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$93+ 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 6/3. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — SJU
Apr 20 — Apr 271
Sun 4/20
Sun 4/27
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 April 15, 2025.

Round-trip from

$199
(Cheapflightsfares)

One-way from

$93
(Cheapflightsfares)

Popular in

December

Cheapest in

September

Average price

$404
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. 9% potential increase in price ($42 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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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 April 15, 2025.

This Travelocity deal was found by Cheapflights users on 4/14. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/35:54 amPIT - STT
1 stop7h 42mSpirit Airlines
Wed 6/1110:52 amSTT - PIT
1 stop13h 02mSpirit Airlines
Deal found 4/14$197
This Delta deal was found by Cheapflights users on 4/15. 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.
Tue 9/2311:49 amPIT - SJU
1 stop10h 53mDelta
Mon 9/292:28 pmSJU - PIT
1 stop8h 41mDelta
Deal found 4/15$215
This American Airlines deal was found by Cheapflights users on 4/14. 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.
Mon 8/256:38 amPIT - STX
1 stop8h 32mAmerican Airlines
Fri 8/291:55 pmSTX - PIT
1 stop9h 52mAmerican Airlines
Deal found 4/14$235
This United Airlines deal was found by Cheapflights users on 4/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/32:10 pmPIT - SJU
2 stops9h 47mUnited Airlines
Mon 5/51:05 amSJU - PIT
2 stops12h 09mUnited Airlines
Deal found 4/15$253
This Delta deal was found by Cheapflights users on 4/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/126:00 amPIT - STT
1 stop7h 39mDelta
Mon 9/152:49 pmSTT - PIT
1 stop8h 20mDelta
Deal found 4/14$279
This American Airlines deal was found by Cheapflights users on 4/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/118:06 amPIT - SJU
1 stop14h 24mAmerican Airlines
Thu 5/152:30 pmSJU - PIT
1 stop9h 48mAmerican Airlines
Deal found 4/15$295
This Frontier deal was found by Cheapflights users on 4/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/252:30 pmPIT - SJU
1 stop11h 13mFrontier
Sun 5/113:56 amSJU - PIT
1 stop13h 28mFrontier
Deal found 4/15$298
This JetBlue deal was found by Cheapflights users on 4/15. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/117:00 amPIT - SJU
1 stop9h 15mJetBlue
Thu 5/1512:30 pmSJU - PIT
1 stop10h 12mJetBlue
Deal found 4/15$302
This Mytrip deal was found by Cheapflights users on 4/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/115:20 pmPIT - SJU
2 stops29h 18mMultiple Airlines
Thu 5/158:12 pmSJU - PIT
2 stops19h 46mMultiple Airlines
Deal found 4/15$303
This Booking.com deal was found by Cheapflights users on 4/15. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/117:00 amPIT - SJU
1 stop12h 07mSpirit Airlines
Wed 5/141:59 amSJU - PIT
1 stop9h 37mSpirit Airlines
Deal found 4/15$307
This Mytrip deal was found by Cheapflights users on 4/14. 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.
Tue 6/312:31 pmPIT - STT
2 stops21h 26mMultiple Airlines
Wed 6/112:41 pmSTT - PIT
3 stops32h 20mMultiple Airlines
Deal found 4/14$311
This FlightHub deal was found by Cheapflights users on 4/14. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/36:30 amPIT - STX
1 stop9h 48mSpirit Airlines
Mon 11/106:13 pmSTX - PIT
1 stop6h 51mSpirit Airlines
Deal found 4/14$318

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 April 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

PittsburghSaint Thomas Island

PIT - STT

PITSTT

Pittsburgh

Tue 6/3

5:54 am-1:36 pm

1 stop7h 42m

Saint Thomas Island Cyril E King

Wed 6/11

10:52 am-11:54 pm

1 stop13h 02m

$197

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Tue 9/23

11:49 am-10:42 pm

1 stop10h 53m

San Juan Luis Munoz Marin Intl

Mon 9/29

2:28 pm-11:09 pm

1 stop8h 41m

$215

PittsburghChristiansted

PIT - STX

PITSTX

Pittsburgh

Mon 8/25

6:38 am-3:10 pm

1 stop8h 32m

Christiansted Henry Rohlsen

Fri 8/29

1:55 pm-11:47 pm

1 stop9h 52m

$235

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Sat 5/3

2:10 pm-11:57 pm

2 stops9h 47m

San Juan Luis Munoz Marin Intl

Mon 5/5

1:05 am-1:14 pm

2 stops12h 09m

$253

PittsburghSaint Thomas Island

PIT - STT

PITSTT

Pittsburgh

Fri 9/12

6:00 am-1:39 pm

1 stop7h 39m

Saint Thomas Island Cyril E King

Mon 9/15

2:49 pm-11:09 pm

1 stop8h 20m

$279

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Sun 5/11

8:06 am-10:30 pm

1 stop14h 24m

San Juan Luis Munoz Marin Intl

Thu 5/15

2:30 pm-12:18 am

1 stop9h 48m

$295

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Fri 4/25

2:30 pm-1:43 am

1 stop11h 13m

San Juan Luis Munoz Marin Intl

Sun 5/11

3:56 am-5:24 pm

1 stop13h 28m

$298

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Sun 5/11

7:00 am-4:15 pm

1 stop9h 15m

San Juan Luis Munoz Marin Intl

Thu 5/15

12:30 pm-10:42 pm

1 stop10h 12m

$302

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Sun 5/11

5:20 pm-10:38 pm

2 stops29h 18m

San Juan Luis Munoz Marin Intl

Thu 5/15

8:12 pm-3:58 pm

2 stops19h 46m

$303

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Sun 5/11

7:00 am-7:07 pm

1 stop12h 07m

San Juan Luis Munoz Marin Intl

Wed 5/14

1:59 am-11:36 am

1 stop9h 37m

$307

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/15

Showing 1-10 of 52 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 December is currently the most expensive (average of $336). 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 April 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.

Rainfall in Caribbean by month

Plan your trip to Caribbean by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean when rainfall is around 2.2 in.

Temperature in Caribbean by month

Plan your trip to Caribbean by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

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 April 15, 2025.
Southwest
8.0
Very good
4,279 reviews

Boarding

8.2

Crew

8.6

Entertainment

7.6

Comfort

8.0

Food

7.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,279 reviews
Southwest
8.0
Very good
4,279 reviews

Boarding

8.2

Crew

8.6

Entertainment

7.6

Comfort

8.0

Food

7.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,918 reviews
Southwest
8.0
Very good
4,279 reviews

Boarding

8.2

Crew

8.6

Entertainment

7.6

Comfort

8.0

Food

7.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Copa Airlines
7.6
Good
1,408 reviews
Southwest
8.0
Very good
4,279 reviews

Boarding

8.2

Crew

8.6

Entertainment

7.6

Comfort

8.0

Food

7.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
LATAM Airlines
7.5
Good
1,758 reviews
Southwest
8.0
Very good
4,279 reviews

Boarding

8.2

Crew

8.6

Entertainment

7.6

Comfort

8.0

Food

7.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
8,658 reviews
Southwest
8.0
Very good
4,279 reviews

Boarding

8.2

Crew

8.6

Entertainment

7.6

Comfort

8.0

Food

7.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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.

  • 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 $93. However, be on the lookout for offers from Delta and American 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 - 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 December is currently the most expensive (average of $336). 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 April 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$100Average$295FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$146Average$404FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$238Average$574FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$260Average$560FlexibilityNo cancel feeOn-time69%
DeltaCheapest$273Average$498FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$285Average$573FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$306Average$655FlexibilityNo cancel feeOn-time63%
Air CanadaCheapest$446Average$581FlexibilityNo cancel feeOn-time67%

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