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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 11/9. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — SJU
Nov 13 — Nov 201
Thu 11/13
Thu 11/20
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 October 14, 2025.

Round-trip from

$213
(CheapOair)

One-way from

$113
(American Airlines)

Popular in

December

Cheapest in

September

Average price

$305

Good round-trip deal

$466 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. 6% potential increase in price ($27 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Price to beat on a round-trip 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 October 14, 2025.

This CheapOair deal was found by Cheapflights users on 10/12. 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.
Wed 11/57:10 amPIT - SJU
1 stop13h 54mJetBlue
Wed 11/126:45 amSJU - PIT
1 stop17h 03mJetBlue
Deal found 10/12$213
This Priceline deal was found by Cheapflights users on 10/11. 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.
Fri 11/77:10 amPIT - SJU
1 stop26h 25mJetBlue
Tue 11/1111:30 amSJU - PIT
1 stop12h 18mJetBlue
Deal found 10/11$220
This American Airlines deal was found by Cheapflights users on 10/12. 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 12/94:05 pmPIT - SJU
1 stop17h 04mAmerican Airlines
Tue 12/165:56 pmSJU - PIT
1 stop7h 08mAmerican Airlines
Deal found 10/12$225
This CheapOair deal was found by Cheapflights users on 10/14. 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 11/137:10 amPIT - SJU
1 stop12h 08mJetBlue
Wed 11/1912:30 pmSJU - PIT
1 stop12h 28mJetBlue
Deal found 10/14$229
This Priceline deal was found by Cheapflights users on 10/14. 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.
Mon 11/107:10 amPIT - SJU
1 stop26h 25mJetBlue
Wed 11/191:59 amSJU - PIT
1 stop8h 51mJetBlue
Deal found 10/14$236
This United Airlines deal was found by Cheapflights users on 10/11. 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 10/316:00 amPIT - SJU
1 stop7h 40mUnited Airlines
Mon 11/38:10 amSJU - PIT
1 stop8h 10mUnited Airlines
Deal found 10/11$240
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 10/256:51 pmPIT - SJU
1 stop16h 05mMultiple Airlines
Sat 11/15:51 pmSJU - PIT
1 stop13h 30mMultiple Airlines
Deal found 10/12$241
This JetBlue deal was found by Cheapflights users on 10/13. 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.
Tue 10/285:37 pmPIT - SJU
1 stop9h 11mJetBlue
Sat 11/17:00 amSJU - PIT
1 stop9h 42mJetBlue
Deal found 10/13$242
This Priceline deal was found by Cheapflights users on 10/14. 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.
Wed 10/295:37 pmPIT - SJU
1 stop9h 11mJetBlue
Sun 11/211:30 amSJU - PIT
1 stop12h 16mJetBlue
Deal found 10/14$244
This United Airlines deal was found by Cheapflights users on 10/13. 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.
Wed 11/1211:00 amPIT - SJU
2 stops12h 36mUnited Airlines
Wed 11/195:50 pmSJU - PIT
1 stop6h 37mUnited Airlines
Deal found 10/13$249
This Priceline deal was found by Cheapflights users on 10/12. 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.
Wed 10/296:00 amPIT - SJU
1 stop14h 54mJetBlue
Fri 10/316:20 pmSJU - PIT
1 stop22h 22mJetBlue
Deal found 10/12$250
This Kiwi.com deal was found by Cheapflights users on 10/13. 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.
Fri 11/1410:06 pmPIT - SJU
1 stop28h 27mMultiple Airlines
Wed 11/196:17 pmSJU - PIT
1 stop13h 49mMultiple Airlines
Deal found 10/13$253

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 October 14, 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

Mon 11/17

6:00 am-5:26 pm

1 stop10h 26m

San Juan Luis Munoz Marin Intl

Wed 11/19

7:15 am-4:54 pm

1 stop10h 39m

$225

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Sun 12/7

12:01 pm-11:20 pm

1 stop10h 19m

San Juan Luis Munoz Marin Intl

Wed 12/10

3:32 pm-12:19 am

1 stop9h 47m

$240

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Tue 12/9

12:00 pm-11:20 pm

1 stop10h 20m

San Juan Luis Munoz Marin Intl

Thu 12/11

7:19 am-5:00 pm

1 stop10h 41m

$240

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Mon 11/17

6:00 am-5:26 pm

1 stop10h 26m

San Juan Luis Munoz Marin Intl

Tue 11/18

6:36 pm-12:21 am

1 stop6h 45m

$240

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Tue 11/11

5:37 pm-3:48 am

1 stop9h 11m

San Juan Luis Munoz Marin Intl

Fri 11/14

3:34 pm-11:58 pm

1 stop9h 24m

$242

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Tue 10/28

5:37 pm-2:48 am

1 stop9h 11m

San Juan Luis Munoz Marin Intl

Sat 11/1

7:00 am-4:42 pm

1 stop9h 42m

$242

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Mon 10/20

6:00 am-2:54 pm

1 stop8h 54m

San Juan Luis Munoz Marin Intl

Tue 10/28

7:00 am-11:58 pm

1 stop16h 58m

$262

PittsburghSaint Thomas Island

PIT - STT

PITSTT

Pittsburgh

Sun 1/4

5:54 pm-12:05 pm

2 stops17h 11m

Saint Thomas Island Cyril E King

Sun 1/11

6:39 pm-11:09 am

1 stop17h 30m

$265

PittsburghSaint Thomas Island

PIT - STT

PITSTT

Pittsburgh

Wed 12/31

6:51 pm-12:40 pm

1 stop16h 49m

Saint Thomas Island Cyril E King

Thu 1/8

6:39 pm-9:58 am

2 stops16h 19m

$265

PittsburghSaint Thomas Island

PIT - STT

PITSTT

Pittsburgh

Tue 1/6

6:44 pm-3:06 pm

2 stops19h 22m

Saint Thomas Island Cyril E King

Sun 1/11

6:39 pm-11:09 am

1 stop17h 30m

$265

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/14

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, February is the cheapest month in which you can book a flight from Pittsburgh to Caribbean (average of $200). Flying from Pittsburgh to Caribbean in June is currently the most expensive (average of $307). 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 October 14, 2025.

It’s typically best to fly out from Pittsburgh to Caribbean in the evening. Doing so could potentially save you 28% on the flight price compared to flying in the afternoon, which is usually more expensive.

What is the cheapest day to fly from Pittsburgh to Caribbean?

Use this chart to determine the cheapest time to fly round-trip from Pittsburgh to Caribbean. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Pittsburgh to Caribbean flight should consider departing on Sunday evenings when fares are most often at their lowest. Saturday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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 October 14, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and United 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
4,238 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,975 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,976 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,042 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,096 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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?

    Delta, JetBlue, and American Airlines can get you from Pittsburgh to Caribbean in just under 9h 11m. Your travel time can differ by up to 8h. The distance between Pittsburgh and Caribbean is about 1742 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 American Airlines, with whom users have recently found tickets for as low as $113. However, be on the lookout for offers from Spirit Airlines and JetBlue, 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 - Punta Cana or Pittsburgh - Oranjestad Reina Beatrix 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, February is the cheapest month in which you can book a flight from Pittsburgh to Caribbean (average of $200). Flying from Pittsburgh to Caribbean in June is currently the most expensive (average of $307). 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 October 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$159Average$410FlexibilityNo cancel feeOn-time65%
FrontierCheapest$160Average$315FlexibilityNo cancel feeOn-time62%
DeltaCheapest$213Average$504FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$225Average$642FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$247Average$540FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$277Average$571FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$281Average$528FlexibilityNo cancel feeOn-time62%
Air CanadaCheapest$446Average$583FlexibilityNo cancel feeOn-time67%

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