$94 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 11/14. 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

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Cheap Flights from Pittsburgh to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$292
Santo Domingo
Santo Domingo1 stop$360
Montego Bay
Montego Bay2 stops$313
Oranjestad
Oranjestad1 stop$272
Nassau
Nassau1 stop$289
Kingston
Kingston1 stop$350
Simpson Bay
Simpson Bay1 stop$304
Providenciales
Providenciales1 stop$440
Port of Spain
Port of Spain1 stop$739
Bridgetown
Bridgetown1 stop$441
George Town
George Town1 stop$290
Willemstad
Willemstad1 stop$353
St. John's
St. John's1 stop$399
Puerto Plata
Puerto Plata1 stop$408
Aguadilla
Aguadilla2 stops$225
Punta Cana
Punta Cana1 stop$292
Santo Domingo
Santo Domingo1 stop$360
Montego Bay
Montego Bay2 stops$313
Oranjestad
Oranjestad1 stop$272
Nassau
Nassau1 stop$289
Kingston
Kingston1 stop$350
Simpson Bay
Simpson Bay1 stop$304
Providenciales
Providenciales1 stop$440
Port of Spain
Port of Spain1 stop$739
Bridgetown
Bridgetown1 stop$441
George Town
George Town1 stop$290
Willemstad
Willemstad1 stop$353
St. John's
St. John's1 stop$399
Puerto Plata
Puerto Plata1 stop$408
Aguadilla
Aguadilla2 stops$225

Book Cheap Pittsburgh to Caribbean 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 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

Tue, Nov 18 - Thu, Dec 4
Delta Logo
6:26 am - 2:10 pmPIT-SJU
6h 44m1 stop
Delta Logo
6:38 pm - 12:12 amSJU-PIT
6h 34m1 stop
$225Delta
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Thu, Nov 13 - Wed, Nov 19
JetBlue Logo
7:10 am - 8:18 pmPIT-SJU
12h 08m1 stop
JetBlue Logo
6:45 am - 10:48 pmSJU-PIT
17h 03m1 stop
$230JetBlue
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Tue, Dec 9 - Tue, Dec 16
American Airlines Logo
6:00 am - 10:09 pmPIT-SJU
15h 09m1 stop
American Airlines Logo
6:00 am - 3:34 pmSJU-PIT
10h 34m1 stop
$240American Airlines
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Sat, Jan 31 - Sat, Feb 7
Spirit Airlines Logo
8:31 pm - 12:28 pmPIT-STT
14h 57m1 stop
Spirit Airlines Logo
1:33 pm - 7:36 pmSTT-PIT
7h 03m1 stop
$248Spirit Airlines
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Sun, Jan 18 - Thu, Jan 22
American Airlines Logo
1:25 pm - 11:56 pmPIT-SJU
9h 31m2 stops
American Airlines Logo
3:49 pm - 11:29 pmSJU-PIT
8h 40m1 stop
$250American Airlines
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Sun, Nov 9 - Wed, Nov 19
United Airlines Logo
11:00 am - 9:00 pmPIT-SJU
9h 00m1 stop
United Airlines Logo
2:05 am - 11:04 amSJU-PIT
9h 59m1 stop
$253United Airlines
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Tue, Nov 11 - Fri, Nov 14
United Airlines Logo
6:00 am - 4:36 pmPIT-SJU
9h 36m1 stop
United Airlines Logo
4:52 pm - 11:44 pmSJU-PIT
7h 52m1 stop
$255United Airlines
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Thu, Jan 22 - Tue, Jan 27
Spirit Airlines Logo
6:40 am - 3:45 pmPIT-AUA
8h 05m1 stop
Spirit Airlines Logo
4:50 pm - 10:37 pmAUA-PIT
6h 47m1 stop
$272Spirit Airlines
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Sat, Feb 28 - Thu, Mar 5
Southwest Logo
11:35 am - 9:40 pmPIT-SJU
9h 05m1 stop
Southwest Logo
6:00 am - 3:10 pmSJU-PIT
10h 10m2 stops
$284Southwest
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Tue, Nov 11 - Fri, Nov 14
Southwest Logo
4:05 pm - 11:20 pmPIT-SJU
6h 15m1 stop
Southwest Logo
6:40 am - 5:20 pmSJU-PIT
11h 40m2 stops
$299Southwest
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Booking Insights

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?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Caribbean from Pittsburgh found in the last 72 hours was to Punta Cana, at $392 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 $392.

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 $269 (return) on average. On the other hand, the most expensive months are December and August, when the average cost of round-trip tickets is $513 and $474 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 1 week before departure. For the absolute cheapest price, our data suggests you should book 20 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$94
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly with an average 2% increase in price.
Flight from Pittsburgh to Nassau

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.

Reviews of the 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 4241 reviews
8.0Comfort
8.1Boarding
7.0Food
7.5Entertainment
8.6Crew
Airline reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

8.0 ExcellentGreg, Oct 2025OAK - BUR
Read more Southwest reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

Delays delays delays. Late taking off, late landing, wait for a gate, etc.

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

Flight was delayed due to plane not passing inspection And one of the crew had to time out and we had to wait for another one A 3 hour delay

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

They ended up paying for the bag twice, but the counter wouldn't take my baggage receipt. Left it to me to resolve. Not sure how to resolve the issue.

The customer service before board was very rude and when I expressed my concerns about making the connecting flight she laughed and told me I bought the wrong ticket. I explained once it showed the flight was delayed it no longer let me change seats or anything. I was trying to upgrade to make sure I would get to the next gate on time.

Non stop on long haul is the way to go. Great experience

The aircraft interior is old and tired on this aircraft. The entertainment system never worked despite the crews attempt to reset the system.

The flight used a B767 with a very old interior from before 2014. The entertainment system did not work at all during the flight despite attempts to reset the system. It was like they flew this route just to be competitive.

Old plane and old configuration/seats but still comfortable for a morning flight

They changed planes and the new plane couldn’t carry enough fuel to fly across the country so we had to stop in Kansas City to refuel. Flight was delayed .

Flight was too crowded and seats are too small, especially since passengrs are getting larger. Having a middle seat is ALWAYS tough! Woman on my left was large & kept creeping in to my space. Flight personnel were great! Have more savory rather than sweet snacks please.

Flight was crowded and the woman sitting on my left was large & kept crouching in to my space. You need bigger seats or smaller passengers to fit into the seats you DO have! Snack were OK. Would appreciate if airlines had more savory rather than sweet snacks, thank you!

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

The person I bought the ticket for didn’t make the flight.

Lately I like the planes have been exceptionally filthy. There’s lines of dust and dirt all across the ceiling in the vents, and the cracks in between the seats are literally full of food. It’s definitely not the quality of service that I was used to with United. I’m also very disappointed with the Wi-Fi! All I wanna do is knock out a few work jobs while I’m trapped in my seat And it spools so bad. They did provide me with a refund, but the process of getting that refund is so complicated. It’s unfortunate.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.

Same as last comment. Food sucks. Quality. Not surprising most people have no clue about nourishment Clearly

Not the fault of United—weather, reroute around weather, time sitting on tarmac, arrived couple hours late, too late for train into city necessitating a much pricier cab but weather…can’t be helped.

Friendly and professional flight crew. Aside from departure delay after boarding, easy flight and smooth landing.

Great smooth flight. Had a seating change, but that was an improvement. Thanks United Airways Crew.

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.

Flight delays numerous times. Everytime we would get close to boarding it would be delayed again. Strung along the entire time.

the plane was not full so the flight attendant had me move to an empty row which made for a good flight. The software for logging on and booking and confirming the flight is much too cumbersome.

Always comes in handy when I want a quick weekend getaway.

For the price I could have taken a “name brand” airline. No drink no snack and constant emails trying to get addition money for EVERYTHING other airlines include in the price. It looks cheaper but it’s Judy bait and switch and emails non stop!

The gate agents for spirit at EWR wouldn’t give me my ticket to board when I arrived 50 min from the flight, saying that I wouldn’t make my flight. They tried to reschedule me to arrive at my destination 14 hours after the original flight, which included a 10 hr layover in another city. I rebooked with another airline and it took me a total of 5 min to go through security. Then I see a charge on my card for a $100 change fee that I did not approve. Beware of this horrible place and these horrible people

Excessive fees for flight delays. What a Scam. I was not able to attend the wedding I needed to go.

Waited at the airport for over 4 hours to board this flight. Terrible airline

Was supposed to take off 8:00 last night. Got delayed till 8:00 this morning

It was terrible, we had to board and unboard the flight with a hour delay that caused me to miss an appointment and a surprise for my wife

When the flight ticket is expensive and you have to purchase check in luggage and there is no snacks, no entertainment, tight seats stuffed in the back of the plane not such good experience. I would like some to reach out to me . I paid for check luggage when I bought the ticket they made me pay again on the return flight extra $70. Very frustrating.

Excellent experience when I am looking for a budget airline where the main expectation is getting me from point A to point B with no frills.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports

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