Caribbean

$116+ 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 8/30. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — SJU
Jun 22 — Jun 291
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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 May 23, 2026.

This United Airlines deal was found by Cheapflights users on 5/21. 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.
Sat 8/299:00 am
PIT
-
STT
1 stop6h 43m
United Airlines
Sat 9/54:45 pm
STT
-
PIT
1 stop6h 45m
United Airlines
Deal found 5/21$250
This American Airlines deal was found by Cheapflights users on 5/21. 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.
Sat 8/296:52 am
PIT
-
STT
1 stop8h 09m
American Airlines
Sat 9/52:00 pm
STT
-
PIT
1 stop9h 50m
American Airlines
Deal found 5/21$275
This American Airlines deal was found by Cheapflights users on 5/20. 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.
Sat 8/226:14 am
PIT
-
STT
1 stop6h 38m
American Airlines
Sat 8/291:49 pm
STT
-
PIT
1 stop10h 05m
American Airlines
Deal found 5/20$290
This American Airlines deal was found by Cheapflights users on 5/21. 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 8/195:40 pm
PIT
-
STT
2 stops19h 12m
American Airlines
Mon 8/244:42 pm
STT
-
PIT
2 stops17h 42m
American Airlines
Deal found 5/21$295
This Kiwi.com deal was found by Cheapflights users on 5/20. 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.
Mon 8/36:00 am
PIT
-
SJU
1 stop8h 00m
Multiple Airlines
Thu 8/136:45 am
SJU
-
PIT
1 stop16h 01m
Multiple Airlines
Deal found 5/20$311
This United Airlines deal was found by Cheapflights users on 5/18. 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.
Tue 11/106:10 am
PIT
-
GCM
1 stop10h 20m
United Airlines
Fri 11/205:45 pm
GCM
-
PIT
2 stops16h 13m
United Airlines
Deal found 5/18$316
This United Airlines deal was found by Cheapflights users on 5/19. 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.
Fri 5/296:10 am
PIT
-
GCM
1 stop7h 20m
United Airlines
Mon 6/11:35 pm
GCM
-
PIT
1 stop9h 24m
United Airlines
Deal found 5/19$317
This Kiwi.com deal was found by Cheapflights users on 5/18. 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 6/412:04 pm
PIT
-
SJU
1 stop26h 29m
Multiple Airlines
Sat 6/67:00 am
SJU
-
PIT
1 stop28h 41m
Multiple Airlines
Deal found 5/18$317
This American Airlines deal was found by Cheapflights users on 5/20. 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.
Mon 8/247:41 am
PIT
-
SJU
1 stop16h 18m
American Airlines
Tue 8/2510:33 am
SJU
-
PIT
2 stops10h 27m
American Airlines
Deal found 5/20$318
This American Airlines deal was found by Cheapflights users on 5/22. 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 11/106:41 am
PIT
-
GCM
1 stop5h 59m
American Airlines
Fri 11/201:00 pm
GCM
-
PIT
1 stop10h 38m
American Airlines
Deal found 5/22$321
This Kiwi.com deal was found by Cheapflights users on 5/19. 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.
Mon 6/16:00 am
PIT
-
SJU
1 stop8h 33m
Multiple Airlines
Wed 6/37:00 am
SJU
-
PIT
1 stop28h 41m
Multiple Airlines
Deal found 5/19$322
This JetBlue deal was found by Cheapflights users on 5/20. 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.
Mon 9/286:00 am
PIT
-
PUJ
1 stop6h 45m
JetBlue
Wed 10/71:50 pm
PUJ
-
PIT
1 stop7h 33m
JetBlue
Deal found 5/20$322

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 May 23, 2026.

Round-trip from

$250
(United Airlines)

One-way from

$116
(American Airlines)

Popular in

December

Cheapest in

October

Average price

$366
From Pittsburgh to Caribbean
One-way flight from Pittsburgh to Caribbean
Highest demand for flights based on searches. 4% potential increase in price ($17 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
Average for round-trip flights in May 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 May 23, 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

PittsburghGeorge Town

PIT - GCM

PITGCM

Pittsburgh

Tue 11/10

6:10 am-4:30 pm

1 stop10h 20m

George Town Owen Roberts Intl

Fri 11/20

5:45 pm-9:58 am

2 stops16h 13m

$316

PittsburghGeorge Town

PIT - GCM

PITGCM

Pittsburgh

Fri 6/5

5:40 am-11:54 am

1 stop7h 14m

George Town Owen Roberts Intl

Mon 6/8

12:59 pm-12:55 am

1 stop10h 56m

$317

PittsburghGeorge Town

PIT - GCM

PITGCM

Pittsburgh

Sat 6/6

5:40 am-11:54 am

1 stop7h 14m

George Town Owen Roberts Intl

Wed 6/10

12:59 pm-12:55 am

1 stop10h 56m

$317

PittsburghPunta Cana

PIT - PUJ

PITPUJ

Pittsburgh

Mon 8/24

6:00 am-12:55 pm

1 stop6h 55m

Punta Cana

Thu 8/27

2:05 pm-9:26 pm

1 stop7h 21m

$322

PittsburghGeorge Town

PIT - GCM

PITGCM

Pittsburgh

Thu 6/4

6:38 am-11:30 am

1 stop5h 52m

George Town Owen Roberts Intl

Mon 6/8

5:12 pm-12:08 pm

2 stops17h 56m

$326

PittsburghGeorge Town

PIT - GCM

PITGCM

Pittsburgh

Fri 6/5

7:33 pm-10:22 am

1 stop15h 49m

George Town Owen Roberts Intl

Mon 6/8

5:12 pm-12:08 pm

2 stops17h 56m

$326

PittsburghGeorge Town

PIT - GCM

PITGCM

Pittsburgh

Wed 6/3

6:37 am-11:30 am

1 stop5h 53m

George Town Owen Roberts Intl

Tue 6/9

12:01 pm-11:58 pm

1 stop10h 57m

$326

PittsburghGeorge Town

PIT - GCM

PITGCM

Pittsburgh

Sat 6/6

7:59 pm-11:30 am

1 stop16h 31m

George Town Owen Roberts Intl

Wed 6/10

5:12 pm-10:16 am

2 stops16h 04m

$326

PittsburghPunta Cana

PIT - PUJ

PITPUJ

Pittsburgh

Thu 8/27

6:10 am-12:40 pm

1 stop6h 30m

Punta Cana

Mon 8/31

3:35 pm-9:36 am

1 stop18h 01m

$338

PittsburghNassau

PIT - NAS

PITNAS

Pittsburgh

Tue 9/1

6:00 am-1:48 pm

1 stop7h 48m

Nassau Intl

Wed 9/2

3:02 pm-9:26 pm

1 stop6h 24m

$340

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/22

Showing 1-10 of 60 resultsSorted by cheapest first
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6

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, August is the cheapest month in which you can book a flight from Pittsburgh to Caribbean (average of $109). Flying from Pittsburgh to Caribbean in October is currently the most expensive (average of $1,350). 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.

How far ahead should I book a flight from Pittsburgh to Caribbean?

Booking 4 days in advance of your planned departure date is, on average, the best time to get cheap flights from Pittsburgh to Caribbean. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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 23, 2026.
Peruse reviews from past customers who have flown with Southwest,Delta, andUnited 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.

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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, Delta, and JetBlue can get you from Pittsburgh to Caribbean in just under 6h 55m. Your travel time can differ by up to 3h 25m. The distance between Pittsburgh and Caribbean is about 1670 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 Frontier, 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, August is the cheapest month in which you can book a flight from Pittsburgh to Caribbean (average of $109). Flying from Pittsburgh to Caribbean in October is currently the most expensive (average of $1,350). 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.

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 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$123Average$428FlexibilityNo cancel feeOn-time65%
FrontierCheapest$135Average$319FlexibilityNo cancel feeOn-time62%
DeltaCheapest$141Average$443FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$141Average$487FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$225Average$614FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$225Average$483FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$232Average$551FlexibilityNo cancel feeOn-time71%
Air CanadaCheapest$406Average$492FlexibilityNo cancel feeOn-time67%

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