$113 Find Cheap Flights from Pittsburgh to Caribbean

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Pittsburgh to Caribbean departing on 10/7. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

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Cheap Flights from Pittsburgh to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$279
Santo Domingo
Santo Domingo1 stop$351
Montego Bay
Montego Bay1 stop$277
Oranjestad
Oranjestad1 stop$337
Nassau
Nassau1 stop$393
Simpson Bay
Simpson Bay1 stop$427
Kingston
Kingston1 stop$380
Providenciales
Providenciales1 stop$424
Port of Spain
Port of Spain1 stop$490
Bridgetown
Bridgetown1 stop$441
George Town
George Town1 stop$315
Willemstad
Willemstad2 stops$371
St. John's
St. John's1 stop$455
Puerto Plata
Puerto Plata1 stop$405
Aguadilla
Aguadilla2 stops$295
Punta Cana
Punta Cana1 stop$279
Santo Domingo
Santo Domingo1 stop$351
Montego Bay
Montego Bay1 stop$277
Oranjestad
Oranjestad1 stop$337
Nassau
Nassau1 stop$393
Simpson Bay
Simpson Bay1 stop$427
Kingston
Kingston1 stop$380
Providenciales
Providenciales1 stop$424
Port of Spain
Port of Spain1 stop$490
Bridgetown
Bridgetown1 stop$441
George Town
George Town1 stop$315
Willemstad
Willemstad2 stops$371
St. John's
St. John's1 stop$455
Puerto Plata
Puerto Plata1 stop$405
Aguadilla
Aguadilla2 stops$295

Book Cheap Pittsburgh to Caribbean Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Pittsburgh to Caribbean that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Pittsburgh to Caribbean

Wed, Nov 19 - Wed, Dec 3
 Logo
8:00 am - 5:54 pmPIT-SJU
8h 54m1 stop
 Logo
9:30 pm - 7:50 pmSJU-PIT
23h 20m1 stop
Fri, Oct 17 - Thu, Oct 23
Frontier Logo
2:45 pm - 12:29 amPIT-SJU
9h 44m1 stop
Frontier Logo
1:59 am - 1:50 pmSJU-PIT
11h 51m1 stop
$219Frontier
Find Deal
Mon, Oct 20 - Sat, Oct 25
Delta Logo
6:35 am - 1:12 pmPIT-SJU
6h 37m1 stop
Delta Logo
5:43 pm - 12:32 amSJU-PIT
6h 49m1 stop
$225Delta
Find Deal
Thu, Oct 16 - Mon, Oct 20
Spirit Airlines Logo
6:51 pm - 9:56 amPIT-STT
15h 05m1 stop
Spirit Airlines Logo
11:01 am - 11:16 pmSTT-PIT
12h 15m1 stop
$239Spirit Airlines
Find Deal
Sat, Oct 4 - Tue, Oct 7
United Airlines Logo
8:35 am - 8:38 pmPIT-SJU
12h 03m2 stops
United Airlines Logo
1:05 am - 9:26 amSJU-PIT
8h 21m2 stops
$240United Airlines
Find Deal
Sat, Oct 25 - Fri, Oct 31
Spirit Airlines Logo
6:51 pm - 9:56 amPIT-STT
15h 05m1 stop
Spirit Airlines Logo
11:01 am - 5:46 pmSTT-PIT
6h 45m1 stop
$243Spirit Airlines
Find Deal
Tue, Nov 11 - Tue, Nov 18
United Airlines Logo
11:00 am - 12:36 amPIT-SJU
12h 36m2 stops
United Airlines Logo
8:30 am - 2:02 pmSJU-PIT
6h 32m1 stop
$250United Airlines
Find Deal
Tue, Dec 9 - Tue, Dec 16
American Airlines Logo
7:40 am - 11:52 pmPIT-SJU
15h 12m1 stop
American Airlines Logo
12:49 pm - 10:30 pmSJU-PIT
10h 41m2 stops
$255American Airlines
Find Deal
Mon, Oct 20 - Sat, Oct 25
American Airlines Logo
5:10 pm - 12:00 pmPIT-STT
18h 50m2 stops
American Airlines Logo
5:20 pm - 9:33 amSTT-PIT
16h 13m2 stops
$265American Airlines
Find Deal
Mon, Feb 23 - Fri, Feb 27
Delta Logo
7:20 am - 4:51 pmPIT-SJU
8h 31m1 stop
Delta Logo
6:15 am - 12:55 pmSJU-PIT
7h 40m1 stop
$291Delta
Find Deal
Booking Insights

KAYAK's insights & trends for Pittsburgh to Caribbean flights

Get data-powered insights and trends into flights from Pittsburgh to Caribbean to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Pittsburgh to Caribbean flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Caribbean from Pittsburgh found in the last 72 hours was to Punta Cana, at $418 round-trip. The most popular route is from Pittsburgh (PIT) to Punta Cana (PUJ), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $418.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Pittsburgh to Caribbean, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Pittsburgh to Caribbean is September, when tickets cost $285 (return) on average. On the other hand, the most expensive months are December and August, when the average cost of round-trip tickets is $498 and $474 respectively.

What’s the cheapest day of the week to fly from Pittsburgh to Caribbean?

The average price of all round-trip flights from Pittsburgh to Caribbean clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Caribbean on a Tuesday and more expensive on a Saturday. On your return trip to Pittsburgh, you should consider flying back on a Thursday, and avoid Sundays for better deals.

How far in advance should I book a flight from Pittsburgh to Caribbean?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Pittsburgh to Caribbean, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Pittsburgh to Caribbean, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 20 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$113
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly with an average 2% increase in price.
Flight from Pittsburgh to San Juan

FAQs - booking Caribbean flights

  • How does KAYAK find such low prices on flights from Pittsburgh to Caribbean?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Pittsburgh to Caribbean.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Pittsburgh to Caribbean?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Pittsburgh to Caribbean is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Pittsburgh to Caribbean?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Pittsburgh to Caribbean with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Pittsburgh to Caribbean?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Pittsburgh to Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Caribbean?

    The cheapest time of day to fly to Caribbean is generally at night, when round-trip flights cost $280 on average. Morning departures are around 1% cheaper than evening flights, on average. The most expensive time of day to fly to Caribbean is generally in the evening, which is peak travel time and where the average cost of a ticket is $433.

Reviews of the top 5 airlines serving from Pittsburgh to Caribbean

 
Need help choosing which airline to fly with from Pittsburgh to Caribbean? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4245 reviews
7.5Entertainment
8.0Comfort
7.0Food
8.1Boarding
8.6Crew
Airline reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

10.0 ExcellentG, Sep 2025LAS - ATL
Read more Southwest reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

The food was terrible especially for a 15 hour international flight. The crew was unpleasant as well.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

Quick check in. Everything went smooth. I don't know what can be done about airline food.

Crew was good. The reservation got mixed up and they didn't have my TSA number. I am also a Silver Medallion and wasn't able to use Sky Priority.

Delta made it easy, comfortable and timely. The crew was fantastic.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Nothing special. The crew never went out of their way for anything.

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

We had to deboard 2 times due to maintenance issues. They changed the plane, and then we got deviated to LAX due to maibtenance issues on the other plane, had to sleep at LAX and los a full day.

Everything was good, except the seats in economy were so close together, you could barely get out when the seat in front of your was reclined. If the airlines keep jamming in more and more seats, it will become intolerable. I will look for another airline that considers customer comfort and does not keep adding more rows of seats for more profit.

The newer screen was super cool and had the option to watch many different shows or movies. Crew was polite and helpful. However again, many children screaming bloody murder and kicking my seat, and parents doing nothing about it as usual.

Flight was good and crew was super polite. However, there were around 5 kids screaming the WHOLE 2 hours. I understand kids have to come but parents need to do something to control their children. They make the experience terrible, especially after finishing 16 hour shifts at the hospital I needed some sleep, which I did not get.

IAD with the archaic people movers is just a place to be avoided.

Great service on board. Boarding a bit slow due to process. Food was pretty average.

Tastless food and too obvious lack of enthusiasm for service in the economy vesus business class

All of the United employees I interacted with were professional and courteous. The aircraft was clean, the food on the flight was good. No complaints here.

I had no checked baggage but was required to hand over carry on baggage at the door of the plane. There was a lot of overboard space in the plane and I was one of the last ones. I ran to get my carry on but it was gone. I was given back at the plane door in Toronto, so the wait was not as long as it would have been at the carousel.

Armrest controller on my seat 35D and nextbooennseat 35E did not work right. Hard to press buttons to recognize and 35D had constantnpressure either upmost down somit was nearly impossible to make selections. .

Flight was delayed not sure why no explanation given and no apologies either. Otherwise the flight was fine

Did not get the seat I selected and paid for.

The flight was canceled 3 hours after original take off time

Plane was delayed for 6 hours, at first by weather, which is understandable, but was further delayed with NO given reason for 2 1/2 hours more. We had no clue when we were going to depart actually until they opened the ramp. VERY POOR to ZERO COMMUNICATION!!!

Flight was delayed and after being in the airport for like seven hours, it was canceled.

Flight delays numerous times. Everytime we would get close to boarding it would be delayed again. Strung along the entire time.

Overall very good, only complaint I have is the crew from CLT to SAT could have collected trash sooner.

Above and beyond effort from this crew in a tough situation. So helpful and understanding. Thank you!

We started with trouble checking in 24 hours early. Then my husband did not get his TSA precheck. Finally flight delayed due to no crew. I know things happen

Most miserable flight ever. We waited almost 2 hours on the runway because the flight was oversold. American offered $1200 credit. Then there was some nonsense about weight distribution. Ridiculous. No food for 8 plus hours on the flight. I will be writing a letter.

Everything was fine. I'm average height and I pack light. I'm ready for my Spirit flight.

Changing the flight time to 6:15 am on the return flight is extremely inconvenient. The flight was okay. It was on time. The crew was friendly. The seats were uncomfortable. All the upsells are annoying, and I would prefer paying a single higher fee and not have to purchase so much extra.

Spirit Airlines was ok but TRAVELHELPDESK, the 3rd party travel agent IS A JOKE! VERY RUDE CUSTOMER AGENTS ont he phone. NO HELP AT ALL. But the airlines was ok.

No Tumberlence smooth flight. Try to change the menu on Snacks.

Cancelled my flight last minute and did not help me rebook. It was a horrible experience.

No frills - because you get what you pay for. The crew was amazing!! I had plenty of room to spread out because the flight was half full. Which made it easy to sleep.

The terminal crew is so rude cabin crew is extremely rude flight is very good

Spirit is low fare air line. Food also cost you. No free food.

The flight was delayed twice with minimal explanation. The terminal and airplane were filthy. The food voucher didn’t even cover a tiny pizza from a kiosk in the terminal. All in all, a pretty miserable experience for a flight to attend a funeral

I will use spirit more New clean aircraft Excellent crew ! Quick boarding process !

Everything you need to know for your flight to Caribbean

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