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$101+ 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 9/24. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — SJU
jul. 12 — jul. 191
sáb. 7/12
sáb. 7/19
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 julio 7, 2025.

Round-trip from

$234
(Priceline)

One-way from

$101
(American Airlines)

Popular in

December

Cheapest in

September

Average price

$414

Good round-trip deal

$418 or less

Good one-way deal

$200 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. 5% potential increase in price ($24 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 July 2025
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Price to beat on a round-trip flight from Pittsburgh to Caribbean.
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Price to beat on a one-way 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 julio 7, 2025.

This Delta deal was found by Cheapflights users on 7/7. 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.
mié. 10/86:00 amPIT - SJU
1 stop7h 23mDelta
mié. 10/157:30 amSJU - PIT
1 stop9h 36mDelta
Deal found 7/7$225
This American Airlines deal was found by Cheapflights users on 7/6. 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.
mié. 10/85:32 amPIT - SJU
2 stops10h 23mAmerican Airlines
mié. 10/157:00 amSJU - PIT
2 stops10h 57mAmerican Airlines
Deal found 7/6$230
This Priceline deal was found by Cheapflights users on 7/6. 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.
dom. 7/206:20 amPIT - SJU
1 stop14h 49mMultiple Airlines
sáb. 7/2612:59 amSJU - PIT
1 stop13h 30mMultiple Airlines
Deal found 7/6$234
This FlightHub deal was found by Cheapflights users on 7/6. 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. 7/216:20 amPIT - SJU
1 stop14h 49mSpirit Airlines
mié. 7/303:50 pmSJU - PIT
1 stop7h 25mSpirit Airlines
Deal found 7/6$238
This United Airlines deal was found by Cheapflights users on 7/6. 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.
mar. 10/76:15 amPIT - SJU
1 stop6h 19mUnited Airlines
sáb. 10/111:05 amSJU - PIT
2 stops12h 00mUnited Airlines
Deal found 7/6$260
This Cheapflightsfares deal was found by Cheapflights users on 7/7. 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. 8/88:21 pmPIT - STT
1 stop16h 09mSpirit Airlines
sáb. 8/1612:18 pmSTT - PIT
1 stop10h 52mSpirit Airlines
Deal found 7/7$260
This Priceline deal was found by Cheapflights users on 7/7. 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.
dom. 8/39:56 amPIT - SJU
1 stop16h 43mFrontier
jue. 8/73:40 amSJU - PIT
1 stop15h 08mFrontier
Deal found 7/7$264
This American Airlines deal was found by Cheapflights users on 7/6. 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.
lun. 7/217:02 pmPIT - STT
2 stops17h 44mAmerican Airlines
vie. 7/2511:34 amSTT - PIT
1 stop10h 23mAmerican Airlines
Deal found 7/6$267
This Travelocity deal was found by Cheapflights users on 7/5. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 8/26:20 amPIT - STX
1 stop9h 09mSpirit Airlines
mar. 8/510:52 amSTX - PIT
1 stop12h 23mSpirit Airlines
Deal found 7/5$284
This American Airlines deal was found by Cheapflights users on 7/6. 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.
lun. 7/215:50 pmPIT - STX
2 stops21h 25mAmerican Airlines
vie. 7/254:10 pmSTX - PIT
2 stops16h 58mAmerican Airlines
Deal found 7/6$289
This Cheapflightsfares deal was found by Cheapflights users on 7/7. 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.
sáb. 8/237:00 amPIT - PUJ
1 stop8h 00mSpirit Airlines
sáb. 8/304:05 pmPUJ - PIT
1 stop7h 05mSpirit Airlines
Deal found 7/7$296
This Southwest deal was found by Cheapflights users on 7/7. 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.
mar. 9/24:20 pmPIT - SJU
1 stop6h 25mSouthwest
lun. 9/85:00 amSJU - PIT
1 stop13h 15mSouthwest
Deal found 7/7$300

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 julio 7, 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

mié. 10/8

6:00 am-1:23 pm

1 stop7h 23m

San Juan Luis Munoz Marin Intl

mié. 10/15

7:30 am-5:06 pm

1 stop9h 36m

$225

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

mié. 10/8

5:32 am-3:55 pm

2 stops10h 23m

San Juan Luis Munoz Marin Intl

mié. 10/15

7:00 am-5:57 pm

2 stops10h 57m

$230

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

dom. 7/20

6:20 am-9:09 pm

1 stop14h 49m

San Juan Luis Munoz Marin Intl

sáb. 7/26

12:59 am-2:29 pm

1 stop13h 30m

$234

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

lun. 7/21

6:20 am-9:09 pm

1 stop14h 49m

San Juan Luis Munoz Marin Intl

mié. 7/30

3:50 pm-11:15 pm

1 stop7h 25m

$238

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

mar. 10/7

6:15 am-12:34 pm

1 stop6h 19m

San Juan Luis Munoz Marin Intl

sáb. 10/11

1:05 am-1:05 pm

2 stops12h 00m

$260

PittsburghSaint Thomas Island

PIT - STT

PITSTT

Pittsburgh

vie. 8/8

8:21 pm-12:30 pm

1 stop16h 09m

Saint Thomas Island Cyril E King

sáb. 8/16

12:18 pm-11:10 pm

1 stop10h 52m

$260

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

dom. 8/3

9:56 am-2:39 am

1 stop16h 43m

San Juan Luis Munoz Marin Intl

jue. 8/7

3:40 am-6:48 pm

1 stop15h 08m

$264

PittsburghSaint Thomas Island

PIT - STT

PITSTT

Pittsburgh

lun. 7/21

7:02 pm-12:46 pm

2 stops17h 44m

Saint Thomas Island Cyril E King

vie. 7/25

11:34 am-9:57 pm

1 stop10h 23m

$267

PittsburghChristiansted

PIT - STX

PITSTX

Pittsburgh

sáb. 8/2

6:20 am-3:29 pm

1 stop9h 09m

Christiansted Henry Rohlsen

mar. 8/5

10:52 am-11:15 pm

1 stop12h 23m

$284

PittsburghChristiansted

PIT - STX

PITSTX

Pittsburgh

lun. 7/21

5:50 pm-3:15 pm

2 stops21h 25m

Christiansted Henry Rohlsen

vie. 7/25

4:10 pm-9:08 am

2 stops16h 58m

$289

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/7

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 julio 7, 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 julio 7, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and Copa 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
4,257 reviews

Crew

8.6

Overall

8.0

Entertainment

7.6

Food

7.0

Boarding

8.2

Comfort

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
4,257 reviews
Southwest
8.0
Very good
4,257 reviews

Crew

8.6

Overall

8.0

Entertainment

7.6

Food

7.0

Boarding

8.2

Comfort

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
7,962 reviews
Southwest
8.0
Very good
4,257 reviews

Crew

8.6

Overall

8.0

Entertainment

7.6

Food

7.0

Boarding

8.2

Comfort

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
1,469 reviews
Southwest
8.0
Very good
4,257 reviews

Crew

8.6

Overall

8.0

Entertainment

7.6

Food

7.0

Boarding

8.2

Comfort

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
8,844 reviews
Southwest
8.0
Very good
4,257 reviews

Crew

8.6

Overall

8.0

Entertainment

7.6

Food

7.0

Boarding

8.2

Comfort

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
2,909 reviews
Southwest
8.0
Very good
4,257 reviews

Crew

8.6

Overall

8.0

Entertainment

7.6

Food

7.0

Boarding

8.2

Comfort

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. 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 $101. 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 - Saint Thomas Island Cyril E King 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 julio 7, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$100Average$241FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$141Average$393FlexibilityNo cancel feeOn-time65%
DeltaCheapest$235Average$492FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$238Average$568FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$245Average$557FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$280Average$640FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$284Average$554FlexibilityNo cancel feeOn-time71%
Air CanadaCheapest$446Average$583FlexibilityNo cancel feeOn-time67%

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