$139 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 11/24. 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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Everything you should know

Cheapest round-trip
$330
Overall average: $452
Spirit Airlines
Mon 12/29Tue 1/6
SJU - PNS • 1 stop
Cheapest one-way
$139
Typical prices: $222-$283
Frontier
Mon 11/24
SJU - PNS • 2 stops
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Flight Deals
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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

Mon, Dec 29 - Tue, Jan 6
Spirit Airlines Logo
4:10 am - 1:03 pmSJU-PNS
10h 53m1 stop
Spirit Airlines Logo
1:58 pm - 11:58 amPNS-SJU
20h 00m1 stop
$330Spirit Airlines
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Mon, Dec 29 - Mon, Jan 5
Spirit Airlines Logo
4:10 am - 1:03 pmSJU-PNS
10h 53m1 stop
Spirit Airlines Logo
7:09 pm - 11:58 amPNS-SJU
14h 49m1 stop
$341Spirit Airlines
Find Deal
Tue, Mar 10 - Tue, Mar 17
Delta Logo
6:15 am - 2:26 pmSJU-PNS
9h 11m1 stop
Delta Logo
1:59 pm - 9:58 pmPNS-SJU
6h 59m1 stop
$345Delta
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Wed, Nov 26 - Sun, Nov 30
Multiple Airlines Logo
6:01 am - 12:49 pmSJU-PNS
32h 48m2 stops
Multiple Airlines Logo
8:16 pm - 11:44 pmPNS-SJU
25h 28m1 stop
$352Multiple Airlines
Find Deal
Thu, Feb 19 - Thu, Feb 26
American Airlines Logo
10:57 am - 6:10 pmSJU-PNS
9h 13m2 stops
American Airlines Logo
8:29 am - 9:35 pmPNS-SJU
11h 06m1 stop
$365American Airlines
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Fri, Mar 6 - Tue, Mar 10
United Airlines Logo
3:20 pm - 9:30 pmMBJ-PNS
7h 10m1 stop
United Airlines Logo
7:00 am - 1:05 pmPNS-MBJ
6h 05m1 stop
$445United Airlines
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Fri, Mar 6 - Tue, Mar 10
United Airlines Logo
2:48 pm - 8:30 pmMBJ-PNS
30h 42m1 stop
United Airlines Logo
10:30 am - 1:05 pmPNS-MBJ
26h 35m1 stop
$461United Airlines
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Mon, Dec 22 - Sun, Dec 28
Multiple Airlines Logo
1:19 pm - 4:04 pmKIN-PNS
51h 45m2 stops
Multiple Airlines Logo
7:09 pm - 12:14 pmPNS-KIN
16h 05m1 stop
$497Multiple Airlines
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Wed, Dec 17 - Mon, Jan 12
American Airlines Logo
1:42 pm - 11:49 pmKIN-PNS
11h 07m1 stop
American Airlines Logo
6:05 am - 12:47 pmPNS-KIN
5h 42m1 stop
$575American Airlines
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Fri, Mar 6 - Tue, Mar 10
Delta Logo
9:00 am - 6:21 pmKIN-PNS
10h 21m1 stop
Delta Logo
8:00 am - 8:00 pmPNS-KIN
12h 00m1 stop
$587Delta
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Useful Info

Good to know

Low seasonOctober
Cheapest flight$139
Best time to beat the crowds but there is an average 13% 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 8007 reviews
8.1Boarding
7.9Entertainment
7.3Food
7.9Comfort
8.5Crew
Airline reviews

The ticket agents in West Palm Beach on Friday afternoon Nov. 7th were incredible in getting us on an earlier plane to Atlanta during the government shutdown. Had the taken our original flight we would have missed our connection. She did this on her own, We didn't even have to ask, and she did it all with a smile and showing genuine concern that we would be taken care of. We are very grateful and thankful. We fly often, and now we will be sure to fly Delta.

10.0 ExcellentDuane, Nov 2025PBI - ATL
Read more Delta reviews

The ticket agents in West Palm Beach on Friday afternoon Nov. 7th were incredible in getting us on an earlier plane to Atlanta during the government shutdown. Had the taken our original flight we would have missed our connection. She did this on her own, We didn't even have to ask, and she did it all with a smile and showing genuine concern that we would be taken care of. We are very grateful and thankful. We fly often, and now we will be sure to fly Delta.

the over had ligth did not work'd for the all way

Flight delayed then cancelled. Misplaced luggage. Still do not have. Rented car 1100 mile drive. I had to buy some overnight Hotels clothes toiletries gas food at my expense. Still not home. Not sure where luggage is. Over 4 hours on hold to Felta

I truly love flying with Delta. They have always treated me with the upmost respect

Our flight attendant in FIRST CLASS was one of the worst I’ve ever had. She was not at all pleasant, nor particularly good at her service.

The flight was an hour and a half late departing which was inconvenient

The flight was great. The gate location was way to far away!!!

The flight attendant in first class was beyond rude and didn't care at all about her job. AND the gate agent was even worse than the flight attendant for rudeness. She was awful.

Movie selection was meh. Food was great. Crew as always great. I paid for premium because that’s the only way not to feel like a sardine. That’s how economy should be imo. Sadly passengers have to pay an extra $1000 to get what they should at base price but that’s all airlines. The airline industry in general treats passengers as cargo.

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.

Delays to take off and to leave the plane after landing added a lot of time to this flight.

It was a red eye flight, so no meals were provided, but it was fine with snacks. The seats felt cramped and almost too narrow.

We didn't take off until an hour after we boarded.

Wish they had the seat-back video screens for watching movies or playing games.

Very good but wish they had the seat-back video screens for movies & games

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.

The pilot would speak it was painfully load a d the crew had to know this! Maybe the were hesitant to tell him. It was just a mediocre experience and I was in Spirit first class!

My flight was cancelled last minute and I had to pay $1600 for flights, when my original flights were $300. It was a terrible experience.

Excessive fees for flight delays. What a Scam. I was not able to attend the wedding I needed to go.

It was terrible, we had to board and unboard the flight with a hour delay that caused me to miss an appointment and a surprise for my wife

They didn't let me board with a proper boarding pass. I threw away my bags so that I can board and was defined boarding. Had to take the next flight after paying more.

Great! I intend to use Spirit for future flights. No complaints .

They cancelled the flight 3 hours prior departure. Had to spend $400 for a ne way flight with Delta Airlines! Spirit Airlines are not serios!

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.

Over SOLD flight. It does not matter that you were able to check in 24 Hours before and confirm your flight. At the airport, the company SPIRIT rep wanted to remove people who pay for lower fares.

The entire staff from check in agents to flight attendants were pleasant and professional. Would suggest a complimentary water.

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