HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean

$68+ 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 12/8. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — SJU
Dec 26 — Jan 21
Fri 12/26
Fri 1/2
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 26, 2025.

Round-trip from

$227
(American Airlines)

One-way from

$68
(Super.com)

Popular in

December

Cheapest in

October

Average price

$409

Good round-trip deal

$403 or less
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 ($49 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($17 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 26, 2025.

This American Airlines deal was found by Cheapflights users on 11/25. 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 12/316:00 amPIT - STT
1 stop10h 39mAmerican Airlines
Thu 1/86:39 pmSTT - PIT
1 stop17h 31mAmerican Airlines
Deal found 11/25$227
This Super.com deal was found by Cheapflights users on 11/25. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/87:59 amPIT - PUJ
1 stop7h 51mSpirit Airlines
Thu 12/116:08 pmPUJ - PIT
1 stop7h 33mSpirit Airlines
Deal found 11/25$229
This Kiwi.com deal was found by Cheapflights users on 11/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/1410:53 amPIT - SJU
1 stop24h 39mMultiple Airlines
Fri 12/196:00 amSJU - PIT
1 stop28h 58mMultiple Airlines
Deal found 11/25$234
This Kiwi.com deal was found by Cheapflights users on 11/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/135:05 pmPIT - SJU
1 stop18h 27mMultiple Airlines
Tue 12/236:00 amSJU - PIT
1 stop28h 58mMultiple Airlines
Deal found 11/24$237
This Priceline deal was found by Cheapflights users on 11/24. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/293:09 pmPIT - SJU
1 stop8h 20mMultiple Airlines
Fri 1/164:40 pmSJU - PIT
1 stop8h 04mMultiple Airlines
Deal found 11/24$239
This United Airlines deal was found by Cheapflights users on 11/25. 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.
Sun 12/76:15 amPIT - SJU
1 stop6h 02mUnited Airlines
Wed 12/102:05 amSJU - PIT
2 stops12h 01mUnited Airlines
Deal found 11/25$240
This Priceline deal was found by Cheapflights users on 11/25. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/113:10 pmPIT - SJU
1 stop18h 37mMultiple Airlines
Mon 12/224:10 amSJU - PIT
1 stop6h 48mMultiple Airlines
Deal found 11/25$248
This Mytrip deal was found by Cheapflights users on 11/25. 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.
Thu 12/1110:53 amPIT - SJU
3 stops31h 57mSpirit Airlines
Thu 1/224:40 pmSJU - PIT
1 stop8h 04mSpirit Airlines
Deal found 11/25$249
This Kiwi.com deal was found by Cheapflights users on 11/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/1410:53 amPIT - SJU
1 stop24h 39mSpirit Airlines
Thu 12/186:28 pmSJU - PIT
1 stop16h 30mSpirit Airlines
Deal found 11/25$250
This United Airlines deal was found by Cheapflights users on 11/25. 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 12/611:10 amPIT - SJU
2 stops10h 12mUnited Airlines
Wed 12/102:05 amSJU - PIT
1 stop9h 15mUnited Airlines
Deal found 11/25$255
This Priceline deal was found by Cheapflights users on 11/25. 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 Priceline 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
Thu 12/251:59 amSJU - PIT
1 stop13h 12mFrontier
Deal found 11/25$258
This Kiwi.com deal was found by Cheapflights users on 11/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3110:53 amPIT - SJU
1 stop10h 12mMultiple Airlines
Sat 1/178:00 amSJU - PIT
1 stop16h 44mMultiple Airlines
Deal found 11/24$259

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 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

Wed 12/31

6:00 am-5:39 pm

1 stop10h 39m

Saint Thomas Island Cyril E King

Thu 1/8

6:39 pm-11:10 am

1 stop17h 31m

$227

PittsburghSaint Thomas Island

PIT - STT

PITSTT

Pittsburgh

Thu 1/22

6:10 am-1:56 pm

1 stop6h 46m

Saint Thomas Island Cyril E King

Thu 1/29

1:02 pm-11:38 pm

2 stops11h 36m

$227

PittsburghSaint Thomas Island

PIT - STT

PITSTT

Pittsburgh

Tue 1/27

7:36 am-3:06 pm

1 stop6h 30m

Saint Thomas Island Cyril E King

Mon 2/2

6:39 pm-11:10 am

1 stop17h 31m

$227

PittsburghSaint Thomas Island

PIT - STT

PITSTT

Pittsburgh

Mon 1/19

7:19 am-3:05 pm

1 stop6h 46m

Saint Thomas Island Cyril E King

Thu 1/22

3:10 pm-9:20 pm

1 stop7h 10m

$229

PittsburghSaint Thomas Island

PIT - STT

PITSTT

Pittsburgh

Sun 1/11

8:00 am-3:14 pm

1 stop6h 14m

Saint Thomas Island Cyril E King

Thu 1/15

1:52 pm-7:51 pm

1 stop6h 59m

$229

PittsburghSaint Thomas Island

PIT - STT

PITSTT

Pittsburgh

Sun 2/8

7:19 am-3:05 pm

1 stop6h 46m

Saint Thomas Island Cyril E King

Wed 2/18

4:15 pm-11:23 pm

1 stop8h 08m

$229

PittsburghSaint Thomas Island

PIT - STT

PITSTT

Pittsburgh

Sun 1/11

8:00 am-3:14 pm

1 stop6h 14m

Saint Thomas Island Cyril E King

Wed 1/14

4:15 pm-10:56 pm

1 stop7h 41m

$229

PittsburghSaint Thomas Island

PIT - STT

PITSTT

Pittsburgh

Fri 1/23

7:19 am-4:10 pm

1 stop7h 51m

Saint Thomas Island Cyril E King

Mon 1/26

4:32 pm-11:35 pm

1 stop8h 03m

$229

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Sun 12/7

6:15 am-1:17 pm

1 stop6h 02m

San Juan Luis Munoz Marin Intl

Wed 12/10

2:05 am-1:06 pm

2 stops12h 01m

$240

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

Fri 1/23

7:30 am-5:05 pm

1 stop8h 35m

San Juan Luis Munoz Marin Intl

Mon 1/26

2:35 pm-9:40 pm

1 stop8h 05m

$248

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/23

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 $178). Flying from Pittsburgh to Caribbean in June is currently the most expensive (average of $254). 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 26, 2025.

It’s typically best to fly out from Pittsburgh to Caribbean at noon. Doing so could potentially save you 23% 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 26, 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
4,254 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

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
4,254 reviews
Southwest
8.0
Very good
4,254 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

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
4,254 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

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
9,050 reviews
Southwest
8.0
Very good
4,254 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

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
11,037 reviews
Southwest
8.0
Very good
4,254 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

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
8,156 reviews
Southwest
8.0
Very good
4,254 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

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?

    American Airlines, United Airlines, and Southwest can get you from Pittsburgh to Caribbean in just under 6h 46m. Your travel time can differ by up to 3h 53m. The distance between Pittsburgh and Caribbean is about 1778 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 Spirit Airlines, with whom users have recently found tickets for as low as $80. However, be on the lookout for offers from American Airlines and United 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 - Punta Cana, Pittsburgh - San Juan Luis Munoz Marin Intl 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 $178). Flying from Pittsburgh to Caribbean in June is currently the most expensive (average of $254). 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 Cancún flights
John F Kennedy Intl to Fort Lauderdale flights
Newark to Miami flights
John F Kennedy Intl to Miami flights
LaGuardia to Fort Lauderdale flights
LaGuardia to Miami flights
Newark to Cancún flights
John F Kennedy Intl to Los Angeles flights
John F Kennedy Intl to Orlando flights
John F Kennedy Intl to Las Vegas flights
John F Kennedy Intl to Luis Munoz Marin Intl flights
John F Kennedy Intl to Dallas/Fort Worth flights
Newark to West Palm Beach flights
John F Kennedy Intl to Heathrow flights
LaGuardia to Dallas/Fort Worth flights
Newark to Dallas/Fort Worth flights
Newark to Las Vegas flights
John F Kennedy Intl to West Palm Beach flights
Newark to Mexico City flights
Newark to Luis Munoz Marin Intl flights
Newark to Heathrow flights
Newark to Orlando flights
John F Kennedy Intl to San Francisco flights
John F Kennedy Intl to Mexico City flights
John F Kennedy Intl to Santo Domingo flights
John F Kennedy Intl to Charles de Gaulle flights
John F Kennedy Intl to Santiago de los Caballeros flights
LaGuardia to Cancún flights
Dulles Intl to Cancún flights
LaGuardia to Hobby flights
Newark to Los Angeles flights
Newark to Hobby flights
Dulles Intl to Dallas/Fort Worth flights
LaGuardia to Orlando flights
John F Kennedy Intl to Haneda flights
Newark to Tampa flights
Reagan-National to Miami flights
Philadelphia to Orlando flights
John F Kennedy Intl to Sky Harbor Intl flights
John F Kennedy Intl to Tel Aviv flights
Newark to Charles de Gaulle flights
LaGuardia to Tampa flights
John F Kennedy Intl to Tampa flights
LaGuardia to Los Angeles flights
John F Kennedy Intl to Hobby flights
John F Kennedy Intl to Atlanta flights
Newark to San Francisco flights
Newark to Haneda flights
LaGuardia to Atlanta 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 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$149Average$315FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$159Average$381FlexibilityNo cancel feeOn-time65%
DeltaCheapest$207Average$511FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$225Average$628FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$226Average$533FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$234Average$541FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$274Average$577FlexibilityNo 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.