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$67+ 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 3/4. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — SJU
ene. 26 — feb. 21
dom. 1/26
dom. 2/2
1 adult, Economy
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Cheap flight deals from Pittsburgh to Caribbean

Discover tips and strategies to find the most affordable flight options for your journey from Pittsburgh (PIT) to Caribbean (0CB). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated enero 21, 2025.

Round-trip from

$156
(Cheapflightsfares)

One-way from

$67
(Cheapflightsfares)
From Pittsburgh to Caribbean
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One-way 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 enero 21, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 1/20. 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.
mié. 2/196:18 pmPIT - STT
1 stop15h 28mSpirit Airlines
mié. 2/2611:41 amSTT - PIT
1 stop12h 10mSpirit Airlines
Deal found 1/20$156
This Mytrip deal was found by Cheapflights users on 1/21. 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.
vie. 2/282:55 pmPIT - SJU
2 stops31h 47mMultiple Airlines
mar. 3/45:22 pmSJU - PIT
1 stop6h 29mMultiple Airlines
Deal found 1/21$265
This FlightHub deal was found by Cheapflights users on 1/20. 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.
dom. 3/910:14 amPIT - SJU
1 stop16h 09mSpirit Airlines
mié. 3/125:45 pmSJU - PIT
1 stop6h 46mSpirit Airlines
Deal found 1/20$266
This Delta deal was found by Cheapflights users on 1/20. 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.
mar. 4/2910:52 amPIT - SJU
1 stop6h 36mDelta
vie. 5/912:49 pmSJU - PIT
1 stop8h 23mDelta
Deal found 1/20$275
This American Airlines deal was found by Cheapflights users on 1/20. 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.
sáb. 2/17:26 pmPIT - STT
1 stop17h 34mAmerican Airlines
mié. 2/54:10 pmSTT - PIT
1 stop7h 44mAmerican Airlines
Deal found 1/20$279
This American Airlines deal was found by Cheapflights users on 1/20. 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.
mié. 2/191:01 pmPIT - SJU
2 stops8h 34mAmerican Airlines
mié. 2/266:00 amSJU - PIT
1 stop7h 22mAmerican Airlines
Deal found 1/20$281
This FlightHub deal was found by Cheapflights users on 1/21. 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.
vie. 2/288:36 pmPIT - SJU
1 stop16h 52mFrontier
sáb. 3/83:44 amSJU - PIT
1 stop29h 02mFrontier
Deal found 1/21$285
This JetBlue Airways deal was found by Cheapflights users on 1/21. 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 Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 2/254:07 pmPIT - SJU
1 stop7h 52mJetBlue
lun. 3/33:26 amSJU - PIT
1 stop8h 08mJetBlue
Deal found 1/21$290
This United Airlines deal was found by Cheapflights users on 1/21. 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.
mié. 4/29:00 amPIT - SJU
2 stops11h 38mUnited Airlines
mié. 4/91:25 pmSJU - PIT
1 stop7h 35mUnited Airlines
Deal found 1/21$295
This CheapOair deal was found by Cheapflights users on 1/21. 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.
sáb. 2/226:18 pmPIT - MBJ
1 stop19h 25mSpirit Airlines
jue. 2/272:48 pmMBJ - PIT
1 stop24h 32mSpirit Airlines
Deal found 1/21$297
This Southwest deal was found by Cheapflights users on 1/20. 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.
lun. 2/244:45 pmPIT - SJU
1 stop7h 05mSouthwest
jue. 2/275:35 amSJU - PIT
2 stops11h 25mSouthwest
Deal found 1/20$335
This FlightHub deal was found by Cheapflights users on 1/20. 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.
mié. 3/126:45 amPIT - SXM
1 stop6h 43mSpirit Airlines
lun. 3/172:33 pmSXM - PIT
1 stop9h 58mSpirit Airlines
Deal found 1/20$351

Find flights from Pittsburgh to Caribbean within your budget

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 enero 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

PittsburghSaint Thomas Island

PIT - STT

PITSTT

Pittsburgh

mié. 2/19

6:18 pm-10:46 am

1 stop15h 28m

Saint Thomas Island Cyril E King

mié. 2/26

11:41 am-10:51 pm

1 stop12h 10m

$156

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

vie. 2/28

2:55 pm-11:42 pm

2 stops31h 47m

San Juan Luis Munoz Marin Intl

mar. 3/4

5:22 pm-10:51 pm

1 stop6h 29m

$265

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

dom. 3/2

2:45 pm-11:25 pm

3 stops31h 40m

San Juan Luis Munoz Marin Intl

mié. 3/5

4:12 pm-4:11 pm

3 stops24h 59m

$267

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

mar. 4/29

10:52 am-5:28 pm

1 stop6h 36m

San Juan Luis Munoz Marin Intl

vie. 5/9

12:49 pm-9:12 pm

1 stop8h 23m

$275

PittsburghSaint Thomas Island

PIT - STT

PITSTT

Pittsburgh

sáb. 2/1

7:26 pm-2:00 pm

1 stop17h 34m

Saint Thomas Island Cyril E King

mié. 2/5

4:10 pm-10:54 pm

1 stop7h 44m

$279

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

vie. 5/2

2:45 pm-1:50 am

1 stop11h 05m

San Juan Luis Munoz Marin Intl

dom. 5/4

3:56 am-5:14 pm

1 stop13h 18m

$280

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

lun. 2/24

7:30 am-7:04 pm

1 stop10h 34m

San Juan Luis Munoz Marin Intl

mié. 2/26

3:26 am-10:34 am

1 stop8h 08m

$290

PittsburghMontego Bay

PIT - MBJ

PITMBJ

Pittsburgh

sáb. 2/22

6:18 pm-1:43 pm

1 stop19h 25m

Montego Bay Sangster Intl

jue. 2/27

2:48 pm-3:20 pm

1 stop24h 32m

$297

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

mié. 2/26

8:09 am-5:29 pm

2 stops8h 20m

San Juan Luis Munoz Marin Intl

mar. 3/4

4:44 pm-11:11 pm

1 stop7h 27m

$300

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

mar. 2/18

3:05 pm-10:22 pm

1 stop6h 17m

San Juan Luis Munoz Marin Intl

lun. 2/24

2:05 am-4:49 pm

2 stops15h 44m

$347

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Showing 1-10 of 58 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.

Travel insights for flights from Pittsburgh to Caribbean

Get recent, data-driven insights about flights from Pittsburgh to Caribbean including ideal travel times, pricing trends, and more.

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 March is currently the most expensive (average of $378). 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 enero 21, 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 enero 21, 2025.
Southwest
8.1
Very good
4,662 reviews

Food

7.2

Comfort

8.1

Crew

8.7

Boarding

8.2

Entertainment

7.7

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,662 reviews
Southwest
8.1
Very good
4,662 reviews

Food

7.2

Comfort

8.1

Crew

8.7

Boarding

8.2

Entertainment

7.7

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Alaska Airlines
8.0
Very good
9,706 reviews
Southwest
8.1
Very good
4,662 reviews

Food

7.2

Comfort

8.1

Crew

8.7

Boarding

8.2

Entertainment

7.7

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,521 reviews
Southwest
8.1
Very good
4,662 reviews

Food

7.2

Comfort

8.1

Crew

8.7

Boarding

8.2

Entertainment

7.7

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Copa Airlines
7.7
Good
1,662 reviews
Southwest
8.1
Very good
4,662 reviews

Food

7.2

Comfort

8.1

Crew

8.7

Boarding

8.2

Entertainment

7.7

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

JetBlue
7.4
Good
3,200 reviews
Southwest
8.1
Very good
4,662 reviews

Food

7.2

Comfort

8.1

Crew

8.7

Boarding

8.2

Entertainment

7.7

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 $67. However, be on the lookout for offers from Frontier and Delta, 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, 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 March is currently the most expensive (average of $378). 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

Browse thousands of different options on Cheapflights for your next trip

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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 enero 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$109Average$288FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$170Average$373FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$238Average$543FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$272Average$567FlexibilityNo cancel feeOn-time69%
DeltaCheapest$273Average$500FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$292Average$560FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$306Average$665FlexibilityNo cancel feeOn-time63%
Air CanadaCheapest$583Average$648FlexibilityNo cancel feeOn-time67%
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