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$92+ 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 11/2. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — SJU
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$238
(FlightHub)

One-way from

$112
(American Airlines)

Popular in

December

Cheapest in

September

Average price

$454

Good round-trip deal

$430 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. 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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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 June 12, 2025.

This FlightHub deal was found by Cheapflights users on 6/12. 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.
Fri 7/187:25 pmPIT - SJU
1 stop13h 34mMultiple Airlines
Fri 7/2511:59 pmSJU - PIT
1 stop23h 30mMultiple Airlines
Deal found 6/12$238
This Frontier deal was found by Cheapflights users on 6/12. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/198:55 pmPIT - SJU
1 stop11h 04mFrontier
Wed 10/221:11 amSJU - PIT
1 stop12h 15mFrontier
Deal found 6/12$239
This Delta deal was found by Cheapflights users on 6/11. 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.
Sun 10/196:00 amPIT - SJU
1 stop10h 18mDelta
Tue 10/287:00 amSJU - PIT
1 stop8h 46mDelta
Deal found 6/11$245
This Mytrip deal was found by Cheapflights users on 6/10. 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.
Fri 7/186:30 amPIT - SJU
1 stop16h 30mSpirit Airlines
Mon 7/2111:59 pmSJU - PIT
2 stops23h 16mSpirit Airlines
Deal found 6/10$253
This Cheapflightsfares deal was found by Cheapflights users on 6/12. 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.
Fri 9/125:25 amPIT - STT
1 stop7h 27mSpirit Airlines
Mon 9/151:47 pmSTT - PIT
1 stop10h 08mSpirit Airlines
Deal found 6/12$262
This Southwest deal was found by Cheapflights users on 6/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/206:00 amPIT - SJU
1 stop6h 15mSouthwest
Sat 10/255:45 amSJU - PIT
1 stop10h 15mSouthwest
Deal found 6/10$275
This United Airlines deal was found by Cheapflights users on 6/10. 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.
Wed 9/1010:59 amPIT - SJU
2 stops12h 58mUnited Airlines
Sat 9/133:56 pmSJU - PIT
1 stop7h 48mUnited Airlines
Deal found 6/10$298
This American Airlines deal was found by Cheapflights users on 6/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/236:50 amPIT - SJU
2 stops9h 02mAmerican Airlines
Mon 9/2912:01 pmSJU - PIT
2 stops10h 19mAmerican Airlines
Deal found 6/12$300
This Cheapflightsfares deal was found by Cheapflights users on 6/10. 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.
Tue 7/226:20 amPIT - PUJ
1 stop8h 10mSpirit Airlines
Wed 7/303:25 pmPUJ - PIT
1 stop7h 50mSpirit Airlines
Deal found 6/10$307
This JetBlue deal was found by Cheapflights users on 6/11. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/76:00 amPIT - SJU
1 stop8h 54mJetBlue
Sat 10/1112:59 amSJU - PIT
1 stop9h 01mJetBlue
Deal found 6/11$320
This Delta deal was found by Cheapflights users on 6/11. 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.
Tue 9/26:00 amPIT - STT
1 stop8h 10mDelta
Wed 9/103:23 pmSTT - PIT
1 stop7h 47mDelta
Deal found 6/11$325
This SmartFares deal was found by Cheapflights users on 6/9. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/87:00 amPIT - MBJ
1 stop5h 02mSpirit Airlines
Tue 7/1512:10 pmMBJ - PIT
1 stop10h 05mSpirit Airlines
Deal found 6/9$329

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 June 12, 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

Fri 7/18

7:25 pm-8:59 am

1 stop13h 34m

San Juan Luis Munoz Marin Intl

Fri 7/25

11:59 pm-11:29 pm

1 stop23h 30m

$238

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Sun 10/19

8:55 pm-7:59 am

1 stop11h 04m

San Juan Luis Munoz Marin Intl

Wed 10/22

1:11 am-1:26 pm

1 stop12h 15m

$239

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Sun 10/19

6:00 am-4:18 pm

1 stop10h 18m

San Juan Luis Munoz Marin Intl

Tue 10/28

7:00 am-3:46 pm

1 stop8h 46m

$245

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Fri 7/18

6:30 am-11:00 pm

1 stop16h 30m

San Juan Luis Munoz Marin Intl

Mon 7/21

11:59 pm-11:15 pm

2 stops23h 16m

$253

PittsburghSaint Thomas Island

PIT - STT

PITSTT

Pittsburgh

Wed 7/9

8:21 pm-12:30 pm

1 stop16h 09m

Saint Thomas Island Cyril E King

Wed 7/16

10:43 am-11:15 pm

1 stop12h 32m

$269

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Mon 10/20

6:00 am-12:15 pm

1 stop6h 15m

San Juan Luis Munoz Marin Intl

Sat 10/25

5:45 am-4:00 pm

1 stop10h 15m

$275

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Wed 9/10

10:59 am-11:57 pm

2 stops12h 58m

San Juan Luis Munoz Marin Intl

Fri 9/12

1:05 am-9:48 am

2 stops8h 43m

$298

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Tue 9/23

6:50 am-3:52 pm

2 stops9h 02m

San Juan Luis Munoz Marin Intl

Mon 9/29

12:01 pm-10:20 pm

2 stops10h 19m

$300

PittsburghPunta Cana

PIT - PUJ

PITPUJ

Pittsburgh

Tue 7/22

6:20 am-2:30 pm

1 stop8h 10m

Punta Cana

Wed 7/30

3:25 pm-11:15 pm

1 stop7h 50m

$307

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Tue 10/7

6:00 am-2:54 pm

1 stop8h 54m

San Juan Luis Munoz Marin Intl

Sat 10/11

12:59 am-10:00 am

1 stop9h 01m

$320

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/12

Showing 1-10 of 59 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 June 12, 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.

Rainfall in Caribbean by month

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

In terms of precipitation, rainfall in Caribbean 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 when rainfall is around 2.2 in.

Temperature in Caribbean by month

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

If weather is an important factor for your trip to Caribbean, 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

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 June 12, 2025.
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Overall

8.0

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Crew

8.6

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
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Overall

8.0

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Crew

8.6

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
7,950 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Overall

8.0

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Crew

8.6

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
1,451 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Overall

8.0

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Crew

8.6

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
8,790 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Overall

8.0

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Crew

8.6

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
2,925 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Overall

8.0

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Crew

8.6

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. 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 American Airlines, with whom users have recently found tickets for as low as $112. However, be on the lookout for offers from Delta and Spirit Airlines, 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 - Punta Cana 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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$100Average$199FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$139Average$390FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$238Average$571FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$245Average$552FlexibilityNo cancel feeOn-time69%
DeltaCheapest$246Average$494FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$284Average$555FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$309Average$644FlexibilityNo cancel feeOn-time63%
Air CanadaCheapest$446Average$581FlexibilityNo cancel feeOn-time67%

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