HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean

$69+ 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 12/7. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — SJU
Dec 7 — Dec 141
Sun 12/7
Sun 12/14
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 November 7, 2025.

Round-trip from

$234
(Cheapflightsfares)

One-way from

$69
(Frontier)

Popular in

December

Cheapest in

September

Average price

$412

Good round-trip deal

$518 or less
From Pittsburgh to Caribbean
Search Deals
One-way flight from Pittsburgh to Caribbean
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($30 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals
Price to beat on a round-trip flight from Pittsburgh to Caribbean.
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 November 7, 2025.

This Delta deal was found by Cheapflights users on 11/5. 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 12/96:25 amPIT - SJU
1 stop6h 34mDelta
Tue 12/166:38 pmSJU - PIT
1 stop6h 34mDelta
Deal found 11/5$240
This Frontier deal was found by Cheapflights users on 11/5. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/113:10 pmPIT - SJU
1 stop8h 39mFrontier
Sat 12/131:59 amSJU - PIT
1 stop13h 12mFrontier
Deal found 11/5$241
This Kiwi.com deal was found by Cheapflights users on 11/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/239:14 amPIT - SJU
1 stop13h 29mMultiple Airlines
Thu 11/279:54 pmSJU - PIT
1 stop17h 48mMultiple Airlines
Deal found 11/6$246
This Kiwi.com deal was found by Cheapflights users on 11/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/249:14 amPIT - SJU
1 stop10h 13mMultiple Airlines
Thu 11/272:25 amSJU - PIT
1 stop13h 17mMultiple Airlines
Deal found 11/6$247
This American Airlines deal was found by Cheapflights users on 11/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/296:00 amPIT - STT
1 stop10h 27mAmerican Airlines
Fri 12/55:29 pmSTT - PIT
1 stop16h 58mAmerican Airlines
Deal found 11/5$265
This Kiwi.com deal was found by Cheapflights users on 11/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/259:14 amPIT - SJU
1 stop13h 30mMultiple Airlines
Thu 11/272:25 amSJU - PIT
1 stop13h 17mMultiple Airlines
Deal found 11/6$267
This American Airlines deal was found by Cheapflights users on 11/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/137:39 amPIT - SJU
1 stop15h 13mAmerican Airlines
Wed 11/196:25 amSJU - PIT
1 stop7h 41mAmerican Airlines
Deal found 11/5$268
This Kiwi.com deal was found by Cheapflights users on 11/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/43:10 pmPIT - SJU
1 stop18h 37mMultiple Airlines
Wed 12/107:10 amSJU - PIT
2 stops18h 31mMultiple Airlines
Deal found 11/6$272
This CheapOair deal was found by Cheapflights users on 11/6. 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.
Tue 12/92:55 pmPIT - SJU
1 stop7h 59mJetBlue
Tue 12/1611:34 amSJU - PIT
1 stop12h 07mJetBlue
Deal found 11/6$273
This American Airlines deal was found by Cheapflights users on 11/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/99:45 amPIT - SJU
1 stop11h 24mAmerican Airlines
Tue 12/165:56 pmSJU - PIT
1 stop17h 15mAmerican Airlines
Deal found 11/5$274
This Priceline deal was found by Cheapflights users on 11/7. 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.
Sun 12/77:59 amPIT - PUJ
1 stop7h 51mSpirit Airlines
Thu 12/116:08 pmPUJ - PIT
1 stop7h 33mSpirit Airlines
Deal found 11/7$274
This Kiwi.com deal was found by Cheapflights users on 11/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/239:14 amPIT - SJU
1 stop10h 13mMultiple Airlines
Thu 12/412:00 pmSJU - PIT
1 stop27h 50mMultiple Airlines
Deal found 11/6$277

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 November 7, 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

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Tue 12/9

6:25 am-1:59 pm

1 stop6h 34m

San Juan Luis Munoz Marin Intl

Tue 12/16

6:38 pm-12:12 am

1 stop6h 34m

$240

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Tue 4/7

1:50 pm-9:58 pm

1 stop8h 08m

San Juan Luis Munoz Marin Intl

Tue 4/14

6:15 am-12:56 pm

1 stop6h 41m

$240

PittsburghSaint Thomas Island

PIT - STT

PITSTT

Pittsburgh

Sun 1/25

7:00 am-4:18 pm

1 stop8h 18m

Saint Thomas Island Cyril E King

Wed 2/18

3:05 pm-11:44 pm

1 stop9h 39m

$265

PittsburghSaint Thomas Island

PIT - STT

PITSTT

Pittsburgh

Tue 1/27

6:44 pm-3:06 pm

2 stops19h 22m

Saint Thomas Island Cyril E King

Mon 2/2

6:39 pm-9:33 am

2 stops15h 54m

$265

PittsburghSaint Thomas Island

PIT - STT

PITSTT

Pittsburgh

Tue 1/6

7:36 am-3:06 pm

1 stop6h 30m

Saint Thomas Island Cyril E King

Sun 1/11

6:39 pm-11:10 am

1 stop17h 31m

$265

PittsburghSaint Thomas Island

PIT - STT

PITSTT

Pittsburgh

Mon 1/19

7:14 am-4:10 pm

1 stop7h 56m

Saint Thomas Island Cyril E King

Mon 1/26

4:15 pm-11:35 pm

1 stop8h 20m

$265

PittsburghSaint Thomas Island

PIT - STT

PITSTT

Pittsburgh

Thu 1/1

6:00 am-4:25 pm

1 stop9h 25m

Saint Thomas Island Cyril E King

Thu 1/8

4:15 pm-11:06 pm

1 stop7h 51m

$265

PittsburghSaint Thomas Island

PIT - STT

PITSTT

Pittsburgh

Thu 1/1

7:30 am-3:05 pm

1 stop6h 35m

Saint Thomas Island Cyril E King

Fri 1/9

4:15 pm-11:06 pm

1 stop7h 51m

$265

PittsburghSaint Thomas Island

PIT - STT

PITSTT

Pittsburgh

Sun 1/18

5:32 am-2:52 pm

1 stop8h 20m

Saint Thomas Island Cyril E King

Sat 1/24

6:15 pm-9:40 am

1 stop16h 25m

$277

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Fri 1/16

7:05 am-4:52 pm

1 stop8h 47m

San Juan Luis Munoz Marin Intl

Wed 1/21

7:30 am-3:58 pm

1 stop9h 28m

$284

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/6

Showing 1-10 of 60 results
1
2
3
...
6

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, December is the cheapest month in which you can book a flight from Pittsburgh to Caribbean (average of $197). Flying from Pittsburgh to Caribbean in June is currently the most expensive (average of $307). 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 November 7, 2025.

It’s typically best to fly out from Pittsburgh to Caribbean in the evening. Doing so could potentially save you 28% on the flight price compared to flying in the afternoon, which is usually more expensive.

What is the cheapest day to fly from Pittsburgh to Caribbean?

Use this chart to determine the cheapest time to fly round-trip from Pittsburgh to Caribbean. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Pittsburgh to Caribbean flight should consider departing on Sunday evenings when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

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 November 7, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and United Airlines from Pittsburgh to Caribbean to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
7.9
Good
8,003 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
9,009 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,044 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,127 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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.

  • How long is the flight from Pittsburgh to Caribbean?

    Delta, United Airlines, and American Airlines can get you from Pittsburgh to Caribbean in just under 6h 34m. Your travel time can differ by up to 12h 48m. The distance between Pittsburgh and Caribbean is about 1742 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    The cheapest airline one-way is Frontier, with whom users have recently found tickets for as low as $69. However, be on the lookout for offers from Delta and Southwest, 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, December is the cheapest month in which you can book a flight from Pittsburgh to Caribbean (average of $197). Flying from Pittsburgh to Caribbean in June is currently the most expensive (average of $307). 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.
Newark to Fort Lauderdale flights
John F Kennedy Intl to Fort Lauderdale flights
John F Kennedy Intl to Cancún flights
John F Kennedy Intl to Los Angeles flights
John F Kennedy Intl to Orlando flights
LaGuardia to Fort Lauderdale flights
John F Kennedy Intl to Miami flights
Newark to Miami flights
John F Kennedy Intl to Dallas/Fort Worth flights
Newark to Cancún flights
John F Kennedy Intl to Las Vegas flights
LaGuardia to Miami flights
Newark to Los Angeles flights
Newark to Dallas/Fort Worth flights
Newark to Orlando flights
LaGuardia to Dallas/Fort Worth flights
Newark to Las Vegas flights
John F Kennedy Intl to San Francisco flights
John F Kennedy Intl to Luis Munoz Marin Intl flights
John F Kennedy Intl to Heathrow flights
Newark to Mexico City flights
Newark to Heathrow flights
John F Kennedy Intl to Mexico City flights
LaGuardia to Hobby flights
John F Kennedy Intl to O'Hare Intl flights
John F Kennedy Intl to West Palm Beach flights
Newark to Luis Munoz Marin Intl flights
Newark to West Palm Beach flights
LaGuardia to Orlando flights
Newark to Hobby flights
John F Kennedy Intl to Haneda flights
Newark to Tampa flights
John F Kennedy Intl to Charles de Gaulle flights
Dulles Intl to Dallas/Fort Worth flights
John F Kennedy Intl to Tampa flights
Dulles Intl to Cancún flights
Newark to San Francisco flights
LaGuardia to Tampa flights
John F Kennedy Intl to Santo Domingo flights
LaGuardia to Cancún flights
LaGuardia to West Palm Beach flights
LaGuardia to Atlanta flights
LaGuardia to Los Angeles flights
John F Kennedy Intl to Sky Harbor Intl flights
Dulles Intl to Miami flights
Philadelphia to Orlando flights
John F Kennedy Intl to New Orleans flights
Newark to Santo Domingo flights
Reagan-National to Miami flights
John F Kennedy Intl to Tel Aviv 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 November 7, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$146Average$398FlexibilityNo cancel feeOn-time65%
FrontierCheapest$149Average$315FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$184Average$523FlexibilityNo cancel feeOn-time62%
DeltaCheapest$209Average$480FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$225Average$644FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$245Average$543FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$275Average$571FlexibilityNo cancel feeOn-time71%
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.