$143 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 2/21. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Pensacola

Travelers love KAYAK
41.299.237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$259
Overall average: $365
Spirit Airlines
Sun 1/25Sat 1/31
SJU - PNS • 1 stop
Cheapest one-way
$143
Typical prices: $153-$183
Spirit Airlines
Sat 2/21
SJU - PNS • 1 stop
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Pensacola!
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

Sun, Jan 25 - Sat, Jan 31
Spirit Airlines Logo
6:00 am - 4:37 pm
SJU
-
PNS
12h 37m1 stop
Spirit Airlines Logo
5:33 pm - 9:47 am
PNS
-
SJU
14h 14m1 stop
$259Spirit 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
$260Spirit 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
$272Spirit Airlines
Thu, Jan 22 - Sun, Feb 1
Multiple Airlines Logo
11:52 am - 10:38 am
SJU
-
PNS
48h 46m2 stops
Multiple Airlines Logo
1:18 pm - 12:34 am
PNS
-
SJU
9h 16m1 stop
$274Multiple Airlines
Thu, Jan 22 - Sat, Jan 31
Multiple Airlines Logo
6:00 am - 4:37 pm
SJU
-
PNS
12h 37m1 stop
Multiple Airlines Logo
11:18 am - 9:54 am
PNS
-
SJU
20h 36m2 stops
$275Multiple Airlines
Sun, Jan 25 - Sat, Jan 31
Multiple Airlines Logo
6:00 am - 4:37 pm
SJU
-
PNS
12h 37m1 stop
Multiple Airlines Logo
11:18 am - 9:54 am
PNS
-
SJU
20h 36m2 stops
$276Multiple Airlines
Wed, Jan 28 - Sun, Feb 1
Multiple Airlines Logo
1:55 pm - 4:37 pm
SJU
-
PNS
28h 42m2 stops
Multiple Airlines Logo
1:18 pm - 12:34 am
PNS
-
SJU
9h 16m1 stop
$278Multiple Airlines
Sat, Jan 24 - Sun, Feb 1
Multiple Airlines Logo
7:00 pm - 4:37 pm
SJU
-
PNS
23h 37m2 stops
Multiple Airlines Logo
1:18 pm - 12:34 am
PNS
-
SJU
9h 16m1 stop
$280Multiple Airlines
Mon, May 25 - Tue, Sep 1
Delta Logo
9:00 am - 11:06 pm
KIN
-
PNS
14h 06m1 stop
Delta Logo
9:25 am - 8:04 pm
PNS
-
KIN
10h 39m1 stop
$554Delta
Mon, May 25 - Tue, Sep 1
American Airlines Logo
12:26 pm - 11:48 pm
KIN
-
PNS
11h 22m1 stop
American Airlines Logo
6:04 am - 7:55 pm
PNS
-
KIN
13h 51m2 stops
$602American Airlines
Useful Info

Good to know

Low seasonOctober
Cheapest flight$143
Best time to beat the crowds but there is an average 18% increase in price.
Most popular time to fly with an average 6% 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 8019 reviews
7.3Food
8.5Crew
7.9Comfort
8.1Boarding
7.9Entertainment
Airline reviews

Did not realize internet screen was hidden between seats and no info printed!!!!

6.0 GoodAnonymous, Dec 2025
BOS - MSP
Read more Delta reviews

Did not realize internet screen was hidden between seats and no info printed!!!!

I went to washroom twice and once there was no toilet seat cover and the other no toilet paper at all. I don't think it was ever replenished or checked before we boarded as it was very early on in the flight.

2 of the seats in row 31 the entertainment system was not working, and one seat the tray table did not go all the way down. Flight arrived early and departed on time which was great.

Very good flight crew and very nice people staff were incredible especially the gate agent

Waited at the usual crowded gate at DCA where one ends up standing up because there aren't enough seats.

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

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.

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

Delays due to a "power bank removal", no wifi, pilot said wrong arrival city, stewardess mumbled the word drinks as she rushed past, loud passengers with no enforcement of rules (blasting music out loud on their phones), screaming children

Flight was cancelled with no help From spirit or kayak. Please refund asap

A flight attendant was extremely friendly and offered to move me to a row that was less crowded

My flight was cancelled for “weather”. There was absolutely no bad weather along the course of my flight track. I missed my entire vacation with my family. I will never book a flight with spirit again

First time in a decade I threw up on the flight, turbulence was terrible!! The staff were kinda rude at times.

I really liked the personalized treatment at the MDE airport, where someone from SPIRIT received me at the entrance of the counter line to ask if the weight of my luggage was accurate or if I wanted a better seat, gave me a name tag for my luggage and walked me to the counter. Thank you.

The most horrible flight ever not only Spirit delayed our flight 2 hours departure time for a 1 hour flight — that I could have driven FLL to TPA and spend less time on the road —- and they did the same on the return with 2-hr delay again!!! Then to top all, the rubber like and most unconfortable seats in the industry with no leg room!!! There should be an award for these kinds of companies measuring % of returning customers!!!

I can't rate food or entertainment when previously you know the lowest rate doesn't have any of that included. However I want to congratulate the crew and specially the flight attendants for their kindness and free smile even knowing is the end of a long day. I had the opportunity to chat to Hailey, Despise her busy job, she had the time to chat with me and even when she asked me to stop using my phone, not with words but with her sweet face expression, was as MasterCard said, a priceless moment. She even told me she learned from the best teacher, her Mom Ruth, a flight attendant working in the same flight, Definitely, with people like them, the real Americans, this country will overcome the worst moment in USA history falling in the hands of the biggest senil Psycho felon. God bless America!!!!

Horrible. Arrived at my gate at 6:37 for a 6:50 flight and was denied by staff to board. Literally watched my flight leave from the window and it didn’t take off until after 7am. Tried to talk to staff and they were rude beyond compare. Will never fly with this airline again.

We had to sit and wait for almost an hour after landing and taxiing to the gate. The jet bridge was broken so we just waited and waited and waited and it was inconvenient, hot, and unnecessary.

Traveling to a place near Pensacola?

Book flights to Pensacola if you plan to visit one of these locations
Evergreen

Everything you need to know for your flight to Pensacola

Information on the airport you'll fly into in Pensacola