$175 Find Cheap Flights from Caribbean to Pensacola

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Pensacola departing on 9/25. 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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Flight Deals

Cheap Flights from Caribbean to Pensacola

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

Fri, Jul 31 - Mon, Aug 3
Multiple Airlines Logo
6:00 am - 6:52 pm
SJU
-
PNS
13h 52m
1 stop
Multiple Airlines Logo
1:17 pm - 12:41 am
PNS
-
SJU
10h 24m
1 stop
$353Multiple Airlines
Thu, Oct 1 - Mon, Oct 5
Multiple Airlines Logo
4:39 pm - 8:18 am
SJU
-
PNS
16h 39m
1 stop
Multiple Airlines Logo
1:25 pm - 11:57 pm
PNS
-
SJU
9h 32m
1 stop
$366Multiple Airlines
Wed, Nov 4 - Sun, Nov 8
Frontier Logo
3:55 am - 2:18 pm
SJU
-
PNS
12h 23m
1 stop
Frontier Logo
3:15 pm - 2:50 am
PNS
-
SJU
9h 35m
1 stop
$373Frontier
Wed, Nov 4 - Sun, Nov 8
Frontier Logo
3:55 am - 2:18 pm
SJU
-
PNS
12h 23m
1 stop
Frontier Logo
3:15 pm - 2:50 am
PNS
-
SJU
9h 35m
1 stop
$374Frontier
Sat, Jul 18 - Tue, Jul 21
American Airlines Logo
5:14 pm - 10:53 am
MBJ
-
PNS
17h 39m
2 stops
American Airlines Logo
4:42 pm - 11:47 am
PNS
-
MBJ
19h 05m
2 stops
$504American Airlines
Sat, Jul 18 - Tue, Jul 21
Delta Logo
2:31 pm - 10:42 pm
MBJ
-
PNS
8h 11m
1 stop
Delta Logo
7:00 am - 3:34 pm
PNS
-
MBJ
8h 34m
1 stop
$512Delta
Sat, Jul 18 - Tue, Jul 21
American Airlines Logo
5:14 pm - 10:53 am
MBJ
-
PNS
17h 39m
2 stops
American Airlines Logo
7:10 am - 1:31 pm
PNS
-
MBJ
6h 21m
1 stop
$515American Airlines
Sun, Jul 5 - Sun, Jul 12
United Airlines Logo
2:40 pm - 10:01 pm
MBJ
-
PNS
7h 21m
1 stop
United Airlines Logo
7:00 am - 3:26 pm
PNS
-
MBJ
8h 26m
1 stop
$532United Airlines
Sun, Jul 5 - Sun, Jul 12
United Airlines Logo
2:40 pm - 10:01 pm
MBJ
-
PNS
7h 21m
1 stop
United Airlines Logo
7:00 am - 3:26 pm
PNS
-
MBJ
8h 26m
1 stop
$535United Airlines
Thu, Oct 1 - Sat, Oct 31
Delta Logo
9:00 am - 2:59 pm
KIN
-
PNS
5h 59m
1 stop
Delta Logo
9:25 am - 7:30 pm
PNS
-
KIN
10h 05m
1 stop
$660Delta
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$175
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly and prices are also 3% 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.
7.9
DeltaOverall score based on 8396 reviews
8.5Crew
7.8Comfort
7.2Food
8.1Boarding
7.8Entertainment
Airline reviews

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

8.0 ExcellentAnonymous, Jun 2026
ATL - GNV
Read more Delta reviews

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

No service flight that took 5 hrs and a stop at an unscheduled airport. Crew and pilots did their jobs

I continue to be satisfied with Delta’s excellent service out of LGA. The digit id works well and gets me through security in no time. Whenever possible, I choose Delta.

Was revoked with Jet Blue due to delay from Kenya Air

Everything could and should be better. We are paying for, it's not a favor, it's a service and should involve quality, responsibility and respect.

Overall Good! The weather delayed our takeoff from Atlanta and our arrival in Miami! If Mother Nature can mess up a flight she will do it every time!

N Everything was perfect from boarding to assistance to baggage in Tampa

I lost my plane and spend 5 hours at the airport arriving at Buffalo at 1 am taxis are very expensive at that time.

Snacks and included beverages were appreciated. Boarding went smoothly. Plenty of overhead bin space. Seats get very uncomfortable after a couple of hours. After waiting 10 painful minutes for my walker, a very nice Delta guest agent pushed me in a wheelchair to the gate. It was finally delivered to me after another 15 minutes . Our checked bag was on the carousel long b4 I was able to retrieve it. Fortunately it was still there but somewhere along the way the straps we used to secure it were removed and and were not reattached. Wish I had made note of the agents name.

The whole experience was excellent. As it most often is with Delta

Referencing ANA'S service to Japan and the return on UA, the pillow was awful, the crew was not very attentive, and the food was bizarre and tasted okay. Whoever's idea it was to make vegetable tempera in a steam capsule should probably revisit that. Since it was the vegetarian option, it was my only choice.

Crew was great! Good meals. Had room to stretch out

Our flight was delayed 2.5 hours from Lisbon to DC so we missed our connection to Seattle that would have arrived at about 9 PM. The agent initially said we had to stay overnight in DC and there were no other options to put us on to get us to Seattle. While on board I discovered a flight via American he could have put us in but by the time we arrived in DC that was sold out. We were then put on a flight to San Francisco that was also delayed then arrived in San Francisco and our flight to Seattle was also delayed so we ended up not arriving until 2:15 am. Our son could not pick us up so we ended up having to pay over $100 to Uber home. This is the second trip with United that the flight has been delayed causing us to miss an evening in Las Vegas and we were given nothing.

Boarding was smooth and efficient. The only food was some pretzels, but it was a short flight. Not much to order if you were hungry.

Crew were welcoming, accommodating and they worked hard to find places for all carry on.

Packed flight, which makes it tough on crew and boarding staff (and the customers of course). But this was great boarding, clear instructions, etc. Traveling on the weekends are always fraught with danger as you have families and less frequent flyers thus more confusion. But this flight went as planned.

Destroyed my suitcase. Tired of talking about it. Cancelling my unite mileage plus account.

Read the fine print. This was my flight home. I booked my flight for the quickest way home. Had a carry-on and a personal item. Same as my outbound flight. Apparently I needed to pre-pay extra for my carry-on. When I checked in, I was told that I had to check it. I said I’ll pay for it, and was told that this wasn’t an option anymore. They said I still had to pay $50 to check my carry-on. I told them I’ll pay whatever to just carry it in as intended. I was not allowed, so eventually I paid $50 to check my carry-on under a plane that was half full, with overhead compartments that were even less full. My white carry-on suitcase was practically destroyed getting from Idaho falls to Denver to Orange County. The low price air fair was a bait and switch. Got me to the gate, made me pay extra, then didn’t even allow me to pay for a carry on. Not to mention that I paid the $8 for WiFi that didn’t work. All to get my suitcase destroyed. I don’t think I’m going to even keep my Untied mileage plus membership and card. Apparently, membership does not have its privileges for this one.

The flight was delayed, they didn’t even have water for the toilets or for drinks

Even through the flight was delayed due to storms near IAH The flight was great! The crew was so hospitable and professional

Little time between flight from Dallas to flight to Gainesville. We chose this one, 43 minutes between, because the price for a connection with at least an hour between, was so much higher. Had to ask passengers on the Dallas flight to please allow us to deplane ahead of them. The economy passengers allowed this. We had to walk very fast to the next gate, 35 gates away. Thankfully all in the same terminal. Getting to the small Gainesville plane was a little confusing as you enter an area that is boarding many small planes at the same time. We stood in the wrong line for about 15 seconds before realizing it was not our Gainesville flight. Since I had boarded at this gate in the past, I knew to check the signs carefully so we weren’t lost. The first class seat experience was wonderful. I really enjoyed the upgrade. We were offered an alcohol drink as soon as we sat down. I got something different but it was a great gesture especially since we really had to hurry to make the flight. We had packed expecting we might miss this connection, but made it. Our luggage didn’t miss the flight. American Airlines delivered our bags to our home the next day. That was very convenient!

The plane was large, not full, but one with 3 seats near each window and 4 in a row in the middle of the plane. There were screens on the backs of the seats for entertainment and information. To use the entertainment one needs ear plugs that physically plug into the screen. My husband had some he let me use as I only had blue tooth type. The stewards gave out some headphones to some, but when my neighbor asked for some, the steward said no. So maybe they ran out? Idk. Bring the old kind of headphones or earbuds if you want entertainment in case this is the type of entertainment offered. We had a very tight connection in Miami. 43 minutes. The other economy passengers allowed us to get ahead of them because I asked if we could since we were near boarding time for our next flight and 35 gates away. They were extremely kind. First class wasn’t going to allow us to pass through. We did make the next flight. Our baggage didn’t, but they were delivered to us the next day and we were prepared with essentials in our carry on packs.

We departed early and arrived early The plane was clean and the crew was incredibly efficient another positive experience with American airlines for me.

Flight left on time. Captain provided relevant announcements. We had to wait 45 minutes to desembark due to the ramp closed because of lightening.

So overall the flight was just average and nothing special. They overbooked some of the flights and they ended up running out of overhead storage space so we had to check our carry-ons which wasn't terrible but we were inconvenienced because of the second connecting flight with a long layover we couldn't get our bags until the final destination. Most of the flight attendants were pretty good and overall the meals were not that great because the chicken was dry and overcooked. They also didn't provide butter or any kind of spread with the bread which is cheap and concerning. The American airlines staff at the check-in counter was kind of unprofessional because this lady just started singing in the middle of checking us in and that's weird. The worst part of the flights was the terrible conditions of the bathrooms which were unclean and did not have toilet paper or toilet tissue available which is kind of insane for a 14-hour and 8 and 1/2 hour flight.

Everything was fine except the end of the flight. We spent more than an hour circling around Miami due to weather conditions. That was not good.

They lost my bag. ... And I asked them 3 times to 3 different people if my checked bag will maKe it all the way - they all confirmed and at the end it was left at the connection... Bravo

Cancelled BOYH legs of our flight home 30 min before initial boarding

Poor... food was horrible, boarding very slow, service on board mediocre

Flight left early and arrived 30 MINUTES early at the destination. Smooth trip.

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