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Caribbean Islands

$108+ Cheap flights from Pittsburgh (PIT) to Caribbean Islands

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 5/10. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — SJU
Apr 22 — Apr 291
Tue 4/22
Tue 4/29
1 adult, Economy
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Cheap flight deals from Pittsburgh to Caribbean Islands

Keep the following information in mind while searching for Pittsburgh to Caribbean Islands flight deals. Data was last updated April 17, 2025.

Round-trip from

$215
(United Airlines)

One-way from

$108
(American Airlines)

Popular in

December

Cheapest in

September

Average price

$404
From Pittsburgh to Caribbean Islands
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One-way flight from Pittsburgh to Caribbean Islands
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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 Islands

Cheapest flights from Pittsburgh to Caribbean Islands
Explore the most affordable flight options available from Pittsburgh to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 17, 2025.

This United Airlines deal was found by Cheapflights users on 4/16. 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.
Tue 5/136:15 amPIT - SJU
1 stop6h 19mUnited Airlines
Sat 5/177:25 amSJU - PIT
2 stops13h 10mUnited Airlines
Deal found 4/16$215
This Delta deal was found by Cheapflights users on 4/16. 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 9/237:20 amPIT - SJU
1 stop8h 58mDelta
Mon 9/292:28 pmSJU - PIT
1 stop8h 41mDelta
Deal found 4/16$225
This American Airlines deal was found by Cheapflights users on 4/16. 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 4/276:02 amPIT - STX
1 stop8h 13mAmerican Airlines
Fri 5/24:55 pmSTX - PIT
2 stops16h 41mAmerican Airlines
Deal found 4/16$239
This FlightHub deal was found by Cheapflights users on 4/17. 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.
Thu 6/127:00 amPIT - STX
1 stop8h 49mSpirit Airlines
Mon 6/164:45 pmSTX - PIT
1 stop6h 35mSpirit Airlines
Deal found 4/17$264
This American Airlines deal was found by Cheapflights users on 4/17. 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.
Fri 9/126:00 amPIT - STT
2 stops10h 30mAmerican Airlines
Mon 9/155:20 pmSTT - PIT
1 stop6h 29mAmerican Airlines
Deal found 4/17$279
This American Airlines deal was found by Cheapflights users on 4/17. 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 5/157:15 amSJU - PIT
1 stop8h 55mAmerican Airlines
Deal found 4/17$295
This Mytrip deal was found by Cheapflights users on 4/17. 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 5/137:00 amPIT - SJU
2 stops28h 31mSpirit Airlines
Fri 5/161:59 amSJU - PIT
1 stop12h 31mSpirit Airlines
Deal found 4/17$296
This Frontier deal was found by Cheapflights users on 4/17. 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.
Thu 5/82:45 pmPIT - SJU
1 stop11h 05mFrontier
Thu 5/156:00 amSJU - PIT
1 stop7h 55mFrontier
Deal found 4/17$298
This Mytrip deal was found by Cheapflights users on 4/16. 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 6/17:00 amPIT - STT
1 stop26h 57mSpirit Airlines
Wed 6/42:41 pmSTT - PIT
2 stops33h 13mSpirit Airlines
Deal found 4/16$299
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/32:00 pmPIT - SJU
1 stop8h 25mSouthwest
Thu 5/83:25 pmSJU - PIT
1 stop7h 55mSouthwest
Deal found 4/15$300
This Delta deal was found by Cheapflights users on 4/17. 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 4/17$304
This Mytrip deal was found by Cheapflights users on 4/16. 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 5/187:00 amPIT - SJU
1 stop12h 07mMultiple Airlines
Sat 5/241:39 pmSJU - PIT
2 stops27h 34mMultiple Airlines
Deal found 4/16$306

Cheapflights Fare Finder

Customize your flight search to find flights from Pittsburgh to Caribbean Islands 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 17, 2025.
Use the filters below to find and compare flights from Pittsburgh to Caribbean Islands that are best for you.

Fly from

Pittsburgh

Fly to

Caribbean Islands

Route

Depart

Return

Price

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Tue 5/13

6:15 am-12:34 pm

1 stop6h 19m

San Juan Luis Munoz Marin Intl

Sat 5/17

7:25 am-8:35 pm

2 stops13h 10m

$215

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Tue 9/23

7:20 am-4:18 pm

1 stop8h 58m

San Juan Luis Munoz Marin Intl

Mon 9/29

2:28 pm-11:09 pm

1 stop8h 41m

$225

PittsburghChristiansted

PIT - STX

PITSTX

Pittsburgh

Sun 4/27

6:02 am-2:15 pm

1 stop8h 13m

Christiansted Henry Rohlsen

Fri 5/2

4:55 pm-9:36 am

2 stops16h 41m

$239

PittsburghChristiansted

PIT - STX

PITSTX

Pittsburgh

Thu 6/12

7:00 am-3:49 pm

1 stop8h 49m

Christiansted Henry Rohlsen

Mon 6/16

4:45 pm-11:20 pm

1 stop6h 35m

$264

PittsburghSaint Thomas Island

PIT - STT

PITSTT

Pittsburgh

Fri 9/12

6:00 am-4:30 pm

2 stops10h 30m

Saint Thomas Island Cyril E King

Mon 9/15

5:20 pm-11:49 pm

1 stop6h 29m

$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

7:15 am-4:10 pm

1 stop8h 55m

$295

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Tue 5/13

7:00 am-11:31 am

2 stops28h 31m

San Juan Luis Munoz Marin Intl

Fri 5/16

1:59 am-2:30 pm

1 stop12h 31m

$296

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Thu 5/8

2:45 pm-1:50 am

1 stop11h 05m

San Juan Luis Munoz Marin Intl

Thu 5/15

6:00 am-1:55 pm

1 stop7h 55m

$298

PittsburghSaint Thomas Island

PIT - STT

PITSTT

Pittsburgh

Sun 6/1

7:00 am-9:57 am

1 stop26h 57m

Saint Thomas Island Cyril E King

Wed 6/4

2:41 pm-11:54 pm

2 stops33h 13m

$299

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Sat 5/3

2:00 pm-10:25 pm

1 stop8h 25m

San Juan Luis Munoz Marin Intl

Thu 5/8

3:25 pm-11:20 pm

1 stop7h 55m

$300

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/17

Showing 1-10 of 52 results
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Best time to book a flight from Pittsburgh to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands 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 Islands

What is the cheapest month to book a flight from Pittsburgh to Caribbean Islands?

Currently, September is the cheapest month in which you can book a flight from Pittsburgh to Caribbean Islands (average of $254). Flying from Pittsburgh to Caribbean Islands 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 EPX?

Find hourly flight availability from Pittsburgh to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 17, 2025.

When flying from Pittsburgh to Caribbean Islands, 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 Islands by month

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

In terms of precipitation, rainfall in Caribbean Islands 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 Islands when rainfall is around 2.2 in.

Temperature in Caribbean Islands by month

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

If weather is an important factor for your trip to Caribbean Islands, 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 Islands

Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated April 17, 2025.
Read through reviews of airlines operating flights from Pittsburgh to Caribbean Islands, such as Southwest, Delta and Copa Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,280 reviews

Comfort

8.0

Boarding

8.2

Crew

8.6

Food

7.1

Entertainment

7.6

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
4,280 reviews
Southwest
8.0
Very good
4,280 reviews

Comfort

8.0

Boarding

8.2

Crew

8.6

Food

7.1

Entertainment

7.6

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
7,916 reviews
Southwest
8.0
Very good
4,280 reviews

Comfort

8.0

Boarding

8.2

Crew

8.6

Food

7.1

Entertainment

7.6

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
1,409 reviews
Southwest
8.0
Very good
4,280 reviews

Comfort

8.0

Boarding

8.2

Crew

8.6

Food

7.1

Entertainment

7.6

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
8,667 reviews
Southwest
8.0
Very good
4,280 reviews

Comfort

8.0

Boarding

8.2

Crew

8.6

Food

7.1

Entertainment

7.6

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.
JetBlue
7.3
Good
2,926 reviews
Southwest
8.0
Very good
4,280 reviews

Comfort

8.0

Boarding

8.2

Crew

8.6

Food

7.1

Entertainment

7.6

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 Islands. 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 Islands?

    Located just 13.5 mi from the city center, Pittsburgh (PIT) is the airport most travelers will use when flying to Caribbean Islands from Pittsburgh.

  • What are the cheapest airlines to fly from Pittsburgh to Caribbean Islands one-way?

    One-way options have recently been found by users for as low as $108 on American Airlines. Other airlines that offer cheap prices include Delta from $113 and Spirit Airlines from $127 one-way.

  • What are the most popular routes from Pittsburgh to Caribbean Islands?

    While some choose either Pittsburgh - Punta Cana or Pittsburgh - Oranjestad Reina Beatrix, Pittsburgh - San Juan Luis Munoz Marin Intl is the most popular route from Pittsburgh to Caribbean Islands.

  • Can I find deals for flights from Pittsburgh to Caribbean Islands that include hotel bookings?

    Yes. In addition to deals on Pittsburgh to Caribbean Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Pittsburgh to Caribbean Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Pittsburgh to Caribbean Islands.

  • Can I find deals for business class flights from Pittsburgh to Caribbean Islands?

    Yes. Cheapflights offers flight deals from Pittsburgh to Caribbean Islands 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 Islands?

    Currently, September is the cheapest month in which you can book a flight from Pittsburgh to Caribbean Islands (average of $254). Flying from Pittsburgh to Caribbean Islands 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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Top 8 airlines flying from Pittsburgh to Caribbean Islands

Discover the top 8 airlines that operate flights from Pittsburgh to Caribbean Islands. 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 17, 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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