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Cheap flights from Pensacola to Caribbean Islands from $120

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 2/2. 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.
Multiple Airlines Logo
1:58 pm - 11:44 pm
PNS
-
SJU
7h 46m1 stop
Multiple Airlines Logo
8:05 pm - 4:37 pm
SJU
-
PNS
22h 32m1 stop
$245Multiple Airlines
Tue, Jan 6 - Fri, Jan 9
Multiple Airlines Logo
1:58 pm - 11:44 pm
PNS
-
SJU
7h 46m1 stop
Multiple Airlines Logo
8:05 pm - 4:37 pm
SJU
-
PNS
22h 32m1 stop
$246Multiple Airlines
Tue, Jan 6 - Fri, Jan 9
Spirit Airlines Logo
4:03 pm - 9:47 am
PNS
-
SJU
15h 44m2 stops
Spirit Airlines Logo
6:00 am - 4:37 pm
SJU
-
PNS
12h 37m1 stop
$273Spirit Airlines
Thu, Feb 5 - Mon, Feb 9
Spirit Airlines Logo
4:03 pm - 9:47 am
PNS
-
SJU
15h 44m2 stops
Spirit Airlines Logo
2:59 am - 3:08 pm
SJU
-
PNS
14h 09m2 stops
$278Spirit Airlines
Thu, Feb 5 - Sun, Feb 8
Delta Logo
7:15 am - 4:45 pm
PNS
-
NAS
8h 30m1 stop
Delta Logo
5:08 pm - 11:06 pm
NAS
-
PNS
6h 58m1 stop
$447Delta
Sun, Apr 12 - Fri, Apr 17
Breeze Airways Logo
10:26 am - 9:25 am
PNS
-
MBJ
22h 59m1 stop
Breeze Airways Logo
7:26 pm - 8:11 am
MBJ
-
PNS
12h 45m1 stop
$469Breeze Airways
Sat, May 23 - Wed, Jun 3
American Airlines Logo
7:26 pm - 11:02 am
PNS
-
NAS
14h 36m1 stop
American Airlines Logo
1:10 pm - 11:24 pm
NAS
-
PNS
11h 14m1 stop
$472American Airlines
Fri, Apr 3 - Wed, Apr 8
American Airlines Logo
7:05 pm - 12:21 pm
PNS
-
SDQ
15h 16m1 stop
American Airlines Logo
6:00 am - 6:34 pm
SDQ
-
PNS
14h 34m1 stop
$478American Airlines
Sat, Jan 17 - Sat, Jan 24
Breeze Airways Logo
10:26 am - 9:25 am
PNS
-
MBJ
22h 59m1 stop
Breeze Airways Logo
7:26 pm - 8:11 am
MBJ
-
PNS
12h 45m1 stop
$480Breeze Airways
Sat, May 23 - Wed, Jun 10
Delta Logo
7:00 am - 5:02 pm
PNS
-
NAS
9h 02m1 stop
Delta Logo
6:27 pm - 11:11 pm
NAS
-
PNS
5h 44m1 stop
$500Delta
Fri, Feb 20 - Wed, Feb 25

Spirit Airlines flights from Pensacola to Caribbean Islands

Our best Spirit Airlines deals on Pensacola to Caribbean Islands flight tickets
Spirit Airlines
Feb 9
PNS5:33 pmPensacola
14h 14m
1 stop
SJU9:47 amSan Juan Luis Munoz Marin Intl
Feb 12
SJU11:52 amSan Juan Luis Munoz Marin Intl
7h 50m
1 stop
PNS5:42 pmPensacola
$270
Find similar
Spirit Airlines
Feb 5
PNS4:03 pmPensacola
15h 44m
2 stops
SJU9:47 amSan Juan Luis Munoz Marin Intl
Feb 9
SJU6:00 amSan Juan Luis Munoz Marin Intl
12h 37m
1 stop
PNS4:37 pmPensacola
$273
Find similar
Spirit Airlines
Jan 29
PNS4:03 pmPensacola
15h 44m
2 stops
SJU9:47 amSan Juan Luis Munoz Marin Intl
Feb 2
SJU6:00 amSan Juan Luis Munoz Marin Intl
12h 37m
1 stop
PNS4:37 pmPensacola
$282
Find similar

American Airlines flights from Pensacola to Caribbean Islands

Our best American Airlines deals on Pensacola to Caribbean Islands flight tickets
American Airlines
Jan 17
PNS7:05 pmPensacola
15h 16m
1 stop
SDQ12:21 pmSanto Domingo Las Americas
Jan 24
SDQ6:00 amSanto Domingo Las Americas
14h 34m
1 stop
PNS6:34 pmPensacola
$478
Find similar
American Airlines
Mar 31
PNS6:00 amPensacola
6h 02m
1 stop
STT1:02 pmSaint Thomas Island Cyril E King
Apr 7
STT5:10 pmSaint Thomas Island Cyril E King
7h 14m
1 stop
PNS11:24 pmPensacola
$479
Find similar
American Airlines
Jan 17
PNS4:15 pmPensacola
18h 06m
2 stops
SDQ12:21 pmSanto Domingo Las Americas
Jan 24
SDQ1:23 pmSanto Domingo Las Americas
7h 11m
1 stop
PNS6:34 pmPensacola
$482
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 December 18, 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

Tue 1/6

1:58 pm-11:44 pm

1 stop7h 46m

San Juan Luis Munoz Marin Intl

Fri 1/9

8:05 pm-4:37 pm

1 stop22h 32m

$245

PensacolaSan Juan

PNS - SJU

PNSSJU

Pensacola

Tue 1/6

1:58 pm-11:44 pm

1 stop7h 46m

San Juan Luis Munoz Marin Intl

Fri 1/9

8:05 pm-4:37 pm

1 stop22h 32m

$246

PensacolaSan Juan

PNS - SJU

PNSSJU

Pensacola

Thu 2/5

4:03 pm-9:47 am

2 stops15h 44m

San Juan Luis Munoz Marin Intl

Mon 2/9

6:00 am-4:37 pm

1 stop12h 37m

$273

PensacolaSan Juan

PNS - SJU

PNSSJU

Pensacola

Thu 2/5

4:03 pm-9:47 am

2 stops15h 44m

San Juan Luis Munoz Marin Intl

Sun 2/8

2:59 am-3:08 pm

2 stops14h 09m

$278

PensacolaNassau

PNS - NAS

PNSNAS

Pensacola

Sun 4/12

7:15 am-4:45 pm

1 stop8h 30m

Nassau Intl

Fri 4/17

5:08 pm-11:06 pm

1 stop6h 58m

$447

PensacolaMontego Bay

PNS - MBJ

PNSMBJ

Pensacola

Sat 5/23

10:26 am-9:25 am

1 stop22h 59m

Montego Bay Sangster Intl

Wed 6/3

7:26 pm-8:11 am

1 stop12h 45m

$469

PensacolaNassau

PNS - NAS

PNSNAS

Pensacola

Fri 4/3

7:26 pm-11:02 am

1 stop14h 36m

Nassau Intl

Wed 4/8

1:10 pm-11:24 pm

1 stop11h 14m

$472

PensacolaSanto Domingo

PNS - SDQ

PNSSDQ

Pensacola

Sat 1/17

7:05 pm-12:21 pm

1 stop15h 16m

Santo Domingo Las Americas

Sat 1/24

6:00 am-6:34 pm

1 stop14h 34m

$478

PensacolaMontego Bay

PNS - MBJ

PNSMBJ

Pensacola

Sat 5/23

10:26 am-9:25 am

1 stop22h 59m

Montego Bay Sangster Intl

Wed 6/10

7:26 pm-8:11 am

1 stop12h 45m

$480

PensacolaNassau

PNS - NAS

PNSNAS

Pensacola

Fri 2/20

7:00 am-5:02 pm

1 stop9h 02m

Nassau Intl

Wed 2/25

6:27 pm-11:11 pm

1 stop5h 44m

$500

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 $398. The month of January is another great option to travel to Caribbean Islands, with average flight prices from Pensacola averaging around $425.

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 $504 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

Fastest flight time

4h 07m

Direct flights

None
The fastest flight from Pensacola to Caribbean Islands takes 4h 07m
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
8,190 reviews
Search Spirit Airlines flights
DeltaPriceFrom $276Free CancellationRating
7.9
8,005 reviews
Search Delta flights
American AirlinesPriceFrom $359Free CancellationRating
7.2
11,054 reviews
Search American Airlines flights
United AirlinesPriceFrom $380Free CancellationRating
7.4
9,091 reviews
Search United Airlines flights
SouthwestPriceFrom $381Free CancellationRating
7.9
4,250 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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