$106 Find Cheap Flights from Caribbean Islands to Pittsburgh

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Pittsburgh departing on 5/7. 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 Caribbean Islands to Pittsburgh

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

Thu, May 7 - Sun, May 10
Frontier Logo
9:09 am - 7:20 pm
SJU
-
PIT
10h 11m
1 stop
Frontier Logo
8:15 pm - 8:04 am
PIT
-
SJU
11h 49m
1 stop
$212Frontier
Tue, Apr 28 - Tue, May 5
American Airlines Logo
10:03 am - 11:59 pm
SJU
-
PIT
13h 56m
1 stop
American Airlines Logo
6:05 am - 12:03 pm
PIT
-
SJU
5h 58m
1 stop
$227American Airlines
Wed, Apr 22 - Mon, Apr 27
Multiple Airlines Logo
12:57 pm - 11:59 pm
SJU
-
PIT
11h 02m
1 stop
Multiple Airlines Logo
3:00 pm - 2:01 am
PIT
-
SJU
11h 01m
1 stop
$247Multiple Airlines
Wed, Apr 8 - Sun, Apr 12
Spirit Airlines Logo
7:54 pm - 9:38 am
SJU
-
PIT
13h 44m
1 stop
Spirit Airlines Logo
6:00 am - 6:55 pm
PIT
-
SJU
12h 55m
1 stop
$270Spirit Airlines
Fri, Apr 24 - Sat, Apr 25
Spirit Airlines Logo
12:57 pm - 11:59 pm
SJU
-
PIT
11h 02m
1 stop
Spirit Airlines Logo
6:35 am - 7:22 pm
PIT
-
SJU
12h 47m
1 stop
$271Spirit Airlines
Fri, Sep 4 - Wed, Sep 16
Delta Logo
5:45 pm - 12:22 am
SJU
-
PIT
6h 37m
1 stop
Delta Logo
6:00 am - 4:31 pm
PIT
-
SJU
10h 31m
1 stop
$275Delta
Thu, Apr 16 - Wed, Apr 22
Delta Logo
1:10 pm - 12:35 am
AUA
-
PIT
11h 25m
1 stop
Delta Logo
7:05 pm - 11:10 am
PIT
-
AUA
16h 05m
1 stop
$350Delta
Wed, Apr 22 - Tue, Apr 28
United Airlines Logo
12:15 am - 9:34 am
BQN
-
PIT
9h 19m
2 stops
United Airlines Logo
8:54 am - 11:09 pm
PIT
-
BQN
14h 15m
2 stops
$350United Airlines
Thu, Apr 23 - Mon, Apr 27
Multiple Airlines Logo
4:10 pm - 10:45 pm
BQN
-
PIT
6h 35m
1 stop
Multiple Airlines Logo
3:00 pm - 1:43 am
PIT
-
BQN
10h 43m
1 stop
$357Multiple Airlines
Wed, May 27 - Wed, Jun 3
United Airlines Logo
3:10 pm - 5:05 pm
AUA
-
PIT
25h 55m
2 stops
United Airlines Logo
6:49 am - 3:10 pm
PIT
-
AUA
8h 21m
1 stop
$365United Airlines
Useful Info

Good to know

Low seasonFebruary
Cheapest flight$106
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly with an average 6% increase in price.
Flight from San Juan to Pittsburgh

FAQs for booking flights from Caribbean Islands to Pittsburgh

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

    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 Caribbean Islands to Pittsburgh.

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

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

    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 Pittsburgh with an airline and back to Caribbean Islands with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Caribbean Islands to Pittsburgh?

    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 Pittsburgh from 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 3 airlines serving from Caribbean Islands to Pittsburgh

 
Need help choosing which airline to fly with from Caribbean Islands to Pittsburgh? 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.
7.9
DeltaOverall score based on 8291 reviews
8.1Boarding
7.8Entertainment
7.9Comfort
7.2Food
8.5Crew
Airline reviews

We landed and sat on the tarmac for 45 minutes because they only have one gate at the airport and there was another plane running late so we had to wait

2.0 MediocreSusan, Mar 2026
JAX - ATL
Read more Delta reviews

We landed and sat on the tarmac for 45 minutes because they only have one gate at the airport and there was another plane running late so we had to wait

The WiFi was not working. That made for a long flight.

Absolutely no communication on why there's a delay and multiple flight time reschedules. I would have canceled the flight and drove back home if I known it was going to be rescheduled 3 or 4 times.

Another late night flight and MORE men belligerently drinking and yelling. I had to move from first to economy because they were so obnoxious and disruptive. Crazy to go from a cozy chair to cardboard when you were supposed to be in first. Delta allows was too much drinking which leads to belligerent behavior.

I was in first class and literally the men behind me were so aggressively loud I moved myself to economy. This has become so common on Delta - people using audio without headphones, and men on 12am / late night flights drinking and yelling to talk to each other which prevents anyone around them from resting. Pretty crazy to have to move from first to economy (poorer service, less comfort...). Wild wild. Looking into other airlines.

Love delta smaller commuter plane so no entertainment and paid wifi on MKE-LGA leg was extremely unreliable and slow

Stop changing gates. Stop cancelling flights Stop moving my seat.

Extremely disappointed with Delta. They canceled flight last minute and then I rebooked the other flights and with which were delayed as well

Could not get my connecting flight boarding pass until four hrs before departure! Ver annoying especially since the staff could not explain why!

The flight was flying with 30% capacity. The flight my seat from preferred seating to back of the seat. Even though i can understand that this was to balance the flight weight. The flight attendance decided to do the serving near my seat and in the middle , their noices woke me up from sleep , when i realized that the service has ended and when they were going back asked for a coffee, for which they answered they have completed teh service in my location. That really upset me as they woke me up and also rejected the coffee i asked. I ended up landing with a headache, thanks to the crew that screwed up my travel

Staff and aircraft were good. However, weather in Houston lee to a ground stop. We were looking at circling behind three other planes until the stop was lifted. Pilot said we didn’t have enough fuel for that. So we flew on to New Orleans as the closest port with immigration and customs staff. Landed there and sat in the plane for two hours plus while staff was sorted. Turned away by ICE. Waited for pilots to be switched out, but after they were approved by ICE. Then had to wait to get a runway because so many planes were ahead of us. Finally took off and flew back to Houston. We all missed our connecting flights because it took too long. Hotel voucher from United was only a link to booking site. Total BS. Finally got a flight out the next day after a night without sleep because all the Houston hotels were booked by rodeo and spring break crowds.

Wifi Bluetooth features for watching in flight movie was horrible. Screen kept blacking out no connection of sound although it said connected. Other than that smooth trip .

I paid $7,000 to fly round trip to Porto. I thought it was for business class. But on the leg from Miami to Newark, and again from Newark to Miami, i was in coach. One time in the middle seat of coach. From Newark to Porto I was in business class as expected, and it was fine. I fly to Portugal once per month, often paying $5,000 for business class. Usually i fly American Airlines. I'd be happy to fly more with United Airlines. But my experience was disappointing because i was put in the coach for almost half the flights.

The travel company that you have on your site did me so wrong. I don’t know how it happened, but they put my son‘s name on my plane ticket flying to Vietnam. Along with his birthday. They would not have let me fly from Fort Myers to Ho Chi Minh City. I don’t think that I can ever use your service again. I typed my information into the browser along with my passport number and four days before I’m leaving I have to quickly search another ticket to fly out here.

Seats are uncomfortable. This has been a trend in the industry for decades. Trying to fit more seats on each plane to increase profits at the expense of the passenger.

The flight was delayed so we were dead tired, and after that the turbulence was horrible. I was very scared.

It was okay, the food was good, but after the landing there was not enough time for luggage and security to catch a connection. It was crowded on board.

It’s always a great time flying with united airlines.

Good flight. Efficient boarding and competent flight crew. No problems until we arrived at our destination gate. We were early so there was an aircraft at the gate that had to move before we could pull in. Then, due to the type of aircraft we flew, the cabin door could not be opened until some luggage from the cargo bay was offloaded to preserve center of gravity characteristics. So, that further delayed deplaning. Despite being 20 minutes early on landing, we ended up being 5 to 10 minutes late after all the delays.

It was amazing. I had several upgraded seats on my flight out. Everything went smooth with no delays.

Older airplane with worn out seats. No entertainment system at all. Connecting to Wi-Fi was problematic and hit and miss.

I didn't end up taking this flight. I got up at 4am for a flight that was supposed to board at 6am - at 5:55am you delayed the flight to 10am. The airport is under construction so I switched to a later flight as I wasn't going to sit in the airport for 4 hours. They said the delay was due to the crew needing rest from a flight coming in late the night before - if that was the case then I think you should have delayed the flight much sooner so that passengers wouldn't get up so early and get to the airport to sit and wait.

I very rarely fly American and my experience today reenforces that is the correct decision. While the staff were all very courteous, our flight was first thing in the morning so there was no reason to be delayed, yet appropriate maintenance checks weren’t completed prior to our flight so we were delayed multiple times. Not a great showing, American Airlines.

Boarding is always an ordeal. Less dogs on flights. I am highly allergic to dogs and cats. Why are there so many animals these days?

I was on a small regional flight from Detroit to Philadelphia. When we landed the outside cruise needed to turn something off with the engine, which took quite a long time. Then, when they allowed us to get off the plane it was outside. They took their time, unloading all the luggage and waited till they unloaded all the luggage before they brought it over to us. It was 9 o’clock at night freezing cold out, and there was no proactive hustle to try to get people their luggage. It was really one of the worst experiences I think I’ve ever had with American until a manager came over. I don’t think they were going to even consider pulling the luggage over to the people that had been waiting outside for at least 10 minutes in the freezing cold.

Awful. Original flight was delayed 5 hours. Had to to take a connecting flight instead of direct. Had a 4 hour layover. I missed all of my morning meetings getting in 5 hours later than I was supposed to and had to change to take a later flight the next day to get them back in which cia time another $150.

I was trying to take 2 one and a half hour one way trips and I experienced almost 20 delays over the course of those two trips. Only a few of them were due to weather the rest was disorganization

The attendants were kind and helpful. A sugar-free drink would have been very welcome.

The entertainment options were at best, fair. It was exactly the same as my outbound flight. It would have been more entertaining if there were some series from Apple TV, HBO, Showtime or other carriers for me to catch up with.

The seat cushions were very worn so they were extremely uncomfortable.

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