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Caribbean Islands

$107+ 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 11/16. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — SJU
Nov 5 — Nov 121
Wed 11/5
Wed 11/12
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 October 6, 2025.

Round-trip from

$213
(CheapOair)

One-way from

$107
(CheapOair)

Popular in

December

Cheapest in

September

Average price

$305
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. 5% potential increase in price ($22 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 October 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 October 6, 2025.

This CheapOair deal was found by Cheapflights users on 10/4. 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 stop10h 03mJetBlue
Wed 11/1912:30 pmSJU - PIT
1 stop11h 18mJetBlue
Deal found 10/4$213
This CheapOair deal was found by Cheapflights users on 10/6. 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 stop13h 54mJetBlue
Mon 11/179:00 pmSJU - PIT
1 stop26h 48mJetBlue
Deal found 10/6$220
This Priceline deal was found by Cheapflights users on 10/5. 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 10/206:51 pmPIT - STT
1 stop15h 05mSpirit Airlines
Sat 10/2511:01 amSTT - PIT
1 stop12h 15mSpirit Airlines
Deal found 10/5$223
This Delta deal was found by Cheapflights users on 10/5. 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 12/911:52 amPIT - SJU
1 stop11h 07mDelta
Tue 12/166:38 pmSJU - PIT
1 stop6h 41mDelta
Deal found 10/5$225
This JetBlue deal was found by Cheapflights users on 10/5. 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.
Wed 11/127:10 amPIT - SJU
1 stop10h 03mJetBlue
Sat 11/158:05 amSJU - PIT
1 stop9h 37mJetBlue
Deal found 10/5$227
This CheapOair deal was found by Cheapflights users on 10/5. 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.
Mon 11/107:10 amPIT - SJU
1 stop27h 25mJetBlue
Sat 11/158:05 amSJU - PIT
1 stop9h 37mJetBlue
Deal found 10/5$236
This Delta deal was found by Cheapflights users on 10/5. 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.
Wed 10/225:11 pmPIT - SJU
1 stop6h 45mDelta
Tue 10/287:00 amSJU - PIT
1 stop9h 53mDelta
Deal found 10/5$240
This JetBlue deal was found by Cheapflights users on 10/5. 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.
Mon 10/206:05 pmPIT - SJU
1 stop6h 52mJetBlue
Fri 10/242:25 pmSJU - PIT
1 stop9h 24mJetBlue
Deal found 10/5$242
This JetBlue deal was found by Cheapflights users on 10/5. 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 11/115:37 pmPIT - SJU
1 stop9h 11mJetBlue
Thu 11/133:34 pmSJU - PIT
1 stop9h 24mJetBlue
Deal found 10/5$246
This Delta deal was found by Cheapflights users on 10/5. 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.
Sat 10/185:11 pmPIT - SJU
1 stop6h 45mDelta
Tue 10/287:00 amSJU - PIT
1 stop9h 53mDelta
Deal found 10/5$253
This United Airlines deal was found by Cheapflights users on 10/5. 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.
Mon 10/206:15 amPIT - SJU
1 stop9h 27mUnited Airlines
Fri 10/241:05 amSJU - PIT
2 stops8h 26mUnited Airlines
Deal found 10/5$255
This Kiwi.com deal was found by Cheapflights users on 10/3. 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 12/58:00 amPIT - SJU
1 stop15h 03mMultiple Airlines
Fri 12/123:00 pmSJU - PIT
1 stop29h 50mMultiple Airlines
Deal found 10/3$256

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 October 6, 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

Sun 2/8

10:49 am-10:22 pm

2 stops10h 33m

San Juan Luis Munoz Marin Intl

Wed 2/11

8:10 am-2:04 pm

1 stop6h 54m

$225

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Tue 12/9

11:52 am-11:59 pm

1 stop11h 07m

San Juan Luis Munoz Marin Intl

Tue 12/16

7:00 am-4:21 pm

1 stop10h 21m

$225

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Wed 2/4

7:20 am-4:51 pm

1 stop8h 31m

San Juan Luis Munoz Marin Intl

Wed 2/11

7:00 am-4:40 pm

1 stop10h 40m

$225

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Wed 11/12

7:10 am-6:13 pm

1 stop10h 03m

San Juan Luis Munoz Marin Intl

Thu 11/13

3:34 pm-11:58 pm

1 stop9h 24m

$229

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Mon 10/20

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

$240

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Tue 10/21

6:00 am-2:54 pm

1 stop8h 54m

San Juan Luis Munoz Marin Intl

Fri 10/24

1:25 pm-11:49 pm

1 stop10h 24m

$242

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Sun 10/19

6:00 am-2:54 pm

1 stop8h 54m

San Juan Luis Munoz Marin Intl

Sat 10/25

1:25 pm-11:49 pm

1 stop10h 24m

$242

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Mon 10/20

6:05 pm-12:57 am

1 stop6h 52m

San Juan Luis Munoz Marin Intl

Fri 10/24

1:25 pm-11:49 pm

1 stop10h 24m

$242

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Sun 10/19

6:00 am-2:54 pm

1 stop8h 54m

San Juan Luis Munoz Marin Intl

Fri 10/24

1:25 pm-11:49 pm

1 stop10h 24m

$242

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Sat 10/18

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

$253

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/5

Showing 1-10 of 60 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 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 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 October 6, 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.

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 October 6, 2025.
Peruse reviews from past customers who have flown with Delta, United Airlines, and American Airlines from Pittsburgh to Caribbean Islands to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,970 reviews

Boarding

8.2

Entertainment

7.9

Crew

8.5

Overall

8.0

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,970 reviews
Delta
8.0
Very good
7,970 reviews

Boarding

8.2

Entertainment

7.9

Crew

8.5

Overall

8.0

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,953 reviews
Delta
8.0
Very good
7,970 reviews

Boarding

8.2

Entertainment

7.9

Crew

8.5

Overall

8.0

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
11,041 reviews
Delta
8.0
Very good
7,970 reviews

Boarding

8.2

Entertainment

7.9

Crew

8.5

Overall

8.0

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
JetBlue
7.2
Good
2,907 reviews
Delta
8.0
Very good
7,970 reviews

Boarding

8.2

Entertainment

7.9

Crew

8.5

Overall

8.0

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Spirit Airlines
6.3
Okay
8,077 reviews
Delta
8.0
Very good
7,970 reviews

Boarding

8.2

Entertainment

7.9

Crew

8.5

Overall

8.0

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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.

  • How long is the flight from Pittsburgh to Caribbean Islands?

    A quick flight from Pittsburgh to Caribbean Islands can take about 10h 03m. Delta provides one of the quickest options available for as low as $229. Airlines will cover a distance of 1742 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 $107 on JetBlue. Other airlines that offer cheap prices include United Airlines from $113 and Delta from $113 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 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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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 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 October 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$149Average$318FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$159Average$394FlexibilityNo cancel feeOn-time65%
DeltaCheapest$214Average$513FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$226Average$640FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$245Average$549FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$279Average$581FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$289Average$571FlexibilityNo cancel feeOn-time62%
Air CanadaCheapest$446Average$583FlexibilityNo cancel feeOn-time67%

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