$113 Find Cheap Flights from Pittsburgh to Caribbean

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 5/27. 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.
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Best Caribbean Flight Deals from Pittsburgh

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

Punta Cana
Punta Cana1 stop$301
Santo Domingo
Santo Domingo1 stop$386
Montego Bay
Montego Bay1 stop$317
Oranjestad
Oranjestad1 stop$334
Nassau
Nassau1 stop$355
Kingston
Kingston1 stop$525
Simpson Bay
Simpson Bay1 stop$471
Providenciales
Providenciales1 stop$432
Bridgetown
Bridgetown2 stops$421
Port of Spain
Port of Spain1 stop$417
George Town
George Town1 stop$424
Willemstad
Willemstad1 stop$550
St. John's
St. John's1 stop$433
Puerto Plata
Puerto Plata2 stops$539
Aguadilla
Aguadilla2 stops$580
Punta Cana
Punta Cana1 stop$301
Santo Domingo
Santo Domingo1 stop$386
Montego Bay
Montego Bay1 stop$317
Oranjestad
Oranjestad1 stop$334
Nassau
Nassau1 stop$355
Kingston
Kingston1 stop$525
Simpson Bay
Simpson Bay1 stop$471
Providenciales
Providenciales1 stop$432
Bridgetown
Bridgetown2 stops$421
Port of Spain
Port of Spain1 stop$417
George Town
George Town1 stop$424
Willemstad
Willemstad1 stop$550
St. John's
St. John's1 stop$433
Puerto Plata
Puerto Plata2 stops$539
Aguadilla
Aguadilla2 stops$580

Cheap Flight Deals from Pittsburgh to Caribbean (PIT-0CB)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Pittsburgh to Caribbean 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.

Recent round-trip flight deals from Pittsburgh to Caribbean

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Pittsburgh to Caribbean.
Discover the best prices for you by selecting your travel dates on KAYAK.
Delta Logo
7:20 am - 4:18 pmPIT-SJU
8h 58m1 stop
Delta Logo
2:28 pm - 9:09 pmSJU-PIT
6h 41m1 stop
$225Delta
Find Deal
Tue, Sep 23 - Mon, Sep 29
Delta Logo
6:25 am - 12:45 pmPIT-SJU
6h 20m1 stop
Delta Logo
7:00 am - 4:55 pmSJU-PIT
9h 55m1 stop
$245Delta
Find Deal
Mon, May 26 - Fri, May 30
Spirit Airlines Logo
7:00 am - 3:00 pmPIT-SJU
8h 00m1 stop
Spirit Airlines Logo
1:59 am - 11:36 amSJU-PIT
9h 37m1 stop
$254Spirit Airlines
Find Deal
Tue, May 27 - Tue, Jun 3
Spirit Airlines Logo
7:00 am - 7:07 pmPIT-SJU
12h 07m1 stop
Spirit Airlines Logo
1:59 am - 11:36 amSJU-PIT
9h 37m1 stop
$257Spirit Airlines
Find Deal
Mon, May 26 - Thu, May 29
United Airlines Logo
4:04 pm - 11:54 pmPIT-SJU
7h 50m1 stop
United Airlines Logo
1:05 am - 9:36 amSJU-PIT
8h 31m2 stops
$299United Airlines
Find Deal
Tue, Jun 10 - Mon, Jun 16
American Airlines Logo
10:39 am - 8:09 pmPIT-SJU
9h 30m2 stops
American Airlines Logo
6:10 am - 10:48 pmSJU-PIT
16h 38m1 stop
$305American Airlines
Find Deal
Tue, May 20 - Wed, May 28
American Airlines Logo
6:05 am - 12:55 pmPIT-STX
6h 50m1 stop
American Airlines Logo
1:37 pm - 11:13 pmSTX-PIT
9h 36m1 stop
$315American Airlines
Find Deal
Thu, Aug 14 - Thu, Aug 21
United Airlines Logo
8:45 am - 11:57 pmPIT-SJU
15h 12m2 stops
United Airlines Logo
1:05 am - 4:55 pmSJU-PIT
15h 50m2 stops
$315United Airlines
Find Deal
Tue, Sep 23 - Tue, Sep 30
Southwest Logo
10:10 am - 8:45 pmPIT-SJU
10h 35m2 stops
Southwest Logo
2:40 pm - 10:15 pmSJU-PIT
7h 35m1 stop
$340Southwest
Find Deal
Fri, Sep 26 - Mon, Sep 29
Southwest Logo
10:10 am - 8:45 pmPIT-SJU
10h 35m2 stops
Southwest Logo
5:50 am - 5:00 pmSJU-PIT
11h 10m2 stops
$438Southwest
Find Deal
Thu, Sep 18 - Mon, Sep 22
Useful Info

KAYAK's insights & trends for Pittsburgh to Caribbean flights

Get data-powered insights and trends into flights from Pittsburgh to Caribbean to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Pittsburgh to Caribbean flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Pittsburgh to Caribbean.

The cheapest ticket to Caribbean from Pittsburgh found in the last 72 hours was to Punta Cana, at $480 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 $480.

What is the cheapest month to fly from Pittsburgh to Caribbean?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Pittsburgh to Caribbean, 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 is September, when tickets cost $294 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $513 and $451 respectively.

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

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

Your flight ticket price will generally be cheaper if you fly to Caribbean 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?

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, 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, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 6 weeks before departure.


Good to know

Low seasonSeptember
High seasonJune
Cheapest flight$113
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly and prices are also 0% lower on average.
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 from Pittsburgh to Caribbean 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 from Pittsburgh to Caribbean 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?

    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 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?

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

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
SouthwestOverall score based on 4293 reviews
8.6Crew
7.6Entertainment
8.2Boarding
8.0Comfort
7.1Food
Airline reviews

It is southwest seat was ok. Not the most comfortable seat

8.0 ExcellentJohn, Apr 2025PVD - FLL
Read more Southwest reviews

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

The seats were a bit cramped and worn, but otherwise okay.

I would have liked to arrive on time - not 5 hours late!

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

It was a perfect flight in all aspects! Both legs!

Only one drink pass through the cabin for a 4 hour flight. Quite rough and bumpy landing.

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

Flight was delayed due to weather. Crew did a nice job of making us comfortable. No complain complaints.

Our bag was lost so that made unnecessary chaos On our trip

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

It was an overnight flight and I desperately needed coffee before we landed, but Delta does only one beverage service, and that is shortly after takeoff, not before landing at 5 am.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Everything is good except the dinner and breakfast. The sandwich is very delicious. Toilet is clean, I only use one of them. Flight attendants are very nice. 👍👍

A bit rush for transit. Food and entertainment are not available

Boarding was a little difficult. The gate area at O'Hare was very small and crowded due to multiple gates in the area. Could not hear the intercom, so had to rely on signage to see when my group was boarding and the signage was blocked by passengers standing in the gate. Flight was great and we arrived in Montreal on time.

Multiple delays and not straight answer from the United team

For economy, it was very good. Staff was great, they even let some of us change seats for more leg room... Put an empty seat between us which was fantastic for a 12hr flight. Onboard entertainment was excellent, I think over 200 choices of movies/tv/etc The bad was the barely/nonfunctional wifi that cost either $16.99 or 1700 miles (full flight). It was atrocious... Definitely the worst of the last 3 long haul major airlines I was on the last few months.

Stewardess spilled orange juice on my clothes/seat no help no apology just threw napkins at me to clean the mess up. Not Happy.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

The plane pushed back from the gate on time. However, it stopped on the ramp, and we waited for over 20 minutes before the aircraft pulled back to the gate. Apparently, something of importance had to be removed from the aircraft by the gate agent. I found this to be odd. The delay was not significant, but I felt that whatever was on the aircraft that had to be taken off, should’ve been done before we pushed back from the gate.

I didn’t get on plane. Passport being processed by consulate with visa application. Tried to cancel through underpricer after purchasing cacelling for any reason. No dice, they are thieves.

Electric plugs didn't work. Entertainment system wasn't working

Everything about the flight was lovely…We left early, arrived early, cabin crew were efficient and helpful. Flight was easy and most pleasant.

Everyone was nice. It was on time and the food was. Airplane food, but not horrible

One bottle of water and a package of cookies for comfort plus. We had to literally beg a flight attendant for an extra bottle of water later in the flight due to feeling dehydrated.

late again! but its my only option to not take 9 hours to get to Memphis

Almost everything was outstanding. First, we boarded on time and the flight crew did a great job getting everyone seated. Then the pilots took their time and care to make sure the plane was full de-iced three times as there was a bad ice storm a few hours earlier. The plane ride was smooth and comfortable and even the economy seats had decent room and comfort. Flight Attendant Lisa went above and beyond to make sure I was comfortable - she is outstanding. The only thing wrong with the flight, and it is something which needs to be addressed, is that the gate to gate time was over 6.5 hours and not one meal was served. The only thing offered to eat were two small cookies for a transcontinental flight - unacceptable. Charge me more but give me a meal for a long flight. Thankfully Lisa found something for me.

Very poor. Our special services attendant gave us incorrect information. I also was mishandled at landing. There was no wheelchair waiting. I fell deboarding the plane. Appalling!

I had a very unpleasant encounter with one man from customer service: he was extremely rude and miserable. And his condition was reflected on his decision to send me to the worst airport hotel and get an awful flight connection. My hotel shuttle had never arrived and I had to book another hotel. People served by other representatives got a much better treatment and deal.

The flight left a bit late, but arrived close to time expected…With the flight being close to full the crew did well serving drinks to all in a very timely fashion. The flight was a pleasure…

They didn't have any gluten-free snacks, oddly, which I require...or any flavored soda water or decaf tea options, which seems to be standard.

My flight back my reservations were list because they said I didn't pay my pet fee when I had a receipt

I mean, it’s Spirit. But it was frustrating to have our flight canceled, get bumped to a later flight, and then Spirit was unwilling to check our bag until 4 hours before our flight… tell us we could not sit in the waiting area’s chairs… and really negative experience getting checked in and dropping the bag.

Not having it be changed after we bought the flight tickets from a direct flight getting in at a reasonable time to a connecting flight red eye of 9 hours, so that we would lose our 35 dollars in nonrefundable insurance would've been great! Our country really does need low-cost carrier options, but this type of "service" ain't it. Fortunately, had a little better success with them flying to and from San Juan PR last month at least.

All was good expecting the seats need a bit of cushion. Besides that I can’t complain.

You get what you pay for, and the flights went smoothly. There’s no reclining chairs, no screens, And there isn’t always wifi, but the plane was clean and staff was friendly and the takeoff/landing were smooth.

The only positive is that the flight made it both ways. Getting charged for every little thing after the cost of the ticket itself is comical, considering how the plane and services are as bottom-tier as possible. The self check-in kiosks are useless. It’s nice to think that you can print your boarding pass, tag your checked bag, and then just drop it off. But no, they still make you go through the line once you finish- what’s the point of the self check-in then? Any questions for the staff seem like the biggest inconvenience and were met with condescending responses. This was my first and now last time ever flying with Spirit. After all the extra costs, subpar plane and staff, I see no value. I’d rather drive the 13 hours than give Spirit another dime.

The flight was fine however what started as a reasonable priced ticket could have become an overpriced ticket with additional charge for carry on as well as checked bag $79 per bag per person each way. Additional charge for choosing one’s seat, additional charge for beverage and snack, we were on what was described as a new plane yet there were no audio/visual on the jet. A bare bones service but not at a bare bones price. Will think twice before flying Spirit again. 😕

Flight was delayed a bit, but that was expected (and updated), so really not bad at all for the price. Could’ve used one less email asking me to upgrade my seat; otherwise no significant complaints

I love Spirit. New aircraft, great cabin service, the airfares are low cost which helps me visit my hospitalized daughter anytime I can without paying a fortune.

Flight was 2hours late they had no crew or the pilot.

I paid for streaming wifi and the connection was poor.

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