HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean Islands

$88+ 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 10/7. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — SJU
ago. 12 — ago. 191
mar. 8/12
mar. 8/19
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Pittsburgh to Caribbean Islands 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 Islands

Keep the following information in mind while searching for Pittsburgh to Caribbean Islands flight deals. Data was last updated agosto 7, 2025.

Round-trip from

$175
(United Airlines)

One-way from

$88
(American Airlines)

Popular in

December

Cheapest in

September

Average price

$474
From Pittsburgh to Caribbean Islands
Search Deals
One-way flight from Pittsburgh to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($18 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 August 2025
Search Deals

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 agosto 7, 2025.

This United Airlines deal was found by Cheapflights users on 8/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/2110:29 amPIT - SJU
2 stops13h 28mUnited Airlines
mar. 10/281:20 pmSJU - PIT
1 stop7h 22mUnited Airlines
Deal found 8/6$175
This American Airlines deal was found by Cheapflights users on 8/6. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/1512:14 pmPIT - SJU
2 stops9h 56mAmerican Airlines
mié. 10/221:35 pmSJU - PIT
2 stops9h 18mAmerican Airlines
Deal found 8/6$178
This American Airlines deal was found by Cheapflights users on 8/6. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/88:00 amPIT - SJU
1 stop15h 59mAmerican Airlines
mié. 10/155:30 amSJU - PIT
1 stop17h 23mAmerican Airlines
Deal found 8/6$179
This United Airlines deal was found by Cheapflights users on 8/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 9/156:00 amPIT - SJU
1 stop7h 45mUnited Airlines
vie. 9/191:05 amSJU - PIT
2 stops12h 00mUnited Airlines
Deal found 8/6$189
This American Airlines deal was found by Cheapflights users on 8/5. 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.
sáb. 10/114:19 pmPIT - SJU
1 stop6h 46mAmerican Airlines
mar. 10/145:30 amSJU - PIT
1 stop17h 23mAmerican Airlines
Deal found 8/5$200
This Delta deal was found by Cheapflights users on 8/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 10/207:05 amPIT - SJU
1 stop9h 20mDelta
mar. 10/287:00 amSJU - PIT
1 stop9h 37mDelta
Deal found 8/7$205
This Delta deal was found by Cheapflights users on 8/5. 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.
vie. 10/176:00 amPIT - SJU
1 stop7h 19mDelta
mar. 10/287:00 amSJU - PIT
1 stop9h 37mDelta
Deal found 8/5$220
This Southwest deal was found by Cheapflights users on 8/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 9/2412:05 pmPIT - SJU
1 stop10h 25mSouthwest
dom. 9/285:05 amSJU - PIT
1 stop6h 20mSouthwest
Deal found 8/7$228
This Delta deal was found by Cheapflights users on 8/5. 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.
vie. 10/106:00 amPIT - SJU
1 stop10h 33mDelta
mié. 10/155:43 pmSJU - PIT
1 stop6h 49mDelta
Deal found 8/5$230
This FlightHub deal was found by Cheapflights users on 8/6. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/127:10 amPIT - STT
1 stop7h 47mSpirit Airlines
lun. 9/154:02 pmSTT - PIT
1 stop17h 28mSpirit Airlines
Deal found 8/6$240
This FlightHub deal was found by Cheapflights users on 8/6. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 9/157:10 amPIT - STT
1 stop7h 47mSpirit Airlines
vie. 9/194:02 pmSTT - PIT
1 stop17h 28mSpirit Airlines
Deal found 8/6$250
This Expedia deal was found by Cheapflights users on 8/6. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/57:10 amPIT - STT
1 stop7h 47mSpirit Airlines
lun. 9/2210:49 amSTT - PIT
1 stop12h 34mSpirit Airlines
Deal found 8/6$254

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 agosto 7, 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

mar. 10/21

10:29 am-11:57 pm

2 stops13h 28m

San Juan Luis Munoz Marin Intl

mar. 10/28

1:20 pm-8:42 pm

1 stop7h 22m

$175

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

mié. 10/15

12:14 pm-10:10 pm

2 stops9h 56m

San Juan Luis Munoz Marin Intl

mié. 10/22

1:35 pm-10:53 pm

2 stops9h 18m

$178

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

mié. 10/8

8:00 am-11:59 pm

1 stop15h 59m

San Juan Luis Munoz Marin Intl

mié. 10/15

5:30 am-10:53 pm

1 stop17h 23m

$179

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

lun. 9/15

6:00 am-1:45 pm

1 stop7h 45m

San Juan Luis Munoz Marin Intl

vie. 9/19

1:05 am-1:05 pm

2 stops12h 00m

$189

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

sáb. 10/11

4:19 pm-11:05 pm

1 stop6h 46m

San Juan Luis Munoz Marin Intl

mar. 10/14

5:30 am-10:53 pm

1 stop17h 23m

$200

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

lun. 10/20

7:05 am-4:25 pm

1 stop9h 20m

San Juan Luis Munoz Marin Intl

vie. 10/24

5:43 pm-12:32 am

1 stop6h 49m

$205

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

vie. 10/17

6:00 am-1:19 pm

1 stop7h 19m

San Juan Luis Munoz Marin Intl

mar. 10/28

7:00 am-4:37 pm

1 stop9h 37m

$220

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

mié. 9/24

12:05 pm-10:30 pm

1 stop10h 25m

San Juan Luis Munoz Marin Intl

dom. 9/28

5:05 am-11:25 am

1 stop6h 20m

$228

PittsburghSan Juan

PIT - SJU

PITSJU

Pittsburgh

vie. 10/10

6:00 am-4:33 pm

1 stop10h 33m

San Juan Luis Munoz Marin Intl

mié. 10/15

5:43 pm-12:32 am

1 stop6h 49m

$230

PittsburghSaint Thomas Island

PIT - STT

PITSTT

Pittsburgh

vie. 9/12

7:10 am-2:57 pm

1 stop7h 47m

Saint Thomas Island Cyril E King

lun. 9/15

4:02 pm-9:30 am

1 stop17h 28m

$240

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/6

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

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 agosto 7, 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 agosto 7, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and Finnair 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.
Southwest
8.0
Very good
4,247 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,247 reviews
Southwest
8.0
Very good
4,247 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,987 reviews
Southwest
8.0
Very good
4,247 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Finnair
7.6
Good
1,319 reviews
Southwest
8.0
Very good
4,247 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,916 reviews
Southwest
8.0
Very good
4,247 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,247 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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.

  • 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 $88 on American Airlines. Other airlines that offer cheap prices include Delta from $103 and Spirit Airlines from $112 one-way.

  • What are the most popular routes from Pittsburgh to Caribbean Islands?

    While some choose either Pittsburgh - Oranjestad Reina Beatrix or Pittsburgh - Saint Thomas Island Cyril E King, 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

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 Islands

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to Cancún flights
John F Kennedy Intl to Miami flights
John F Kennedy Intl to O'Hare Intl flights
Newark to Fort Lauderdale flights
John F Kennedy Intl to Las Vegas flights
John F Kennedy Intl to Los Angeles flights
Newark to Cancún flights
LaGuardia to Fort Lauderdale flights
Newark to Los Angeles flights
LaGuardia to O'Hare Intl flights
Newark to Miami flights
Newark to O'Hare Intl flights
Newark to Las Vegas flights
John F Kennedy Intl to Orlando flights
LaGuardia to Dallas/Fort Worth flights
John F Kennedy Intl to Fort Lauderdale flights
LaGuardia to Miami flights
John F Kennedy Intl to San Francisco flights
Newark to Orlando flights
Newark to San Francisco flights
LaGuardia to Orlando flights
Newark to Seattle flights
John F Kennedy Intl to Mexico City flights
John F Kennedy Intl to West Palm Beach flights
Dulles Intl to Cancún flights
John F Kennedy Intl to Seattle flights
Newark to Mexico City flights
John F Kennedy Intl to Atlanta flights
LaGuardia to Las Vegas flights
LaGuardia to Los Angeles flights
John F Kennedy Intl to Dallas/Fort Worth flights
Newark to Dallas/Fort Worth flights
John F Kennedy Intl to Ontario flights
LaGuardia to Denver flights
LaGuardia to Cancún flights
Reagan-National to Boston flights
LaGuardia to Atlanta flights
John F Kennedy Intl to Sky Harbor Intl flights
Reagan-National to Los Angeles flights
Reagan-National to O'Hare Intl flights
Dulles Intl to Seattle flights
Reagan-National to Dallas/Fort Worth flights
Dulles Intl to Miami flights
Dulles Intl to Las Vegas flights
LaGuardia to Seattle flights
Philadelphia to Orlando flights
LaGuardia to Tampa flights
Newark to Atlanta flights
Reagan-National to Seattle flights
LaGuardia to San Francisco flights

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 agosto 7, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$100Average$298FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$153Average$386FlexibilityNo cancel feeOn-time65%
DeltaCheapest$231Average$509FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$238Average$547FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$257Average$635FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$260Average$549FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$284Average$570FlexibilityNo cancel feeOn-time71%
Air CanadaCheapest$446Average$583FlexibilityNo 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.