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Find cheap flights from Pittsburgh to Caribbean from $87

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 4/21. 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 4/18
Thu 4/25

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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 Cana2 stops$258
Montego Bay
Montego Bay1 stop$250
Santo Domingo
Santo Domingo1 stop$250
Nassau
Nassau1 stop$318
Oranjestad
Oranjestad1 stop$255
Kingston
Kingston1 stop$333
Providenciales
Providenciales2 stops$440
Simpson Bay
Simpson Bay1 stop$303
Port of Spain
Port of Spain1 stop$486
Bridgetown
Bridgetown1 stop$532
George Town
George Town1 stop$485
Aguadilla
Aguadilla1 stop$234
Willemstad
Willemstad2 stops$510
St. John's
St. John's1 stop$546
Port Au Prince
Port Au Prince1 stop$258

Good to know

Low season

September

High season

June

Cheapest flight

$87
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 Saint Thomas Island

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 2% cheaper 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 KAYAK reviews.
8.0
DeltaOverall score based on 11551 reviews
75food
86crew
81entertainment
81overall
82boarding
79comfort
Airline reviews

Boarding was a sh!t show. JFK BOARDING was awful. The agent called three sections at a time Clogging the area then yelling at people to not block the walk way. How are you going to call delta one , premium select and comfort plus at once and the yell at highest paying passengers. Need to do a lot better and the flight attendants in the galley need to understand that their voices travel. They were talking about others and everyone in the cabin heard them

Read more about Delta

Boarding was a sh!t show. JFK BOARDING was awful. The agent called three sections at a time Clogging the area then yelling at people to not block the walk way. How are you going to call delta one , premium select and comfort plus at once and the yell at highest paying passengers. Need to do a lot better and the flight attendants in the galley need to understand that their voices travel. They were talking about others and everyone in the cabin heard them

Uncomfortable seats on 14 hour flight. Mediocre food. On time and great crew.

Please see my lengthy description on MSP to Atlanta survey. Tailbone is killing me from old hard seats. Seat would not recline and were not near exit row. Entertainment did not work properly and couldn’t use. No audio and touch screen failed. 3 plus hours of discomfort in narrower seats than previous flight not in comfort plus. Very dissatisfied and deserve comfort plus charges refunds, at the very least, for both my wife and I. The plane needs to be retired. Please feel free to contact me directly for further details.

MSP to Atlanta was much better than Atlanta to St. Kitts. Paid $180 each for myself and wife for Delta comfort from Atlanta to St. Kitts. Seats were more narrow and obviously old and worn out. Tailbone is killing me. Seat would not recline. Seats behind reclined and we were not an exit row or in front of an exit row. Entertainment did not work in that the movie jumped forward and back and there was no audio. The plug in the arm rest was loose. Flight attendant tried “resetting” the video for my seat but no good. She never checked back. Someone else near me had the same issue. Touch screen was unresponsive. No where near as comfortable as MSP to Atlanta flight. 3 plus hrs. flight time without the basic amenities and not even remotely close to comfortable but paid for Comfort plus. I will be very disappointed if I have the same on my return “Comfort Plus” flight St. Kitts to Atlanta. At the very least my wife and I should be refunded for round trip “Comfort Plus” charges. Please feel free to contact me directly for more details.

public website still broken for years randomly blocking browsers with privacy options active after loading a page maybe once. check-in on laptop was almost impossible but eventually randomly worked. had to print pass at airport since couldn't get back in to load digital pass on mobile firefox or chrome. red eye flight so smooth onboarding, plenty of room to spread out, easy offboarding. onboard wifi instructions mention vpn can cause problems connecting but fails to also mention private dns. no printed or built in menu list, seems weird to require personal device to point at qr code link for menu which does not even allow direct ordering. people with health condition risk related dietary restrictions trying to avoid for example cholesterol and sugar are left guessing what they can order either way without nutritional info highlights (cranberry juice was minute maid cocktail with as much suger as typical can of soda). tap to pay wasn't working and always seems sketchy to manually enter card info. good movie variety, so limited tv was okay.

It wasn't really their fault it was the horrible winds and we just got unlucky.

Great experience overall. Check in at Austin was congested as they only have about 6 check in kiosks, one was broken, and there was a lot of Spring Break travelers.

The main person that was coordinating everything was a short white/light skin Spanish man and he was very rude. It honestly made me feel like it was everyone’s First day at work. His announcements were very not reasonable and they did not make sense. The stewardess on the flight that made the announcements she didn’t even know what she was talking about she sounded inebriated. There were no snacks or drinks on our flight there wasn’t even much turbulence. This flight was not enjoyable nor was it what a Delta flight should be and just this past week I flew with Delta 3 times.

The landing was bad and the hostess came two times and i was sleeping but when she served the person that nexts to me I woke up and she didn’t even asked me if I need any drink or snacks two times!!!!

The helpful attitude of the staff, and being a wheelchair passenger everyone was helpful and understanding. The trip was made comfortable by the upgraded seat which was given without my request, that was a great surprise. Thank you Delta.

Another horrible Jet Blue experience. This airline has suffered the biggest decline of all from best to worst. TVs didn’t work (again). internet was temperamental. Boarded late and couldn’t get organized to serve snacks.

I hate their constant delays! It’s as if I cannot confidently make plans for timing when I'm traveling with them. I slept through it, so all I can say is it was good.

The staff at JFK were rude and unhelpful. I was harassed for the same bag that I used on my flight to jfk with no issues claiming it was the inappropriate size. The women then allowed my travel companion to board with the same size bag because they thought she was more “humble”. Also on the flight when informing the flight attendant that nationals no longer have to fill out the Bahamas immigration form my statement was met with eye rolling and attitude.

The free wi-fi was great. But, the flight delay was not sustainable. It definitely impacted people schedules and JetBlue didn’t do anything to compensate clients for it

One of the crew members, a male complained about my bag being too heavy, which I felt was really unnecessary. I am disabled and would have carried it myself if I thought it was going to be a problem. In addition the landing was rough because everyone gasped in unison which it touched down.

Need a 2nd round of water for a 4+ hour flight

I loved the wifi, much better than Delta. Seats were old. and bathrooms dingy.

My tv was broken on the flight which is disappointing when you pay for a seat and expect a service

Always delays from Boston to Salt lake but this time was very long. Don’t understand while they board the passengers and then make them sit in the plane

The boarding and flight were ok, but there were several painful issues. The flight was 3:20 in the air and almost four hours door to door, but they only had snack packs on the plane. They really need to have food on longer flights or make it clear to everyone that they won’t have food. They also advertise free WiFi, but it did not work for 90% of this flight. Again, almost four hours door to door. If I had known I was flying spirit for JetBlue prices then I would have planned differently.

Flight was on time. Staff were friendly. I paid for Economy Plus but was required to check my standard carry-on luggage due to lack of space on the aircraft. This cost me 30 minutes, unexpectedly, in waiting at the baggage claim. This experience did not meet my expectations.

737 Max was leaking water into the cabin through the windows. Overhead bins opened on landing. Bad bad plane.

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

Very bad , airplain had problem with engines , had to evacuate, had a delay on my trip for almost 4 hours , lost my rental car in london..

The plane boarded and deplaned twice before the crew timed out. Flight was 7 hours late departing. Horrible experience!

Aircraft has better leg room than any of United's larger planes. We had requested mobility assistance for this and related flights. United's response to all was superb.

No snacks served! Seating in the kast row in uncomfortable.

Over two hours wait to get wheelchair assistance from arrival to the departure gate for LA was unreasonable even though there appreared to be heavy demand.

Everything was very good. Boarding and takeoff were on time and organized. Had a good flight

Wouldn’t let me check in said couldn’t find a ticket had to wait very long Time

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

Terrible Ticketing and Check in process. I learned that AA unilaterally cancelled my premium seating from PHL to CLT and from CLT to JAN. They did, however, refund my money, but my seating was subsequently severely downgraded. They didn’t have a seat for my unless I paid for it! Not cool! Consequently, Check-in took 45 min. AA is usually great, but this was my worst experience with AA ever. Appalling they they arbitrarily cancel my seats threatening loss of flight if I didn’t pay for a seat!!!! -John

We liked quick boarding and on time departure. Seats were very uncomfortable.

Great flight. Quick boarding and departure. No problems. Flight crew were very friendly and professional.

heat was on full blast. It was like the Tropics inside the plan.

Delayed several times. Flight was to arrive at midnight and it arrive at 3 am. A 3 hour delay is already bad but one that has you arriving in the wee hour is just disruptive and overall unacceptable. The complete lack of restitution is a joke in keeping with Spirit’s reputation of ranking bottom-low in the pecking order.

Awful experience. Both flights were delayed several times with weather but also crew members being the official cause. The vouchers are unusable and insufficient ($50 voucher to fly the same crappy airline is a joke for putting me on a red-eye that landed at 3:00 am). The aircrafts were old and uncomfortable (have a real pocket on the seat, for crying out loud!).

Its so random that they only allow 40 pounds on checked bags when all airlines take 55. They then charge you for each 10 extra pounds, so my checked suitcase was $130 and the flight $30 ... its like whattt, im for sure not traveling with Spirit again

Cancelled my flight last minute and had to end up driving to Texas from Atlanta last minute. I’m going to miss another day of work, drive back to Atlanta , in my own car and spirit doesn’t want to refund the money. First time I tried flying anyone else but delta and I get ripped off . And I had. To pay for seats for a flight that didn’t happen. Usually you could say you get what you pay for but in this case, didn’t get anything and paid for everything never flying spirit again, or even attempting it or thinking about it.

Actual CLT experience was rough. I've never seen the airport as bad in regards to security lines and wait. (For not being a holiday) A lot of folks missed their flight this morning. Spirit is fine. But wasnt offered a beverage somehow. No worries but some how I missed it.

the landing was terrible. the plane touched down and had take off. the plane flew around and landed a second time.i understand the weather might of been the problem. It was a scary experience and no explanation from the captain.

Flight was canceled and rebooked for the next day. Had to cancel the entire vacation.

It wasn’t as horrible as I would have expected, however, to not provide water and change so much for bags is a ripoff to say the least.

Flight from Tampa to Houston was canceled. SPIRIT rebooked me and they double booked my seat. Conclusion I COULD NOT TRAVEL TO HOUSTON. I MISSED MY GRANDDAUGHTER BIRTHDAY. I would not recommend this company. I will file a complaint. I will never consider SPIRIT as an airline . It’s a faker.

I like strict carry on policy. Quick to board, quick to leave. Less time at gate and get there quicker

Book cheap flights from Pittsburgh to Caribbean

Recent round-trip flight deals

4/12Fri
1 stopSpirit Airlines
12h 20mPIT-STT
4/16Tue
1 stopSpirit Airlines
13h 25mSTT-PIT
$175
4/10Wed
1 stopSpirit Airlines
12h 20mPIT-STT
4/13Sat
1 stopSpirit Airlines
13h 25mSTT-PIT
$177
4/24Wed
1 stopAmerican Airlines
8h 10mPIT-AUA
5/1Wed
1 stopAmerican Airlines
15h 48mAUA-PIT
$295
4/24Wed
2 stopsAmerican Airlines
10h 45mPIT-AUA
5/1Wed
2 stopsAmerican Airlines
20h 18mAUA-PIT
$300
5/6Mon
1 stopDelta
17h 42mPIT-SXM
5/9Thu
1 stopDelta
18h 44mSXM-PIT
$310
4/27Sat
1 stopDelta
5h 56mPIT-NAS
5/1Wed
1 stopDelta
9h 13mNAS-PIT
$321
4/13Sat
2 stopsUnited Airlines
17h 38mPIT-NAS
4/20Sat
1 stopUnited Airlines
7h 49mNAS-PIT
$386
4/13Sat
1 stopUnited Airlines
5h 23mPIT-NAS
4/21Sun
1 stopUnited Airlines
20h 08mNAS-PIT
$387
7/31Wed
1 stopJetBlue
8h 59mPIT-AUA
8/8Thu
1 stopJetBlue
9h 34mAUA-PIT
$643
4/15Mon
1 stopJetBlue
9h 50mPIT-SDQ
4/16Tue
1 stopJetBlue
12h 10mSDQ-PIT
$732

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Recent one-way flight deals

4/21Sun
1 stopSpirit Airlines
12h 20mPIT-STT
$87
4/20Sat
1 stopSpirit Airlines
16h 30mPIT-STT
$91
4/29Mon
1 stopSpirit Airlines
14h 30mPIT-SJU
$95
6/17Mon
1 stopAmerican Airlines
16h 07mPIT-MBJ
$166
6/17Mon
2 stopsAmerican Airlines
19h 13mPIT-MBJ
$172
7/16Tue
1 stopDelta
7h 35mPIT-STT
$221
7/15Mon
1 stopDelta
6h 49mPIT-SXM
$226
7/16Tue
2 stopsUnited Airlines
25h 15mPIT-AUA
$248
7/16Tue
1 stopJetBlue
8h 59mPIT-AUA
$307
7/18Thu
2 stopsUnited Airlines
25h 15mPIT-AUA
$353

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Last minute flights from Pittsburgh to Caribbean

Last minute flight, train and bus deals

3/24Sun
multi-stopSpirit Airlines
12h 40mPIT-SJU
4/3Wed
multi-stopSpirit Airlines
9h 00mSJU-PIT
$325
3/24Sun
multi-stopSpirit Airlines
12h 40mPIT-SJU
4/2Tue
multi-stopSpirit Airlines
24h 29mSJU-PIT
$338
3/22Fri
multi-stopSpirit Airlines
17h 12mPIT-SJU
4/3Wed
multi-stopSpirit Airlines
9h 00mSJU-PIT
$369
3/20Wed
multi-stopAir Canada
20h 50mPIT-GCM
3/25Mon
multi-stopAir Canada
19h 03mGCM-PIT
$372
3/23Sat
multi-stopAmerican Airlines
5h 46mPIT-MBJ
3/26Tue
multi-stopAmerican Airlines
7h 42mMBJ-PIT
$381
3/23Sat
multi-stopAmerican Airlines
10h 02mPIT-MBJ
3/26Tue
multi-stopAmerican Airlines
12h 57mMBJ-PIT
$384
3/24Sun
multi-stopAir Canada
25h 55mPIT-PUJ
3/28Thu
multi-stopAir Canada
19h 53mPUJ-PIT
$545
3/20Wed
multi-stopUnited Airlines
10h 10mPIT-GCM
3/24Sun
multi-stopUnited Airlines
9h 04mGCM-PIT
$578
3/20Wed
multi-stopUnited Airlines
9h 35mPIT-GCM
3/24Sun
multi-stopUnited Airlines
9h 04mGCM-PIT
$673
3/20Wed
multi-stopDelta
6h 25mPIT-GCM
3/24Sun
multi-stopDelta
6h 41mGCM-PIT
$681

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