$133 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 2/3. 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
$182
Typical prices: $462-$508
Frontier
Thu 2/19Mon 2/23
SJU - PNS • 1 stop
Cheapest one-way
$133
Typical prices: $153-$183
Spirit Airlines
Tue 2/3
SJU - PNS • 1 stop
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Flight Deals
Useful Info
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

Thu, Feb 19 - Mon, Feb 23
Frontier Logo
4:25 pm - 8:50 am
SJU
-
PNS
18h 25m1 stop
Frontier Logo
2:23 pm - 12:43 am
PNS
-
SJU
8h 20m1 stop
$182Frontier
Fri, Jan 23 - Sun, Jan 25
Spirit Airlines Logo
6:00 am - 4:37 pm
SJU
-
PNS
12h 37m1 stop
Spirit Airlines Logo
4:03 pm - 6:58 pm
PNS
-
SJU
24h 55m1 stop
$240Spirit Airlines
Thu, Feb 19 - Mon, Feb 23
Spirit Airlines Logo
11:52 am - 5:42 pm
SJU
-
PNS
7h 50m1 stop
Spirit Airlines Logo
6:37 pm - 10:17 am
PNS
-
SJU
13h 40m1 stop
$253Spirit Airlines
Fri, Jan 16 - Sun, Jan 25
Multiple Airlines Logo
6:00 am - 3:08 pm
SJU
-
PNS
11h 08m1 stop
Multiple Airlines Logo
5:33 pm - 9:47 am
PNS
-
SJU
14h 14m1 stop
$258Multiple Airlines
Thu, Feb 19 - Thu, Feb 26
Spirit Airlines Logo
11:52 am - 5:42 pm
SJU
-
PNS
7h 50m1 stop
Spirit Airlines Logo
6:37 pm - 10:17 am
PNS
-
SJU
13h 40m1 stop
$259Spirit Airlines
Thu, Feb 19 - Mon, Feb 23
Multiple Airlines Logo
11:52 am - 5:42 pm
SJU
-
PNS
7h 50m1 stop
Multiple Airlines Logo
6:37 pm - 1:24 am
PNS
-
SJU
28h 47m2 stops
$284Multiple Airlines
Tue, Mar 3 - Tue, Mar 10
American Airlines Logo
11:07 am - 8:18 pm
MBJ
-
PNS
10h 11m2 stops
American Airlines Logo
3:16 pm - 9:07 am
PNS
-
MBJ
17h 51m2 stops
$501American Airlines
Sat, Jan 17 - Tue, Jan 27
American Airlines Logo
6:29 pm - 11:46 pm
SDQ
-
PNS
7h 17m1 stop
American Airlines Logo
6:05 am - 5:23 pm
PNS
-
SDQ
9h 18m1 stop
$572American Airlines
Mon, Jun 8 - Mon, Jun 15
Delta Logo
8:50 pm - 10:45 am
STI
-
PNS
14h 55m2 stops
Delta Logo
7:15 pm - 12:40 pm
PNS
-
STI
16h 25m2 stops
$652Delta
Thu, Jan 22 - Mon, Jan 26
WestJet Logo
5:30 pm - 5:18 pm
POP
-
PNS
25h 48m2 stops
WestJet Logo
11:25 am - 4:33 pm
PNS
-
POP
27h 08m2 stops
$1,823WestJet
Useful Info

Good to know

Low seasonOctober
Cheapest flight$133
Best time to beat the crowds but there is an average 26% increase in price.
Most popular time to fly with an average 9% 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 8018 reviews
7.9Comfort
7.8Entertainment
7.2Food
8.1Boarding
8.5Crew
Airline reviews

Delta canceled our flight and we had to scramble to find another airline to get home. Phoenix is not a delta hub so they didn’t have another plane. It would have been a red eye though Salt Lake City. Getting in at 5am. No bueno.

2.0 MediocreAnonymous, Jan 2026
PHX - JFK
Read more Delta reviews

Delta canceled our flight and we had to scramble to find another airline to get home. Phoenix is not a delta hub so they didn’t have another plane. It would have been a red eye though Salt Lake City. Getting in at 5am. No bueno.

Delta is a good airline. I've never had an issue with Delta. I'll continue to fly with them until they show me that I shouldn't.

Flight was operated by Virgin Atlantic and it was up to their usual high standard. Minor grips about some issues, but they are really first world issues and as a whole, was an excellent flight.

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

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!!!

Original flight was canceled and rescheduled for the next day. Cancelation notice was sent in the middle of the night (only saw it in the morning), leaving no room to find other options. No offers to reimburse for the extra expenses or compensations. My flight to Rio on 12/12 was also delayed for 16 hours. This seems to be the new normal for AA.

I got sick nothing contagious but distressing and the care I received by Kayla? Keighly the flight attendant will be memorable for ever. Thank You

Waaay too small plane. They also need to up the size of the overhead bins. I would love to keep me 3k with of camera equipment in my hard case baggahe instead of it being thrown into the belly of the plane

Attendants were pleasant and the flight was smooth and relaxed.

It was fine. No drinks nor snacks offered though. I thought that was unusual.

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.

Bad experience with gate agent. I asked what group she was boarding. She gave me a face and said, with attitude, group 1. I stood back and waited for my group, group 2 to be called. After an awful lot of people boarded she took the mic and announced, now boarding group 5. The lack of professionalism amongst spirit staff is astounding.

Boarding process was slightly delayed but took an extra long time which caused a 30 minutes delay.

Flight cancelled. Only options are to a different city or wait 2 days for a flight to same destination

Our flight was canceled at the last minute after delaying for hours and our whole holiday had to be canceled they could not get another flight next day we had so much planned 3 hotels, Disney tickets, car rental. It was canceled due to cabin crew not showing up.

I like that our first flight wasn’t delayed or canceled. The trip went downhill from there. If you’re presented with the opportunity to fly Spirit Airlines before they go out of business, please consider other options.

Spirit Airlines has a reputation for being a terrible, cheap airline, this is why. I took a gamble on them, having never flown with them before, and the flight got cancelled. First they delayed the flight about 4 times before finally canceling it because a flight attendant didn’t show up to work that day. That’s so stupid. When I asked a ticketing agent she said that’s “company policy”. A company policy that inconveniences hundreds of passengers because a single flight attendant didn’t show is ridiculous and inefficient. I will never, ever try flying Spirit Airlines again.

The traffic controllers had cancelled some flights, I wish they'd done it sooner so we didn't have to sit at the airport for 3 hours.

I liked that the crew looked well put together. I also liked that there were little turbulences.

The front desk personnel at ORF ticketing were the only good experience I had during my round trip. I encourage spirit to re-assess all aspects of their internal operations. This includes their website with constant issues connecting to their data base and questionable system practices. The employees of spirit airlines I will not comment on, as I believe primary issues had been a direct result of poor work conditions and expectations placed upon them. The holidays cause high emotions for everyone, this is an excellent time to take the opportunity to provide solutions for them, not take monetary advantage.

Absolute disaster. Was delayed, delayed again, then delayed while loaded, causing many to miss connecting flights. However, spirit had only one person to process over 20 missed flights, taking forever. They then provided little guidance. No wonder they are bankrupt

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