HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean

$97+ 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 4/21. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — SJU
Mar 31 — Apr 71
Mon 3/31
Mon 4/7
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Pittsburgh to Caribbean with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 March 26, 2025.

Round-trip from

$207
(CheapOair)

One-way from

$97
(Cheapflightsfares)

Popular in

December

Cheapest in

September

Average price

$455
From Pittsburgh to Caribbean
Search Deals
One-way flight from Pittsburgh to Caribbean
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($51 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2025
Search Deals

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 March 26, 2025.

This CheapOair deal was found by Cheapflights users on 3/24. 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 5/57:00 amPIT - STT
1 stop27h 00mSpirit Airlines
Tue 5/1310:52 amSTT - PIT
1 stop12h 27mSpirit Airlines
Deal found 3/24$207
This Delta deal was found by Cheapflights users on 3/25. 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 4/306:55 amPIT - SJU
1 stop9h 32mDelta
Wed 5/77:00 amSJU - PIT
1 stop9h 26mDelta
Deal found 3/25$215
This Mytrip deal was found by Cheapflights users on 3/25. 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 4/87:17 pmPIT - SJU
2 stops28h 22mSpirit Airlines
Thu 4/102:40 pmSJU - PIT
2 stops19h 03mSpirit Airlines
Deal found 3/25$226
This United Airlines deal was found by Cheapflights users on 3/25. 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
Fri 5/91:05 amSJU - PIT
2 stops12h 09mUnited Airlines
Deal found 3/25$228
This Mytrip deal was found by Cheapflights users on 3/25. 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 4/88:18 amPIT - SJU
1 stop8h 16mMultiple Airlines
Wed 4/912:57 amSJU - PIT
2 stops20h 32mMultiple Airlines
Deal found 3/25$235
This Southwest deal was found by Cheapflights users on 3/25. 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.
Sun 4/276:25 pmPIT - SJU
1 stop6h 50mSouthwest
Fri 5/23:25 pmSJU - PIT
1 stop7h 55mSouthwest
Deal found 3/25$245
This American Airlines deal was found by Cheapflights users on 3/25. 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.
Wed 8/205:39 amPIT - STT
2 stops9h 11mAmerican Airlines
Wed 8/275:25 pmSTT - PIT
2 stops16h 18mAmerican Airlines
Deal found 3/25$279
This deal was found by Cheapflights users on 3/25. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/77:00 amPIT - SJU
1 stop9h 15mJetBlue
Tue 5/136:00 amSJU - PIT
1 stop7h 05mJetBlue
Deal found 3/25$288
This Cheapflightsfares deal was found by Cheapflights users on 3/25. 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.
Mon 5/127:00 amPIT - MBJ
1 stop5h 02mSpirit Airlines
Tue 5/1312:07 pmMBJ - PIT
1 stop10h 12mSpirit Airlines
Deal found 3/25$292
This American Airlines deal was found by Cheapflights users on 3/25. 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 4/276:52 pmPIT - SJU
1 stop16h 07mAmerican Airlines
Wed 4/306:21 amSJU - PIT
2 stops9h 56mAmerican Airlines
Deal found 3/25$295
This Frontier deal was found by Cheapflights users on 3/25. 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.
Wed 4/911:48 amPIT - SJU
1 stop9h 50mFrontier
Mon 4/1412:59 amSJU - PIT
1 stop12h 21mFrontier
Deal found 3/25$296
This United Airlines deal was found by Cheapflights users on 3/25. 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 5/136:00 amPIT - NAS
1 stop9h 58mUnited Airlines
Sat 5/172:53 pmNAS - PIT
1 stop8h 53mUnited Airlines
Deal found 3/25$345

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 March 26, 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

Mon 5/5

7:00 am-10:00 am

1 stop27h 00m

Saint Thomas Island Cyril E King

Tue 5/13

10:52 am-11:19 pm

1 stop12h 27m

$207

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Wed 4/30

6:55 am-4:27 pm

1 stop9h 32m

San Juan Luis Munoz Marin Intl

Wed 5/7

7:00 am-4:26 pm

1 stop9h 26m

$215

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Tue 4/8

7:17 pm-11:39 pm

2 stops28h 22m

San Juan Luis Munoz Marin Intl

Thu 4/10

2:40 pm-9:43 am

2 stops19h 03m

$226

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Sat 5/3

2:10 pm-11:54 pm

1 stop9h 44m

San Juan Luis Munoz Marin Intl

Fri 5/9

1:05 am-1:14 pm

2 stops12h 09m

$228

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Tue 4/8

8:18 am-4:34 pm

1 stop8h 16m

San Juan Luis Munoz Marin Intl

Wed 4/9

12:57 am-9:29 pm

2 stops20h 32m

$235

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Sun 4/27

6:25 pm-1:15 am

1 stop6h 50m

San Juan Luis Munoz Marin Intl

Fri 5/2

3:25 pm-11:20 pm

1 stop7h 55m

$245

PittsburghSaint Thomas Island

PIT - STT

PITSTT

Pittsburgh

Wed 8/20

5:39 am-2:50 pm

2 stops9h 11m

Saint Thomas Island Cyril E King

Wed 8/27

5:25 pm-9:43 am

2 stops16h 18m

$279

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Tue 4/8

12:40 pm-9:47 pm

1 stop9h 07m

San Juan Luis Munoz Marin Intl

Tue 4/15

5:01 am-3:34 pm

1 stop10h 33m

$286

PittsburghMontego Bay

PIT - MBJ

PITMBJ

Pittsburgh

Mon 5/12

7:00 am-11:02 am

1 stop5h 02m

Montego Bay Sangster Intl

Tue 5/13

12:07 pm-11:19 pm

1 stop10h 12m

$292

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Sun 4/27

6:52 pm-10:59 am

1 stop16h 07m

San Juan Luis Munoz Marin Intl

Wed 4/30

6:21 am-4:17 pm

2 stops9h 56m

$295

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/26

Showing 1-10 of 49 results
1
2
3
...
5

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 March 26, 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 March 26, 2025.
Southwest
8.1
Very good
4,274 reviews

Crew

8.6

Boarding

8.2

Overall

8.1

Food

7.1

Comfort

8.1

Entertainment

7.6

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
8.1
Very good
4,274 reviews
Southwest
8.1
Very good
4,274 reviews

Crew

8.6

Boarding

8.2

Overall

8.1

Food

7.1

Comfort

8.1

Entertainment

7.6

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
7,891 reviews
Southwest
8.1
Very good
4,274 reviews

Crew

8.6

Boarding

8.2

Overall

8.1

Food

7.1

Comfort

8.1

Entertainment

7.6

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
1,393 reviews
Southwest
8.1
Very good
4,274 reviews

Crew

8.6

Boarding

8.2

Overall

8.1

Food

7.1

Comfort

8.1

Entertainment

7.6

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
8,608 reviews
Southwest
8.1
Very good
4,274 reviews

Crew

8.6

Boarding

8.2

Overall

8.1

Food

7.1

Comfort

8.1

Entertainment

7.6

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
2,923 reviews
Southwest
8.1
Very good
4,274 reviews

Crew

8.6

Boarding

8.2

Overall

8.1

Food

7.1

Comfort

8.1

Entertainment

7.6

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 $97. 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 - 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 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Pittsburgh to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
LaGuardia to Fort Lauderdale flights
Newark to Fort Lauderdale flights
Newark to Cancún flights
John F Kennedy Intl to Cancún flights
LaGuardia to Miami flights
John F Kennedy Intl to Miami flights
Newark to Miami flights
John F Kennedy Intl to Heathrow flights
John F Kennedy Intl to Las Vegas flights
Newark to Heathrow flights
Newark to Las Vegas flights
John F Kennedy Intl to Fort Lauderdale flights
Newark to Los Angeles flights
John F Kennedy Intl to Gatwick flights
John F Kennedy Intl to Charles de Gaulle flights
Newark to Charles de Gaulle flights
Newark to Luis Munoz Marin Intl flights
John F Kennedy Intl to Orlando flights
John F Kennedy Intl to Leonardo da Vinci/Fiumicino flights
Newark to Orlando flights
John F Kennedy Intl to West Palm Beach flights
John F Kennedy Intl to Haneda flights
John F Kennedy Intl to Luis Munoz Marin Intl flights
John F Kennedy Intl to Los Angeles flights
LaGuardia to Dallas/Fort Worth flights
LaGuardia to Orlando flights
Newark to Leonardo da Vinci/Fiumicino flights
Newark to Seattle flights
Newark to Dallas/Fort Worth flights
Newark to Athens flights
Dulles Intl to Cancún flights
Newark to Tampa flights
LaGuardia to Los Angeles flights
LaGuardia to Heathrow flights
LaGuardia to Atlanta flights
Newark to Haneda flights
LaGuardia to Las Vegas flights
John F Kennedy Intl to Athens flights
LaGuardia to Cancún flights
Dulles Intl to Dallas/Fort Worth flights
Newark to Hobby flights
Newark to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Newark to Narita flights
Newark to West Palm Beach flights
John F Kennedy Intl to London City flights
John F Kennedy Intl to Punta Cana flights
John F Kennedy Intl to Lisbon flights
Newark to Mexico City flights
Dulles Intl to Miami flights

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 March 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$141Average$295FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$146Average$375FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$238Average$580FlexibilityNo cancel feeOn-time62%
DeltaCheapest$273Average$500FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$277Average$572FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$282Average$553FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$308Average$642FlexibilityNo cancel feeOn-time63%
Air CanadaCheapest$446Average$581FlexibilityNo cancel feeOn-time67%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.