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$95+ Cheap flights from Pittsburgh (PIT) to Caribbean

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/16. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — SJU
ago. 19 — ago. 261
mar. 8/19
mar. 8/26
1 adult, Economy
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Cheap flight deals from Pittsburgh to Caribbean

Keep the following information in mind while searching for Pittsburgh to Caribbean flight deals. Data was last updated agosto 14, 2025.

Round-trip from

$205
(Southwest)

One-way from

$95
(Cheapflightsfares)

Popular in

December

Cheapest in

September

Average price

$490

Good round-trip deal

$468 or less
From Pittsburgh to Caribbean
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One-way flight from Pittsburgh to Caribbean
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Highest demand for flights based on searches. 4% potential increase in price ($21 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Pittsburgh to Caribbean.
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Find flight deals from Pittsburgh to Caribbean

Cheapest flights from Pittsburgh to Caribbean
Explore the most affordable flight options available from Pittsburgh to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on agosto 14, 2025.

This Delta deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 10/207:05 amPIT - SJU
1 stop9h 20mDelta
mar. 10/287:00 amSJU - PIT
1 stop9h 53mDelta
Deal found 8/14$205
This Delta deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 10/196:00 amPIT - SJU
1 stop10h 33mDelta
mié. 10/227:18 amSJU - PIT
1 stop9h 35mDelta
Deal found 8/14$220
This American Airlines deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/118:00 amPIT - SJU
1 stop15h 05mAmerican Airlines
dom. 10/195:30 amSJU - PIT
1 stop17h 23mAmerican Airlines
Deal found 8/14$230
This United Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/2711:04 amPIT - SJU
2 stops12h 53mUnited Airlines
lun. 9/291:05 amSJU - PIT
2 stops8h 21mUnited Airlines
Deal found 8/12$238
This Delta deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/217:05 amPIT - SJU
1 stop9h 20mDelta
sáb. 10/257:00 amSJU - PIT
1 stop9h 53mDelta
Deal found 8/14$243
This Priceline deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/92:26 pmPIT - SJU
1 stop10h 19mFrontier
dom. 10/121:59 amSJU - PIT
1 stop11h 51mFrontier
Deal found 8/12$249
This Delta deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 11/97:20 amPIT - SJU
1 stop8h 50mDelta
mar. 11/111:50 pmSJU - PIT
1 stop10h 19mDelta
Deal found 8/12$250
This FlightHub deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 9/157:10 amPIT - STT
1 stop7h 47mSpirit Airlines
vie. 9/194:02 pmSTT - PIT
1 stop17h 28mSpirit Airlines
Deal found 8/12$250
This Priceline deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/62:38 pmPIT - SJU
1 stop9h 03mFrontier
dom. 11/92:11 amSJU - PIT
1 stop12h 42mFrontier
Deal found 8/12$255
This Priceline deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/232:26 pmPIT - SJU
1 stop10h 19mFrontier
sáb. 10/253:40 amSJU - PIT
1 stop8h 25mFrontier
Deal found 8/13$256
This Cheapflightsfares deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/127:10 amPIT - STT
1 stop7h 47mSpirit Airlines
lun. 9/1510:49 amSTT - PIT
1 stop8h 09mSpirit Airlines
Deal found 8/12$256
This Delta deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 10/196:00 amPIT - SJU
1 stop10h 33mDelta
sáb. 10/257:00 amSJU - PIT
1 stop9h 53mDelta
Deal found 8/14$258

Cheapflights Fare Finder

 
Customize your flight search to find flights from Pittsburgh to Caribbean 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, Cheapflights users made 2,558,603 searches. Data last updated agosto 14, 2025.
Use the filters below to find and compare flights from Pittsburgh to Caribbean that are best for you.

Fly from

Pittsburgh

Fly to

Caribbean

Route

Depart

Return

Price

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

sáb. 11/8

5:11 pm-1:15 am

1 stop7h 04m

San Juan Luis Munoz Marin Intl

mié. 11/12

7:00 am-4:37 pm

1 stop10h 37m

$205

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

mar. 9/23

6:15 am-8:38 pm

2 stops14h 23m

San Juan Luis Munoz Marin Intl

vie. 9/26

1:05 am-9:31 am

2 stops8h 26m

$205

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

mar. 1/27

11:45 am-8:30 pm

1 stop7h 45m

San Juan Luis Munoz Marin Intl

mié. 2/4

3:30 pm-9:11 pm

1 stop6h 41m

$205

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

mié. 1/28

7:20 am-4:51 pm

1 stop8h 31m

San Juan Luis Munoz Marin Intl

jue. 2/5

2:12 pm-9:26 pm

1 stop8h 14m

$205

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

jue. 10/16

7:05 am-4:25 pm

1 stop9h 20m

San Juan Luis Munoz Marin Intl

mié. 10/22

7:00 am-4:53 pm

1 stop9h 53m

$205

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

vie. 10/17

6:00 am-1:21 pm

1 stop7h 21m

San Juan Luis Munoz Marin Intl

mié. 10/22

7:18 am-4:53 pm

1 stop9h 35m

$205

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

lun. 10/6

7:05 am-4:25 pm

1 stop9h 20m

San Juan Luis Munoz Marin Intl

sáb. 10/11

5:43 pm-12:32 am

1 stop6h 49m

$205

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

lun. 10/20

5:11 pm-11:56 pm

1 stop6h 45m

San Juan Luis Munoz Marin Intl

jue. 10/23

1:06 pm-9:27 pm

1 stop8h 21m

$205

PittsburghSaint Thomas Island

PIT - STT

PITSTT

Pittsburgh

lun. 9/15

7:10 am-2:57 pm

1 stop7h 47m

Saint Thomas Island Cyril E King

vie. 9/19

4:02 pm-9:30 am

1 stop17h 28m

$250

PittsburghSaint Thomas Island

PIT - STT

PITSTT

Pittsburgh

vie. 9/12

7:10 am-2:57 pm

1 stop7h 47m

Saint Thomas Island Cyril E King

lun. 9/15

10:49 am-6:58 pm

1 stop8h 09m

$256

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/13

Showing 1-10 of 60 results
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Best time to book a flight from Pittsburgh to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean from Pittsburgh with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Pittsburgh to Caribbean

What is the cheapest month to book a flight from Pittsburgh to Caribbean?

Currently, September is the cheapest month in which you can book a flight from Pittsburgh to Caribbean (average of $254). Flying from Pittsburgh to Caribbean in June is currently the most expensive (average of $339). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from PIT to CB?

Find hourly flight availability from Pittsburgh to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated agosto 14, 2025.

When flying from Pittsburgh to Caribbean, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated agosto 14, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and United Airlines from Pittsburgh to Caribbean to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Delta
8.0
Very good
7,980 reviews
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
United Airlines
7.4
Good
8,916 reviews
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Spirit Airlines
6.3
Okay
8,046 reviews
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

Related info for your journey

Find useful and relevant information for your journey from Pittsburgh to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Pittsburgh to Caribbean?

    Pittsburgh (PIT) is the airport you will fly out of if you book a flight from Pittsburgh to Caribbean. It is only a 13.5 mi journey to Pittsburgh (PIT) from Pittsburgh’s city center.

  • What are the cheapest airlines to fly from Pittsburgh to Caribbean one-way?

    The cheapest airline one-way is Spirit Airlines, with whom users have recently found tickets for as low as $95. However, be on the lookout for offers from American Airlines and Delta, as they are both options that can get you from Pittsburgh to Caribbean for a low price.

  • What are the most popular routes from Pittsburgh to Caribbean?

    When deciding which route to take from Pittsburgh to Caribbean consider Pittsburgh - San Juan Luis Munoz Marin Intl, Pittsburgh - Oranjestad Reina Beatrix or Pittsburgh - Willemstad Hato Int. as they are the most popular.

  • Can I find deals for flights from Pittsburgh to Caribbean that include hotel bookings?

    Yes. In addition to deals on Pittsburgh to Caribbean flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Pittsburgh to Caribbean?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Pittsburgh to Caribbean.

  • Can I find deals for business class flights from Pittsburgh to Caribbean?

    Yes. Cheapflights offers flight deals from Pittsburgh to Caribbean by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Pittsburgh to Caribbean?

    Currently, September is the cheapest month in which you can book a flight from Pittsburgh to Caribbean (average of $254). Flying from Pittsburgh to Caribbean in June is currently the most expensive (average of $339). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Pittsburgh to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
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Top 8 airlines flying from Pittsburgh to Caribbean

Discover the top 8 airlines that operate flights from Pittsburgh to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated agosto 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$109Average$314FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$153Average$383FlexibilityNo cancel feeOn-time65%
DeltaCheapest$227Average$509FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$238Average$543FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$257Average$635FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$270Average$551FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$284Average$571FlexibilityNo cancel feeOn-time71%
Air CanadaCheapest$446Average$583FlexibilityNo cancel feeOn-time67%

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