$184 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 12/8. 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

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Everything you should know

Cheapest round-trip
$345
Overall average: $384
Delta
Fri 2/27Sun 3/1
SJU - PNS • 1 stop
Cheapest one-way
$184
Typical prices: $187-$375
Multiple Airlines
Mon 12/8
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, Feb 27 - Sun, Mar 1
Delta Logo
6:15 am - 2:26 pmSJU-PNS
10h 11m1 stop
Delta Logo
1:59 pm - 11:49 pmPNS-SJU
7h 50m1 stop
$345Delta
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Thu, Nov 13 - Thu, Nov 20
Spirit Airlines Logo
3:37 pm - 7:11 pmSJU-PNS
5h 34m1 stop
Spirit Airlines Logo
1:44 pm - 12:24 amPNS-SJU
8h 40m1 stop
$361Spirit Airlines
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Tue, Dec 23 - Tue, Jan 6
American Airlines Logo
10:03 pm - 7:58 amSJU-PNS
11h 55m1 stop
American Airlines Logo
4:42 pm - 10:48 amPNS-SJU
16h 06m1 stop
$365American Airlines
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Tue, Jan 13 - Sat, Jan 17
American Airlines Logo
1:24 pm - 6:35 pmSJU-PNS
7h 11m1 stop
American Airlines Logo
4:42 pm - 10:48 amPNS-SJU
16h 06m1 stop
$371American Airlines
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Thu, Nov 13 - Thu, Nov 20
Spirit Airlines Logo
3:37 pm - 7:11 pmSJU-PNS
5h 34m1 stop
Spirit Airlines Logo
8:16 pm - 10:49 amPNS-SJU
36h 33m2 stops
$405Spirit Airlines
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Fri, Feb 27 - Sun, Mar 1
Southwest Logo
5:30 am - 4:00 pmSJU-PNS
12h 30m2 stops
Southwest Logo
10:25 am - 10:30 pmPNS-SJU
10h 05m2 stops
$445Southwest
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Thu, Feb 19 - Thu, Feb 26
Southwest Logo
7:00 am - 3:45 pmSJU-PNS
10h 45m2 stops
Southwest Logo
7:20 am - 10:30 pmPNS-SJU
13h 10m2 stops
$475Southwest
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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
$475United Airlines
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Tue, Mar 10 - Wed, Mar 11
Delta Logo
6:15 am - 12:53 pmSJU-PNS
7h 38m1 stop
Delta Logo
1:59 pm - 9:58 pmPNS-SJU
6h 59m1 stop
$495Delta
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Wed, Jan 14 - Sun, Jan 18
United Airlines Logo
2:05 am - 7:58 pmSJU-PNS
19h 53m2 stops
United Airlines Logo
6:35 am - 4:36 pmPNS-SJU
8h 01m1 stop
$563United Airlines
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Useful Info

Good to know

Low seasonJanuary
Cheapest flight$184
Best time to beat the crowds but there is an average 5% 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 7977 reviews
8.5Crew
8.2Boarding
7.9Comfort
7.9Entertainment
7.3Food
Airline reviews

Delayed flight (1hour) plus a long layover after an overnight flight with no backup plane available.

6.0 GoodFernando, Oct 2025SAN - ATL
Read more Delta reviews

Delayed flight (1hour) plus a long layover after an overnight flight with no backup plane available.

We were delayed, which I think had to do with air traffic control. Otherwise, everything was great.

The boarding process needs to be refined. Sometimes the gate crew calls out the zones and then flip to showing the.zones boarding on the gate monitor display. So, unless you are huddled around the gate lanes watching the monitor, you could miss your boarding zone. Suggest the zones be announced each time a new zone is allowed to board.

The boarding process needs to be refined. Sometimes the gate crew call out the boarding zone, and then flip to the monitor to show which zones are boarding. So unless everyone is gathered around to see the monitor there is usually confusion as wi which zones are boarding.

On time flight. Seat comfort could be better in the Comfort section.

My issue was with TSA agents for delta airlines. My luggage got flagged. The agent was going thru another persons first. He took 20 min to go thru hers. I asked them to bring mine closer so I could sit down . They said you can go sit it will be fine. I said I am supposed to keep my eyes on my bags at all times. The agent was meticulously unwrapping 2 gifts that the lady had and then tried to re warp it. He was trying to be kind i get it but 20 min for me to stand watching him do that was ridiculous. It was 6 am and there were a ton of travelers. Mine was flagged for some air packed tea that I bought in Turkey. My previous delta flight and 2 others before didn’t flag it. Consistency would be nice. Also on the flight the window shades were down for take off and landing - I thought that was very odd I thought they had to remain open for take off and landing.

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

Delay in SLC jammed us up in Chicago. Got caught up in rush hour traffic

The crew took good care of us. The flight from ATL to SFO is a longer one, and there were multiple beverage offerings. I like the 757's that Delta uses. Good airplane that is comfortable. I do wish Delta would separate Priority boarding from the better seats. I would gladly take a smaller seat in an open row than be jammed into Comfort just to get priority boarding, just to make sure I don't have to check a bag.

The crew was not very visible. This might be a good thing for people who wanted to sleep but seemed odd when compared to the Atlantic crossing where they are more present in the cabin. The Food (beef) was not good. Tough and tasteless. Would love to see more choices on a long flight like that.

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.

This flight never occurred because AA couldn’t get their act together.

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.

Very easy boarding! Crew was fantastic and offered us refreshments quickly and efficiently. Quick, nice flight!

My baggage broke and they did not offer me anything. No conversation

It was not good at all, I think the crew could be kinder

Cheap flight but really uncomfortable. Seat cushions flimsy. Jammed in middle seat when flight is not full. They don’t even give you water

I don’t like the idea of having to buy everything including a bottle of water when the other airlines are giving it to us

My initial flight got overbooked whilst waiting at the gate, and they rebooked me on a later INDIRECT flight!. No offer of a refund

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