$156 Find Cheap Flights from Caribbean Islands 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 1/9. 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
$250
Overall average: $365
Multiple Airlines
Fri 1/16Mon 1/19
SJU - PNS • 1 stop
Cheapest one-way
$156
Typical prices: $248-$417
Multiple Airlines
Fri 1/9
SJU - PNS • 2 stops
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Flight Deals
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Flight Deals

Cheap Flights from Caribbean Islands to Pensacola

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

Fri, Jan 16 - Mon, Jan 19
Multiple Airlines Logo
6:00 am - 3:08 pmSJU-PNS
11h 08m1 stop
Multiple Airlines Logo
4:03 pm - 3:35 pmPNS-SJU
21h 32m1 stop
$250Multiple Airlines
Find Deal
Thu, Dec 25 - Sat, Jan 10
Spirit Airlines Logo
6:28 pm - 6:14 pmSJU-PNS
25h 46m1 stop
Spirit Airlines Logo
5:33 pm - 9:47 amPNS-SJU
14h 14m1 stop
$271Spirit Airlines
Find Deal
Tue, Dec 30 - Tue, Jan 6
Multiple Airlines Logo
6:00 am - 1:03 pmSJU-PNS
9h 03m1 stop
Multiple Airlines Logo
1:58 pm - 11:44 pmPNS-SJU
7h 46m1 stop
$282Multiple Airlines
Find Deal
Fri, Jan 30 - Mon, Feb 2
Spirit Airlines Logo
6:00 am - 4:37 pmSJU-PNS
12h 37m1 stop
Spirit Airlines Logo
5:33 pm - 9:47 amPNS-SJU
14h 14m1 stop
$286Spirit Airlines
Find Deal
Fri, Jan 16 - Mon, Jan 19
Multiple Airlines Logo
6:00 am - 3:08 pmSJU-PNS
11h 08m1 stop
Multiple Airlines Logo
5:33 pm - 3:35 pmPNS-SJU
20h 02m2 stops
$287Multiple Airlines
Find Deal
Thu, Jan 29 - Sun, Feb 1
Delta Logo
4:45 pm - 11:13 pmMBJ-PNS
7h 28m1 stop
Delta Logo
6:07 pm - 11:13 amPNS-MBJ
16h 06m1 stop
$495Delta
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Fri, Jan 23 - Sun, Feb 1
American Airlines Logo
4:16 pm - 10:50 amMBJ-PNS
19h 34m2 stops
American Airlines Logo
5:24 pm - 12:58 pmPNS-MBJ
18h 34m2 stops
$499American Airlines
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Thu, Jan 29 - Mon, Feb 2
Delta Logo
3:46 pm - 11:13 pmSDQ-PNS
9h 27m1 stop
Delta Logo
7:00 am - 2:21 pmPNS-SDQ
5h 21m1 stop
$516Delta
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Fri, Jan 30 - Wed, Feb 4
American Airlines Logo
12:33 pm - 11:46 pmMBJ-PNS
12h 13m2 stops
American Airlines Logo
5:24 pm - 12:58 pmPNS-MBJ
18h 34m2 stops
$524American Airlines
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Thu, Jan 29 - Mon, Feb 2
Air Canada Logo
4:15 pm - 9:40 amANU-PNS
43h 25m2 stops
Air Canada Logo
6:35 am - 3:20 pmPNS-ANU
30h 45m2 stops
$1,094Air Canada
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Useful Info

Good to know

Low seasonOctober
Cheapest flight$156
Best time to beat the crowds but there is an average 12% increase in price.
Most popular time to fly with an average 3% increase in price.
Flight from San Juan to Pensacola

FAQs for booking flights from Caribbean Islands to Pensacola

  • How does KAYAK find such low prices on flights from Caribbean Islands 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 Islands to Pensacola.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Caribbean Islands to Pensacola?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Pensacola from Caribbean Islands 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 Islands 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 Islands with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Caribbean Islands 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 Islands 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 Islands to Pensacola

 
Need help choosing which airline to fly with from Caribbean Islands 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 8011 reviews
8.5Crew
7.3Food
7.9Comfort
8.1Boarding
7.9Entertainment
Airline reviews

Very smooth, on-time, and pleasantly uneventful flight. The team at the gate and on board were professional and genuinely courteous. The pilot kept us well updated throughout, and both takeoff and landing were steady and enjoyable without any drama. Just a good, solid flight. Thank you! 💗

10.0 ExcellentHartaj, Nov 2025LGA - RDU
Read more Delta reviews

Very smooth, on-time, and pleasantly uneventful flight. The team at the gate and on board were professional and genuinely courteous. The pilot kept us well updated throughout, and both takeoff and landing were steady and enjoyable without any drama. Just a good, solid flight. Thank you! 💗

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

No lunch on a x-country flight scheduled for 10:50 am departure, arrived 5+ hrs later. That requires a black box label before you pay for the tickets. Worst, when I checked in online, it's specifically said that lunch was served on his flight for economy Plus passengers.

We had a lot of really rough weather but that was not Delta's fault. Pilot was amazing.

First, Delta needs more flights to/from Miami. Second, a 1000pm leaving at 1230pm is unacceptable from their biggest airport world hub. Another aircraft could have been used such as the aircraft scheduled to be used in the morning for that exact same route. Yes, I did get me there but the lack of sleep the next day didn't help me enjoy my entire trip since I was busy with activities during the weekend. This can be and is expected from Spirit (going bankrupt) and Frontier (despite they're nickel and dimers). But from Delta's World Hub? That's totally unacceptable!

Service in business class was not impressive. I ordered coffee with dinner and then watched other people get 2 refills before I got my 1 cup of coffee, and only after I pressed the attendant button overhead. Furthermore, the seats in the forward cabin need maintenance on this 737-800: the upholstery is detaching from the seat frame, at least on the backs of seats 1C, 1D.

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!!!

I like how the crew and pilot kept us updated Even though our flight was slightly delayed. We made up time for it in the air. I really did enjoy my seat and amenities and my trip and value overall.

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.

I hope you continue to be one of the great company

I stopped flying spirit as much because they are crooks and thieves. It's not like other airlines where you can at least get credits they just take your money.

The checkin in laguardia was a disaster, scrambling left and right, it was constantly a trying to sell you something, better seat, constantly selling

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!

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