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Find cheap flights from Pittsburgh to Caribbean from $49

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 5/15. 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
Thu 5/30
Thu 6/6

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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$211
Montego Bay
Montego Bay1 stop$287
Santo Domingo
Santo Domingo1 stop$268
Oranjestad
Oranjestad1 stop$277
Nassau
Nassau1 stop$290
Kingston
Kingston1 stop$343
Simpson Bay
Simpson Bay1 stop$303
Providenciales
Providenciales1 stop$413
Port of Spain
Port of Spain1 stop$381
Bridgetown
Bridgetown2 stops$534
George Town
George Town1 stop$405
Aguadilla
Aguadilla1 stop$569
Willemstad
Willemstad2 stops$537
St. John's
St. John's1 stop$650

Good to know

Low season

September

High season

June

Cheapest flight

$49
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly with an average 13% 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

  • Morning departure is around 24% more expensive than an evening flight, on average*.
*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 10895 reviews
8.0Entertainment
7.9Comfort
7.4Food
8.6Crew
8.2Boarding
Airline reviews

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

6.0 GoodJames, Apr 2024TPA - RDU
Read more about Delta reviews

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

Big plane, long flight, absolutely no leg room and basically non existent air! I am 5”4’ and always travel Main Cabin, I was miserable on this plane and could barely move when we arrived in Cabo due to the cramped leg area!

From Atlanta to Cabo I would have hoped on a plane that size I would have been able to breathe and wiggle my feet a little! The leg room in that plane is non existent and I am only 5”4’. And the air vent either wasn’t working very well or just could not blow air from the ceiling to the seat area as I was suffocating through the entire flight! And please don’t say I would have been more comfortable in first class because I cannot afford those rates and have always travelled Main Cabin without issues !

The pilots were good. Disappointing when planes don't have electrical ports

I liked the piloting of the aircraft. Very disappointed about lack of electrical ports. Also, although a short flight. there was enough time to hand out snacks to comfort + seats as was done for first class.

I had a wonderful experience flying with delta. The gentleman taking care of us on our flight was so nice, accommodating, and attentive. He always was smiling and giving pins to the kids which made me smile. The flight was quick too and without turbulence. Thank you for the great flying experience.

Delta is one of the best airlines I have flown

Made the Atlanta to Pittsburgh trip many times, with Delta no issues

I always fly with Delta. My friends tell me their horror stories of flying with other airlines. I just smile and say, “You should fly Delta”

Great. Loved that there was WiFi on flight to keep in touch and excellent service of beverages and snacks.

Business class is great. New airplane, very comfortable, better than some of the major airlines I am used to

Terrible. Flight was cancelled due to the weather in the east and sout east(florida). Did not get any compesation of any kind. According to them, it was not under their control so I lost all the money paid for the 2 fairs from Raleigh, NC to Orlando, Fl.

great flight. Pilot was communicative, flight attendants were excellent. Really nice experience except my tv didn’t work.

Overall, the flight was better than the flight I took to go to Florida, which had a bunch of problems. The crew is really nice and the plane was new so it had a small problem when we were on the runway, but the flight itself was great. They even made some time back up, which is always a good thing.

at the time for boarding the lady just call Group A and no other goups and everybody from A to F go inside without the right turn,and when we get in theres no more spsce for carry on , the ones that get in at not correct group from the back occupy our space !!!!! a mess !!!!

There were multiple delays but JetBlue tried to make the boarding and departure process as quick and efficient as possible. The crew was as detached from reality as could be, meaning: not very friendly and just doing things by the numbers.

I had back trouble prior to my flight and everyone was great about helping me.

Jetblue needs to improve on Onboarding as it seems to always be behind on departing. It never leaves on time. I would recommend to have an earlier Onboarding in order to leave on time and respect your customers time as well.

40 minute delay before take off after boarding flight. Bright lights throughout night flight due Issues with light panels. In flight Entertainment nonfunctional

Do not like the feeling of being in the basic economy. Everyone should feel good no matter what.

All flights were on time and boarding was issue free

Terrible! The plane was old and you are required to connect your own device to their Wi-Fi rather than have entertainment options in the back of the seat in front of you. The Wi-Fi went out during the flight and there was only one plug for the devices every two seats. Three out of five surrounding my family did not work. The seats and spaces under them were so small I could not fit my backpack, which I’ve always brought on flights and fit before no problem. The crew were unpleasant and patronizing.

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Food was terrible Not many options Stewards dont care Delay

Water service would be great. The way they board is terrible. Slow passengers first😂😂 They need to smart up a bit

Our original business class flight was cancelled so we not only downgraded but we were also spread out across the plane not sitting together in separate middle seats. My poor kids were scared and couldn’t see me on the flight and the crew wasn’t sensitive to the situation and what the airlines did to us. Very dissatisfied with United airlines.

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.

The ride was good but no food ot entertainment hence, it was just over an hour flight.

There was a group of school age passengers that were very loud and unruly with their chaperones were no where to be found.

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!!

We experience delays on departure and connecting flights resulting in 14 hour to our next departure. We were accommodated with a night's stay but was only provided a 12 dollar meals accommodation. The airlines rules state.at least 50 dollars. In any case, it can not make up for the whole day missed on our vacation in Sydney Australia.

Flight from PHL to PHX arrived 50 minutes early and a gate was available. First class flight attendant Stephanie was very friendly and polite. Sanitizing wipes should be provided with meals in addition to refresher towels.

flight delayed so missed connection and this had to rebook for next day

Flight departed PHL one hour late due to late arrival of aircraft. On board services were okay. First class menu does not offer any new items; same desserts (cheese & crackers or Mango sorbet). At least there were no credit card promotions during the flight.

After sitting on plane for 7+ hours, flight was canceled. And to makes matters worse, my suitcase is in baggage hell!

Some of the crew members were rude for no good reason

The guy with severe body odor sat next to me. For the whole duration of the flight it was a torture. The airline should have better policy on limiting people with bad body odor to board the flight. Passengers should not be the ones to endure bad odor for the whole duration of the flight. The airline should be e the one to ensure decent air quality for ever passenger.

Overall it was a miserable experience... I will never fly spirit for more than a 3 hour flight or overnight.

The boarding attendant was slightly rude when I asked about checking our stroller. Made me feel like I was bothering her.

My wife and I are both handicapped and at boarding they upgraded us to a seat closer to the front rather than all the way towards the back. Much appreciated.

Not much seat room, but that was unexpected. But the seat headrest was very uncomfortable.

First the good, everyone was friendly and efficient. Flight was smooth and plane was very clean and new. Now the bad, seats have almost no padding on your behind. I was in exit row so I had tons of leg room for a 6' 2" bean pole with long legs. Everything was extra - water, soda, snacks everything besides oxygen. Ya get what you pay for, and my flight was cheap as you could ever want it, so no worries.

First the good, everyone was friendly and efficient. Flight was smooth and plane was very clean and new. Now the bad, seats have almost no padding on your behind. I was in exit row so I had tons of leg room for a 6' 2" bean pole with long legs. Everything was extra - water, soda, snacks everything besides oxygen. Ya get what you pay for, and my flight was cheap as you could ever want it, so no worries. They dont really bother you about carry-on size, I brought a descent sized backpack and they didnt even check.

Spirit canceled the flight in March and never notified me!

Seats suck, not enough room, overcrowded planes, hectic situation all together.

Pretty good. Would’ve been excellent if we would have left on time and the crew wasn’t late.

Book cheap flights from Pittsburgh to Caribbean

Recent round-trip flight deals

5/20Mon
1 stopFrontier
11h 09mPIT-SJU
5/23Thu
1 stopFrontier
6h 36mSJU-PIT
$170
5/21Tue
1 stopSpirit Airlines
16h 35mPIT-SJU
5/31Fri
1 stopSpirit Airlines
27h 51mSJU-PIT
$177
6/6Thu
2 stopsAmerican Airlines
11h 21mPIT-SJU
6/14Fri
1 stopAmerican Airlines
9h 57mSJU-PIT
$272
5/30Thu
1 stopAmerican Airlines
4h 54mPIT-NAS
6/3Mon
1 stopAmerican Airlines
12h 59mNAS-PIT
$290
7/18Thu
1 stopDelta
6h 07mPIT-NAS
7/22Mon
1 stopDelta
9h 43mNAS-PIT
$293
7/25Thu
1 stopDelta
16h 22mPIT-NAS
7/30Tue
1 stopDelta
5h 19mNAS-PIT
$298
5/31Fri
2 stopsUnited Airlines
22h 03mPIT-NAS
6/3Mon
2 stopsUnited Airlines
20h 16mNAS-PIT
$388
5/12Sun
2 stopsUnited Airlines
9h 38mPIT-NAS
5/20Mon
2 stopsUnited Airlines
30h 59mNAS-PIT
$394
9/1Sun
2 stopsAir Canada
46h 30mPIT-BGI
9/9Mon
1 stopAir Canada
24h 40mBGI-PIT
$534
9/10Tue
2 stopsAir Canada
22h 30mPIT-BGI
9/13Fri
2 stopsAir Canada
23h 46mBGI-PIT
$537

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Recent one-way flight deals

5/15Wed
1 stopSpirit Airlines
10h 51mPIT-SJU
$49
5/14Tue
1 stopSpirit Airlines
16h 35mPIT-SJU
$79
5/15Wed
2 stopsSpirit Airlines
18h 23mPIT-SJU
$82
5/29Wed
1 stopAmerican Airlines
4h 54mPIT-NAS
$92
6/23Sun
1 stopAmerican Airlines
16h 34mPIT-SJU
$136
5/29Wed
3 stops
34h 33mPIT-NAS
$180
6/23Sun
2 stops
29h 00mPIT-SJU
$190
7/6Sat
1 stopDelta
10h 15mPIT-STT
$193
7/10Wed
1 stopDelta
7h 22mPIT-SJU
$201
5/6Mon
2 stopsUnited Airlines
9h 01mPIT-STT
$377

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Last minute flights from Pittsburgh to Caribbean

Last minute flight, train and bus deals

5/3Fri
multi-stopSpirit Airlines
17h 05mPIT-SJU
5/6Mon
multi-stopSpirit Airlines
25h 23mSJU-PIT
$296
5/3Fri
multi-stopSpirit Airlines
17h 05mPIT-SJU
5/5Sun
multi-stopSpirit Airlines
16h 34mSJU-PIT
$329
5/3Fri
multi-stop
15h 20mPIT-SJU
5/6Mon
multi-stop
28h 48mSJU-PIT
$368
5/3Fri
multi-stop
15h 20mPIT-SJU
5/5Sun
multi-stop
16h 34mSJU-PIT
$390
5/2Thu
multi-stopAmerican Airlines
9h 00mPIT-SJU
5/5Sun
multi-stopAmerican Airlines
15h 03mSJU-PIT
$408
5/3Fri
multi-stopAmerican Airlines
6h 15mPIT-PUJ
5/4Sat
multi-stopAmerican Airlines
7h 49mPUJ-PIT
$412
5/3Fri
multi-stopUnited Airlines
11h 30mPIT-SJU
5/5Sun
multi-stopUnited Airlines
8h 21mSJU-PIT
$538
5/4Sat
multi-stopAir Canada
19h 55mPIT-PLS
5/11Sat
multi-stopAir Canada
26h 51mPLS-PIT
$549
5/5Sun
multi-stopAir Canada
22h 25mPIT-BGI
5/10Fri
multi-stopAir Canada
24h 40mBGI-PIT
$562
5/5Sun
multi-stopUnited Airlines
20h 00mPIT-AUA
5/11Sat
multi-stopUnited Airlines
19h 44mAUA-PIT
$650

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