Caribbean

$88+ 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 5/10. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — SJU
May 10 — May 171
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Cheap 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 April 10, 2026.

This CheapOair deal was found by Cheapflights users on 4/5. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/266:15 pm
PIT
-
SJU
1 stop25h 07m
Spirit Airlines
Thu 4/3012:57 pm
SJU
-
PIT
1 stop11h 02m
Spirit Airlines
Deal found 4/5$226
This Kiwi.com deal was found by Cheapflights users on 4/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/236:15 pm
PIT
-
SJU
1 stop18h 08m
Multiple Airlines
Thu 4/3012:57 pm
SJU
-
PIT
1 stop11h 02m
Multiple Airlines
Deal found 4/7$227
This CheapOair deal was found by Cheapflights users on 4/7. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/1812:53 pm
PIT
-
SJU
1 stop13h 08m
Multiple Airlines
Sat 5/212:57 pm
SJU
-
PIT
1 stop11h 02m
Multiple Airlines
Deal found 4/7$228
This Mytrip deal was found by Cheapflights users on 4/6. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/206:35 am
PIT
-
SJU
1 stop12h 47m
Spirit Airlines
Sat 4/255:45 am
SJU
-
PIT
2 stops18h 14m
Spirit Airlines
Deal found 4/6$229
This Delta deal was found by Cheapflights users on 4/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/105:40 am
PIT
-
STT
1 stop9h 37m
Delta
Thu 5/213:01 pm
STT
-
PIT
1 stop9h 44m
Delta
Deal found 4/6$230
This CheapOair deal was found by Cheapflights users on 4/7. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/236:15 pm
PIT
-
SJU
1 stop25h 07m
Spirit Airlines
Thu 4/3012:57 pm
SJU
-
PIT
1 stop11h 02m
Spirit Airlines
Deal found 4/7$231
This CheapOair deal was found by Cheapflights users on 4/6. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/296:00 am
PIT
-
SJU
1 stop12h 59m
Multiple Airlines
Sat 6/63:58 pm
SJU
-
PIT
1 stop27h 22m
Multiple Airlines
Deal found 4/6$235
This CheapOair deal was found by Cheapflights users on 4/7. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/249:44 am
PIT
-
SJU
1 stop13h 04m
Multiple Airlines
Wed 4/2912:57 pm
SJU
-
PIT
1 stop11h 02m
Multiple Airlines
Deal found 4/7$237
This Kiwi.com deal was found by Cheapflights users on 4/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/256:15 pm
PIT
-
SJU
1 stop18h 08m
Multiple Airlines
Tue 4/287:01 pm
SJU
-
PIT
2 stops28h 58m
Multiple Airlines
Deal found 4/8$239
This Delta deal was found by Cheapflights users on 4/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/125:40 am
PIT
-
STT
1 stop9h 37m
Delta
Wed 5/203:01 pm
STT
-
PIT
1 stop9h 44m
Delta
Deal found 4/9$250
This Delta deal was found by Cheapflights users on 4/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/156:00 am
PIT
-
STT
1 stop7h 51m
Delta
Mon 4/201:59 pm
STT
-
PIT
1 stop7h 37m
Delta
Deal found 4/5$255
This FlightHub deal was found by Cheapflights users on 4/8. 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.
Sat 5/26:35 am
PIT
-
SXM
1 stop7h 02m
Spirit Airlines
Sat 5/92:35 pm
SXM
-
PIT
1 stop7h 32m
Spirit Airlines
Deal found 4/8$263

Find flight deals from Pittsburgh to Caribbean

Keep the following information in mind while searching for Pittsburgh to Caribbean flight deals. Data was last updated April 10, 2026.

Round-trip from

$226
(CheapOair)

One-way from

$88
(Frontier)

Popular in

December

Cheapest in

October

Average price

$363
From Pittsburgh to Caribbean
One-way flight from Pittsburgh to Caribbean
Highest demand for flights based on searches. 6% potential increase in price ($27 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Average for round-trip flights in April 2026

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 April 10, 2026.
Use the filters below to find and compare flights from Pittsburgh to Caribbean that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PittsburghSaint Thomas Island

PIT - STT

PITSTT

Pittsburgh

Mon 4/20

7:00 am-3:31 pm

1 stop8h 31m

Saint Thomas Island Cyril E King

Fri 4/24

4:45 pm-11:20 pm

1 stop6h 35m

$230

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Tue 7/7

7:20 am-4:38 pm

1 stop9h 18m

San Juan Luis Munoz Marin Intl

Fri 7/10

7:30 am-3:50 pm

1 stop8h 20m

$282

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Tue 7/28

11:58 am-11:53 pm

1 stop11h 55m

San Juan Luis Munoz Marin Intl

Tue 8/4

2:42 pm-12:42 am

1 stop10h 00m

$282

PittsburghSaint Thomas Island

PIT - STT

PITSTT

Pittsburgh

Mon 5/11

5:40 am-3:17 pm

1 stop9h 37m

Saint Thomas Island Cyril E King

Tue 5/19

3:01 pm-12:45 am

1 stop9h 44m

$300

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Tue 5/5

6:00 am-4:23 pm

1 stop10h 23m

San Juan Luis Munoz Marin Intl

Tue 5/12

5:43 pm-12:45 am

1 stop7h 02m

$313

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Fri 7/24

7:20 am-4:38 pm

1 stop9h 18m

San Juan Luis Munoz Marin Intl

Sun 8/2

5:56 pm-12:50 am

1 stop6h 54m

$313

PittsburghSaint Thomas Island

PIT - STT

PITSTT

Pittsburgh

Sat 5/2

7:35 pm-11:35 am

2 stops16h 00m

Saint Thomas Island Cyril E King

Tue 5/5

3:30 pm-8:00 am

2 stops16h 30m

$318

PittsburghWillemstad

PIT - CUR

PITCUR

Pittsburgh

Wed 5/6

6:00 am-1:37 pm

1 stop7h 37m

Willemstad Hato Int.

Thu 5/7

2:42 pm-12:07 am

1 stop9h 25m

$357

PittsburghOranjestad

PIT - AUA

PITAUA

Pittsburgh

Tue 5/5

7:47 pm-12:40 pm

2 stops16h 53m

Oranjestad Reina Beatrix

Tue 5/12

4:30 pm-9:31 am

1 stop17h 01m

$357

PittsburghSimpson Bay

PIT - SXM

PITSXM

Pittsburgh

Tue 6/2

6:00 am-1:54 pm

1 stop7h 54m

Simpson Bay Princess Juliana

Sat 6/6

6:00 pm-11:33 am

1 stop17h 33m

$358

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/9

Showing 1-10 of 60 resultsSorted by cheapest first
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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, April is the cheapest month in which you can book a flight from Pittsburgh to Caribbean (average of $145). Flying from Pittsburgh to Caribbean in July is currently the most expensive (average of $251). 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 April 10, 2026.

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 April 10, 2026.
Peruse reviews from past customers who have flown with Delta,United Airlines, andJetBlue 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.

Crew

8.5

Food

7.2

Boarding

8.1

Comfort

7.9

Entertainment

7.8

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Crew

8.5

Food

7.2

Boarding

8.1

Comfort

7.9

Entertainment

7.8

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Crew

8.5

Food

7.2

Boarding

8.1

Comfort

7.9

Entertainment

7.8

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Crew

8.5

Food

7.2

Boarding

8.1

Comfort

7.9

Entertainment

7.8

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Crew

8.5

Food

7.2

Boarding

8.1

Comfort

7.9

Entertainment

7.8

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Crew

8.5

Food

7.2

Boarding

8.1

Comfort

7.9

Entertainment

7.8

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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.

  • How long is the flight from Pittsburgh to Caribbean?

    United Airlines, Spirit Airlines, and Delta can get you from Pittsburgh to Caribbean in just under 7h 02m. Your travel time can differ by up to 2h 16m. The distance between Pittsburgh and Caribbean is about 1855 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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 $60. However, be on the lookout for offers from United Airlines 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?

  • 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, April is the cheapest month in which you can book a flight from Pittsburgh to Caribbean (average of $145). Flying from Pittsburgh to Caribbean in July is currently the most expensive (average of $251). 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

Browse thousands of different options on Cheapflights for your next trip

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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.

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 April 10, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$135Average$315FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$141Average$462FlexibilityNo cancel feeOn-time62%
DeltaCheapest$152Average$488FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$153Average$408FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$225Average$629FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$225Average$489FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$232Average$563FlexibilityNo cancel feeOn-time71%
Air CanadaCheapest$406Average$494FlexibilityNo cancel feeOn-time67%

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