$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 1/5. 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$256
Santo Domingo
Santo Domingo1 stop$278
Montego Bay
Montego Bay1 stop$256
Oranjestad
Oranjestad1 stop$223
Nassau
Nassau1 stop$319
Kingston
Kingston1 stop$354
Simpson Bay
Simpson Bay1 stop$254
Providenciales
Providenciales1 stop$364
Port of Spain
Port of Spain2 stops$273
Bridgetown
Bridgetown1 stop$361
George Town
George Town1 stop$252
Willemstad
Willemstad1 stop$273
St. John's
St. John's1 stop$428
Puerto Plata
Puerto Plata1 stop$340
Aguadilla
Aguadilla2 stops$211
Punta Cana
Punta Cana1 stop$256
Santo Domingo
Santo Domingo1 stop$278
Montego Bay
Montego Bay1 stop$256
Oranjestad
Oranjestad1 stop$223
Nassau
Nassau1 stop$319
Kingston
Kingston1 stop$354
Simpson Bay
Simpson Bay1 stop$254
Providenciales
Providenciales1 stop$364
Port of Spain
Port of Spain2 stops$273
Bridgetown
Bridgetown1 stop$361
George Town
George Town1 stop$252
Willemstad
Willemstad1 stop$273
St. John's
St. John's1 stop$428
Puerto Plata
Puerto Plata1 stop$340
Aguadilla
Aguadilla2 stops$211

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, Jan 23 - Sat, Jan 31
American Airlines Logo
10:23 am - 11:56 pm
PIT
-
SJU
12h 33m1 stop
American Airlines Logo
7:12 pm - 11:10 am
SJU
-
PIT
16h 58m1 stop
$223American Airlines
Sun, Jan 11 - Sat, Jan 17
Spirit Airlines Logo
6:00 am - 3:45 pm
PIT
-
AUA
8h 45m1 stop
Spirit Airlines Logo
4:40 pm - 11:44 pm
AUA
-
PIT
8h 04m1 stop
$223Spirit Airlines
Sat, Feb 7 - Tue, Feb 10
Spirit Airlines Logo
5:32 am - 11:33 pm
PIT
-
SJU
17h 01m1 stop
Spirit Airlines Logo
4:40 pm - 11:44 pm
SJU
-
PIT
8h 04m1 stop
$224Spirit Airlines
Tue, Jan 6 - Mon, Jan 12
Delta Logo
6:00 am - 4:10 pm
PIT
-
STT
9h 10m1 stop
Delta Logo
3:10 pm - 10:56 pm
STT
-
PIT
8h 46m1 stop
$229Delta
Sun, Jan 11 - Wed, Jan 14
United Airlines Logo
5:46 pm - 6:11 am
PIT
-
SJU
11h 25m2 stops
United Airlines Logo
8:10 am - 2:04 pm
SJU
-
PIT
6h 54m1 stop
$239United Airlines
Tue, Jan 6 - Tue, Jan 13
Delta Logo
6:00 am - 4:10 pm
PIT
-
STT
9h 10m1 stop
Delta Logo
4:15 pm - 10:56 pm
STT
-
PIT
7h 41m1 stop
$247Delta
Tue, Feb 24 - Thu, Mar 5
United Airlines Logo
8:06 pm - 1:15 pm
PIT
-
GCM
17h 09m2 stops
United Airlines Logo
2:25 pm - 11:30 pm
GCM
-
PIT
9h 05m1 stop
$296United Airlines
Sat, Jan 10 - Wed, Jan 14
JetBlue Logo
6:00 am - 12:46 pm
PIT
-
NAS
6h 46m1 stop
JetBlue Logo
1:55 pm - 11:55 pm
NAS
-
PIT
10h 00m1 stop
$319JetBlue
Wed, Feb 4 - Sat, Feb 7
JetBlue Logo
6:00 am - 3:53 pm
PIT
-
UVF
8h 53m1 stop
JetBlue Logo
2:45 pm - 11:53 pm
UVF
-
PIT
10h 08m1 stop
$319JetBlue
Sun, Jan 25 - Thu, Jan 29
Air Canada Logo
5:55 pm - 12:25 pm
PIT
-
GCM
18h 30m1 stop
Air Canada Logo
1:30 pm - 5:14 pm
GCM
-
PIT
27h 44m1 stop
$361Air Canada
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 $403 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 $403.

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 $343, 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 August and June, when the average cost of round-trip tickets is $474 and $461 respectively.

What’s the cheapest day of the week to fly from Pittsburgh to Caribbean Islands?

The average price of all round-trip flights from Pittsburgh to Caribbean Islands clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Caribbean Islands 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 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$90
Best time to beat the crowds with an average 16% 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.

  • What is the cheapest time of day to fly to Caribbean Islands?

    The cheapest time of day to fly to Caribbean Islands 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 Islands is generally in the evening, which is peak travel time and where the average cost of a ticket is $433.

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 8010 reviews
8.1Boarding
7.9Comfort
7.9Entertainment
7.3Food
8.5Crew
Airline reviews

None of the airplane features were available during the flight.

4.0 OkayAnonymous, Dec 2025
JFK - SDQ
Read more Delta reviews

None of the airplane features were available during the flight.

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

Lady Pilot was perfect in every way wheels up to wheels down communication, professionalism, excellent on time departure and on time arrival, excellent communication! Fantastic job with Superb attitude!!

The food is terrible. The staff is wonderful. Comfort is good.

Left on time, a bit delayed due to headwinds most of the trip.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

Getting to the flight was arduous and lengthy. The flight itself was good but the food option wasn’t a good selection. I need to do a Kosher option on my return. Flight crew were nice

Good seats in Main cabin, excellent service and excellent landing

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

Very smooth, on-time, and pleasantly uneventful flight. The team at the gate and on board were professional and genuinely courteous. The pilot kept us well updated throughout, and both takeoff and landing were steady and enjoyable without any drama. Just a good, solid flight. Thank you! 💗

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

Not great experience - we were super late boarding due to issues with aircraft. Then when we finally all got onboard and seated and they started taxiing out to the runway they just stopped then turned around and went back to the airport. Apparently the crew “ran out of time” to legally fly us. They mentioned that they were about 2 minutes away from taking off. I understand the rules and safety but kinda wonder why they would have bothered boarding us in the first place? Had to go all the way back and de plane and then wait in a HUGE line to get a hotel (this is somewhere around 2:30am) finally got to hotel by Uber (no shuttle after 20min so gave up) and they ended up putting us all back on the same aircraft at 10am next morning so got about 2.5 hours sleep. They did give us. $250 credit, but it was a São Paulo Brazil flight out of Dulles. The flight and everything was fine.

United overall experience is great these days. Airport experience was very organized. Staff on flight were great. App and information as good as it gets.

United have really come back. Airport and boarding process is clear and good, app and information also very good

They charged a fee for 1st bag checked. Others in same party were free.

Flight was delayed 8 times. We were sitting at the airport for 14 hours. We got 2 hours of sleep (if that) on what was not meant to be a red-eye.

The movies offered were great. Staff were very pleasant and very efficient.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very bad! They kept delaying my flight and wouldn’t do anything about it

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

Airport in MXP is crazy. Get there at least 2 hours before flight.

Flight was delayed not sure why no explanation given and no apologies either. Otherwise the flight was fine

Did not get the seat I selected and paid for.

The flight was canceled 3 hours after original take off time

Plane was delayed for 6 hours, at first by weather, which is understandable, but was further delayed with NO given reason for 2 1/2 hours more. We had no clue when we were going to depart actually until they opened the ramp. VERY POOR to ZERO COMMUNICATION!!!

Flight was delayed and after being in the airport for like seven hours, it was canceled.

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 flight was two hours late due to a computer fault and resulting maintenance. Nothing was offered as compensation beyond bottles of water during the time we were deplaned and waiting in the terminal.

Very pleasant flight attendants. Gate crew rather loud chatting with each other.

Four plus hour flight delay in New York caused us to take off after 11:30pm. We didn’t arrive at our hotel until five hours after check in. Started the trip off feeling exhausted.

Plane was in bad shape. TV’s and WiFi didn’t work. Plane need a refresh. Not enough room for bags.

There was a fowl odour coming from the lavatory the entire flight

Everything was great. I liked the text updates so that I never miss a gate change & I have all the latest info.

I don’t usually fly budget airlines or airlines in the United States. It was as good as any other airline. The seats are comfortable and the airline attendants are not rude & surly. Very nice flight (s).

No internet on a flight over three hours in this age is criminal. Staff inattentive and dismissive

We had to sit and wait for almost an hour after landing and taxiing to the gate. The jet bridge was broken so we just waited and waited and waited and it was inconvenient, hot, and unnecessary.

Flight was in time, very smooth ride and surprisingly lots of legroom in the cabin so I certainly will fly with spirit again

The seats are the most uncomfortable seats I’ve ever sat in. Don’t believe I’ll ever fly spirit again!!

Flight was canceled and instead of rescheduling at the gate we had to go out to the ticket counter. Unruly kids kicking the back of my rows chair with staff to inattentive to say something.

Customer feedback I sent to Spirited today: “I will never fly Spirit Airlines again and will work hard to convince my friends and family to boycott/avoid Spirit Airlines at all costs. I booked three seats for me and my 8 and 10 year old children on NK 1222 from Orlando to Kansas City for 12/7/25 leaving Orlando at 10:37AM. This itinerary was abandoned by Spirit and we were rebooked onto Spirit flight NK 213 leaving at 9:06PM without any notice. Then the nightmare really began. Flight 213 was delayed a total of 12 times, finally leaving at 6:35AM the following day. The gate was changed 5 times and our electronic boarding passes were invalidated at midnight. The worst part was that the 12 separate delays were incremental making it impossible to plan for accommodations for my family. My kids missed a day of school and barely slept under the harsh lights with lots of noise on the filthy airport floor. The customer service agent at Spirit Airlines told us we would be emailed a voucher for a hotel which never happened. I asked about it multiple times and it never arrived in my email inbox. This whole unfortunate situation could’ve been avoided if spirit had taken a realistic approach and delayed the flight from 9 PM until 6 AM from the beginning. My son gleefully deleted the Spirit app from my phone once we landed and we will never fly with Spirit again.”

Honestly horrible. The plane on the way back was delayed 6 times with no explanation on why. When I asked for a refund or some money back because I had to miss a day of work because of the desk, they told me no. Because of how poorly it was handled I will most likely never take spirit again

I love a flight without turbulence and you guys deliver It’d be nice to have comfier seats and maybe some inflight entertainment and snacks but that’s for Delta

30 minute delay, Also there was a medical emergency on the flight. The flight crew was on top of the situation and assisted the medical professionals that happened to be on the flight.

This was my first time on a budget airline and I couldn't even sit down all the way because my knees would embed in the seat in front of me. I'm only 6' tall with a 32" inseam. There's no upside other than y'all are cheap. I'm glad it was only a 2 hour flight. Lesson learned! I get why everybody talks down on budget airlines. The staff was outstanding, the flight went as well as possible, great pilot, great boarding, smooth sailing. Zero chance I'll be back though.

Everything was smoothly and convenient! Just stay in this way!

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports