$112 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 10/27. 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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Best Caribbean Flight Deals from Pittsburgh

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$307
Santo Domingo
Santo Domingo1 stop$355
Montego Bay
Montego Bay1 stop$309
Oranjestad
Oranjestad1 stop$353
Nassau
Nassau1 stop$331
Kingston
Kingston1 stop$362
Simpson Bay
Simpson Bay1 stop$373
Providenciales
Providenciales1 stop$418
Port of Spain
Port of Spain1 stop$534
Bridgetown
Bridgetown2 stops$400
George Town
George Town1 stop$423
Willemstad
Willemstad1 stop$636
St. John's
St. John's1 stop$463
Puerto Plata
Puerto Plata2 stops$519
Aguadilla
Aguadilla1 stop$320
Punta Cana
Punta Cana1 stop$307
Santo Domingo
Santo Domingo1 stop$355
Montego Bay
Montego Bay1 stop$309
Oranjestad
Oranjestad1 stop$353
Nassau
Nassau1 stop$331
Kingston
Kingston1 stop$362
Simpson Bay
Simpson Bay1 stop$373
Providenciales
Providenciales1 stop$418
Port of Spain
Port of Spain1 stop$534
Bridgetown
Bridgetown2 stops$400
George Town
George Town1 stop$423
Willemstad
Willemstad1 stop$636
St. John's
St. John's1 stop$463
Puerto Plata
Puerto Plata2 stops$519
Aguadilla
Aguadilla1 stop$320

Cheap Flights from Pittsburgh to Caribbean

 
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

Sun, Jul 6 - Sat, Jul 12
Frontier Logo
3:14 pm - 9:54 amPIT-SJU
18h 40m1 stop
Frontier Logo
9:30 pm - 9:01 amSJU-PIT
11h 31m1 stop
$185Frontier
Find Deal
Fri, Jul 4 - Wed, Jul 9
Frontier Logo
3:49 pm - 11:59 pmPIT-SJU
8h 10m1 stop
Frontier Logo
12:59 am - 2:29 pmSJU-PIT
13h 30m1 stop
$193Frontier
Find Deal
Fri, Jul 4 - Thu, Jul 10
Spirit Airlines Logo
10:32 am - 7:19 pmPIT-SJU
32h 47m2 stops
Spirit Airlines Logo
11:59 pm - 11:29 pmSJU-PIT
23h 30m1 stop
$219Spirit Airlines
Find Deal
Mon, Oct 20 - Tue, Oct 28
Delta Logo
7:20 am - 4:25 pmPIT-SJU
9h 05m1 stop
Delta Logo
7:00 am - 3:46 pmSJU-PIT
8h 46m1 stop
$225Delta
Find Deal
Mon, Jul 21 - Fri, Jul 25
Spirit Airlines Logo
6:20 am - 9:09 pmPIT-SJU
14h 49m1 stop
Spirit Airlines Logo
11:59 pm - 11:29 pmSJU-PIT
23h 30m1 stop
$237Spirit Airlines
Find Deal
Sun, Oct 19 - Fri, Oct 24
Delta Logo
6:00 am - 4:18 pmPIT-SJU
10h 18m1 stop
Delta Logo
12:57 pm - 9:09 pmSJU-PIT
8h 12m1 stop
$245Delta
Find Deal
Tue, Oct 21 - Tue, Oct 21
United Airlines Logo
7:05 am - 2:44 pmPIT-SJU
7h 39m1 stop
United Airlines Logo
1:05 am - 1:05 pmSJU-PIT
12h 00m2 stops
$310United Airlines
Find Deal
Tue, Oct 21 - Tue, Oct 28
United Airlines Logo
11:04 am - 11:57 pmPIT-SJU
12h 53m2 stops
United Airlines Logo
1:20 pm - 11:27 pmSJU-PIT
10h 07m2 stops
$315United Airlines
Find Deal
Wed, Jul 9 - Wed, Jul 16
American Airlines Logo
5:46 am - 3:55 pmPIT-STT
10h 09m2 stops
American Airlines Logo
5:05 pm - 9:19 amSTT-PIT
16h 14m2 stops
$319American Airlines
Find Deal
Mon, Oct 20 - Sat, Oct 25
American Airlines Logo
7:34 pm - 2:45 pmPIT-STT
19h 11m2 stops
American Airlines Logo
5:15 pm - 11:46 pmSTT-PIT
6h 31m1 stop
$325American Airlines
Find Deal
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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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Pittsburgh to Caribbean.

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 June, when the average cost of round-trip tickets is $508 and $454 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 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 22 weeks before departure.


Good to know

Low seasonSeptember
High seasonMarch
Cheapest flight$112
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly with an average 3% increase in price.
Flight from Pittsburgh to Nassau

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.

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 4278 reviews
7.1Food
8.2Boarding
8.0Comfort
7.6Entertainment
8.6Crew
Airline reviews

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

10.0 ExcellentMichael, Jun 2025SMF - SEA
Read more Southwest reviews

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

The flight was scheduled for 2:30 PM. Early in the morning we got a text message saying the flight was delayed and rescheduled for 3:00 PM. We got to the airport with that in mind. Then we got a message during check-in at the flight was rescheduled again for 2:30 PM. We almost missed our flight. In fact, our bags Were told that they would not make it. At the end, everything worked out. But it is very stressful.

Overall, aside from the baggage issue, it was as good as one expects.

Most aspects were good however if they assign boarding zones they ought to enforce them or why bother? My luggage from SAN-JFK-MAD was lost in NY so I without my main bag for two days upon arrival in Spain. They were helpful in tracking it and eventually delivered it to my hotel. The flub was because of a delay upon arrival in NYC. I had booked 2 1/2 hours between flights but we had to hold on the taxiway for an hour after landing while waiting for a clear gate which likely caused the baggage error.

I want to single out flight attendant Mitch who was in the Premium Economy section. When my wife’s hearing aide dropped through the cushion under the seat he was able to locate it and return it to her. Food was a different matter. Dinner was fine. Breakfast was another matter. They had a yogurt dish that the ran out of and the alternative was not very good according to those we talked to.

Excellent check-in. Crew was good. Excellent communication from flight deck.

Great overall. There was a bit of turbulence so they could only serve water because too much turbulence for the carts. Was glad they prioritized safety though

Excellent flight, the planes were newer, they did a nice job with boarding, great service overall.

Flight was delayed long enough that I was misding my connecting flight. The agents could not get me on a comparable flight, nor could they get me s Main Cabin seat I had paid for, nor could they get me on a comparable connecting flight. The gate agent would not issue meal vouchers, even though I was delayed over six hours! I had to spend over an hour and 15 minutes with customer service on the phone to See if they could get me on a better flight and get a meal voucher. Customer service was not helpful enough in trying to find alternate flights and it Ended up taking me 24 hours for a 12 hour trip!! Delta does not provide upgrades NOR will they even give you a pass for a few hours to their lounge. They claim that they do not issue daily passes to their lounge anymore. I call BS since this would be no extra cost to them to provide excellent customer service and give you a few hours to relax in comfort when you’re sitting in a crowded airport and your flight has been screwed up for that many hours.

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

United airlines, mediocre at best. No issues , nothing great . Worked for me

Boarding experience was smooth. Flight attendants were friendly and helpful. Entertainment system on the Houston-Edmonton flight did not function for passengers on the left side of the aisle. On the bird's eye flight from Quito to Houston, they should not serve a meal. No one needs to eat after midnight and it is disturbing for those passengers trying to sleep.

it was so bad. I tried to board my flight from vancouver to saskatoon. And to my surprise they did not board me cause the flight was changed and no email was send to me. and on my boarding pass which i got from seattle says different flight. I did not knew anyone from Vancouver, air canada crew was rude, i asked for today flight but they were rude and i had early morning dental appointment in saskatoon. I was so much in pain and my whole day is wasted today. and i suffered alot. They did provide me hotel but they did not provide me any food. I am really really disappointed first time had so bad experience with air canada. I may think twice to book it again. If i can get any reply or any composition that would be great. Thanks

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

Terrible. Out flight was delayed for 21 (twenty one) hours. United is a joke.

Boarding was mayhem. Late boarding by 15 minutes because of lack of staff (missing 1 flight attendant. We had to wait for an arrival of another plane before we could board). Flight was a little rough, but cannot blame on airlines.

Impressed with the service despite turbulence because of the weather. Both flights arrived before their scheduled times.

Very comfortable (upgraded to business class). The audio on my screen didn’t work, but I managed to play the audio through my phone while watching the screen.

The food was the worst I’ve had on any flight I’ve ever been on.

Great experience…left a bit behind schedule but made up fir that in the air and landed 10 minutes early 😁

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.

Honestly, I haven’t flown American in years, probably due to the pandemic and my being unable to travel for certain periods in the last two years, but it was a good experience to dig out or obtain a new American Airlines account after many years of traveling for business with American in the past.

It’s a great flight. Service is good. Staff is awesome.

Again flight was awesome except British Airways lost both gate checked luggage’s. Still missing

Everything about the flight was lovely…We left early, arrived early, cabin crew were efficient and helpful. Flight was easy and most pleasant.

Everyone was nice. It was on time and the food was. Airplane food, but not horrible

One bottle of water and a package of cookies for comfort plus. We had to literally beg a flight attendant for an extra bottle of water later in the flight due to feeling dehydrated.

late again! but its my only option to not take 9 hours to get to Memphis

Almost everything was outstanding. First, we boarded on time and the flight crew did a great job getting everyone seated. Then the pilots took their time and care to make sure the plane was full de-iced three times as there was a bad ice storm a few hours earlier. The plane ride was smooth and comfortable and even the economy seats had decent room and comfort. Flight Attendant Lisa went above and beyond to make sure I was comfortable - she is outstanding. The only thing wrong with the flight, and it is something which needs to be addressed, is that the gate to gate time was over 6.5 hours and not one meal was served. The only thing offered to eat were two small cookies for a transcontinental flight - unacceptable. Charge me more but give me a meal for a long flight. Thankfully Lisa found something for me.

Very poor. Our special services attendant gave us incorrect information. I also was mishandled at landing. There was no wheelchair waiting. I fell deboarding the plane. Appalling!

Great! We boarded on time! Everything went so smoothly! The flight was so smooth

Spirit gets you there; it's no worse than any other aircraft, all things considered. (It's not like everyone else is such a hero). But - holy moses - do they nickel and dime you to absolutely every nickel - I was really expecting to have to pay to use the bathroom. And when the captain comes on with a 5 minute sales pitch about getting "points", that was like something on Bizarro world. Other than that, everyone else was professional and worked hard to get us from point A to point B. I'm not loving all the "self-service" stuff but there it is - just when the machines don't work you don't have anyone to talk to.

Boarding was a breeze, however, two of the flights that I boarded with Spirit did not have Wi-Fi available.

Seats uncomfortable, hard to check luggage, etc. It was like the last flight out of Hanoi

Need screens for tv/movies. Seats are more cramped than any other airlines. Seats are hard. They don’t recline. And in flight time should not be used for sales pitches.

Good experience except for the drunk woman who was with a child. Sad

The ease of booking the flight was very good. Speaking with customer service was also good. However, the crew people are unfriendly and unwelcoming which I found this as unprofessional. As far as comfort it was mediocre. This was my first time flying Spirit and I chose them because of the flight times met my needs and my budget. However, I would be reluctant to fly on Spirit again. In addition, if the crew were more friendly and at least appeared somewhat happy and welcoming personally it would probably make the experience of flying with Spirit better.

Tell them to chose a better, less bumpy route :( my seat had no window all the way at the end 😔

Seats too hard, too much lumbar. Space between rows was extremely tight, so tight hard to place item under seat in front of me. No tv screens. Zero plugs for charging phones. Too many sales pitches

Prepaid for 1 bag but my prior airline did not provide it to me in time to check it with Spirit and I could not get my $75 refunded.

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