$90 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 2/22. 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 Cana2 stops$319
Santo Domingo
Santo Domingo1 stop$250
Montego Bay
Montego Bay1 stop$280
Oranjestad
Oranjestad1 stop$260
Nassau
Nassau1 stop$349
Kingston
Kingston1 stop$360
Simpson Bay
Simpson Bay1 stop$293
Providenciales
Providenciales2 stops$326
Port of Spain
Port of Spain2 stops$274
Bridgetown
Bridgetown1 stop$362
George Town
George Town1 stop$290
Willemstad
Willemstad1 stop$245
St. John's
St. John's1 stop$422
Puerto Plata
Puerto Plata1 stop$341
Aguadilla
Aguadilla2 stops$328
Punta Cana
Punta Cana2 stops$319
Santo Domingo
Santo Domingo1 stop$250
Montego Bay
Montego Bay1 stop$280
Oranjestad
Oranjestad1 stop$260
Nassau
Nassau1 stop$349
Kingston
Kingston1 stop$360
Simpson Bay
Simpson Bay1 stop$293
Providenciales
Providenciales2 stops$326
Port of Spain
Port of Spain2 stops$274
Bridgetown
Bridgetown1 stop$362
George Town
George Town1 stop$290
Willemstad
Willemstad1 stop$245
St. John's
St. John's1 stop$422
Puerto Plata
Puerto Plata1 stop$341
Aguadilla
Aguadilla2 stops$328

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

Tue, Mar 3 - Wed, Mar 4
Spirit Airlines Logo
6:00 am - 4:34 pm
PIT
-
STT
9h 34m
1 stop
Spirit Airlines Logo
3:36 pm - 11:25 pm
STT
-
PIT
8h 49m
1 stop
$153Spirit Airlines
Tue, Feb 17 - Tue, Feb 24
Spirit Airlines Logo
6:00 am - 4:34 pm
PIT
-
STT
9h 34m
1 stop
Spirit Airlines Logo
3:36 pm - 11:25 pm
STT
-
PIT
8h 49m
1 stop
$155Spirit Airlines
Wed, Feb 18 - Wed, Feb 25
Delta Logo
11:55 am - 11:58 pm
PIT
-
SJU
11h 03m
1 stop
Delta Logo
6:15 am - 12:36 pm
SJU
-
PIT
7h 21m
1 stop
$216Delta
Wed, Apr 22 - Tue, Apr 28
American Airlines Logo
6:00 am - 10:05 pm
PIT
-
SJU
16h 05m
1 stop
American Airlines Logo
6:00 am - 4:54 pm
SJU
-
PIT
10h 54m
1 stop
$218American Airlines
Mon, Mar 2 - Wed, Mar 4
JetBlue Logo
6:00 am - 2:47 pm
PIT
-
CUR
7h 47m
1 stop
JetBlue Logo
3:54 pm - 11:49 pm
CUR
-
PIT
8h 55m
1 stop
$245JetBlue
Mon, Mar 2 - Wed, Mar 4
American Airlines Logo
6:15 am - 3:03 pm
PIT
-
CUR
7h 48m
1 stop
American Airlines Logo
4:03 pm - 9:12 am
CUR
-
PIT
18h 09m
1 stop
$279American Airlines
Wed, Apr 1 - Wed, Apr 8
United Airlines Logo
7:00 am - 12:45 pm
PIT
-
GCM
6h 45m
1 stop
United Airlines Logo
1:50 pm - 1:05 pm
GCM
-
PIT
22h 15m
1 stop
$303United Airlines
Fri, Feb 27 - Thu, Mar 5
Delta Logo
6:00 am - 12:29 pm
PIT
-
GCM
6h 29m
1 stop
Delta Logo
1:54 pm - 9:20 pm
GCM
-
PIT
7h 26m
1 stop
$311Delta
Sat, Feb 7 - Tue, Feb 10
United Airlines Logo
7:00 am - 5:25 pm
PIT
-
PUJ
9h 25m
2 stops
United Airlines Logo
4:25 pm - 11:44 pm
PUJ
-
PIT
8h 19m
1 stop
$319United Airlines
Mon, Feb 23 - Thu, Feb 26
JetBlue Logo
6:00 am - 1:51 pm
PIT
-
MBJ
7h 51m
1 stop
JetBlue Logo
12:22 pm - 11:49 pm
MBJ
-
PIT
11h 27m
1 stop
$334JetBlue
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 $298 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 $298.

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 $334, 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 $266 (return) on average. On the other hand, the most expensive months are August and December, when the average cost of round-trip tickets is $474 and $460 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 20 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$90
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 3% increase in price.
Flight from Pittsburgh to Saint Thomas Island

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 8124 reviews
7.9Comfort
7.8Entertainment
7.2Food
8.1Boarding
8.5Crew
Airline reviews

Timing, quality of service, promptness and courtesy of the staff

10.0 ExcellentAjai, Jan 2026
DFW - ATL
Read more Delta reviews

Timing, quality of service, promptness and courtesy of the staff

It was last minute due to weather - considering - it was amazing! Good smiles, friendly staff and they were making sure we knew what was going on when and where.

delta last minute gave me a boarding pass for a different flight with no confirmation that they were changing it

The flight was comfortable and uneventful, which is what I desire

The service from the flight attendants were of supreme quality. They greeted and treated everyone with a wide smile. This is totally absent nowadays. Kudos to them!!!!

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

was sitting in the jet bridge for 10 minutes in -20 degree weather waiting for my bag

Outdated equipment in disrepair, wifi inoperable. Broken seats, taped air vents, generally poor condition, the 717 showed its age and lack of upkeep.

My flight out of Baton Rouge to Atlanta was delayed by a half hour. This got us into Atlanta airport 30 minutes late. I ran through the airport to get to my connecting flight. As I approached the boarding gate, I saw the boarding door was still open and a passenger was being checked in. But when I got to the gate, the boarding agent told me they had already given away my seat and there were no empty seats on that flight. So I had to take a later flight. That has never happened to me before. Very frustrating.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

HORRIBLE, my initial flight was cancelled, they made me pay $200 extra dollars and that got cancelled as well! After 6 cancellations I decided to get a refund because I needed to get home to my babies. Out of $1000+ dollars they offered me only $40 in refund! Totally unacceptable! The flight that they cancelled I was able to fly it on another airline. I had to spend $400 on one way tickets just to get home! I’m still getting the runaround.

First class ticket gets you a choice of chips or nuts. . Just like economy Southwest. Also no screen in the seats. This is first class???!

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

The food was terrible this time. Otherwise pleasant, quiet, on-time.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

Flight arrived 30 min early and bag was waiting at the baggage pickup. United Club HNL was one of the nicest in the system

Unfortunately weather delayed our flight waiting for our plane to arrive and due to a little snow time was needed to deice the plane so departure was very delayed and I missed the connecting flight

Very good. Because of the delays with my previous flight, I missed my connection, but I was able to book another flight through the United app easily.

I wish there were outlets to charge my iPhone. The crew was great; we had a female pilot who was great with explaining what was happening and delays,

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 late and boarding was confusing because gate changed and I didn’t get a notification

Not comparable to Qatar Airways services on flights to Doha. Flight attendants provided basic services; I was never recognized by name or as an Executive Platinum member. Restrooms were not kept clean during the flight.

Delays to take off and to leave the plane after landing added a lot of time to this flight.

The Phildalphia to Allentown portion was a BUS, not a plane. All was as expected.

Excellent - explanations were clear staff was nice and flight was comfortable

Terrible. They canceled our early morning flight after midnight on the day of and had no available flights to rebook my family on for the next 72 hours. Yet they still had other flights that were not cancelled from JFK so it couldn’t be based on the weather. It felt like they canceled the flight based on it not being profitable enough for them. I am not interested in traveling with the again. The absolute worse customer service and lack of accountability.

Horribly rude check in at airport, worst in 25 years of flying. All over a simple issue they could have googled to resolve.

First time flying with JetBlue and never again. I went to the counter to request meet and assist because I'm 74 and my wife is 79. I walk with a cane and my wife is handicapped and has her own wheel chair. I told the agent that my wife and luggage was at the entrance door. The ticketing agent said to me that they don't offer meet and assist. I need to bring them our luggage and then go back and get my wife in order to get my boarding pass. As I went back to get my luggage a Southwest agent along with a TSA agent recognized the situation and came over and took my wife and luggage to the JetBlue ticketing counter alongside the line and told the JetBlue agent to issue to take our luggage as soon as they could.

Flight was fine, price was good but food onboard was abysmal. I was on there for breakfast and lunch and dinner 845am EST to 845pm GMT and all I got was a yoghurt parfait, fruit and a piece of cake. Later snacks included an ice-cream brownie and a pizza twist. I was hungry by the time I landed and the airport amenities were closed. Not happy.

1) No pilot available for 1 hour 2) no room for most passengers careyon in overhead—-> stowed below 3) when we landed we had to wait 45 min. Before docking at gate as gate was not ready

Good. No issues except a slight delay. Crew came in late.

Not a pleasant experience, service was poor. Didn't like it

It was good. I prefer JB over other airlines.I just wish we had headphones for the films, but other than that - good.

The ride share experience in JFK is terrible. After traveling on a flight, then you need to take a subway to the last stop to get an uber or lyft. Unacceptable. Bad job JetBlue for permitting JFK and Port Authority to do this to your passengers.

Checking In on JetBlue site was impossible. It hung up on REAL ID. Even my Global Entry did not help. Luckily, on Kayak site it was a breeze. Entire flight the temperature was COLD! Otherwise the crew was great!

The entire experience was so surprisingly pleasant. And the blocked extra seat between us was such an amazing and nice bonus. Great experience all around and I can’t wait to fly with spirit again!

Everything was OK, the deicing took a long time, our connections were almost missed.

All very good except they didn’t load our walker so haven’t gotten it yet

Flight was cancelled. But kayak thought it was still on time.

For the cost you can't e too critical, but the inablitiy to recline the seat and minimal cushioning in the seats made for a less than comfortable flight. Other than that we had an ealry departure and arrival, boarding was smooth.

The flight was delayed by 2 hours and we had no food or water or chargers

Spirit was on time. They maintained updates and information. The crew was friendly and professional. Because this is a budget friendly airline, they have dispensed with a lot of frills and part of that comes with a price, for example, the seats are not quite as comfortable as others. I am ok with a pay for beverage and snack service as I prefer my own anyway so this was not a concern. I thought overall, having a great flight crew and on time service was definitely worth losing some of the frills from other carriers.

Nothing everything cost money a bottle of water is 5 dollars and there wasn't even an outlet to plug 🔌 in my 📱 phone

You can’t beat Spirit’s prices on tickets, especially with the positive experience that comes with it! I appreciated the timeliness of Spirit airlines. The crew in the airport was very kind and wished you a good flight by name. The crew on the flight was attentive and friendly. Overall, I am very pleased with my experience with Spirit.

This was my best experience with spirit. I flew you guys 4 times and I must say this was the BEST

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports