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$113+ 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 5/27. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — SJU
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Round-trip from

$225
(Delta)

One-way from

$113
(United Airlines)

Popular in

December

Cheapest in

September

Average price

$380
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. 9% potential increase in price ($42 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 May 2025
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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 May 1, 2025.

This Delta deal was found by Cheapflights users on 4/29. 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 5/276:25 amPIT - SJU
1 stop6h 20mDelta
Wed 6/47:00 amSJU - PIT
1 stop9h 55mDelta
Deal found 4/29$225
This United Airlines deal was found by Cheapflights users on 4/29. 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.
Sun 5/257:00 amPIT - SJU
1 stop7h 44mUnited Airlines
Wed 5/281:05 amSJU - PIT
1 stop7h 38mUnited Airlines
Deal found 4/29$235
This Cheapflightsfares deal was found by Cheapflights users on 4/29. 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 5/307:00 amPIT - SJU
1 stop12h 07mSpirit Airlines
Sun 6/11:59 amSJU - PIT
1 stop9h 37mSpirit Airlines
Deal found 4/29$252
This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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.
Mon 5/265:54 amPIT - STT
1 stop7h 42mSpirit Airlines
Wed 6/410:52 amSTT - PIT
1 stop13h 02mSpirit Airlines
Deal found 4/30$273
This American Airlines deal was found by Cheapflights users on 4/29. 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.
Wed 5/710:39 amPIT - SJU
2 stops9h 30mAmerican Airlines
Thu 5/86:10 amSJU - PIT
1 stop12h 07mAmerican Airlines
Deal found 4/29$280
This CheapOair deal was found by Cheapflights users on 4/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/307:00 amPIT - SJU
1 stop12h 07mMultiple Airlines
Sat 6/73:40 amSJU - PIT
1 stop14h 20mMultiple Airlines
Deal found 4/30$293
This Cheapflightsfares deal was found by Cheapflights users on 4/29. 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.
Sun 6/17:00 amPIT - MBJ
1 stop5h 02mSpirit Airlines
Fri 6/612:07 pmMBJ - PIT
1 stop10h 47mSpirit Airlines
Deal found 4/29$294
This Frontier deal was found by Cheapflights users on 4/28. 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.
Fri 5/96:14 pmPIT - SJU
1 stop8h 37mFrontier
Mon 5/126:00 amSJU - PIT
1 stop9h 08mFrontier
Deal found 4/28$298
This FlightHub deal was found by Cheapflights users on 4/30. 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 5/307:00 amPIT - PUJ
1 stop7h 17mSpirit Airlines
Wed 6/43:22 pmPUJ - PIT
1 stop8h 32mSpirit Airlines
Deal found 4/30$301
This American Airlines deal was found by Cheapflights users on 4/29. 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.
Thu 8/146:05 amPIT - STX
1 stop6h 50mAmerican Airlines
Thu 8/213:49 pmSTX - PIT
1 stop7h 24mAmerican Airlines
Deal found 4/29$315
This Priceline deal was found by Cheapflights users on 4/29. 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.
Sun 6/17:00 amPIT - AUA
1 stop7h 40mSpirit Airlines
Sat 6/73:45 pmAUA - PIT
1 stop8h 09mSpirit Airlines
Deal found 4/29$319
This Delta deal was found by Cheapflights users on 4/29. 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.
Fri 9/126:00 amPIT - STT
1 stop7h 39mDelta
Mon 9/152:49 pmSTT - PIT
1 stop8h 20mDelta
Deal found 4/29$319

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 May 1, 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

Tue 5/27

6:25 am-12:45 pm

1 stop6h 20m

San Juan Luis Munoz Marin Intl

Wed 6/4

7:00 am-4:55 pm

1 stop9h 55m

$225

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Sun 5/25

7:00 am-2:44 pm

1 stop7h 44m

San Juan Luis Munoz Marin Intl

Wed 5/28

1:05 am-8:43 am

1 stop7h 38m

$235

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Fri 5/30

7:00 am-7:07 pm

1 stop12h 07m

San Juan Luis Munoz Marin Intl

Sun 6/1

1:59 am-11:36 am

1 stop9h 37m

$252

PittsburghSaint Thomas Island

PIT - STT

PITSTT

Pittsburgh

Wed 6/4

5:54 am-1:36 pm

1 stop7h 42m

Saint Thomas Island Cyril E King

Wed 6/11

10:52 am-11:54 pm

1 stop13h 02m

$265

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Fri 5/30

7:00 am-7:07 pm

1 stop12h 07m

San Juan Luis Munoz Marin Intl

Sat 6/7

3:40 am-6:00 pm

1 stop14h 20m

$293

PittsburghMontego Bay

PIT - MBJ

PITMBJ

Pittsburgh

Sun 6/1

7:00 am-11:02 am

1 stop5h 02m

Montego Bay Sangster Intl

Fri 6/6

12:07 pm-11:54 pm

1 stop10h 47m

$294

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Sun 5/11

2:45 pm-1:50 am

1 stop11h 05m

San Juan Luis Munoz Marin Intl

Thu 5/15

3:56 am-5:24 pm

1 stop13h 28m

$298

PittsburghPunta Cana

PIT - PUJ

PITPUJ

Pittsburgh

Fri 5/30

7:00 am-2:17 pm

1 stop7h 17m

Punta Cana

Wed 6/4

3:22 pm-11:54 pm

1 stop8h 32m

$301

PittsburghSaint Thomas Island

PIT - STT

PITSTT

Pittsburgh

Tue 5/13

5:41 am-1:41 pm

1 stop8h 00m

Saint Thomas Island Cyril E King

Tue 5/20

2:51 pm-12:21 am

1 stop9h 30m

$305

PittsburghChristiansted

PIT - STX

PITSTX

Pittsburgh

Thu 8/14

6:05 am-12:55 pm

1 stop6h 50m

Christiansted Henry Rohlsen

Thu 8/21

3:49 pm-11:13 pm

1 stop7h 24m

$315

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 51 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 December is currently the most expensive (average of $336). 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 May 1, 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 May 1, 2025.
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.6

Crew

8.6

Comfort

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,294 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.6

Crew

8.6

Comfort

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,934 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.6

Crew

8.6

Comfort

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
LATAM Airlines
7.5
Good
1,767 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.6

Crew

8.6

Comfort

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Copa Airlines
7.5
Good
1,415 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.6

Crew

8.6

Comfort

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,696 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.6

Crew

8.6

Comfort

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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 United Airlines, with whom users have recently found tickets for as low as $113. However, be on the lookout for offers from Delta and American 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 December is currently the most expensive (average of $336). 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$100Average$295FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$143Average$399FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$238Average$578FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$260Average$560FlexibilityNo cancel feeOn-time69%
DeltaCheapest$273Average$497FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$285Average$569FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$306Average$651FlexibilityNo cancel feeOn-time63%
Air CanadaCheapest$446Average$581FlexibilityNo cancel feeOn-time67%

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