$153 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 10/10. 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 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

Wed, Oct 1 - Fri, Oct 17
 Logo
6:44 am - 6:10 pmSJU-PNS
12h 26m1 stop
 Logo
6:25 pm - 2:30 amPNS-SJU
7h 05m1 stop
Wed, Oct 1 - Fri, Oct 17
Spirit Airlines Logo
6:44 am - 6:10 pmSJU-PNS
12h 26m1 stop
Spirit Airlines Logo
6:25 pm - 12:54 amPNS-SJU
29h 29m1 stop
$335Spirit Airlines
Find Deal
Fri, Oct 31 - Mon, Nov 3
American Airlines Logo
5:00 pm - 11:46 pmSJU-PNS
7h 46m1 stop
American Airlines Logo
8:22 am - 5:05 pmPNS-SJU
6h 43m1 stop
$385American Airlines
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Fri, Oct 31 - Mon, Nov 3
American Airlines Logo
7:45 am - 4:33 pmSJU-PNS
9h 48m1 stop
American Airlines Logo
5:24 am - 1:38 pmPNS-SJU
6h 14m1 stop
$394American Airlines
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Fri, Oct 31 - Mon, Nov 3
Southwest Logo
5:40 am - 4:20 pmSJU-PNS
11h 40m2 stops
Southwest Logo
7:20 am - 9:30 pmPNS-SJU
12h 10m2 stops
$407Southwest
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Thu, Oct 2 - Tue, Oct 7
Southwest Logo
10:05 am - 9:55 pmSJU-PNS
12h 50m2 stops
Southwest Logo
7:40 am - 8:45 pmPNS-SJU
12h 05m2 stops
$445Southwest
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Fri, Mar 6 - Tue, Mar 10
United Airlines Logo
3:20 pm - 9:26 pmMBJ-PNS
7h 06m1 stop
United Airlines Logo
7:00 am - 1:00 pmPNS-MBJ
6h 00m1 stop
$445United Airlines
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Thu, Oct 2 - Tue, Oct 7
United Airlines Logo
2:55 pm - 9:59 pmSJU-PNS
8h 04m1 stop
United Airlines Logo
11:00 am - 8:38 pmPNS-SJU
8h 38m1 stop
$475United Airlines
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Fri, Mar 6 - Tue, Mar 10
Delta Logo
12:35 pm - 6:03 pmMBJ-PNS
6h 28m1 stop
Delta Logo
3:35 pm - 11:47 amPNS-MBJ
20h 12m2 stops
$520Delta
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Tue, Mar 10 - Wed, Mar 11
Delta Logo
6:15 am - 2:26 pmSJU-PNS
9h 11m1 stop
Delta Logo
3:35 pm - 9:58 pmPNS-SJU
5h 23m1 stop
$540Delta
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Everything you should know

Cheapest round-trip
$333
Overall average: $380
Multiple Airlines
Wed 10/1Fri 10/17
SJU - PNS • 1 stop
Cheapest one-way
$153
Typical prices: $181-312
Multiple Airlines
Fri 10/10
SJU - PNS • 1 stop
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Pensacola!
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$153
Best time to beat the crowds but there is an average 5% increase in price.
Most popular time to fly with an average 4% increase in price.
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 7954 reviews
8.5Crew
8.2Boarding
7.9Entertainment
7.9Comfort
7.3Food
Airline reviews

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

10.0 ExcellentAnonymous, Sep 2025CLT - BOS
Read more Delta reviews

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

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.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

Crew was good. The reservation got mixed up and they didn't have my TSA number. I am also a Silver Medallion and wasn't able to use Sky Priority.

The airport crew helped a lot, what I didn’t like? We were not informed that we needed to pick our luggage’s, if the crew at the luggage center didn’t tell me I would have been home without my belongings, I was heading out to my next connecting flight while looking for what gate to go to, I asked one of the crews for help, he told me and he also told me to not forget to grab my luggage’s which was chocking, because on my way out the country that wasn’t required, I just hope none of your customers lost their luggage’s because of this.

Delta made it easy, comfortable and timely. The crew was fantastic.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

The flight crew was friendly. I tried to adjust my seat online ahead of time but no option existed without additional fees. My friend asked at the gate about a seat change and was able to make it happen. That was great! The flight crew moved a very tall gentleman and his companion which allowed us to have more space which was nice. Overall, good experience. Appreciated the blanket and pillow.

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

The delayed flight was awful and moving the departure gate twice was annoying

Flight was delayed not sure why no explanation given and no apologies either. Otherwise the flight was fine

Flight from Miami to Lima was very good, like the free WiFi to get movies and TV.

While waiting to claim my checked luggage, I discovered the airline had lost it. After a long wait and inquiries, I discovered it was on another flight. Fortunately, the airline finally sent my luggage home.

Flight delays numerous times. Everytime we would get close to boarding it would be delayed again. Strung along the entire time.

This flight never occurred because AA couldn’t get their act together.

Flight was good & early meaning the gate was changed. With gate change there were no wheelchairs & the gate attendant left without making sure wheelchairs were coming to the changed gate. I had to go to another attendant at another desk to get this done.

The flight crew were friendly and attentive. Food was good and they passed out ice cream and drinks awhile after Lunch was done. The ice cream was a nice treat! I found several movies to watch during the flight. There was many movies and tv shows to choose from. We flew Premium economy and there was enough leg room to be comfortable. The seats were also comfortable. I would fly AA again if the airfare isn’t expensive.

The pilots are always hauling in the sky. No issues with boarding only problem was layover was shortened too much by weather but luckily the next flight was still boarding and did not missit

During service there was a garbage/beverage spill near our seats that never was cleaned up. On a relatively short flight when we’re fortunate enough to actually have in flight movies available, the flight attendants pitching the AADVANTAGE credit card shouldn’t talk for the last 10 minutes of the flight so that we miss the end of the movie.

Everything was fine. I'm average height and I pack light. I'm ready for my Spirit flight.

The flight was canceled leaving us scrambling to find another airline. I should have known not to trust Spirit

Wow truly top notch airline Efficient nice snacks courteous staff Fast boarding !

My experience with Spirit was good, but the experience with Kayak was not. Based on the Spirit agent Kayak added an additional charge after purchasing the tickets. When I buy the tickets I paid the total amount and I only pay once. This time they added an additional charge because based on Spirit they partially charge the tickets and I still needed to pay a second time. This is not good at all and Unprofessional

Spirit gets such a bad rap. I have never had a bad experience with them and the crew is always friendly and funny. This trip I had knee replacement surgery surgery 10 weeks ago. It is still a little rough to get get from point a to point b. And Spirit was on top of it. When there was a seat available the stewardess asked me if I wanted to move to an open seat so I could elevate my leg on the empty seat? 5 stars all around. They helped me on and helped me off the plane. I can’t say enough about the crew!!

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 staff was excellent and I appreciated the zero tolerance for noise making electronics and the only bad part was It took forever for the luggage to get to the baggage claim. It took over 40 minutes. And Norfolk is a small airport so it was probably airport. Staff’s fault.

The staff was very sarcastic, the flight was delayed. There was no wi-fi o any type of entertainment. The plane was dirty and we have to wait a long time for the luggage to come out.

Booked through kayak, everything seemed normal but when it came time to go, my flight ticket didn’t exist, so I had to purchase another set of tickets at the airport the day of the flight, for about double. When I reached kayaks customer service, they claimed no responsibility, and pushed me onto another 3rd party booking service, airfare assist, where I have had no luck getting any kind of help or refund. I’ve used kayak many times, but I’ll never again after I’ve been burned by this.

The air fares are good, Charging me for every single thing 😩

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