$107 Find Cheap Flights from Caribbean 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 11/18. 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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Everything you should know

Cheapest round-trip
$225
Overall average: $334
Delta
Fri 2/6Sun 2/8
SJU - PIT • 1 stop
Cheapest one-way
$107
Typical prices: $157-$292
JetBlue
Tue 11/18
SJU - PIT • 1 stop
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Flight Deals
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Flight Deals

Cheap Flights from Caribbean to Pittsburgh

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

Fri, Feb 6 - Sun, Feb 8
Delta Logo
3:55 pm - 11:35 pmSJU-PIT
8h 40m1 stop
Delta Logo
11:55 am - 8:57 pmPIT-SJU
8h 02m1 stop
$225Delta
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Fri, Feb 6 - Sun, Feb 8
American Airlines Logo
7:00 am - 10:43 pmSJU-PIT
16h 43m1 stop
American Airlines Logo
1:25 pm - 11:56 pmPIT-SJU
9h 31m2 stops
$229American Airlines
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Fri, Feb 6 - Sun, Feb 8
American Airlines Logo
5:10 pm - 10:43 pmSJU-PIT
6h 33m1 stop
American Airlines Logo
1:25 pm - 11:56 pmPIT-SJU
9h 31m2 stops
$230American Airlines
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Wed, Nov 12 - Sun, Nov 16
Multiple Airlines Logo
6:17 pm - 6:21 amSJU-PIT
13h 04m1 stop
Multiple Airlines Logo
10:06 pm - 3:33 amPIT-SJU
28h 27m1 stop
$239Multiple Airlines
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Tue, Nov 11 - Sun, Nov 16
United Airlines Logo
2:05 am - 1:09 pmSJU-PIT
12h 04m2 stops
United Airlines Logo
6:15 am - 1:17 pmPIT-SJU
6h 02m1 stop
$255United Airlines
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Tue, Jan 27 - Sat, Jan 31
Southwest Logo
6:00 am - 3:45 pmSJU-PIT
10h 45m2 stops
Southwest Logo
3:55 pm - 11:00 pmPIT-SJU
6h 05m1 stop
$262Southwest
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Mon, Nov 24 - Fri, Nov 28
United Airlines Logo
5:20 pm - 9:54 amPUJ-PIT
17h 34m2 stops
United Airlines Logo
8:10 pm - 12:59 pmPIT-PUJ
15h 49m1 stop
$303United Airlines
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Sat, Feb 7 - Tue, Feb 10
Delta Logo
7:00 am - 5:38 pmSJU-PIT
11h 38m1 stop
Delta Logo
6:00 am - 2:10 pmPIT-SJU
7h 10m1 stop
$314Delta
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Fri, Dec 5 - Sat, Dec 13
Spirit Airlines Logo
4:10 am - 4:10 pmSJU-PIT
13h 00m1 stop
Spirit Airlines Logo
5:05 pm - 10:33 amPIT-SJU
40h 28m3 stops
$342Spirit Airlines
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Fri, Dec 5 - Sat, Dec 13
Spirit Airlines Logo
4:10 am - 4:10 pmSJU-PIT
13h 00m1 stop
Spirit Airlines Logo
5:05 pm - 12:32 pmPIT-SJU
18h 27m1 stop
$357Spirit Airlines
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Good to know

Low seasonFebruary
Cheapest flight$107
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 12% increase in price.
Flight from San Juan to Pittsburgh

FAQs for booking flights from Caribbean to Pittsburgh

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

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Pittsburgh from 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 Caribbean 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 with another airline.

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

 
Need help choosing which airline to fly with from Caribbean 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.
8.0
SouthwestOverall score based on 4241 reviews
8.1Boarding
8.6Crew
7.0Food
8.0Comfort
7.5Entertainment
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

DELTA does a terrific job making sure you are well taken care of during the flight, gives you assurance before the flight through numerous email notifications about your upcoming flight & lastly good follow up after the flight making sure your needs were mat. It has been, is & will continue to be my carrier of choice in all my future travels. Good Job DELTA

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

Seats comfortable, service and food very mediocre, staff not very attentive, worse than many other our flights with Delta.

Overall good experience; however, there was one flight attendant who was rather rough compared to everyone else. Everything else was good: entertainment, food. Delta keeps on delivering! Thank you!

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.

Crew blocked exits to front of ship with galley carts. Also split five person family apart on international flight without fixing.

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 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.

Flight left on time. Boarding was easy. Arrived to EWR 30 mins early. Luggage was deplaned in good time. Overall a very good experience.

Flight from Rome to SFO was excellent compared To our flight to Europe from SFO. The food was much tastier. You can see how UNITED is skimping, though. Instead of getting something mid flight you had to ask for it. It was not automatically served. There was a cookie at the end of the arrival meal, for example that tasted like it just came out of a box. They used to serve a little container of nuts, now … a tiny container of nuts, mixed with pretzels. This was business class that you really have to pay for! But this is minor complaints compared to the overall. My major complaint is the position of the even numbered seats by the windows. You have to turn around to see your window & the positioning as some other controls are harder to get at. This is compared to the odd number seat that are perfectly aligned.

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.

The food quality sucks. One must starve if they do not eat flesh Or wheat based products Some variety would be expected. The trivial amount of snacks and or food is inhumane

Excellent all round, first time flying United. App is very helpful.

Nice comfortable flight from Barcelona back to the states. The premium economy offers the extra room we need for my husband. The food was good and our flight attendants were excellent.

the trip to madrid was uncomfortable with my legs touching the seat in front of me

The Phildalphia to Allentown portion was a BUS, not a plane. All was as expected.

Very crowded flight but what can you expect these days?? Crew was accommodating.

Small outdated plane from Philly to Des Moines with very uncomfortable seats. The plane was old, so we had mechanical issues that delayed us for 3 hours with very little communication. It was a very unpleasant experience and I will try to never fly AA again.

The seats in economy were appeared to be quite thin and lack sufficient cushioning to be comfortable. Perhaps it was my seating position but the plane seemed notably load.

Internet was a bit expensive and did not work ask that week otherwise a good flight

They don't make it easy or promote their food options. Dirty plane. Delayed.

International baggage recheck process in Philadelphia was a disaster. Waited 1 hour and 45 minutes to receive our bags. Waited 15 minutes to recheck bags, flight notification boards were blank so we asked an AA representative for our connecting gate and we were directed to the wrong terminal and gate. Our connection window was over 3 hours and we made our flight by 5 minutes. We pulled away from the gate and sat on the runway for 1 1/2 hours. 1 of our 4 bags didn’t make it to Phoenix. The mobile app for lost baggage didn’t work, the AA rep had to manually fix.

I miss my flight and they could not rebook me that day because the other flight was full, and for the next day I had to pay a whole new fee again which I think is unprofessional

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.

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