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Cheap flights from Pensacola to Caribbean Islands from $134

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Pensacola to Caribbean Islands departing on 12/8. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Pensacola to Caribbean Islands

Cheap round-trip flights

Enter your travel dates to find the best prices.
Spirit Airlines Logo
8:16 pm - 8:27 pmPNS-SJU
22h 11m1 stop
Spirit Airlines Logo
4:10 am - 6:14 pmSJU-PNS
16h 04m1 stop
$301Spirit Airlines
Find Deal
Sat, Nov 22 - Fri, Dec 5
Multiple Airlines Logo
1:44 pm - 12:24 amPNS-SJU
8h 40m1 stop
Multiple Airlines Logo
7:10 am - 7:11 pmSJU-PNS
14h 01m2 stops
$307Multiple Airlines
Find Deal
Thu, Nov 20 - Mon, Nov 24
Delta Logo
7:00 am - 2:30 pmPNS-SJU
5h 30m1 stop
Delta Logo
3:55 pm - 8:32 pmSJU-PNS
6h 37m1 stop
$345Delta
Find Deal
Mon, Feb 2 - Thu, Feb 12
Southwest Logo
7:05 am - 12:05 amPNS-SJU
15h 00m2 stops
Southwest Logo
6:00 am - 4:00 pmSJU-PNS
12h 00m2 stops
$365Southwest
Find Deal
Sun, Feb 1 - Fri, Feb 13
Delta Logo
1:59 pm - 9:58 pmPNS-SJU
6h 59m1 stop
Delta Logo
6:15 am - 2:26 pmSJU-PNS
9h 11m1 stop
$375Delta
Find Deal
Wed, Mar 25 - Sat, Apr 4
American Airlines Logo
7:00 am - 10:26 pmPNS-SJU
13h 26m1 stop
American Airlines Logo
10:57 am - 6:50 pmSJU-PNS
9h 53m1 stop
$405American Airlines
Find Deal
Sun, Feb 1 - Fri, Feb 13
American Airlines Logo
6:40 pm - 11:42 amPNS-SJU
15h 02m1 stop
American Airlines Logo
8:19 am - 6:50 pmSJU-PNS
12h 31m1 stop
$415American Airlines
Find Deal
Sun, Feb 15 - Sat, Feb 21
United Airlines Logo
2:15 pm - 1:46 pmPNS-MBJ
22h 31m1 stop
United Airlines Logo
3:20 pm - 10:11 pmMBJ-PNS
7h 51m1 stop
$489United Airlines
Find Deal
Wed, Dec 17 - Wed, Dec 24
Southwest Logo
5:20 am - 6:30 pmPNS-NAS
12h 10m2 stops
Southwest Logo
8:45 am - 5:55 pmNAS-PNS
10h 10m2 stops
$673Southwest
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Sun, Apr 5 - Sat, Apr 11
United Airlines Logo
2:17 pm - 1:46 pmPNS-MBJ
22h 29m1 stop
United Airlines Logo
2:48 pm - 1:15 pmMBJ-PNS
23h 27m1 stop
$683United Airlines
Find Deal
Fri, Nov 21 - Mon, Nov 24

Southwest flights from Pensacola to Caribbean Islands

Our best Southwest deals on Pensacola to Caribbean Islands flight tickets
Southwest
Feb 1
PNS7:05 amPensacola
15h 00m
2 stops
SJU12:05 amSan Juan Luis Munoz Marin Intl
Feb 13
SJU6:00 amSan Juan Luis Munoz Marin Intl
12h 00m
2 stops
PNS4:00 pmPensacola
$365
Find similar
Southwest
Nov 8
PNS2:35 pmPensacola
7h 55m
2 stops
SJU12:30 amSan Juan Luis Munoz Marin Intl
Nov 18
SJU8:55 amSan Juan Luis Munoz Marin Intl
11h 40m
2 stops
PNS6:35 pmPensacola
$514
Find similar
Southwest
Nov 7
PNS12:10 pmPensacola
11h 15m
2 stops
SJU1:25 amSan Juan Luis Munoz Marin Intl
Nov 9
SJU11:55 amSan Juan Luis Munoz Marin Intl
12h 00m
2 stops
PNS9:55 pmPensacola
$619
Find similar

United Airlines flights from Pensacola to Caribbean Islands

Our best United Airlines deals on Pensacola to Caribbean Islands flight tickets
United Airlines
Dec 17
PNS2:15 pmPensacola
22h 31m
1 stop
MBJ1:46 pmMontego Bay Sangster Intl
Dec 24
MBJ3:20 pmMontego Bay Sangster Intl
7h 51m
1 stop
PNS10:11 pmPensacola
$489
Find similar
United Airlines
Nov 21
PNS2:17 pmPensacola
22h 29m
1 stop
MBJ1:46 pmMontego Bay Sangster Intl
Nov 24
MBJ2:48 pmMontego Bay Sangster Intl
23h 27m
1 stop
PNS1:15 pmPensacola
$683
Find similar
United Airlines
Nov 16
PNS11:00 amPensacola
8h 26m
1 stop
SJU9:26 pmSan Juan Luis Munoz Marin Intl
Nov 19
SJU2:05 amSan Juan Luis Munoz Marin Intl
21h 17m
3 stops
PNS9:22 pmPensacola
$714
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Pensacola to Caribbean Islands that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated November 3, 2025.
Use the filters below to find and compare flights from Pensacola to Caribbean Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

PensacolaSan Juan

PNS - SJU

PNSSJU

Pensacola

Sat 11/22

8:16 pm-8:27 pm

1 stop22h 11m

San Juan Luis Munoz Marin Intl

Fri 12/5

4:10 am-6:14 pm

1 stop16h 04m

$301

PensacolaSan Juan

PNS - SJU

PNSSJU

Pensacola

Thu 11/20

1:44 pm-12:24 am

1 stop8h 40m

San Juan Luis Munoz Marin Intl

Mon 11/24

7:10 am-7:11 pm

2 stops14h 01m

$307

PensacolaSan Juan

PNS - SJU

PNSSJU

Pensacola

Mon 2/2

7:00 am-2:30 pm

1 stop5h 30m

San Juan Luis Munoz Marin Intl

Thu 2/12

3:55 pm-8:32 pm

1 stop6h 37m

$345

PensacolaSan Juan

PNS - SJU

PNSSJU

Pensacola

Sun 2/1

7:05 am-12:05 am

2 stops15h 00m

San Juan Luis Munoz Marin Intl

Fri 2/13

6:00 am-4:00 pm

2 stops12h 00m

$365

PensacolaSan Juan

PNS - SJU

PNSSJU

Pensacola

Wed 3/25

1:59 pm-9:58 pm

1 stop6h 59m

San Juan Luis Munoz Marin Intl

Sat 4/4

6:15 am-2:26 pm

1 stop9h 11m

$375

PensacolaSan Juan

PNS - SJU

PNSSJU

Pensacola

Sun 2/1

7:00 am-10:26 pm

1 stop13h 26m

San Juan Luis Munoz Marin Intl

Fri 2/13

10:57 am-6:50 pm

1 stop9h 53m

$405

PensacolaSan Juan

PNS - SJU

PNSSJU

Pensacola

Sun 2/15

6:40 pm-11:42 am

1 stop15h 02m

San Juan Luis Munoz Marin Intl

Sat 2/21

8:19 am-6:50 pm

1 stop12h 31m

$415

PensacolaMontego Bay

PNS - MBJ

PNSMBJ

Pensacola

Wed 12/17

2:15 pm-1:46 pm

1 stop22h 31m

Montego Bay Sangster Intl

Wed 12/24

3:20 pm-10:11 pm

1 stop7h 51m

$489

PensacolaNassau

PNS - NAS

PNSNAS

Pensacola

Sun 4/5

5:20 am-6:30 pm

2 stops12h 10m

Nassau Intl

Sat 4/11

8:45 am-5:55 pm

2 stops10h 10m

$673

PensacolaMontego Bay

PNS - MBJ

PNSMBJ

Pensacola

Fri 11/21

2:17 pm-1:46 pm

1 stop22h 29m

Montego Bay Sangster Intl

Mon 11/24

2:48 pm-1:15 pm

1 stop23h 27m

$683

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Caribbean Islands from

How to get the cheapest flight ticket from Pensacola to Caribbean Islands

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Caribbean Islands?

The month of February is, on average, the cheapest month to fly to Caribbean Islands from Pensacola, with most prices found around $384. The month of January is another great option to travel to Caribbean Islands, with average flight prices from Pensacola averaging around $390.

What is the cheapest day to depart on your flight to Caribbean Islands?

The cheapest day to depart from Pensacola to Caribbean Islands is on a Wednesday. Travelers who choose to depart for Caribbean Islands on a Wednesday will often find tickets for as low as $306. If your travel schedule is flexible, try to avoid departing on a Friday because tickets tend to average around $447. These prices are subject to change though, so be sure to set up a Price Alert for flights to Caribbean Islands.

What is the cheapest time of day to depart on your flight to Caribbean Islands?

According to our data, the cheapest time of day to fly to Caribbean Islands is in the evening. momondo users have found flights departing from Pensacola to Caribbean Islands in the evening for as low as $306. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Try not to purchase tickets at noon because they tend to be around $456. Of course, these prices can vary depending on the time of year and what airport you fly to.

How far in advance should I book a flight to Caribbean Islands?

You are more likely to see cheaper flights to Caribbean Islands from Pensacola when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean Islands for around $481 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean Islands from Pensacola for as low as $390 on momondo.

Can stopping save me money on Pensacola to Caribbean Islands flights?

No. A direct flight is the cheapest option for a flight between Pensacola to Caribbean Islands.

Cheap Pensacola to Caribbean Islands flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Pensacola to Caribbean Islands

Direct flights

None
There are no direct flights from Pensacola to Caribbean Islands. There are no popular flight routes from Pensacola to Caribbean Islands.
Search flight deals

  • When did momondo last update prices for flights from Pensacola Airport to Caribbean Islands?

    Prices for flights from Pensacola Airport to Caribbean Islands refresh daily.

  • How many operators does momondo search for flights from Pensacola Airport to Caribbean Islands?

  • How old do you have to be to fly from Pensacola Airport to Caribbean Islands?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Pensacola Airport to Caribbean Islands.

  • What documentation or ID do you need to fly to Caribbean Islands?

    The travel and health documents required for your trip to Caribbean Islands can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Caribbean Islands. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Pensacola to Caribbean Islands?

Best airlines flying from Pensacola to Caribbean Islands

Compare and see reviews for airlines that fly from Pensacola to Caribbean Islands with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $115Free CancellationRating
6.3
8,115 reviews
Search Spirit Airlines flights
DeltaPriceFrom $300Free CancellationRating
7.9
8,002 reviews
Search Delta flights
American AirlinesPriceFrom $338Free CancellationRating
7.2
11,038 reviews
Search American Airlines flights
United AirlinesPriceFrom $380Free CancellationRating
7.4
8,997 reviews
Search United Airlines flights
SouthwestPriceFrom $381Free CancellationRating
8.0
4,238 reviews
Search Southwest flights

Why use momondo?

Why should I use momondo to find a flight deal from Pensacola to Caribbean Islands?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Pensacola to Caribbean Islands. momondo saves you time and could save you money on your trip.

Can I find flights from Pensacola to Caribbean Islands with flexible booking policies on momondo?

Yes. All flights to Caribbean Islands from Pensacola on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Pensacola to Caribbean Islands?

Once all potential Pensacola to Caribbean Islands flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Pensacola to Caribbean Islands right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Caribbean Islands, momondo offers a useful price alert feature which will track prices for flights to Caribbean Islands from Pensacola and alert you when they change.

An easier way to manage your Caribbean Islands trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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