puerto Plata
Puerto Plata1 stop$780
Aguadilla
Aguadilla1 stop$330
Punta Cana
Punta Cana1 stop$359
Santo Domingo
Santo Domingo1 stop$345
Montego Bay
Montego Bay2 stops$379
Oranjestad
Oranjestad1 stop$534
Nassau
Nassau1 stop$462
Simpson Bay
Simpson Bay2 stops$400
Kingston
Kingston1 stop$405
George Town
George Town1 stop$498
St. John's
St. John's1 stop$555
Puerto Plata
Puerto Plata1 stop$780
Aguadilla
Aguadilla1 stop$330

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

Sat, Sep 27 - Sat, Oct 4
Spirit Airlines Logo
4:44 pm - 9:44 amPNS-STT
16h 00m1 stop
Spirit Airlines Logo
10:49 am - 3:39 pmSTT-PNS
5h 50m1 stop
$278Spirit Airlines
Find Deal
Wed, Oct 8 - Mon, Oct 13
Spirit Airlines Logo
4:36 pm - 10:56 amPNS-SJU
17h 20m1 stop
Spirit Airlines Logo
2:49 am - 3:31 pmSJU-PNS
13h 42m2 stops
$285Spirit Airlines
Find Deal
Sat, Oct 25 - Mon, Oct 27
 Logo
4:36 pm - 2:59 pmPNS-SJU
21h 23m2 stops
 Logo
9:00 am - 3:31 pmSJU-PNS
7h 31m1 stop
Sat, Oct 25 - Mon, Oct 27
 Logo
4:36 pm - 10:56 amPNS-SJU
17h 20m1 stop
 Logo
9:00 am - 3:31 pmSJU-PNS
7h 31m1 stop
Wed, Nov 5 - Mon, Nov 10
American Airlines Logo
6:00 am - 5:52 pmPNS-SJU
9h 52m1 stop
American Airlines Logo
6:42 pm - 10:55 pmSJU-PNS
6h 13m1 stop
$365American Airlines
Find Deal
Tue, Nov 4 - Tue, Nov 25
Southwest Logo
7:20 am - 9:30 pmPNS-SJU
12h 10m2 stops
Southwest Logo
6:35 am - 5:35 pmSJU-PNS
13h 00m2 stops
$380Southwest
Find Deal
Sat, Nov 1 - Sun, Nov 9
Southwest Logo
11:45 am - 11:45 pmPNS-SJU
11h 00m2 stops
Southwest Logo
6:40 am - 3:50 pmSJU-PNS
11h 10m2 stops
$425Southwest
Find Deal
Sat, Nov 1 - Sat, Nov 8
American Airlines Logo
2:38 pm - 12:16 pmPNS-MHH
20h 38m2 stops
American Airlines Logo
5:36 pm - 10:22 amMHH-PNS
17h 46m2 stops
$445American Airlines
Find Deal
Sun, Sep 7 - Sat, Sep 13
Delta Logo
6:00 am - 11:37 amPNS-GCM
5h 37m1 stop
Delta Logo
12:52 pm - 7:17 pmGCM-PNS
6h 25m1 stop
$498Delta
Find Deal
Tue, Dec 30 - Thu, Jan 8
Delta Logo
6:00 am - 2:50 pmPNS-STT
6h 50m1 stop
Delta Logo
3:00 pm - 11:07 pmSTT-PNS
10h 07m1 stop
$509Delta
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 October, when tickets cost $326 (return) on average. On the other hand, the most expensive months are December and July, when the average cost of round-trip tickets is $558 and $525 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 28% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

Good to know

Low seasonAugust
Cheapest flight$144
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly with an average 23% 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 4 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 4244 reviews
8.1Boarding
7.5Entertainment
8.0Comfort
8.6Crew
7.0Food
Airline reviews

Southwest's seats are the least comfortable I have ever sat in.

4.0 OkayDavid, Aug 2025DTW - STL
Read more Southwest reviews

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

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.

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.

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.

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.

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.

The plane was broken so we had to change planes.

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

I liked the check in procedure. The luggage charges and overweight cost can be better.

The flight was delayed be over 3 hours. I tried to get a refund for Vivian Kirby and my session kept being stopped. I was NEVER able to finish the prosses...after 2 hours of attempting.

Again, when I use Kayak I expect to pay the total amount and that´s it. Someone added an additional charge few days later after purchasing the tickets.

For the minimalist experience, it is really a great ride-- feels a little like public transport i guess

I didn’t mind being delayed due to weather, but continuing to post (and not update) that we would be delayed until after the flight was already supposed to have taken off was a bit much. In the future, please announce the delay even if the time is still unknown.

This gate agents are always so rude! I stopped flirting with spirit years ago for that reason I thought it would change by now. It’s so tacky they try to treat you like a school child i hate it

The flight and boarding process was smooth. Wifi was unavailable and I prepaid for it. Have requested a refund

Spirit is a very uncomfortable travel experience. It’s cheap but you are squeezed into the seats like canned meat.

Friendly employees, good seat, on time, Great flight. Pilot and attendants greeted passengers as we deplaned. However, I could not ever understand what the flight attendant was saying on the mic. It was too fast, and too loud.

The flight was delayed four and half hours for paperwork on a maintenance issue. Very frustrating.

Everything you need to know for your flight to Caribbean

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