Caribbean

$127+ 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 6/1. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — SJU
Jun 9 — Jun 161
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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 10, 2026.

This American Airlines deal was found by Cheapflights users on 5/6. 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.
Sat 8/297:39 pm
PIT
-
STT
2 stops17h 13m
American Airlines
Sat 9/53:43 pm
STT
-
PIT
1 stop8h 09m
American Airlines
Deal found 5/6$250
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/189:14 pm
PIT
-
SJU
1 stop12h 50m
Multiple Airlines
Thu 5/217:00 am
SJU
-
PIT
1 stop27h 48m
Multiple Airlines
Deal found 5/5$287
This American Airlines deal was found by Cheapflights users on 5/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/166:14 am
PIT
-
STT
1 stop9h 38m
American Airlines
Fri 8/214:42 pm
STT
-
PIT
2 stops17h 42m
American Airlines
Deal found 5/9$290
This Kiwi.com deal was found by Cheapflights users on 5/6. 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 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
Sat 6/67:00 am
SJU
-
PIT
1 stop28h 41m
Multiple Airlines
Deal found 5/6$291
This CheapOair deal was found by Cheapflights users on 5/5. 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.
Thu 8/207:59 pm
PIT
-
SJU
1 stop12h 10m
Frontier
Wed 8/264:05 pm
SJU
-
PIT
1 stop26h 59m
Frontier
Deal found 5/5$295
This Priceline deal was found by Cheapflights users on 5/8. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/17:10 pm
PIT
-
SJU
1 stop7h 01m
Frontier
Wed 8/56:31 pm
SJU
-
PIT
1 stop23h 44m
Frontier
Deal found 5/8$301
This Delta deal was found by Cheapflights users on 5/8. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/287:20 am
PIT
-
SJU
1 stop9h 18m
Delta
Tue 8/42:59 pm
SJU
-
PIT
1 stop9h 37m
Delta
Deal found 5/8$302
This Super.com deal was found by Cheapflights users on 5/9. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/246:00 am
PIT
-
PUJ
1 stop6h 55m
JetBlue
Fri 8/282:05 pm
PUJ
-
PIT
1 stop7h 21m
JetBlue
Deal found 5/9$302
This Frontier deal was found by Cheapflights users on 5/6. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/187:10 pm
PIT
-
SJU
1 stop12h 47m
Frontier
Fri 7/246:00 am
SJU
-
PIT
1 stop12h 15m
Frontier
Deal found 5/6$303
This Kiwi.com deal was found by Cheapflights users on 5/8. 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.
Mon 8/36:00 am
PIT
-
SJU
1 stop8h 34m
Multiple Airlines
Thu 8/67:00 am
SJU
-
PIT
1 stop15h 46m
Multiple Airlines
Deal found 5/8$306
This American Airlines deal was found by Cheapflights users on 5/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/97:07 am
PIT
-
SJU
2 stops11h 03m
American Airlines
Tue 10/68:35 am
SJU
-
PIT
2 stops9h 22m
American Airlines
Deal found 5/7$307
This American Airlines deal was found by Cheapflights users on 5/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/126:56 pm
PIT
-
STT
2 stops16h 39m
American Airlines
Thu 5/2111:43 am
STT
-
PIT
1 stop9h 04m
American Airlines
Deal found 5/5$315

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 10, 2026.

Round-trip from

$250
(American Airlines)

One-way from

$127
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$367
From Pittsburgh to Caribbean
One-way flight from Pittsburgh to Caribbean
Highest demand for flights based on searches. 5% potential increase in price ($22 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease ($8 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 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

Sun 8/16

6:14 am-3:52 pm

1 stop9h 38m

Saint Thomas Island Cyril E King

Fri 8/21

4:42 pm-10:24 am

2 stops17h 42m

$290

PittsburghWillemstad

PIT - CUR

PITCUR

Pittsburgh

Sat 9/19

6:30 am-1:40 pm

1 stop7h 10m

Willemstad Hato Int.

Sat 9/26

2:50 pm-9:58 am

2 stops19h 08m

$343

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Wed 10/7

5:30 am-4:33 pm

1 stop11h 03m

San Juan Luis Munoz Marin Intl

Wed 10/14

7:30 am-5:05 pm

1 stop9h 35m

$353

PittsburghNassau

PIT - NAS

PITNAS

Pittsburgh

Tue 6/23

6:49 am-2:57 pm

1 stop8h 08m

Nassau Intl

Fri 6/26

3:59 pm-11:59 pm

1 stop8h 00m

$376

PittsburghNassau

PIT - NAS

PITNAS

Pittsburgh

Sun 6/28

8:36 am-2:57 pm

1 stop6h 21m

Nassau Intl

Fri 7/3

2:53 pm-11:59 pm

1 stop9h 06m

$376

PittsburghOranjestad

PIT - AUA

PITAUA

Pittsburgh

Fri 8/28

6:00 am-1:34 pm

1 stop7h 34m

Oranjestad Reina Beatrix

Fri 9/4

2:39 pm-9:26 pm

1 stop6h 47m

$383

PittsburghSimpson Bay

PIT - SXM

PITSXM

Pittsburgh

Sun 9/20

7:00 am-1:50 pm

1 stop6h 50m

Simpson Bay Princess Juliana

Thu 9/24

3:20 pm-12:22 am

1 stop9h 02m

$383

PittsburghSanto Domingo

PIT - SDQ

PITSDQ

Pittsburgh

Mon 6/1

11:54 am-12:41 am

1 stop12h 47m

Santo Domingo Las Americas

Tue 6/16

6:06 am-5:06 pm

1 stop11h 00m

$386

PittsburghSimpson Bay

PIT - SXM

PITSXM

Pittsburgh

Sat 5/30

7:59 pm-3:42 pm

2 stops19h 43m

Simpson Bay Princess Juliana

Fri 6/5

4:43 pm-8:54 am

2 stops16h 11m

$388

PittsburghSimpson Bay

PIT - SXM

PITSXM

Pittsburgh

Sat 10/10

8:19 pm-3:05 pm

2 stops18h 46m

Simpson Bay Princess Juliana

Sat 10/17

4:30 pm-12:32 pm

2 stops20h 02m

$388

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/9

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

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

Booking 67 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.

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 $1,414). 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.

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 10, 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

Food

7.0

Comfort

8.0

Boarding

8.1

Crew

8.6

Overall

8.0

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

Food

7.0

Comfort

8.0

Boarding

8.1

Crew

8.6

Overall

8.0

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

Food

7.0

Comfort

8.0

Boarding

8.1

Crew

8.6

Overall

8.0

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

Food

7.0

Comfort

8.0

Boarding

8.1

Crew

8.6

Overall

8.0

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

Food

7.0

Comfort

8.0

Boarding

8.1

Crew

8.6

Overall

8.0

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

Food

7.0

Comfort

8.0

Boarding

8.1

Crew

8.6

Overall

8.0

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?

    American Airlines, United Airlines, and Delta can get you from Pittsburgh to Caribbean in just under 7h 10m. Your travel time can differ by up to 3h 53m. The distance between Pittsburgh and Caribbean is about 2071 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 $1,414). 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 10, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$123Average$446FlexibilityNo cancel feeOn-time65%
FrontierCheapest$135Average$318FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$141Average$492FlexibilityNo cancel feeOn-time62%
DeltaCheapest$144Average$441FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$225Average$613FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$225Average$484FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$232Average$544FlexibilityNo cancel feeOn-time71%
Air CanadaCheapest$406Average$492FlexibilityNo cancel feeOn-time67%

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