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Caribbean Islands

$111+ Cheap flights from Pittsburgh (PIT) to Caribbean Islands

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 6/20. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — SJU
Jun 22 — Jun 291
So 6/22
So 6/29
1 adult, Economy
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Cheap flight deals from Pittsburgh to Caribbean Islands

Keep the following information in mind while searching for Pittsburgh to Caribbean Islands flight deals. Data was last updated Juni 17, 2025.

Round-trip from

$183
(Priceline)

One-way from

$111
(Priceline)

Popular in

December

Cheapest in

September

Average price

$454
From Pittsburgh to Caribbean Islands
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One-way flight from Pittsburgh to Caribbean Islands
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Highest demand for flights based on searches. 7% potential increase in price ($30 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 June 2025
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Find flight deals from Pittsburgh to Caribbean Islands

Cheapest flights from Pittsburgh to Caribbean Islands
Explore the most affordable flight options available from Pittsburgh to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on Juni 17, 2025.

This Priceline deal was found by Cheapflights users on 6/16. 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.
Mo 7/73:49 pmPIT - SJU
1 stop8h 10mFrontier
Mi 7/912:59 amSJU - PIT
1 stop13h 30mFrontier
Deal found 6/16$183
This Priceline deal was found by Cheapflights users on 6/15. 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.
Mo 6/307:00 amPIT - SJU
1 stop12h 19mMultiple Airlines
Do 7/312:59 amSJU - PIT
1 stop14h 05mMultiple Airlines
Deal found 6/15$204
This Mytrip deal was found by Cheapflights users on 6/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fr 7/410:32 amPIT - SJU
2 stops32h 47mSpirit Airlines
Do 7/1011:59 pmSJU - PIT
1 stop23h 30mSpirit Airlines
Deal found 6/15$219
This United Airlines deal was found by Cheapflights users on 6/16. 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.
Mi 10/227:05 amPIT - SJU
1 stop7h 39mUnited Airlines
Mi 10/221:05 amSJU - PIT
2 stops8h 21mUnited Airlines
Deal found 6/16$220
This Delta deal was found by Cheapflights users on 6/16. 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.
Fr 10/177:20 amPIT - SJU
1 stop9h 05mDelta
Di 10/287:00 amSJU - PIT
1 stop8h 46mDelta
Deal found 6/16$235
This Cheapflightsfares deal was found by Cheapflights users on 6/15. 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.
Fr 9/125:25 amPIT - STT
1 stop7h 27mSpirit Airlines
Mo 9/151:47 pmSTT - PIT
1 stop10h 08mSpirit Airlines
Deal found 6/15$262
This American Airlines deal was found by Cheapflights users on 6/15. 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.
Di 9/236:50 amPIT - SJU
2 stops9h 02mAmerican Airlines
Mo 9/2912:01 pmSJU - PIT
2 stops10h 19mAmerican Airlines
Deal found 6/15$300
This Priceline deal was found by Cheapflights users on 6/16. 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.
Sa 7/126:20 amPIT - PUJ
1 stop9h 35mSpirit Airlines
Mi 7/303:25 pmPUJ - PIT
1 stop7h 50mSpirit Airlines
Deal found 6/16$307
This Cheapflightsfares deal was found by Cheapflights users on 6/17. 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.
Sa 9/66:30 amPIT - MBJ
1 stop6h 11mSpirit Airlines
Sa 9/1310:19 amMBJ - PIT
1 stop12h 45mSpirit Airlines
Deal found 6/17$309
This American Airlines deal was found by Cheapflights users on 6/15. 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.
Mi 7/95:46 amPIT - STT
2 stops10h 09mAmerican Airlines
Mi 7/165:05 pmSTT - PIT
2 stops16h 14mAmerican Airlines
Deal found 6/15$319
This Delta deal was found by Cheapflights users on 6/15. 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.
Di 8/197:10 amPIT - NAS
1 stop6h 30mDelta
Fr 8/223:05 pmNAS - PIT
1 stop6h 57mDelta
Deal found 6/15$331
This American Airlines deal was found by Cheapflights users on 6/16. 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.
Mi 11/510:32 amPIT - NAS
2 stops8h 08mAmerican Airlines
Mi 11/122:45 pmNAS - PIT
1 stop4h 38mAmerican Airlines
Deal found 6/16$335

Cheapflights Fare Finder

Customize your flight search to find flights from Pittsburgh 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, Cheapflights users made 2,558,603 searches. Data last updated Juni 17, 2025.
Use the filters below to find and compare flights from Pittsburgh to Caribbean Islands that are best for you.

Fly from

Pittsburgh

Fly to

Caribbean Islands

Route

Depart

Return

Price

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Mo 7/7

3:49 pm-11:59 pm

1 stop8h 10m

San Juan Luis Munoz Marin Intl

Mi 7/9

12:59 am-2:29 pm

1 stop13h 30m

$183

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Mo 6/30

7:00 am-7:19 pm

1 stop12h 19m

San Juan Luis Munoz Marin Intl

Do 7/3

12:59 am-3:04 pm

1 stop14h 05m

$204

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Fr 7/4

10:32 am-7:19 pm

2 stops32h 47m

San Juan Luis Munoz Marin Intl

Do 7/10

11:59 pm-11:29 pm

1 stop23h 30m

$219

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Di 7/8

7:30 am-3:20 pm

1 stop7h 50m

San Juan Luis Munoz Marin Intl

Mi 7/16

3:45 pm-12:15 am

1 stop8h 30m

$225

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Sa 9/13

1:50 pm-10:08 pm

1 stop8h 18m

San Juan Luis Munoz Marin Intl

Sa 9/20

2:15 pm-10:36 pm

1 stop8h 21m

$235

PittsburghSaint Thomas Island

PIT - STT

PITSTT

Pittsburgh

Fr 9/12

5:25 am-12:52 pm

1 stop7h 27m

Saint Thomas Island Cyril E King

Mo 9/15

1:47 pm-11:55 pm

1 stop10h 08m

$262

PittsburghPunta Cana

PIT - PUJ

PITPUJ

Pittsburgh

Sa 7/12

6:20 am-3:55 pm

1 stop9h 35m

Punta Cana

Mi 7/30

3:25 pm-11:15 pm

1 stop7h 50m

$307

PittsburghMontego Bay

PIT - MBJ

PITMBJ

Pittsburgh

Sa 9/6

6:30 am-11:41 am

1 stop6h 11m

Montego Bay Sangster Intl

Sa 9/13

10:19 am-12:04 am

1 stop12h 45m

$309

PittsburghSaint Thomas Island

PIT - STT

PITSTT

Pittsburgh

Mi 7/9

5:46 am-3:55 pm

2 stops10h 09m

Saint Thomas Island Cyril E King

Mi 7/16

5:05 pm-9:19 am

2 stops16h 14m

$319

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Fr 7/4

6:00 am-10:55 pm

1 stop16h 55m

San Juan Luis Munoz Marin Intl

Mi 7/16

7:54 am-6:21 pm

2 stops10h 27m

$330

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/16

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

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands 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 Islands

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

Currently, September is the cheapest month in which you can book a flight from Pittsburgh to Caribbean Islands (average of $254). Flying from Pittsburgh to Caribbean Islands 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 EPX?

Find hourly flight availability from Pittsburgh to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated Juni 17, 2025.

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

Rainfall in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean Islands ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean Islands when rainfall is around 2.2 in.

Temperature in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean Islands, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

Reviews of airlines servicing Caribbean Islands

Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated Juni 17, 2025.
Read through reviews of airlines operating flights from Pittsburgh to Caribbean Islands, such as Southwest, Delta and Copa Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,279 reviews

Crew

8.6

Food

7.1

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,279 reviews
Southwest
8.0
Very good
4,279 reviews

Crew

8.6

Food

7.1

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,965 reviews
Southwest
8.0
Very good
4,279 reviews

Crew

8.6

Food

7.1

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Copa Airlines
7.5
Good
1,453 reviews
Southwest
8.0
Very good
4,279 reviews

Crew

8.6

Food

7.1

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,809 reviews
Southwest
8.0
Very good
4,279 reviews

Crew

8.6

Food

7.1

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
JetBlue
7.3
Good
2,923 reviews
Southwest
8.0
Very good
4,279 reviews

Crew

8.6

Food

7.1

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Related info for your journey

Find useful and relevant information for your journey from Pittsburgh to Caribbean Islands. 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 Islands?

    Located just 13.5 mi from the city center, Pittsburgh (PIT) is the airport most travelers will use when flying to Caribbean Islands from Pittsburgh.

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

    One-way options have recently been found by users for as low as $111 on Frontier. Other airlines that offer cheap prices include American Airlines from $112 and Delta from $113 one-way.

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

    While some choose either Pittsburgh - Oranjestad Reina Beatrix or Pittsburgh - Punta Cana, Pittsburgh - San Juan Luis Munoz Marin Intl is the most popular route from Pittsburgh to Caribbean Islands.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Pittsburgh to Caribbean Islands 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 Islands?

    Currently, September is the cheapest month in which you can book a flight from Pittsburgh to Caribbean Islands (average of $254). Flying from Pittsburgh to Caribbean Islands 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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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 Islands

Discover the top 8 airlines that operate flights from Pittsburgh to Caribbean Islands. 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 Juni 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$100Average$241FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$134Average$385FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$238Average$575FlexibilityNo cancel feeOn-time62%
DeltaCheapest$239Average$492FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$245Average$549FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$284Average$554FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$307Average$643FlexibilityNo cancel feeOn-time63%
Air CanadaCheapest$446Average$581FlexibilityNo cancel feeOn-time67%

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