$93 Find Cheap Flights from Pittsburgh to Caribbean Islands - Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 21% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Pittsburgh to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Sort by: Cheapest
San Juan
6h 10m2 stops
from $186per person
Saint Thomas Island
6h 25m2 stops
from $290per person
Nassau
4h 44m2 stops
from $306per person
Oranjestad
6h 40m2 stops
from $327per person
George Town
5h 59m2 stops
from $359per person
Simpson Bay
6h 43m2 stops
from $361per person
Providenciales
5h 30m2 stops
from $372per person
Punta Cana
4h 10mNonstop
from $376per person
Explore the map
Booking Insights

KAYAK's insights & trends for Pittsburgh to Caribbean Islands flights

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

What is the cheapest Pittsburgh to Caribbean Islands flight route?

The cheapest ticket to Caribbean Islands from Pittsburgh found in the last 5 days was to Punta Cana, at $406 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 $406.

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

No, with an average price for the route of $389, prices are generally cheapest when you fly direct.

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

The cheapest month for flights from Pittsburgh to Caribbean Islands is January, when tickets cost $428 (return) on average. On the other hand, the most expensive months are November and December, when the average cost of round-trip tickets is $671 and $666 respectively.

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

To get a below average price on the flight from Pittsburgh to Caribbean Islands, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 11 weeks before departure.

Good to know

Low season

September

Cheapest flight

$93
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly with an average 15% increase in price.
Flight from Pittsburgh to San Juan

FAQs - booking Caribbean Islands flights

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

    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 Islands.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Pittsburgh to Caribbean Islands 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 Islands?

    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 Islands 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 Islands?

    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 Islands 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 Islands

 
Need help choosing which airline to fly with from Pittsburgh to Caribbean Islands? 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 4195 reviews
7.5Entertainment
7.0Food
8.1Boarding
8.0Comfort
8.6Crew
Airline reviews

Delayed and once landed waited very long for the luggage

6.0 GoodIngeborg, Sep 2026
Read more Southwest reviews

Delayed and once landed waited very long for the luggage

Nice managed … it was a smaller plane, so the seating wasn’t as comfortable.

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.

Flight Staff: Always great! Checking back vs carry-on: I typically check my bag since so much time is spent stowing the bag, it's heavy, maybe not enough room. Delta is charging $45 to check bags. Yet, the people who have multiple carry-on bags are then asked to check their bags and are offered this service for free. This does not seem fair to a person who is trying to be proactive in improving the process . Boarding: Boarding is always slow and exhausting. With the exception of First Class, Economy, why not board the zone in the back of the plane first??? Seats: Why cross the seat belts? I get that it looks nice, but people waste so much time moving them or sitting on them and then having to move. Seats: On both my flights the seat did not recline. Not a big deal. Smell: There was a horrific smell like the restrooms on my first flight. I thought I was going to be sick. Most flights do not smell great. Does Delta use air purifiers or anything?

The crew were very respectful. And also they were welcoming.they did help us locate our seats.i enjoyed.

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

Like the fact that the boarding was expedited. But the delay and chaos around the onboarding was not appreciated.

The flight crew were very helpful. The seats were very close together. There was barely room to sit without touching the person next to you.

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

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

newer aircraft, ability to connect my headset via blue tooth for entertainment.

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.

Flight was cancelled due to a myriad of operational issues. You guys really suck

Our gate was changed several times, and the gate agents were just as in the dark as all of us in knowing when our plane would arrive at PHL.

mechanical problem delayed more than 2 hours on the run way.

The boarding process was slow and we had a delay on the tarmac, not the fault of the airline. They had ZERO food options available for purchase which shouldn't happen.

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.

Very good flight that left on time and arrived earlier than anticipated, which was a plus! The crew members were very welcoming and helpful. However, the temperature on the flight was very cold - almost to the point of extreme discomfort. Additionally, requiring passengers to pay $8 for headphones to access the JetBlue entertainment was disappointing. Those earbud jacks are not used with most technology and would not be able to be used. There was no option to use Bluetooth for my own earbuds. Beyond those inconveniences, the flight was good.

My original flight was cancelled. My replacement flight was delayed over 2 hours. I lost my whole day in NY

Delays were crazy long (over an hour) both for boarding and baggage claim

awful expereince. boarding was a mess and not communicated, then we sat on a hot plane and were at risk of getting kicked off

2 hour delay and a lack of air conditioning on the plane. Not a good combination

Fabulous! This was the first time we've flown with JetBlue and the entire experience was flawless!

First time flying JetBlue and my perception changed. Love it.

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.

More options for your flight to Caribbean Islands

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