$98 Find Cheap Flights from Pittsburgh to Caribbean - Compare and Save

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Cheap Flights from Pittsburgh to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Punta Cana
Punta Cananonstop$347
Santo Domingo
Santo Domingo1 stop$377
Montego Bay
Montego Bay1 stop$362
Oranjestad
Oranjestad1 stop$302
Nassau
Nassau1 stop$302
Kingston
Kingston2 stops$562
Simpson Bay
Simpson Bay2 stops$290
Providenciales
Providenciales1 stop$516
Port of Spain
Port of Spain1 stop$577
Bridgetown
Bridgetown1 stop$515
George Town
George Town1 stop$412
Aguadilla
Aguadilla1 stop$307
Puerto Plata
Puerto Plata2 stops$596
St. John's
St. John's1 stop$768
Punta Cana
Punta Cananonstop$347
Santo Domingo
Santo Domingo1 stop$377
Montego Bay
Montego Bay1 stop$362
Oranjestad
Oranjestad1 stop$302
Nassau
Nassau1 stop$302
Kingston
Kingston2 stops$562
Simpson Bay
Simpson Bay2 stops$290
Providenciales
Providenciales1 stop$516
Port of Spain
Port of Spain1 stop$577
Bridgetown
Bridgetown1 stop$515
George Town
George Town1 stop$412
Aguadilla
Aguadilla1 stop$307
Puerto Plata
Puerto Plata2 stops$596
St. John's
St. John's1 stop$768
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?

The cheapest ticket to Caribbean from Pittsburgh found in the last 5 days was to Punta Cana, at $376 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 5 days was $376.

Can I save money by flying with a layover from Pittsburgh to Caribbean?

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $711 on average.

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

The cheapest month for flights from Pittsburgh to Caribbean is January, when tickets cost $407 (return) on average. On the other hand, the most expensive months are November and December, when the average cost of round-trip tickets is $615 and $609 respectively.

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

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 14 weeks before departure.

Good to know

Low season

September

Cheapest flight

$98
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly with an average 11% increase in price.
Flight from Pittsburgh to Simpson Bay

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.

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.
7.9
SouthwestOverall score based on 4217 reviews
8.0Comfort
7.0Food
7.4Entertainment
8.1Boarding
8.6Crew
Airline reviews

Delayed over 3 hours, extremely rough landing on all four flights. Would not recommend

2.0 MediocreKevin, Oct 2026
Read more Southwest reviews

Delayed over 3 hours, extremely rough landing on all four flights. Would not recommend

Boarding, crew and inflight entertainment was great. Could have better food options for a long flight. Paid money and got a seat with extra leg space but was asked to keep my carry on under the seat in front of me which defeats the purpose of buying a extra space seat.

Just crazy with times being pushed and pushed and pushed and gate crew at Philly super rude and unprofessional with many under stress with delays.

My experience will Southwest was good. I wish there was more entertainment and the boarding process was slow at time but other than that my experience was great definitely will be flying with SouthWest again.

For my birthday trip this was my second time ever flying, this trip was the best.

I really wish that SW would ask anyone with a carry-on to wait while those who don’t have to access the overhead bins are boarded. Then, reverse that when the plane arrives. Those without the need to clog up the aisle retrieving their bags from the overhead bins wait for those exiting the plane without needing to clog up. The aisle.

We boarded the flight and set two and a half hours on the jetway. Would have been better if they had not boarded us at all. Plane was hot and it was limited ability to access the restrooms or get a drink of water. Very unpleasant experience

The actual flight was great! The 3 hour delay not so much.

Southwest is a garbage airline and the people who fly it are garbage people.

Boarding was easy. Plane wasn’t crowded. Plenty of space. Flight was on time. Crew was pleasant.

Everything was pretty good. I would like to have more drinks (water) during four hours of the flight.

This flight was the flight we missed due to deltas delay at our first airport going TO Atlanta.

This a short easy flight. No food or drink but that was not an issue since we were only in the air for 35 minutes.

No Internet, no backseat screen, no nothing. I bought a Delta ticket and ended up on American Airlines. How did that happen?

Connection flights should be spaced out farther because too close I missed my connection.

The flight was way too HOT! And the plane did not have any in-flight TV entertainment.

The gate attendants and the crew were terrible. Because of high winds, they needed to carry more fuel, so they had to get volunteers to take the next flight at 6 am the next day. They did a terrible job of it - our flight ended up taking off just under 3 hours of the scheduled time. I hope to never fly Delta again.

Great service. Great staff. Boarding was a little slow, but I think there was a service dog slowing things down.

We splurged and decided to fly first class. Seats were roomy. But flight crew arrived late to the airport. That delayed our flight. Most of the passengers had to try to make connections flights. I felt bad for them. We checked 4 bags. We got three from the baggage claim carousel. 4th one was lost. Delta online help wasn’t good. Baggage claim staff were sympathetic and nice but we waited around for almost 2 hours and it had t been found. They did find it several hours later and we had to drive back to airport to retrieve it. I won’t be splurging on 1st. Lass again anytime soon. I think we got worse service. I am also not a huge fan of delta but we have family in ATL so we don’t have a ton of choice. What should have been an easy flight turned into a stressful event due to flight crew tardiness and baggage mishandling.

My flight consistently said it was on time and the plane didn’t arrive until after 30 minutes after take off and nothing was announced to passengers

Just sat on the run way after we arrived early

Stored my cloth purse under seat in front off me as instructed. When I retrieved it, half of it was soaked, along with everything inside it. I don’t really know how that could have been prevented because the area did not look wet, but I was not happy about it.

It was easy to board, and the staff was friendly and helpful. What could have been better is that I shouldn't have to pay extra for a seat that doesn't recline.

Was on the plane sitting longer than the actual flight in air was, boarded at 5:45p and didn't take off until 6:50p flight was only about 30 minutes long. Just was poor experience will booking more with American Airlines.

It was great. All the crew were professional and nice.

Miserable. They moved my seat, but canceled the next leg of my flight. I resolved the issue at my transfer, but that resulted in lost luggage that has taken days off my schedule with no resolution. Worse, they fail to interface effectively with Lufthansa, forcing me to bounce between two equally useless help desks. The apps are unable to handle the situation, the bag dropped off the tracker, and while the call centers are polite, they do not provide written information to assist with cross-airline communication.

The only downside was my cell phone charger wouldn’t work in the charging port but everyone else’s would work in them all. My cell phone cable works fine in my hotel room in Frankfurt.

A three (3) hour flight should have meal service in First Class, not just potato chips!

Crew were fine, drinks and snacks were as well but we were delayed for around 2 hrs which made our entry into Mexico delayed as well with the influx of arrivals at the same time. Sort of wasted our first day of vacation. We left Pittsburgh at 630am and did not arrive in Mexico until late dinner time.

Seats suck. Only one drink service in three hours with the flight attendants being more attendant to their phones than the customer. Painful in the extreme.

The boarding agent and checked bag agent were both rude. It only takes a second to be kind. However, the flight crew was amazing. I got a turkey sandwich and it wasn't bad---not great but not bad. The internet was my biggest problem. This was a work trip and I REALLY needed the internet to meet a deadline but it didn't work for 80% of the trip. Very disappointing.

I tried to check in beforehand from Ireland. The Jet Blue website sent me to the Aer Lingus website and vice versa. I tried to get a boarding pass at Dublin Airport as well, but they said they couldn't help me either. I had to wait until I arrived at the gate in Boston to secure a boarding pass...it was a bit nerve wracking.

Great flight. Best in years. Very clean craft. Easy boarding. Communicative pilot. Friendly flight attendants. Absolutely smooth take off, in flight and landing. Very comfortable seats. Smoothest flight I've experienced in years. THANK YOU JET BLUE!

I was asked to pony up an additional $239 (over the $735 paid originally) for a one way middle seat, which was very uncomfortable. Where did you expect me to sit?

Jet Blue sevice was good. Just don't understand why they charge for earphones to listen to flight entertainment. Other than that, everything was excellent.

Mostly good, flight take off in time and land earlier I can’t ask for more..

The crew was not nice this time. I asked for a drink one time and the girl didn’t say anything to me and just got me the hot drink while walking super fast to the back. We were sitting in the back and she wasn’t doing anything except socializing. She was upset I asked for something and she had to do her job. I also didn’t fully have it in my hands when she handed it to me so it was dangerous. She was abrupt and rude. She wouldn’t allow for people to spread out like previous flights we had been on if they were empty, and there were empty rows. It was strange and she enjoyed being angry at us.

They lost my luggage and refuse to help. Terrible airline. I've never experienced worse customer service in my life. Pretty much just told me too bad that I lost all my luggage, not caring that I am stuck in Europe for 2 weeks with absolutely nothing.

I especially liked the lead crew officer. His boarding and safety announcements were made with a bit of novelty and humor. The flight also left the gate 10 minutes early and we landed about 20 minutes early… It was a delightful flight…

As with all airline's seats, a little more padding would appreciated. Especially on longer flights.

It was a late flight; crew was invisible. Zero air flow - the tiny plane was a sauna; the left the lights on for 1/2 of the flight; there was no water. Never again.

What an amazing plane! We flew a 787 to Miami. Although the Internet was not functioning, it was a wonderful flight.

Plane was in good shape, multiple passes from the drink cart, and one of the smoothest flights I've had in a while.

Smell of jet fuel was overwhelming from inside the plane while on the ground at take off and landing. Gave me a sore throat and a headache. During boarding, de-planing, taxi-ing, waiting in line for take off, etc. Also, the vents didn't have enough cool air coming out (yes, off course I opened it all the way) so the whole flight was hot and stuffy. But just my vent - all the vents.

The flight had a 6 hours delay. This should not happen to anyone. Airlines should provide an alternative with no additional costs.

Seat comfort was poor (no lumbar or lower back support).

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

The American flight was a connecting flight to an international flight. The international flight has a 2 check bag rule. Despite being informed of this, American would only check 1 bag and wanted 100 to check the second (basically a 3rd carry-on) to NYC. Subsequently tsa took a sealed container of maple syrup and a few other things that couldn't be in carry-on plus I had to lug around 3 pieces of luggage for the entire trip. The American reservation was made with the international and American actually checked the one piece the entire way to China. This is one of the reasons that I will avoid American airlines if possible in the future.

The boarding process and flight were great. However, I waited about 40 minutes for my luggage. It did not come up on the designated belt. Instead, everyone’s bags were on a cart. Not sure what the issue was, but we were not informed until another passenger went looking for her bags and found them.

It was a good flight. Of course it was full, but it went well.

More options for your flight to Caribbean

Complete your trip to Caribbean with a hotel stay or car rental