$147 Find Cheap Flights from Caribbean to Pensacola - Compare and Save

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Cheap Flights from Caribbean to Pensacola

 

Cheap flights from Caribbean to Pensacola with top airlines, updated regularly. Compare round-trip, one-way, direct and last-minute deals.

Thu, Nov 12 - Sun, Nov 15
Frontier Logo
3:55 am - 7:19 pmSJU  San Juan Luis Munoz Marin Intl-PNS Pensacola
17h 24m1 stop Orlando
Frontier Logo
8:14 pm - 10:15 amPNS  Pensacola-SJU San Juan Luis Munoz Marin Intl
12h 01m1 stop Orlando
$256Frontier
Fri, Nov 6 - Mon, Nov 9
Multiple Airlines Logo
3:55 pm - 8:18 amSJU  San Juan Luis Munoz Marin Intl-PNS Pensacola
18h 23m2 stops Atlanta Hartsfield-Jackson Tampa
Multiple Airlines Logo
7:46 pm - 3:19 pmPNS  Pensacola-SJU San Juan Luis Munoz Marin Intl
17h 33m1 stop Fort Lauderdale
$267Multiple Airlines
Sat, Oct 31 - Wed, Nov 4
Multiple Airlines Logo
11:22 am - 1:05 pmBQN  Aguadilla Borinquen-PNS Pensacola
26h 43m1 stop Orlando
Multiple Airlines Logo
8:58 am - 10:52 amPNS  Pensacola-BQN Aguadilla Borinquen
23h 54m1 stop Orlando
$301Multiple Airlines
Wed, Nov 4 - Wed, Nov 18
American Airlines Logo
2:01 pm - 10:49 pmSTT  Saint Thomas Island Cyril E King-PNS Pensacola
10h 48m1 stop Charlotte Douglas
American Airlines Logo
6:44 am - 3:38 pmPNS  Pensacola-STT Saint Thomas Island Cyril E King
6h 54m1 stop Charlotte Douglas
$542American Airlines
Wed, Nov 4 - Wed, Nov 18
American Airlines Logo
4:53 pm - 10:27 amSTT  Saint Thomas Island Cyril E King-PNS Pensacola
19h 34m2 stops Miami Charlotte Douglas
American Airlines Logo
6:44 am - 3:38 pmPNS  Pensacola-STT Saint Thomas Island Cyril E King
6h 54m1 stop Charlotte Douglas
$542American Airlines
Wed, Nov 4 - Wed, Nov 18
American Airlines Logo
4:53 pm - 10:27 amSTT  Saint Thomas Island Cyril E King-PNS Pensacola
19h 34m2 stops Miami Charlotte Douglas
American Airlines Logo
3:04 pm - 2:25 pmPNS  Pensacola-STT Saint Thomas Island Cyril E King
21h 21m2 stops Charlotte Douglas Miami
$566American Airlines
Thu, Nov 19 - Thu, Nov 26
Delta Logo
4:20 pm - 11:41 pmSJU  San Juan Luis Munoz Marin Intl-PNS Pensacola
9h 21m1 stop Atlanta Hartsfield-Jackson
Delta Logo
7:01 am - 5:43 pmPNS  Pensacola-SJU San Juan Luis Munoz Marin Intl
8h 42m1 stop Atlanta Hartsfield-Jackson
$571Delta
Mon, Nov 30 - Mon, Dec 7
United Airlines Logo
2:40 pm - 9:40 pmNAS  Nassau Intl-PNS Pensacola
8h 00m1 stop Houston George Bush Intcntl
United Airlines Logo
6:47 am - 1:33 pmPNS  Pensacola-NAS Nassau Intl
5h 46m1 stop Houston George Bush Intcntl
$628United Airlines
Wed, Dec 23 - Tue, Dec 29
Delta Logo
12:33 pm - 4:54 pmNAS  Nassau Intl-PNS Pensacola
5h 21m1 stop Atlanta Hartsfield-Jackson
Delta Logo
7:05 am - 1:28 pmPNS  Pensacola-NAS Nassau Intl
5h 23m1 stop Atlanta Hartsfield-Jackson
$696Delta
Wed, Dec 23 - Tue, Dec 29
United Airlines Logo
2:40 pm - 9:53 pmNAS  Nassau Intl-PNS Pensacola
8h 13m1 stop Houston George Bush Intcntl
United Airlines Logo
6:47 am - 1:33 pmPNS  Pensacola-NAS Nassau Intl
5h 46m1 stop Houston George Bush Intcntl
$742United Airlines

Good to know

Low season

August

Cheapest flight

$147
Best time to beat the crowds but there is an average 3% increase in price.
Most popular time to fly and prices are also 3% lower on average.
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.
7.8
DeltaOverall score based on 8650 reviews
7.2Food
8.5Crew
8.1Boarding
7.8Comfort
7.8Entertainment
Airline reviews

Good but since we got in early we had to wait on runway for our gate. That was kind of a bummer but we still got in earlier than planned For entertainment I was watching a movie and getting close to the end of it with 15 min left but it kept jumping automatically to the next movie before finishing.

8.0 ExcellentLisa, Oct 2026
Read more Delta reviews

Good but since we got in early we had to wait on runway for our gate. That was kind of a bummer but we still got in earlier than planned For entertainment I was watching a movie and getting close to the end of it with 15 min left but it kept jumping automatically to the next movie before finishing.

Delta seems to be getting worse. They are trying to take any comfort away from poorer people to make more money selling it to the rich. I paid for delta comfort and on my flight from Rome to jfk I had a tv that would go on and off automatically and literally no electrical outlets or usbs worked which was advertised in the price of the fare. The infotainment system wasn’t fully working. Luckily the movies worked and the plane was needing a lot of repairs. The jfk to Tampa flight they stuck me next to this really larger guy who was half in my seat and they should have made other accommodations for him because now you’re interfering with the fare class I paid for and act like I shouldn’t care because I didn’t pay for first class. I couldn’t even pull out my tray table because of this guy. The safety video tv screen you couldn’t even see it. It made me a little scared to fly delta anymore, because if these planes are this much in need of servicing, I have to wonder if the plane is going to make it to the destination.

Late flight, screens not working and still had to pay for a drink

They changed my seat assignment from window to middle. I have a physical need to sit by the window because of spinal issues. I unboarded in pain, I also was placed between 2 very large men. I am very disappointed and now dealing with the physical aftermath.

The crew were awesome and ready to help as much as possible. The gate agent in Atlanta was tremendously helpful. The delays were ridiculous. Getting home at 4am when I could have driven home faster was unimpressive. Being delayed for countless hours through the night wasn't a great travel experience.

We sat at the gate for over 30 minutes, with no indication as to why

Flight Staff: Always great! Checking back vs carry-on: I typically check my bag since so much time is spent stowing the bag, it's heavy, maybe not enough room. Delta is charging $45 to check bags. Yet, the people who have multiple carry-on bags are then asked to check their bags and are offered this service for free. This does not seem fair to a person who is trying to be proactive in improving the process . Boarding: Boarding is always slow and exhausting. With the exception of First Class, Economy, why not board the zone in the back of the plane first??? Seats: Why cross the seat belts? I get that it looks nice, but people waste so much time moving them or sitting on them and then having to move. Seats: On both my flights the seat did not recline. Not a big deal. Smell: There was a horrific smell like the restrooms on my first flight. I thought I was going to be sick. Most flights do not smell great. Does Delta use air purifiers or anything?

DL482 did not wait for about 10 of us including a mother and 3 children when we were in the same terminal on DL486, where we were switching from waiting for a jet bridge fix, to moving to a neighboring gate. I understand taxiing delays are ok either but man. We only needed 5 more minutes. DL482 did not adjust from their times at all. This was my first time with Delta.

The actual flight was smooth and we arrived earlier than expected which was great. The flight attendants gave unclear instructions and were rude. They seemed overwhelmed or flustered for the flight. Inflight service was delayed and unsure why.

Paid for wifi that didn't work. No plug in seat to work. No entertainment.

We couldn’t take the direct flight back home in Florida because the flight in Palermo was delayed flor long time and keep us inside the cabin without moving the plane. The plane from Munich to Orlando was still there when we arrived to the gate but they said it was late for us to board the plane. We rushed the most to get there. It was a bad experience and got back exhausted and with pain in all muy body. We are seniors 72 and for us was very bad

The experience with United Airlines was excellent; however, the experience with Houston Intercontinental Airport (IAH) was horrible. Although our flight departed from Terminal B, we had to go through security in Terminal C and then get on a train for travel to Terminal B. Additionally, there was significant walking required to get to the boarding location.

Flight was delayed 5 hours. Updates kept changing. Sears were extremely cramped. Very little leg room. Flight attendant was rushing through with drinks and hit me in the knee either the cart and didn’t apologize. They gave a 15 dollar voucher in airport which doesn’t buy. Much and it was so late that choices were limited.

Always pretty good as far as I see it. Staff was friendly and process was quick to get on and off.

The flight was delayed because they closed several flight ways because of air shows, fire works, etc.

Lost one piece of luggage even though I checked in 2.5 hours before the flight

Horrifying Almost 2 million miles. Bring your own food and drink. One coffee or drink every three hours. Have to order meals on app more than 24 hours ahead Tiny and dirty bathrooms

Left an hour and a half after the listed time. Up side was it had TV screens on the seat.

I've been flying American mostly, and it's been very frustrating. This united flight makes me realize maybe the issue isn't flying, but the airline. United was a significantly better experience. The plane was more comfortable, with a normal amount of leg room (vs the ridiculous reductions AA has made), more comfortable seats, screens to watch movies. It was a much better experience!

Always wish for more healthy, gluten free options. We have to bring our own.

What an amazing plane! We flew a 787 to Miami. Although the Internet was not functioning, it was a wonderful flight.

Seats did not recline as much as I would have expected on a premium economy flight, and the food reminded me of the old days of flying when food was generally tasteless, low quality and small portions.

It was freezing in the cabin. That's on me to be better prepared in the future.

I have posted the comments in the first flight leg.

When we landed, there was only one gate agent to handle three planes, including retrieval of carry on luggage. I was stuck in the jet way waiting on my carry on for almost 20-30 minutes. NOT GOOD

Might want to rethink the snacks you offer in first class they were pretty pathetic

The staff and flight were great! The inflight enteretaintment did not work from EZE to MIA. They attempted to troubleshoot but exhausted all options.

The flight from American side was good, my main issue this was a part of a partner flight with gol, preventing me to use digital boarding passes and doing checking previous of the arrival to the airport.

5 hours delay - minimum communication, no compensation, no support from Airline. Terrible customer experience

Fine. On time, cabin service was fine, bag arrived. All good. Flying into DCA so did not collide with any helicopters, which is also good. Horrid incident that could have and should have been prevented.

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