$114 Find Cheap Flights from Caribbean to Pittsburgh - 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 to Pittsburgh departing on 10/1. 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 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

Sat, Sep 12 - Wed, Sep 16
United Airlines Logo
1:00 am - 9:36 am
SJU
-
PIT
8h 36m
2 stops
United Airlines Logo
6:30 am - 1:53 pm
PIT
-
SJU
7h 23m
1 stop
$228United Airlines
Sat, Sep 5 - Sun, Sep 20
Southwest Logo
2:00 pm - 8:50 pm
SJU
-
PIT
6h 50m
1 stop
Southwest Logo
4:15 pm - 11:55 pm
PIT
-
SJU
7h 40m
1 stop
$228Southwest
Tue, Sep 15 - Fri, Sep 18
Southwest Logo
8:20 am - 2:45 pm
SJU
-
PIT
6h 25m
1 stop
Southwest Logo
4:10 pm - 10:55 pm
PIT
-
SJU
6h 45m
1 stop
$228Southwest
Fri, Aug 28 - Mon, Aug 31
American Airlines Logo
2:33 pm - 9:00 pm
SJU
-
PIT
6h 27m
1 stop
American Airlines Logo
6:21 am - 2:51 pm
PIT
-
SJU
8h 30m
2 stops
$238American Airlines
Fri, Aug 28 - Mon, Aug 31
American Airlines Logo
1:38 pm - 11:50 pm
SJU
-
PIT
10h 12m
2 stops
American Airlines Logo
6:21 am - 2:51 pm
PIT
-
SJU
8h 30m
2 stops
$238American Airlines
Fri, Sep 18 - Mon, Sep 21
United Airlines Logo
2:20 pm - 11:59 pm
SJU
-
PIT
9h 39m
1 stop
United Airlines Logo
6:30 am - 1:45 pm
PIT
-
SJU
7h 15m
1 stop
$238United Airlines
Thu, Aug 27 - Mon, Aug 31
JetBlue Logo
2:30 pm - 9:28 pm
BQN
-
PIT
6h 58m
1 stop
JetBlue Logo
6:15 am - 1:28 pm
PIT
-
BQN
7h 13m
1 stop
$290JetBlue
Fri, Sep 11 - Thu, Sep 17
JetBlue Logo
2:32 pm - 11:20 pm
SJU
-
PIT
8h 48m
1 stop
JetBlue Logo
7:00 am - 3:23 pm
PIT
-
SJU
8h 23m
1 stop
$292JetBlue
Thu, Sep 24 - Thu, Oct 1
Delta Logo
5:59 pm - 12:31 am
SJU
-
PIT
6h 32m
1 stop
Delta Logo
11:16 am - 10:19 pm
PIT
-
SJU
11h 03m
1 stop
$296Delta
Wed, Sep 23 - Sat, Sep 26
Delta Logo
7:30 am - 4:28 pm
SJU
-
PIT
8h 58m
1 stop
Delta Logo
12:10 pm - 11:49 pm
PIT
-
SJU
11h 39m
1 stop
$296Delta
Useful Info

Good to know

Low season

February

Cheapest flight

$114
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly with an average 47% 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 4 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 4227 reviews
8.1Boarding
8.6Crew
8.0Comfort
7.5Entertainment
7.0Food
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.

The flight was fine. Seats were very comfortable. Attendants were very friendly -

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

It was good. Last flight was delayed but I always say that is in God's plan

Red eye from San Diego. Temperature of the cabin was way too warm and the air duct flowed very little air.

Overall good, just screaming kids in the area the whole flight.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

The crew was very nice and respectful and everything went well.

Having a direct flight between Pittsburgh and Austin makes traveling so easy.

Only beverages were offered to first class and I thought the flight attendant could have also served the Delta Comfort as well instead of sitting down and staring at her phone and walking past all of us to the back of the plane to charge her phone more. There was a complete lack of turbulence and was safe enough for flights attendant to walk around in the front of the plane, collect trash and serve a few people water and turn off the seat belt light. Also didn’t enforce people putting their seats into the upright position and allowed two passengers to remain reclined during landing. They seemed out to lunch completely. Usually my experience on Delta is much better.

My tray was broken so i had no place to work or eat except my lap. Flight attendant said I would get an email with some credit or miles, it was a complete waste of time as I could only function at about 20% of normal. I have not received anything yet.

Delayed. Hot. Passenger next to me was so large I couldn’t move.

2+hrs delay without any reason provided and a cramped flight

Originally, I was booked in economy. I paid several hundred additional dollars to upgrade to first class. Then I paid several more hundred dollars to change my flight to a slightly earlier flight. I asked if the changed flight would also seat me in first class, and I was told that it would. When I boarded the plane, however, I was seated in economy. So, I paid $500-600 more than I paid for my original ticket for an upgrade and a changed flight - received the changed flight (which was nice), but did not receive the upgrade. So, I was not completely satisfied.

I noticed that the planes seem to be outdated. There was no entertainment per se. Also, the waiting area did not have any working electrical outlets

Delayed due to thunderstorms and no in-flight service due to rough weather — both of which are out of Delta’s control. Flight was good overall.

This was the second flight this week with flight attendant Marcus I’m not sure if his last name is Lane or Lang but this guy is awesome. He funny, attentive and his service is 5 stars. Marcus makes business travel more enjoyable !

My seat was moved closer to the front of the cabin since I had requested wheelchair assistance to the gate.

Made the Atlanta to Pittsburgh trip many times, with Delta no issues

It was hot and not as comfortable as the flight to Chicago. Must have been a different plane that needs to be worked on or replaced.

My flight was delayed so bad i missed u it so i just said never mind

What would be infinitely better if for Kayak to not offer this flight as if it was completely different airlines rather than United and then filtering me through some creepy discount site.

United didn’t even try to hold the flight for me. They knew I had a tight connection and when I arrived at the gate less than 10 mins after final boarding the flight had already gone. The gate agent wasn’t even notified that I was on my way. She was told I wasn’t at the airport

Everything went well except the turbulence what no one have a control of but pilot and crew handled very good!

I still prefer Delta, but Delta doesn’t fly to State College PA.

This flight was delayed multiple times and eventually canceled around 2-3ish. Original take off time was around 10:30am. By 3, there were no other options out of Houston, so stuck in Houston for from 3pm - 11am the next day.

Nothing bad to say about the actual crew or airline. It was nice to have a complimentary FULL can of soda, as well as a snack. Blankets and earbuds were also provided at no cost for this red eye flight. I especially appreciated the free WiFi and movie selection with the Bluetooth option. It helped the flight pass more quickly. No matter who you fly, boarding and disembarking are always SUCH a pain. As I mentioned, this is on the passengers and not the crew!!

Flight attendants rude and impolite… flight delayed by almost 5 hours.

Ok so apparently the new policy on United Airlines is that customers in the main cabin should NEVER be served more than once and besides picking up trash there should NEVER be another interaction with the customer for any reason.

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. 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. 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. However, the in-flight entertainment screens and the overall interior of the plane were somewhat older. The system did not offer streaming to personal mobile devices, so we had to watch movies on the seatback screens.

The flight was on time and the landing was very smooth. The crew and flight attendants were all very friendly and professional.

Message about flight cancelation was received late due to being in the air. No explanation, just canceled and booked on morning flight. We had to stay in the airport overnight because there was no transportation offered to get to the hotel that AA had available. Actual inflight was fine.

Bag drop was very disorganized in Miami. All main cabin passengers were shunted to just a few lanes and they had an equal number of lanes for first class passengers but there was nobody on those lines. They did nothing to bring the main cab and passengers over to the open lines and they just had employees standing there and doing nothing

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

Staff at the gate were incredibly rude, hostile and threatening. Never fly American Airlines.

Great - quick boarding and landed early with an available gate.

The flight was delayed till next day ! They kept delaying every 30 minutes then after 3 hours they delayed it till next day. We kept waiting in line standing more than an hour to get the hotel and meal vouchers. There was no communication at all. Everything was bad

The flight was great but board was a nightmare. The gate was changed 4 times during the layover period

I don’t think the flight attendants are happy. They do not seem to be friendly or welcoming.

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