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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 10/7. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — SJU
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
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 September 15, 2025.

Round-trip from

$208
(Kiwi.com)

One-way from

$113
(Delta)

Popular in

December

Cheapest in

September

Average price

$285

Good round-trip deal

$430 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. 3% potential increase in price ($15 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 September 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 September 15, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/198:00 amPIT - SJU
1 stop8h 54mMultiple Airlines
Wed 12/39:30 pmSJU - PIT
1 stop23h 20mMultiple Airlines
Deal found 9/14$208
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/172:45 pmPIT - SJU
1 stop9h 44mFrontier
Thu 10/231:59 amSJU - PIT
1 stop11h 51mFrontier
Deal found 9/13$219
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/172:45 pmPIT - SJU
1 stop9h 44mFrontier
Sun 10/262:12 amSJU - PIT
1 stop12h 48mFrontier
Deal found 9/13$222
This Delta deal was found by Cheapflights users on 9/15. 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.
Mon 10/205:11 pmPIT - SJU
1 stop6h 45mDelta
Wed 10/227:18 amSJU - PIT
1 stop9h 35mDelta
Deal found 9/15$225
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
Thu 10/232:26 pmPIT - SJU
1 stop10h 03mFrontier
Sun 10/262:12 amSJU - PIT
1 stop12h 48mFrontier
Deal found 9/13$228
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/156:45 amPIT - SJU
2 stops19h 17mMultiple Airlines
Wed 10/224:51 pmSJU - PIT
1 stop24h 38mMultiple Airlines
Deal found 9/14$235
This CheapOair deal was found by Cheapflights users on 9/14. 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.
Tue 12/97:10 amPIT - SJU
1 stop10h 03mJetBlue
Tue 12/164:26 pmSJU - PIT
1 stop7h 20mJetBlue
Deal found 9/14$237
This Cheapflightsfares deal was found by Cheapflights users on 9/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/166:51 pmPIT - STT
1 stop15h 05mSpirit Airlines
Mon 10/2011:01 amSTT - PIT
1 stop12h 15mSpirit Airlines
Deal found 9/13$239
This Delta deal was found by Cheapflights users on 9/15. 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.
Fri 10/177:21 amPIT - SJU
1 stop9h 04mDelta
Wed 10/227:18 amSJU - PIT
1 stop9h 35mDelta
Deal found 9/15$240
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
Wed 10/226:45 amPIT - SJU
2 stops19h 17mMultiple Airlines
Sun 10/262:12 amSJU - PIT
1 stop12h 48mMultiple Airlines
Deal found 9/13$243
This Expedia deal was found by Cheapflights users on 9/13. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/256:51 pmPIT - STT
1 stop15h 05mSpirit Airlines
Fri 10/3111:01 amSTT - PIT
1 stop6h 45mSpirit Airlines
Deal found 9/13$243
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/206:45 amPIT - SJU
1 stop8h 31mMultiple Airlines
Fri 10/249:00 amSJU - PIT
1 stop14h 16mMultiple Airlines
Deal found 9/15$245

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 September 15, 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

Wed 10/29

11:55 am-9:22 pm

2 stops9h 27m

San Juan Luis Munoz Marin Intl

Thu 10/30

1:05 am-9:38 am

1 stop8h 33m

$225

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Sun 10/26

5:50 am-3:50 pm

1 stop10h 00m

San Juan Luis Munoz Marin Intl

Sun 11/2

5:55 pm-11:45 pm

1 stop6h 50m

$225

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Wed 10/22

7:21 am-4:25 pm

1 stop9h 04m

San Juan Luis Munoz Marin Intl

Tue 10/28

7:00 am-4:53 pm

1 stop9h 53m

$225

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Mon 10/20

5:11 pm-11:56 pm

1 stop6h 45m

San Juan Luis Munoz Marin Intl

Tue 10/28

7:00 am-4:53 pm

1 stop9h 53m

$225

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Wed 12/10

7:10 am-3:30 pm

1 stop7h 20m

San Juan Luis Munoz Marin Intl

Mon 12/15

4:40 pm-9:55 pm

1 stop6h 15m

$225

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Tue 2/24

6:00 am-5:12 pm

1 stop10h 12m

San Juan Luis Munoz Marin Intl

Wed 3/4

7:00 am-4:40 pm

1 stop10h 40m

$225

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Tue 10/21

5:11 pm-11:56 pm

1 stop6h 45m

San Juan Luis Munoz Marin Intl

Tue 10/28

7:00 am-4:53 pm

1 stop9h 53m

$225

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Tue 10/21

11:39 am-9:59 pm

1 stop10h 20m

San Juan Luis Munoz Marin Intl

Sat 10/25

5:43 pm-12:32 am

1 stop6h 49m

$225

PittsburghSaint Thomas Island

PIT - STT

PITSTT

Pittsburgh

Thu 10/16

6:51 pm-9:56 am

1 stop15h 05m

Saint Thomas Island Cyril E King

Mon 10/20

11:01 am-11:16 pm

1 stop12h 15m

$239

PittsburghSaint Thomas Island

PIT - STT

PITSTT

Pittsburgh

Mon 10/20

6:51 pm-9:56 am

1 stop15h 05m

Saint Thomas Island Cyril E King

Sat 10/25

11:01 am-5:46 pm

1 stop6h 45m

$239

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

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, 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 September 15, 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 September 15, 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
4,245 reviews

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Food

7.0

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
4,245 reviews
Southwest
8.0
Very good
4,245 reviews

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Food

7.0

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
7,956 reviews
Southwest
8.0
Very good
4,245 reviews

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Food

7.0

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
8,931 reviews
Southwest
8.0
Very good
4,245 reviews

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Food

7.0

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
10,000 reviews
Southwest
8.0
Very good
4,245 reviews

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Food

7.0

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
8,016 reviews
Southwest
8.0
Very good
4,245 reviews

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Food

7.0

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?

    Southwest, Delta, and Spirit Airlines can get you from Pittsburgh to Caribbean in just under 9h 04m. Your travel time can differ by up to 6h 01m. 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 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?

    When deciding which route to take from Pittsburgh to Caribbean consider Pittsburgh - San Juan Luis Munoz Marin Intl, Pittsburgh - Oranjestad Reina Beatrix or Pittsburgh - Punta Cana 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$109Average$315FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$153Average$392FlexibilityNo cancel feeOn-time65%
DeltaCheapest$215Average$515FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$226Average$636FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$245Average$551FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$281Average$543FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$284Average$579FlexibilityNo cancel feeOn-time71%
Air CanadaCheapest$446Average$583FlexibilityNo cancel feeOn-time67%

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