$114 Find Cheap Flights from Pittsburgh to Caribbean Islands - Compare and Save

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 Islands departing on 8/23. 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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Cheap Flights from Pittsburgh to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana2 stops$390
Santo Domingo
Santo Domingo1 stop$426
Montego Bay
Montego Bay1 stop$389
Oranjestad
Oranjestad1 stop$405
Nassau
Nassau1 stop$374
Kingston
Kingston1 stop$466
Simpson Bay
Simpson Bay1 stop$385
Providenciales
Providenciales1 stop$423
Port of Spain
Port of Spain1 stop$377
Bridgetown
Bridgetown1 stop$407
George Town
George Town2 stops$351
Willemstad
Willemstad2 stops$379
Aguadilla
Aguadilla1 stop$290
St. John's
St. John's1 stop$617
Puerto Plata
Puerto Plata1 stop$530
Punta Cana
Punta Cana2 stops$390
Santo Domingo
Santo Domingo1 stop$426
Montego Bay
Montego Bay1 stop$389
Oranjestad
Oranjestad1 stop$405
Nassau
Nassau1 stop$374
Kingston
Kingston1 stop$466
Simpson Bay
Simpson Bay1 stop$385
Providenciales
Providenciales1 stop$423
Port of Spain
Port of Spain1 stop$377
Bridgetown
Bridgetown1 stop$407
George Town
George Town2 stops$351
Willemstad
Willemstad2 stops$379
Aguadilla
Aguadilla1 stop$290
St. John's
St. John's1 stop$617
Puerto Plata
Puerto Plata1 stop$530

Book Cheap Pittsburgh to Caribbean Islands 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 Islands 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 Islands

Tue, Oct 27 - Tue, Nov 3
United Airlines Logo
6:00 am - 1:40 pm
PIT
-
SJU
7h 40m
1 stop
United Airlines Logo
8:25 am - 3:21 pm
SJU
-
PIT
7h 56m
1 stop
$228United Airlines
Wed, Sep 23 - Mon, Sep 28
United Airlines Logo
6:15 am - 3:12 pm
PIT
-
SJU
8h 57m
1 stop
United Airlines Logo
3:56 pm - 11:59 pm
SJU
-
PIT
8h 03m
1 stop
$228United Airlines
Mon, Oct 26 - Thu, Oct 29
American Airlines Logo
8:19 am - 10:57 pm
PIT
-
SJU
14h 38m
1 stop
American Airlines Logo
3:51 pm - 8:36 am
SJU
-
PIT
16h 45m
1 stop
$238American Airlines
Sun, Aug 23 - Fri, Aug 28
American Airlines Logo
1:16 pm - 12:15 am
PIT
-
SJU
10h 59m
1 stop
American Airlines Logo
7:03 am - 4:55 pm
SJU
-
PIT
9h 52m
1 stop
$238American Airlines
Tue, Sep 15 - Sun, Sep 20
Southwest Logo
4:05 pm - 10:05 pm
PIT
-
SJU
6h 00m
1 stop
Southwest Logo
5:30 am - 12:20 pm
SJU
-
PIT
6h 50m
1 stop
$262Southwest
Sat, Sep 5 - Sat, Sep 12
Southwest Logo
3:30 pm - 10:00 pm
PIT
-
SJU
6h 30m
1 stop
Southwest Logo
10:25 am - 6:40 pm
SJU
-
PIT
8h 15m
1 stop
$262Southwest
Mon, Jan 11 - Thu, Jan 14
Delta Logo
6:00 am - 3:05 pm
PIT
-
STT
8h 05m
1 stop
Delta Logo
1:50 pm - 12:19 am
STT
-
PIT
11h 29m
1 stop
$270Delta
Mon, Jan 18 - Wed, Jan 20
Delta Logo
6:00 am - 4:15 pm
PIT
-
STT
9h 15m
1 stop
Delta Logo
4:15 pm - 12:19 am
STT
-
PIT
9h 04m
1 stop
$270Delta
Wed, Aug 19 - Tue, Aug 25
JetBlue Logo
6:15 am - 4:05 pm
PIT
-
SJU
9h 50m
1 stop
JetBlue Logo
1:48 pm - 9:28 pm
SJU
-
PIT
7h 40m
1 stop
$291JetBlue
Fri, Sep 11 - Sat, Sep 12
JetBlue Logo
7:00 am - 3:23 pm
PIT
-
SJU
8h 23m
1 stop
JetBlue Logo
2:32 pm - 11:20 pm
SJU
-
PIT
8h 48m
1 stop
$295JetBlue
Booking Insights

KAYAK's insights & trends for Pittsburgh to Caribbean Islands flights

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

What is the cheapest Pittsburgh to Caribbean Islands flight route?

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

The cheapest ticket to Caribbean Islands from Pittsburgh found in the last 5 days was to Punta Cana, at $386 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 5 days was $386.

Can I save money by flying with a layover from Pittsburgh to Caribbean Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $372, prices are generally cheapest when you fly direct.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Pittsburgh to Caribbean Islands, 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 Islands is January, when tickets cost $434 (return) on average. On the other hand, the most expensive months are December and November, when the average cost of round-trip tickets is $663 and $635 respectively.

How far in advance should I book a flight from Pittsburgh to Caribbean Islands?

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 Islands, 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 Islands, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 11 weeks before departure.

Good to know

Low season

September

Cheapest flight

$114
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly with an average 12% increase in price.
Flight from Pittsburgh to San Juan

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from Pittsburgh to Caribbean Islands?

    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 Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Pittsburgh to Caribbean Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Pittsburgh to Caribbean Islands 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 Islands?

    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 Islands 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 Islands?

    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 Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 5 airlines serving from Pittsburgh to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from Pittsburgh to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Pittsburgh to Caribbean Islands? 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 4227 reviews
7.5Entertainment
8.0Comfort
8.6Crew
7.0Food
8.1Boarding
Airline reviews

No wifi, seems to be very common with Southwest currently. Everything else was normal.

8.0 ExcellentSean, Jul 2026
HOU - LGB
Read more Southwest reviews

No wifi, seems to be very common with Southwest currently. Everything else was normal.

Poor customer service, no accommodation for passengers when the flight was delayed over 5 hours.

Friendly crew kept coming by to make sure all was ok, provide additional refreshments, etc.

My experience will Southwest was good. I wish there was more entertainment and the boarding process was slow at time but other than that my experience was great definitely will be flying with SouthWest again.

For my birthday trip this was my second time ever flying, this trip was the best.

I really wish that SW would ask anyone with a carry-on to wait while those who don’t have to access the overhead bins are boarded. Then, reverse that when the plane arrives. Those without the need to clog up the aisle retrieving their bags from the overhead bins wait for those exiting the plane without needing to clog up. The aisle.

We boarded the flight and set two and a half hours on the jetway. Would have been better if they had not boarded us at all. Plane was hot and it was limited ability to access the restrooms or get a drink of water. Very unpleasant experience

The actual flight was great! The 3 hour delay not so much.

Southwest is a garbage airline and the people who fly it are garbage people.

Boarding was easy. Plane wasn’t crowded. Plenty of space. Flight was on time. Crew was pleasant.

Flight was delayed for about an hour but overall good experience

Staff is friendly and helpful but flight was delayed by one hour from Detroit, making for tight window in Toronto to clear Canada Customs and pass through security screening in order to get to connecting flight on time.

Delta staff was exceptionally helpful and considerate. However, the first two of three flight legs were delayed making connections tentative and stressful.

No Internet, no backseat screen, no nothing. I bought a Delta ticket and ended up on American Airlines. How did that happen?

Connection flights should be spaced out farther because too close I missed my connection.

The flight was way too HOT! And the plane did not have any in-flight TV entertainment.

The gate attendants and the crew were terrible. Because of high winds, they needed to carry more fuel, so they had to get volunteers to take the next flight at 6 am the next day. They did a terrible job of it - our flight ended up taking off just under 3 hours of the scheduled time. I hope to never fly Delta again.

Great service. Great staff. Boarding was a little slow, but I think there was a service dog slowing things down.

We splurged and decided to fly first class. Seats were roomy. But flight crew arrived late to the airport. That delayed our flight. Most of the passengers had to try to make connections flights. I felt bad for them. We checked 4 bags. We got three from the baggage claim carousel. 4th one was lost. Delta online help wasn’t good. Baggage claim staff were sympathetic and nice but we waited around for almost 2 hours and it had t been found. They did find it several hours later and we had to drive back to airport to retrieve it. I won’t be splurging on 1st. Lass again anytime soon. I think we got worse service. I am also not a huge fan of delta but we have family in ATL so we don’t have a ton of choice. What should have been an easy flight turned into a stressful event due to flight crew tardiness and baggage mishandling.

My flight consistently said it was on time and the plane didn’t arrive until after 30 minutes after take off and nothing was announced to passengers

It was great. All the crew were professional and nice.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

newer aircraft, ability to connect my headset via blue tooth for entertainment.

Miserable. They moved my seat, but canceled the next leg of my flight. I resolved the issue at my transfer, but that resulted in lost luggage that has taken days off my schedule with no resolution. Worse, they fail to interface effectively with Lufthansa, forcing me to bounce between two equally useless help desks. The apps are unable to handle the situation, the bag dropped off the tracker, and while the call centers are polite, they do not provide written information to assist with cross-airline communication.

The only downside was my cell phone charger wouldn’t work in the charging port but everyone else’s would work in them all. My cell phone cable works fine in my hotel room in Frankfurt.

My husband and I recently had an unfortunate experience with Lufthansa. At the Philadelphia International airport, the ground staff refused to board us because we didn’t have a current visa stamped on our passports for Frankfurt. We completely understand that this was our mistake. we should have double-checked the visa requirements before our trip. However, the issue that upset us most was how the situation was handled by the staff. They told us they would mark it as “boarding denied due to visa issue”, but instead they recorded it as “no show”. Because of that incorrect entry, our return flight was automatically cancelled as well, which caused additional stress and expense. Mistakes can happen, but we expected more transparency and accuracy from a reputed airline like Lufthansa. It would have made a big difference if the staff had been more careful and considerate in documenting the situation correctly.

Everything was good, except the seats in economy were so close together, you could barely get out when the seat in front of your was reclined. If the airlines keep jamming in more and more seats, it will become intolerable. I will look for another airline that considers customer comfort and does not keep adding more rows of seats for more profit.

A three (3) hour flight should have meal service in First Class, not just potato chips!

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.

Seats suck. Only one drink service in three hours with the flight attendants being more attendant to their phones than the customer. Painful in the extreme.

Very good, boarded and took off on time and landed early

Boarding and Delays The boarding process for my American Airlines flight from Copenhagen to Philadelphia was a bit tricky. We experienced a gate change that required a long walk to a new area of the airport. Additionally, boarding was not via a jet bridge; we had to take a shuttle bus to the plane and then carry our luggage up the stairs ourselves. Furthermore, the bag drop didn't open until about 12:20 PM, which was only three hours before our scheduled departure. This meant I couldn't drop my bag off early and had to wait outside of security in order to drop off my bag and use the kiosk. The bag drop self-service kiosks also didn't open until about 12:00 PM when an American Airlines employee unlocked them so that we could print out our boarding passes and bag tags, which further created a backlog. The flight was delayed by over an hour because we had to wait for one of the tires on the plane to be changed. Flight Attendant Professionalism On a positive note, the flight attendant was very professional when handling a passenger who was sitting in the wrong seat. Even though the passenger was persistent and reluctant to move, the flight attendant calmly ensured the assigned passenger could take their seat. Kudos to the flight attendant for keeping his calm and composure, not allowing the issue to escalate, and handling it well under pressure while a line of passengers waited in the aisle to board. In-Flight Service The in-flight service was also fast, prompt, and efficient, although service had to be suspended for the last two hours of the flight due to weather and turbulence, which was outside of the crew's control. Limited Flight Options Please note that American Airlines only operates one flight per day in and out of Copenhagen. This means there are limited options available if your flight is delayed or canceled, which is something to take into consideration when booking.

Not much space for someone 6 feet high in normal economy seat. My knee hurt

Getting to Scotland with no luggage (no medicine, no clothes and no club) on golf trip very disappointed

Quick flight again no one illness why there were multiple delays and changing of the gate number.

Seat comfort was poor (no lumbar or lower back support).

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

The American flight was a connecting flight to an international flight. The international flight has a 2 check bag rule. Despite being informed of this, American would only check 1 bag and wanted 100 to check the second (basically a 3rd carry-on) to NYC. Subsequently tsa took a sealed container of maple syrup and a few other things that couldn't be in carry-on plus I had to lug around 3 pieces of luggage for the entire trip. The American reservation was made with the international and American actually checked the one piece the entire way to China. This is one of the reasons that I will avoid American airlines if possible in the future.

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.

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

Flight delayed 4 times on a non-stop from BOS to SFO. Then when landed in SFO had to wait for 30 mins for a gate AT 3:30AM.

Plane was delayed multiple times. I would like to request a refund. Was due to arrive Thursday evening ended up arriving Friday morning.

The seats were roomier than other airplanes I’ve been on.

The crew and the pilots. The pilots were amazing. The landing in Cancun was excellent.

The security line at JFK was one of the longest I’ve ever experienced - probably 45 minutes. I don’t know if JetBlue has control over it, but it detracted from the overall experience. Entertainment had good options, but the volume control was a bit small to tap on and the screen had a fair amount of interference blips. Clearer picture would have been better.

I liked the entertainment on JetBlue, the service from JFK to JAX was terrible at best

I usually dont fly JeTBlue and I dont think I will ever do it again. The flight was delayed fee time, nobody was giving us any info at at the airport, gate changing, the slowest and poorly organized boarding ever, rude staff.. huh

They lost my luggage and refuse to help. Terrible airline. I've never experienced worse customer service in my life. Pretty much just told me too bad that I lost all my luggage, not caring that I am stuck in Europe for 2 weeks with absolutely nothing.

I especially liked the lead crew officer. His boarding and safety announcements were made with a bit of novelty and humor. The flight also left the gate 10 minutes early and we landed about 20 minutes early… It was a delightful flight…

As with all airline's seats, a little more padding would appreciated. Especially on longer flights.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports