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Find cheap flights from Pittsburgh to Caribbean from $103

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 departing on 6/24. 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
0 bags
Sat 6/29
Sat 7/6

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Best Caribbean Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Punta Cana
Punta Cana1 stop$247
Montego Bay
Montego Bay1 stop$297
Santo Domingo
Santo Domingo1 stop$284
Oranjestad
Oranjestad1 stop$291
Nassau
Nassau1 stop$270
Kingston
Kingston1 stop$368
Simpson Bay
Simpson Bay1 stop$278
Providenciales
Providenciales2 stops$418
Port of Spain
Port of Spain1 stop$377
Bridgetown
Bridgetown2 stops$360
George Town
George Town1 stop$450
Aguadilla
Aguadilla2 stops$619
Willemstad
Willemstad2 stops$477
St. John's
St. John's1 stop$595

Good to know

Low season

September

High season

June

Cheapest flight

$103
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 14% increase in price.
Flight from Pittsburgh to San Juan

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 to Caribbean from Pittsburgh 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 to Caribbean with an airline and back to Pittsburgh 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 to Caribbean from Pittsburgh up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Caribbean

  • On average*, there is no price difference when choosing to fly in the morning or the evening on this flight route.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

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.
8.0
DeltaOverall score based on 10457 reviews
7.9Comfort
8.6Crew
8.2Boarding
8.0Entertainment
7.4Food
Airline reviews

I've flown many many times on Northwest and then Delta. The crew on this flight were absolutely the best I've had the pleasure of being looked after by.

10.0 ExcellentAnonymous, May 2024MSP - YVR
Read more about Delta reviews

I've flown many many times on Northwest and then Delta. The crew on this flight were absolutely the best I've had the pleasure of being looked after by.

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

Half the bathrooms assigned to economy were out of action

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

Overall fine but both ways for this trip was delayed.

Flight was delayed by almost 5 hours. Suitcase was not loaded despite the flight being near empty (my colleagues’ suitcases did reach JFK, unlike mine). Had to argue on phone to get JetBlue to deliver the case to my hotel. Never again

The flight was excellent. The crew was welcoming and attentive.

Great! I love Jet Blue. My favorite airline! Very efficient, clean and timely.

Run out of snack choices. Why are the seats not padded for your butt? Are we sitting on blocks of wood or metal for $250-300 a pop? This ain’t spirit. Let’s get it together people

We were told that our flight would be delayed for 90+ minutes because of weather, so we went to get something to eat only to have them randomly start boarding 15 minutes after the announcement, with no warning.

Entertainment... No earphones passed out. Many including me couldn't use the TV. Legroom was good. Crew was indifferent and a bit surly. Free wifi was a nice convenience. Check in desk location was unknown. Gate number on the boarding passes was wrong.

Going through JFK’s security is a mess. The TSA security said no shoes on the bins. So, we place our shoes in the belt and they came out all over the belt. Boarding was delayed and Flight as well.

Safe and on time were the positives. The plane wasn't cleaned before boarding, there was garbage and food on the floor and in the seat pocket. The TV screen was small and the picture fuzzy, audio quality was poor. Seatbelt was fraying and seat did not recline properly. No charging ports near the seats,

Confusing. Delay updates were out of whack At one point it said my flight was 25 hours. Three gate changes and two delays only to change back to original departure time. Gate announcer and on board flight attendant (Alejandro) making the announcements was impossible to understand due to accent and speed of speech. After beverage service the rear flight attendants sat back there on their phones. No refills no checking in, one sweep through for trash collection. Very impersonal. Bring back Coke products

The flight and boarding were easy peasy. I was traveling with my 4-year-old, so a smooth boarding experience was especially appreciated. My only piece of feedback is really about where our gate was in O'Hare. They've shoved four gates into a tiny corner of the B terminal and there isn't early enough room or seating for everyone. Not United's problem, but did dent the overall experience.

We liked the fully reclinable seats. Had center seats, so it was difficult to talk to spouse. Crew was great

Aisle chair was good and liked the foot bar preventing you from putting your foot in the isle, The breakfast on this international flight to Zurich was horrible (Europeans, specially, used to good food) may make this a dealbreaker for booking with United Airlines again. I agreed with my Spanish fellow passenger.

Dinner was okay but the breakfast was not eatable on the flight San Francisco to Zurich.

There was no screens on board AND the WiFi didn’t work. My seat was broken and couldn’t recline so I couldn’t even sleep. The flight attendants didn’t offer anything to make it more comfortable. It was such an old cramped plane, when the person in front of me reclined I couldn’t even open my tray table. All the United ads talk about guaranteeing everyone gets a screen!

The Wi-Fi was unavailable on this flight for some reason.

The flight was delayed almost 2 hours. Bad customer service etc. I will never fly Luthansa. Ever!!!

On time take off…US cabins look tired and need of refresh!

Fine. Though no food or entertainment so the survey needs to be updated with those options.

Backpack should NOT allowed put in the flight bin , only put it under the seat. I can't find space put my carry on luggage!!! and I pay for it ! that was very bad experience

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.

There were delays on both ends. It made it less than excellent. This plane was great though

So uncomfortable to sit in the tiny space on a long, international. Food was rough. Please, less white flour and processed food.

Attendants were rude. Scowling. Seats were miserable and we paid extra.

Tray table was filthy when I sat down. I needed to have someone come clean it because there was food and stains on it WiFi didn’t work after paying for in flight WiFi Food was terrible and was not filling at all Chicken was rubbery Flight attendant had an attitude, interrupted me and wasn’t able to answer basic questions about the food selection such as “does the chicken have red sauce in it”. If your flight attendants are not going to know what is in the meals so we can make an educated decision based on dietary restrictions, they shouldn’t be on the plane. My 1.5 year old niece was sleeping and dropped her binkie. I went on the ground under the chairs looking for it. It was at that time that she came up to me as I’m CLEARLY on all 4s with a flashlight and said “I need to get by”. I said one moment please I’m getting something from under the seat (while my head was literally under the seat). Her reply was “no you need to move now” and proceeded to almost push me out of the way. I looked up and all I saw was her toes under my eyes. When I looked in front of me, her private parts were inches away from my face. I then made a comment “you couldn’t waited 2 seconds?” and her response was, “no I need to use the bathroom”. I understand that and would never want to be the reason someone couldn’t get to the bathroom but I was under the seat. She could’ve gone around the other way instead of harassing me, basically placing her private parts on my head and borderline pushing me out of the way. You don’t pay (especially this much) for this deplorable experience. This was by far the worst experience I have ever had on American. I will be absolutely thinking twice and thrice about flying American Airlines again. I would rather pay more to fly delta because at least I know their WiFi will work and their flight attendants won’t have a terrible attitude for no reason, nor will they act the way this woman did. Unacceptable.

Great crew. Very comfortable business seats with nice bedding. Good food. We were delayed to let late passengers on the flight, but otherwise great experience.

Not being able to purchase my check in baggage online was a negative.

LATE LATE LATE!!! Plagued by late AA flights on this trip. Such a drag. This one was by far the worst.

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

Same basket of unhealthy prepackaged snacks (junk food) which was depleted by the time it got to my row!!

EVERYTHING WAS WONDERFUL HOSPITALITY THE HELP.THE SEATING FRIENDLY ALWAYS HAVE A GOOD RIDE NOT ONE BAD EXPERIENCE WITH THEM

This was the smoothest flight I have had in awhile. I was also offered an exit row seat for a great upgrade cost and was able to sleep almost thr whole flight due to comfort and a smooth flight. We left on time and arrived on time.

No food not even water offered unless you buy it and no usb in the seat but other than that everything was good

Because our flight from marsh Harbor to Fort Lauderdale was over three hours delayed it caused us to miss our flight in Fort Lauderdale. Because we missed that flight, it cost us nearly $100 apiece for four different travelers which totaled nearly $400. We are seeking a reimbursement for the flight that we missed in Fort Lauderdale Florida.

Flight expected to leave at 6:40 pm ended leaving at 8:00 am the following day. I slept in a cold airport. Never again Spirit for me…

Flight was cancelled just 6 days before. No more flights that day, and the following date was sold out. Had to obtain a refund and buy more expensive flights on another airline.

The flight was on time and nice as always for me with spirit but the cabin crew were not good. They left the lights on on a red eye for the entire flight.

This was the return leg of my journey with Spirit Airlines. Despite its reputation, I found no issues as it got me from point A to B safely and without delay, especially with no mechanical delays, which is fantastic in my book! The staff, from ground crew to cabin crew, were all pleasant and hassle-free. The flight was smooth from takeoff to landing. I have absolutely no complaints about this no-frills airline!

I got a one-way, last-minute nonstop flight from PDX to BWI for only $125. Yes, I got nicked $79 more for a checked suitcase and $89 more for the BIG SEAT option, but it was worth it, even with $4.50 for coffee and $10 for a snack (the latter no different than any other airline). The grand total was still less flying on any other airline.

It was the worst ever, i will be filing a lawsuit to get a refund. Our flight was delayed 4 hours so we would miss our connecting flight, we were not rebooked to our destination the same day, we were not offered any options to get home on the same day despite being clear that we absolutely cannot get stranded at night due to family, we were forced to book our own flights on a different airline to get home, and spririt is refusing a refund because our flight wasn't cancelled, only delayed. oh yeah, and they lost our luggage on the first part of the trip and you cannot get a hold of customer service when anything goes wrong, on hold for 30+ minutes. and their app breaks so you can't use that either.

Book cheap flights from Pittsburgh to Caribbean

Recent round-trip flight deals

9/21Sat
1 stopSpirit Airlines
9h 59mPIT-SJU
9/28Sat
1 stopSpirit Airlines
10h 15mSJU-PIT
$156
8/13Tue
1 stopSpirit Airlines
12h 38mPIT-SJU
8/20Tue
1 stopSpirit Airlines
10h 15mSJU-PIT
$165
6/19Wed
1 stopSpirit Airlines
13h 05mPIT-SJU
6/26Wed
1 stopSpirit Airlines
10h 44mSJU-PIT
$169
7/17Wed
1 stopAmerican Airlines
4h 35mPIT-NAS
7/23Tue
1 stopAmerican Airlines
13h 22mNAS-PIT
$270
11/8Fri
1 stopDelta
6h 07mPIT-NAS
11/14Thu
1 stopDelta
6h 51mNAS-PIT
$273
11/9Sat
1 stopDelta
19h 12mPIT-NAS
11/14Thu
1 stopDelta
6h 51mNAS-PIT
$280
6/13Thu
1 stopAmerican Airlines
14h 22mPIT-NAS
6/18Tue
1 stopAmerican Airlines
13h 23mNAS-PIT
$322
8/7Wed
1 stopUnited Airlines
7h 28mPIT-NAS
8/11Sun
2 stopsUnited Airlines
20h 53mNAS-PIT
$338
8/7Wed
1 stopUnited Airlines
5h 41mPIT-NAS
8/11Sun
1 stopUnited Airlines
18h 03mNAS-PIT
$339
11/26Tue
1 stopJetBlue
6h 34mPIT-PUJ
11/29Fri
1 stopJetBlue
8h 57mPUJ-PIT
$955

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Recent one-way flight deals

6/24Mon
1 stopSpirit Airlines
9h 09mPIT-SJU
$103
7/1Mon
1 stopSpirit Airlines
9h 09mPIT-SJU
$104
6/22Sat
1 stopSpirit Airlines
6h 24mPIT-SJU
$108
6/26Wed
1 stopSpirit Airlines
10h 50mPIT-SJU
$111
6/23Sun
1 stopFrontier
12h 39mPIT-SJU
$119
7/11Thu
2 stopsFrontier
19h 52mPIT-SJU
$140
6/25Tue
2 stopsAmerican Airlines
28h 29mPIT-SJU
$159
11/25Mon
2 stopsAmerican Airlines
17h 13mPIT-SJU
$187
7/4Thu
1 stopDelta
7h 51mPIT-KIN
$241
10/11Fri
1 stopJetBlue
8h 46mPIT-PUJ
$323

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Last minute flights from Pittsburgh to Caribbean

Last minute flight, train and bus deals

6/3Mon
multi-stopFrontier
6h 24mPIT-SJU
6/5Wed
multi-stopFrontier
12h 22mSJU-PIT
$284
6/4Tue
multi-stopSpirit Airlines
31h 29mPIT-SJU
6/10Mon
multi-stopSpirit Airlines
16h 18mSJU-PIT
$299
6/3Mon
multi-stop
6h 24mPIT-SJU
6/10Mon
multi-stop
8h 51mSJU-PIT
$313
6/4Tue
multi-stopSpirit Airlines
33h 23mPIT-SJU
6/10Mon
multi-stopSpirit Airlines
25h 19mSJU-PIT
$321
6/4Tue
multi-stopSpirit Airlines
31h 29mPIT-SJU
6/10Mon
multi-stopSpirit Airlines
20h 18mSJU-PIT
$325
6/3Mon
multi-stopAmerican Airlines
9h 09mPIT-SJU
6/5Wed
multi-stopAmerican Airlines
10h 05mSJU-PIT
$452
6/1Sat
multi-stopAir Canada
19h 10mPIT-NAS
6/5Wed
multi-stopAir Canada
9h 40mNAS-PIT
$468
6/3Mon
multi-stopUnited Airlines
7h 09mPIT-SJU
6/4Tue
multi-stopUnited Airlines
8h 35mSJU-PIT
$499
6/3Mon
multi-stopAmerican Airlines
7h 26mPIT-MBJ
6/10Mon
multi-stopAmerican Airlines
22h 19mMBJ-PIT
$516
6/3Mon
multi-stopAlaska Airlines
30h 35mPIT-SJU
6/11Tue
multi-stopAlaska Airlines
23h 14mSJU-PIT
$4,826

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