$81 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 9/25. 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 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

Thu, Oct 16 - Tue, Oct 21
Spirit Airlines Logo
12:06 pm - 6:58 pmSJU-PIT
6h 52m1 stop
Spirit Airlines Logo
6:04 pm - 12:44 amPIT-SJU
6h 40m1 stop
$183Spirit Airlines
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Thu, Sep 11 - Wed, Sep 17
Spirit Airlines Logo
11:59 am - 11:22 pmSJU-PIT
11h 23m1 stop
Spirit Airlines Logo
6:04 pm - 12:44 amPIT-SJU
6h 40m1 stop
$184Spirit Airlines
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Thu, Oct 23 - Sat, Oct 25
Southwest Logo
5:30 pm - 11:35 pmSJU-PIT
6h 05m1 stop
Southwest Logo
2:05 pm - 11:25 pmPIT-SJU
9h 20m1 stop
$205Southwest
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Wed, Sep 10 - Wed, Sep 17
Spirit Airlines Logo
1:59 am - 9:30 amSJU-PIT
7h 31m1 stop
Spirit Airlines Logo
6:04 pm - 12:44 amPIT-SJU
6h 40m1 stop
$207Spirit Airlines
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Thu, Oct 16 - Tue, Oct 21
American Airlines Logo
5:30 am - 11:46 amSJU-PIT
6h 16m1 stop
American Airlines Logo
12:14 pm - 10:10 pmPIT-SJU
9h 56m2 stops
$209American Airlines
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Fri, Nov 7 - Sat, Nov 15
Delta Logo
7:00 am - 4:37 pmSJU-PIT
10h 37m1 stop
Delta Logo
11:49 am - 11:50 pmPIT-SJU
11h 01m1 stop
$215Delta
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Wed, Oct 8 - Mon, Oct 20
American Airlines Logo
11:56 am - 10:53 pmSJU-PIT
10h 57m2 stops
American Airlines Logo
6:54 am - 11:54 pmPIT-SJU
17h 00m1 stop
$220American Airlines
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Thu, Sep 25 - Mon, Sep 29
United Airlines Logo
1:05 am - 9:31 amSJU-PIT
8h 26m2 stops
United Airlines Logo
11:04 am - 11:57 pmPIT-SJU
12h 53m2 stops
$246United Airlines
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Wed, Jan 14 - Wed, Jan 21
Delta Logo
7:00 am - 4:40 pmSJU-PIT
10h 40m1 stop
Delta Logo
7:20 am - 4:51 pmPIT-SJU
8h 31m1 stop
$253Delta
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Fri, Sep 12 - Tue, Sep 16
United Airlines Logo
1:05 am - 4:55 pmSJU-PIT
15h 50m2 stops
United Airlines Logo
6:00 am - 1:45 pmPIT-SJU
7h 45m1 stop
$295United Airlines
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Good to know

Low seasonFebruary
Cheapest flight$81
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly and prices are also 12% lower on average.
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
8.0Comfort
8.1Boarding
7.0Food
8.6Crew
7.5Entertainment
Airline reviews

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

2.0 MediocreAnonymous, Jul 2025AUS - RDU
Read more Southwest reviews

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

Very smooth checking in our luggage with a super pleasant SW agent. I enjoyed a fun entertaining movie.

WiFi did not work. For as outrageous as these flights cost, when they’re advertised with certain services/ features they should be in working order

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

The Southwest employees (all two of them) were very nice and cheerful despite the fact the line to self-check a bag (simply drop it off) was hundreds of people long. Thank God I arrived early to the airport because I stood in this line for at least an hour. Once on the flight that had been delayed by an hour, we had no Wi-Fi and thus no entertainment. Finally, I hope the investor strong arm tactics against Southwest pay off in a short-term windfall to your C-Suite because the rest of you are screwed. I have been a faithful Southwest customer for 15 years due to everything you just got rid of. I'm flying to Idaho and Washington in October, both places I used to simply book with Southwest without a second thought now with Frontier (Washington) and United (Idaho) because they offer everything the "new" Southwest does but cheaper and at better times, destinations, etc. This really makes me sad...

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

It was one and half hour late... Not sure if any other experience matters.

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

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

My experience on any Delta flight is always overshadowed by the time Delta removed me from a flight for no apparent reason.

Check in process was terrible. Lady at counter didn’t know what she was doing

Delayed and took off even later than the scheduled delay time

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

Great experience on Delta. Staff from baggage check to flight attendants were very courteous and professional. My only issue was a personal preference for pretzels instead of the chips and cookies that were offered.

The crew was amazing; Von, Vera and Guadalupe were very friendly and attentive throughout the entire flight. They were friendly and welcoming to everyone. A solid and dedicated team for sure!

Terrible. I was bumped off of my original flight and spent the next six days fighting to get back on it. I lost hours of my vacation trying to get this situation corrected.

There was no problems, just a little uncomfortable with seats that do not lay back a little

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

Flight was delayed, 30+ bags had to be gate checked. Crew were very friendly!

Not good , late, and long. We came home so late and spent so much time flying around and taxiing

Terrible. Delayed 7 hours, and cancelled the flight, leaving me stranded and out of pocket $500 for an alternative last minute flight

Was on time until within 1 hour of flight-how does that happen? Staff very friendly.

Had one staff that was not pleasant. Seems they are stressed with too many people to care for.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Ok. Get a different kosher caterer. The food was odd.

Food was terrible. Crew was kind but skipped over my row for providing sandwiches and beverages.

Our flight was understandably diverted to a small regional airport in Laramie, Wyoming due to weather conditions, which I fully recognize and appreciate. However, the low rating stems from the experience that followed: passengers remained on board for over an hour without the option to deplane and stretch, despite the aircraft being stationary. Although the pilot opened the cabin door, only he was permitted to exit. Meanwhile, passengers grew increasingly uncomfortable as warm summer air entered the cabin through the open door, and being in the second row meant we were impacted immediately. While the flight attendants made efforts to keep everyone at ease, I believe allowing passengers to deplane briefly, given the extended delay, would have significantly improved the overall experience.

I never flew. Flight was canceled. DIA worst airport in the country. Avoid at all costs.

Lost luggage, they need a baggage service representative available all times in Atlanta

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 flight had a delay that made me being in a real rush to take the second flight. The delay was almost for 2 hours. They moved us from gate to gate in 4 times. Once I arrived to Philadelphia, I got to run thorough all the airport, as the train was already closed by that time. So I got sick with asthma for all the running I had to do. And I was the last one to board, when it was almost closed. So irresponsable with the people

Above and beyond effort from this crew in a tough situation. So helpful and understanding. Thank you!

The plane was probably full boarding was easy. We were able to check our carry-on luggage for free. It was a return flight through Philly to LA. Never saw a stewardess do a demonstration of emergency Procedures. I think my flight was pretty full

Overall, a good experience. The food, however, was subpar. The breakfast was a joke.

I was late from Jacksonville, FL but the limited interaction I had with the Philly crew was great.

The delays and cancellations kept me stuck in Miami for an additional 24 hours, and the whole thing seemed extremely disorganized

Everything was great except British airways lost our luggage that was gate checked all the way through to Italy. No one knows currently where one is and the other one may be in route to Amsterdam to meet us but not sure. If you can Hale’s it would be awesome. The website is not helpful.

Seats were roomy. Lavatories were surprisingly big and clean. Plenty of entertainment available. We were fed and offered drinks, multiple times during the flight.

The staff was excellent and I appreciated the zero tolerance for noise making electronics and the only bad part was It took forever for the luggage to get to the baggage claim. It took over 40 minutes. And Norfolk is a small airport so it was probably airport. Staff’s fault.

The flight was 3.5 hrs delayed. I was not notified prior to arriving to the airport via spirit app. or via boarding pass that I already had loaded on my phone. The agent that i saw at the counter didn’t mention anything about the delay either. I only saw the update after logging in to my email account.

The flight and boarding process was smooth. Wifi was unavailable and I prepaid for it. Have requested a refund

Offer snacks for free. You are charging for the flight for the carry on for the seat and for a snack??? Lord

Had a issue with catching flight due to airline, was unable to board flight

Spirit is a very uncomfortable travel experience. It’s cheap but you are squeezed into the seats like canned meat.

Not great. Seats uncomfortable. Crew a little rude. Amenities like wifi and drinks way too expensive.

Late departure by 1:45min. No explanation why. During boarding inconsistent policing of their baggage rules. Before takeoff and lamdimg strange obsession with window shade and armrest positions. Don't know why they care. 15 min tarmac delay on arrival, they blamed airport congestion but we were the o lh flight waiting, it was clear it was due to poor staff planning (only one ground crew to receive airplanes and multiple arrivals) Got there but was rrally lame the whole trip.

The seat belt was lengthy enough that I did not need an extender. Courteous and helpful flight attendants.

We sat on the tarmac for an hour waiting for a gate to deplane.

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