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$112+ 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 1/15. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — SJU
Dec 14 — Dec 211
Sun 12/14
Sun 12/21
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 November 14, 2025.

Round-trip from

$254
(Flightnetwork)

One-way from

$112
(United Airlines)

Popular in

December

Cheapest in

October

Average price

$414

Good round-trip deal

$518 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. 11% potential increase in price ($54 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in November 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 November 14, 2025.

This Flightnetwork deal was found by Cheapflights users on 11/14. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/77:59 amPIT - GCM
1 stop5h 46mSpirit Airlines
Sat 12/135:56 pmGCM - PIT
1 stop16h 02mSpirit Airlines
Deal found 11/14$254
This American Airlines deal was found by Cheapflights users on 11/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/298:35 pmPIT - SJU
1 stop7h 13mAmerican Airlines
Wed 12/32:36 pmSJU - PIT
2 stops8h 54mAmerican Airlines
Deal found 11/14$255
This Priceline deal was found by Cheapflights users on 11/14. 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.
Thu 12/43:10 pmPIT - SJU
1 stop8h 39mFrontier
Fri 3/63:55 amSJU - PIT
1 stop6h 36mFrontier
Deal found 11/14$256
This Kiwi.com deal was found by Cheapflights users on 11/13. 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 12/1210:53 amPIT - SJU
1 stop12h 52mMultiple Airlines
Fri 12/196:00 amSJU - PIT
1 stop28h 58mMultiple Airlines
Deal found 11/13$258
This Mytrip deal was found by Cheapflights users on 11/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/87:10 amPIT - SJU
2 stops16h 35mSpirit Airlines
Thu 12/114:10 amSJU - PIT
1 stop6h 48mSpirit Airlines
Deal found 11/14$264
This United Airlines deal was found by Cheapflights users on 11/13. 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.
Sun 12/147:00 amPIT - STT
1 stop8h 18mUnited Airlines
Wed 12/172:15 pmSTT - PIT
2 stops10h 14mUnited Airlines
Deal found 11/13$265
This Kiwi.com deal was found by Cheapflights users on 11/13. 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.
Sun 12/710:53 amPIT - SJU
1 stop24h 39mMultiple Airlines
Tue 12/93:55 amSJU - PIT
1 stop17h 33mMultiple Airlines
Deal found 11/13$267
This Delta deal was found by Cheapflights users on 11/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/2410:10 amPIT - SJU
1 stop6h 16mDelta
Tue 12/26:38 pmSJU - PIT
1 stop6h 34mDelta
Deal found 11/13$268
This American Airlines deal was found by Cheapflights users on 11/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/297:40 amPIT - STT
1 stop7h 50mAmerican Airlines
Sat 12/66:17 pmSTT - PIT
1 stop6h 41mAmerican Airlines
Deal found 11/13$272
This American Airlines deal was found by Cheapflights users on 11/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/98:03 amPIT - SJU
2 stops8h 49mAmerican Airlines
Tue 12/162:36 pmSJU - PIT
2 stops9h 31mAmerican Airlines
Deal found 11/13$274
This Kiwi.com deal was found by Cheapflights users on 11/13. 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.
Sat 12/135:05 pmPIT - SJU
1 stop18h 27mMultiple Airlines
Sat 12/2010:09 pmSJU - PIT
2 stops44h 00mMultiple Airlines
Deal found 11/13$279
This Cheapflightsfares deal was found by Cheapflights users on 11/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/117:59 amPIT - AUA
1 stop6h 36mSpirit Airlines
Thu 12/184:40 pmAUA - PIT
1 stop7h 02mSpirit Airlines
Deal found 11/14$280

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 November 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

Sat 1/24

3:55 pm-11:00 pm

1 stop6h 05m

San Juan Luis Munoz Marin Intl

Sat 1/31

9:30 am-3:25 pm

1 stop6h 55m

$262

PittsburghSaint Thomas Island

PIT - STT

PITSTT

Pittsburgh

Fri 1/9

6:00 am-5:10 pm

1 stop10h 10m

Saint Thomas Island Cyril E King

Thu 1/15

6:15 pm-9:40 am

1 stop16h 25m

$264

PittsburghSaint Thomas Island

PIT - STT

PITSTT

Pittsburgh

Tue 1/6

6:00 am-3:04 pm

1 stop8h 04m

Saint Thomas Island Cyril E King

Mon 1/12

4:25 pm-11:06 pm

1 stop7h 41m

$265

PittsburghSaint Thomas Island

PIT - STT

PITSTT

Pittsburgh

Sun 12/14

7:00 am-4:18 pm

1 stop8h 18m

Saint Thomas Island Cyril E King

Wed 12/17

2:15 pm-11:29 pm

2 stops10h 14m

$265

PittsburghSaint Thomas Island

PIT - STT

PITSTT

Pittsburgh

Fri 1/2

7:00 pm-12:40 pm

2 stops16h 40m

Saint Thomas Island Cyril E King

Thu 1/8

6:39 pm-11:10 am

1 stop17h 31m

$265

PittsburghSaint Thomas Island

PIT - STT

PITSTT

Pittsburgh

Sun 12/14

5:00 am-3:42 pm

1 stop9h 42m

Saint Thomas Island Cyril E King

Fri 12/19

4:25 pm-11:54 pm

1 stop8h 29m

$265

PittsburghSaint Thomas Island

PIT - STT

PITSTT

Pittsburgh

Wed 1/7

6:00 am-3:04 pm

1 stop8h 04m

Saint Thomas Island Cyril E King

Mon 1/12

4:25 pm-11:06 pm

1 stop7h 41m

$265

PittsburghSaint Thomas Island

PIT - STT

PITSTT

Pittsburgh

Tue 1/27

6:00 am-3:56 pm

1 stop8h 56m

Saint Thomas Island Cyril E King

Mon 2/2

6:39 pm-11:10 am

1 stop17h 31m

$265

PittsburghSaint Thomas Island

PIT - STT

PITSTT

Pittsburgh

Sat 1/31

5:42 pm-1:10 pm

2 stops18h 28m

Saint Thomas Island Cyril E King

Sat 2/7

6:39 pm-9:01 am

2 stops15h 22m

$265

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Mon 11/24

9:14 am-8:27 pm

1 stop10h 13m

San Juan Luis Munoz Marin Intl

Wed 12/3

8:00 am-9:58 am

3 stops26h 58m

$284

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/12

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, December is the cheapest month in which you can book a flight from Pittsburgh to Caribbean (average of $152). Flying from Pittsburgh to Caribbean in June 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 November 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. Sunday afternoons 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 November 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
4,244 reviews

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

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
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

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
7.9
Good
8,012 reviews
Southwest
8.0
Very good
4,244 reviews

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

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
9,017 reviews
Southwest
8.0
Very good
4,244 reviews

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

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
11,049 reviews
Southwest
8.0
Very good
4,244 reviews

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

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
8,142 reviews
Southwest
8.0
Very good
4,244 reviews

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

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, Spirit Airlines, and Delta can get you from Pittsburgh to Caribbean in just under 6h 05m. Your travel time can differ by up to 4h 05m. 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 United Airlines, with whom users have recently found tickets for as low as $112. However, be on the lookout for offers from American Airlines and Spirit 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?

    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, December is the cheapest month in which you can book a flight from Pittsburgh to Caribbean (average of $152). Flying from Pittsburgh to Caribbean in June 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

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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 November 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$146Average$398FlexibilityNo cancel feeOn-time65%
FrontierCheapest$149Average$315FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$184Average$523FlexibilityNo cancel feeOn-time62%
DeltaCheapest$209Average$480FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$225Average$644FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$245Average$543FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$275Average$571FlexibilityNo cancel feeOn-time71%
Air CanadaCheapest$446Average$581FlexibilityNo cancel feeOn-time67%

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