$106 Find Cheap Flights from Pittsburgh to Caribbean Islands

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 Islands departing on 3/24. 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, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Pittsburgh to Caribbean Islands.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Pittsburgh to Caribbean Islands.
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Cheap Flights from Pittsburgh to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$365
Santo Domingo
Santo Domingo1 stop$363
Montego Bay
Montego Bay1 stop$352
Oranjestad
Oranjestad1 stop$333
Nassau
Nassau1 stop$373
Kingston
Kingston1 stop$425
Simpson Bay
Simpson Bay1 stop$359
Providenciales
Providenciales1 stop$341
Port of Spain
Port of Spain1 stop$306
Bridgetown
Bridgetown1 stop$382
George Town
George Town1 stop$347
Willemstad
Willemstad1 stop$307
Puerto Plata
Puerto Plata1 stop$411
St. John's
St. John's1 stop$563
Aguadilla
Aguadilla2 stops$262
Punta Cana
Punta Cana1 stop$365
Santo Domingo
Santo Domingo1 stop$363
Montego Bay
Montego Bay1 stop$352
Oranjestad
Oranjestad1 stop$333
Nassau
Nassau1 stop$373
Kingston
Kingston1 stop$425
Simpson Bay
Simpson Bay1 stop$359
Providenciales
Providenciales1 stop$341
Port of Spain
Port of Spain1 stop$306
Bridgetown
Bridgetown1 stop$382
George Town
George Town1 stop$347
Willemstad
Willemstad1 stop$307
Puerto Plata
Puerto Plata1 stop$411
St. John's
St. John's1 stop$563
Aguadilla
Aguadilla2 stops$262

Book Cheap Pittsburgh to Caribbean Islands 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 Islands 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 Islands

Fri, May 8 - Sun, May 17
Frontier Logo
8:15 pm - 8:04 am
PIT
-
SJU
11h 49m
1 stop
Frontier Logo
3:03 am - 7:20 pm
SJU
-
PIT
16h 17m
1 stop
$223Frontier
Sun, May 3 - Sat, May 9
United Airlines Logo
6:10 am - 12:34 pm
PIT
-
SJU
6h 24m
1 stop
United Airlines Logo
1:00 am - 9:31 am
SJU
-
PIT
8h 31m
2 stops
$227United Airlines
Tue, May 5 - Tue, May 12
Delta Logo
10:20 am - 4:23 pm
PIT
-
SJU
6h 03m
1 stop
Delta Logo
7:05 am - 5:19 pm
SJU
-
PIT
10h 14m
1 stop
$236Delta
Tue, Apr 14 - Wed, Apr 22
American Airlines Logo
10:55 am - 8:51 pm
PIT
-
SJU
9h 56m
2 stops
American Airlines Logo
3:19 pm - 11:21 pm
SJU
-
PIT
8h 02m
1 stop
$240American Airlines
Fri, May 8 - Thu, May 14
American Airlines Logo
7:55 pm - 1:35 pm
PIT
-
STT
17h 40m
1 stop
American Airlines Logo
2:05 pm - 11:59 pm
STT
-
PIT
9h 54m
1 stop
$250American Airlines
Thu, Mar 19 - Wed, Mar 25
Delta Logo
6:00 am - 1:47 pm
PIT
-
STT
7h 47m
1 stop
Delta Logo
12:49 pm - 12:17 am
STT
-
PIT
11h 28m
1 stop
$275Delta
Mon, Apr 13 - Fri, Apr 17
Spirit Airlines Logo
6:00 am - 3:28 pm
PIT
-
STT
9h 28m
1 stop
Spirit Airlines Logo
5:10 pm - 11:59 pm
STT
-
PIT
6h 49m
1 stop
$282Spirit Airlines
Fri, Apr 10 - Fri, Apr 17
Spirit Airlines Logo
6:00 am - 3:28 pm
PIT
-
STT
9h 28m
1 stop
Spirit Airlines Logo
5:10 pm - 11:59 pm
STT
-
PIT
6h 49m
1 stop
$283Spirit Airlines
Mon, Apr 13 - Wed, Apr 22
JetBlue Logo
6:00 am - 1:50 pm
PIT
-
CUR
7h 50m
1 stop
JetBlue Logo
2:41 pm - 11:59 pm
CUR
-
PIT
9h 18m
1 stop
$307JetBlue
Sat, Apr 11 - Thu, Apr 23
JetBlue Logo
7:30 am - 1:50 pm
PIT
-
SXM
6h 20m
1 stop
JetBlue Logo
1:40 pm - 11:59 pm
SXM
-
PIT
10h 19m
1 stop
$361JetBlue
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?

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

The cheapest ticket to Caribbean Islands from Pittsburgh found in the last 72 hours was to Punta Cana, at $324 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 $324.

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

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $364, prices are generally cheapest when you fly direct.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Pittsburgh to Caribbean Islands, 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 Islands is October, when tickets cost $267 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $459 and $444 respectively.

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

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 Islands, 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 Islands, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 25 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$93
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 1% 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

 
See real verified KAYAK customer reviews for airlines flying from Pittsburgh to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
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.
7.9
DeltaOverall score based on 8293 reviews
7.9Comfort
8.5Crew
7.8Entertainment
8.1Boarding
7.2Food
Airline reviews

First class is comfortable. Enjoyed a movie and was able to relax compared to coach.

10.0 ExcellentAnonymous, Mar 2026
ATL - DTW
Read more Delta reviews

First class is comfortable. Enjoyed a movie and was able to relax compared to coach.

Loved flying First Class. Very comfortable. The seat was amazing. Enjoyed a movie and was able to relax so much better than in coach.

We landed and sat on the tarmac for 45 minutes because they only have one gate at the airport and there was another plane running late so we had to wait

The WiFi was not working. That made for a long flight.

With Aeromexico it ended up good but with Delta it was bad because we did everything through Delta... Showed up at the Delta terminal... It was the wrong place! Nothing ever told us to go to the Aeromexico terminal. It said "in partnership with Aeromexico" but I was never instructed to check in with them or go to their terminal. We had to haul @$$ running through the airport and almost didn't make it thanks to this poor communication. 👎🏽

Absolutely no communication on why there's a delay and multiple flight time reschedules. I would have canceled the flight and drove back home if I known it was going to be rescheduled 3 or 4 times.

Another late night flight and MORE men belligerently drinking and yelling. I had to move from first to economy because they were so obnoxious and disruptive. Crazy to go from a cozy chair to cardboard when you were supposed to be in first. Delta allows was too much drinking which leads to belligerent behavior.

I was in first class and literally the men behind me were so aggressively loud I moved myself to economy. This has become so common on Delta - people using audio without headphones, and men on 12am / late night flights drinking and yelling to talk to each other which prevents anyone around them from resting. Pretty crazy to have to move from first to economy (poorer service, less comfort...). Wild wild. Looking into other airlines.

Love delta smaller commuter plane so no entertainment and paid wifi on MKE-LGA leg was extremely unreliable and slow

Stop changing gates. Stop cancelling flights Stop moving my seat.

Both my flight where delayed Had 25min to make it to my transfer flight

Everything was on time and service on the flight was great!

Wifi Bluetooth features for watching in flight movie was horrible. Screen kept blacking out no connection of sound although it said connected. Other than that smooth trip .

The 777’s economy seat’s legroom was more tolerable than expected. I appreciate the reclining mechanism which slides the seat forward to minimize cannibalizing the space behind. The food was terrible: very salty.

The travel company that you have on your site did me so wrong. I don’t know how it happened, but they put my son‘s name on my plane ticket flying to Vietnam. Along with his birthday. They would not have let me fly from Fort Myers to Ho Chi Minh City. I don’t think that I can ever use your service again. I typed my information into the browser along with my passport number and four days before I’m leaving I have to quickly search another ticket to fly out here.

Seats are uncomfortable. This has been a trend in the industry for decades. Trying to fit more seats on each plane to increase profits at the expense of the passenger.

The flight was delayed so we were dead tired, and after that the turbulence was horrible. I was very scared.

It’s always a great time flying with united airlines.

Good flight. Efficient boarding and competent flight crew. No problems until we arrived at our destination gate. We were early so there was an aircraft at the gate that had to move before we could pull in. Then, due to the type of aircraft we flew, the cabin door could not be opened until some luggage from the cargo bay was offloaded to preserve center of gravity characteristics. So, that further delayed deplaning. Despite being 20 minutes early on landing, we ended up being 5 to 10 minutes late after all the delays.

Everything went well except the turbulence what no one have a control of but pilot and crew handled very good!

My check in was stressful. I somehow lost my seat from my original booking, the plane showed no availability/no seat when it was time to check-in. I called and was instructed to try to get a seat at the airport. I asked if it was a full flight and the travel agent said the site showed some seating but was not able to secure one for me. Why not? On my way to the airport the app finally revealed one available seat towards the back of the aircraft that I was able to book. It ended up being an overbooked flight, so glad I wasn't stuck.

Flights with JetBlue from San Diego to Boston are a miserable experience. The flight was delayed about 1.5 hours due to “weather” supposedly but the flights for other airlines left on time so it just have been some kind of weather that only affects JetBlue. I had a small carry on - purse. The crew stored it in a bin 2 rows down from me because they were using the bin next to my seat for other people’s stuff. The TV screen in the emergency row seats does not work. It just was awful from start to finish. When we landed, we had to sit inside the plane for a very long time because the plane had to be moved to a different gate.

They made me check my bag and I didn't need to as there was overhead space available. I paid for a seat towards the front of the plane and it didn't recline. I requested a refund and they declined to give me one.

I have to congratulate Kayak (and Dylan the Chatdeal agent) because because when we decided extended our trip in Florida by two days, there were many direct flights oprions back to Boston available on the Friday we wanted to fly on the JetBlue website, but once I canceled the original JetBlue flight on their website, those direct return options disappeared immediatley! I think it's a game JetBlue plays. . Luckily, I checked Kayak and they had a direct flight that wasn't appearing on JetBlue's website and so I booked it, and we were able to fly home direct through the Kayak booking when JetBlue was offering nothing (even though I have been a True Blue member for 20 years, and also am a Mosaic member). So much for loyalty- their algorithm for booking is like a shell game. JetBlue used to be a good company but now they're worse than anyone. Also I was originally booked this trip to Florida, two months before the departure date, I booked the trip on JetBlue's website and then after the payment part, they said there was a problem and that I needed to do the booking again, so when I immediately went to rebook , the price had gone up 30%! I called them and it sounded like they had heard this so many times before and the guy told me to check back in 10 minutes and the price would be back to where it was when I was booking- it but it never was. How could the price go up 30% in one minute two months before the flight???? They're playing a game with their customers. Anyways, I booked a cheaper flight then at a less convenient time. So fast forward two months the night before the 7 AM flight, they sent me an email at midnight when I was sleeping to let me know that my flight at 7 AM had been canceled. The only thing they offered was a flight that night from from a different airport (Providence) to a different airport in Florida (West Palm Beach) or a flight two days later. No compensation, nothing. They couldn't of tried to get another plane to the Boston airport? They had all night to do it. I passed on their ridiculous options and flew with Delta and it was a great experience. Of course, I had to pay a lot more booking on the same day, but JetBlue doesn't care. I put in a lengthy complaint with the agent who assured me someone would get back to me by email within three days and I haven't heard a thing. JetBlue used to be a good company but now they're among the worst. The only thing they still have is decent legroom, but the corporate bean counters will probably start taking that away too.

We were made to wait in the airport for six hours for a flight that was ultimately canceled.

Both flights were significantly delayed. The flight experience itself was great.

My flight got delayed and eventually canceled, then rescheduled. I and several others had a connection from Boston to Paris and asked several times if we would make it. They assured us we would and then rebooked us mid flight without our consent and closed doors early even though they said they communicated we were a bit delayed. We got stranded in Boston and I opted with being rebooked for a different connection to France since they refused to pay for a Hotel. I've now been in Europe for 5 days and still haven't recieved my bags. There was absolutely no urgency for the fact that I'm in a foreign country with absolutely no change of clothes or any of my medication. Such an overwhelming and frustrating experience.

Automated scanning was slow and somewhat haphazard. Too many people were unfamiliar with the tech and were forced to learn on the fly. The hands off approach of the gate staff made it more uncomfortable. This needs work. Overall the flight and cabin crew were excellent.

The crew for the flight was A+ top notch. They were friendly and professional and made the flight a very relaxing and enjoable.

Rude crew member. She seemed annoyed at me without me saying a single word. Also loudly admonished me for having my bag next to my seat instead of tucked away before landing. Just telling me to put it away and guiding me without giving me a lecture would have been enough.

It would have been nice if American tried to care.

Delayed initially because they couldn’t print the flight details. Poor instruction on delay. When I got on the plane the flight attendant argued with me about whether my carry on would fit (it did, although she didn’t acknowledge that). No greeting (other than arguing with me) getting on or off the plane.

Beverage service was not good. Also just one service in 5 hr 30 min flight. No ask fir water ir anything beside one time beverage service.

They are always late and seats was also not having working charger

Broke my luggage and I can't get a resolution yet.

My flight to London from Philadelphia was cancelled due to weather.

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

This flight captain and crew were amazing, started ahead of time of departure and reached 30 mins before arrival time. Amazing!

Long delays, lack of information about the status of the flight. The flight was delayed 4 times.

Everything about the flight was lovely. My only suggestion would be to offer a few more options of tv series from Apple TV or HBO.

Flight was delayed, then undelayed, then delayed again. Gate was changed to the other side of the airport. Horrible seats with no screens. Spirit os truly awful, even for a budget option.

flight delayed because of poor staffing and organization - confusion from gate agents and flight attendant supervisors scheduling a missing flight attendant. flight delay 1 hr 30 min

I liked the quickness of the boarding process. Things were run smoothly and the staff was very professional. The overall experience was great.

Flight was delayed more than 3 hours, and the metro had stopped running by the time we got to the terminal well past midnight, so I was stranded, alone, with no way to get home until the metro started up the next morning.

We get stuck in the plane when landed during 45min and no communication from the crew People were listening to their phone and music out loud and nobody told them anything I definitely want stop booking spirit flight it is a disaster

When I arrived at the airport at 4:00 in the morning, I was notified that I "hadn't paid" for my ticket (I had paid and had a boarding pass). Then I was told that while I had paid, the ticket was $600 more than it actually was, and that I needed to pay that so I could board. None of this was true, of course, but it took 20 minutes, two crew members behind the desk, and one on the phone to clear up.

The flight was delayed by two hours, then by three hours. Then, at 10:01, a notification that the flight was back on schedule for the original time. I just happened to be getting on a train to go to the airport at 10 just to be extra early for the delayed departure when I saw the update come through. I got to the train terminal at the airport at 11:07. A shuttle immediately arrived and offloaded, but didn't show anyone on before speeding off. It was 30 minutes before another arrived. I finally got to the terminal and through security and to the gate just in time for them to tell me the door had just been locked. Flight closed. I had to wait until the next day to fly out. No or for a hotel, a meal, nothing.

The staff were very helpful. Definitely the stars of my experience. The seats were very uncomfortable.

Good: It was cheap and they got us to our destination safely. Not so Good: Gates experience with many, many nauseatingly (almost) threatening announcements about bags size and how much they were going to charge us if our bag was too big, even to the point of having a gate agent roaming around through the passengers eyeballing bags size and making people go check their bags in the sizers.

For a change, friendly staff at check-in and in flight.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports