$106 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 5/20. 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

Fri, May 15 - Sun, May 17
Frontier Logo
6:09 pm - 6:30 pm
SJU
-
PIT
24h 21m
1 stop
Frontier Logo
8:15 pm - 5:30 pm
PIT
-
SJU
21h 15m
1 stop
$212Frontier
Wed, May 13 - Mon, May 18
Frontier Logo
3:03 am - 6:05 pm
SJU
-
PIT
15h 02m
1 stop
Frontier Logo
8:15 pm - 10:43 pm
PIT
-
SJU
26h 28m
1 stop
$214Frontier
Sat, May 16 - Tue, May 19
American Airlines Logo
6:45 am - 6:22 pm
SJU
-
PIT
11h 37m
1 stop
American Airlines Logo
8:24 am - 6:10 pm
PIT
-
SJU
9h 46m
2 stops
$282American Airlines
Wed, Aug 19 - Wed, Aug 26
American Airlines Logo
10:33 am - 11:54 pm
SJU
-
PIT
13h 21m
1 stop
American Airlines Logo
6:16 am - 4:03 pm
PIT
-
SJU
9h 47m
2 stops
$287American Airlines
Tue, Sep 15 - Wed, Sep 16
JetBlue Logo
1:50 pm - 9:23 pm
PUJ
-
PIT
7h 33m
1 stop
JetBlue Logo
6:00 am - 2:25 pm
PIT
-
PUJ
8h 25m
1 stop
$371JetBlue
Fri, May 15 - Sun, May 17
United Airlines Logo
6:00 am - 11:20 pm
SDQ
-
PIT
17h 20m
1 stop
United Airlines Logo
7:28 am - 10:46 pm
PIT
-
SDQ
15h 18m
1 stop
$409United Airlines
Thu, Aug 27 - Mon, Aug 31
JetBlue Logo
2:30 pm - 9:26 pm
BQN
-
PIT
6h 56m
1 stop
JetBlue Logo
6:00 am - 1:26 pm
PIT
-
BQN
7h 26m
1 stop
$410JetBlue
Mon, Sep 14 - Tue, Sep 22
Delta Logo
7:40 pm - 11:32 am
SDQ
-
PIT
15h 52m
1 stop
Delta Logo
7:00 am - 1:41 pm
PIT
-
SDQ
6h 41m
1 stop
$412Delta
Thu, May 14 - Mon, May 18
United Airlines Logo
6:45 pm - 11:20 pm
PUJ
-
PIT
28h 35m
1 stop
United Airlines Logo
4:02 pm - 3:12 pm
PIT
-
PUJ
23h 10m
1 stop
$415United Airlines
Wed, Jun 3 - Wed, Jun 17
Delta Logo
6:05 am - 5:19 pm
SDQ
-
PIT
11h 14m
1 stop
Delta Logo
7:22 am - 12:42 am
PIT
-
SDQ
17h 20m
1 stop
$490Delta
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 4% 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 4317 reviews
8.0Comfort
7.0Food
8.1Boarding
7.5Entertainment
8.6Crew
Airline reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

10.0 Excellentlarry, Apr 2026
LGB - PHX
Read more Southwest reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den

We waited in the airplane for over 45 min for a southwest employee to make the flight. This cause over half the plane to miss their connecting flight in Denver. When we confronted the desk upon arrival, they told us the only flight they had was the next day leaving at 8:50 pm!!! Or they offered to get us to Burbank or LA, but after that we were on our own to get back to Santa Barbara. I paid for a flight from sba to bna bna to sba. My re entry into mom mode has been 💯 rough because of southwest mistake with my flight. And now I’m leaving to Reno tomorrow for a vballl tournament and just discovered that my leg in Vegas has me and my 3 kids on a stand by flight even though I had booked these ticket last year November!! Do better southwest!

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

Round trip flight to Canada and back to the US was smooth and efficient.

The agent at check in and at the gate were less than thrilled to be at work. I'm not a fan of Kayak's placement on the plane. I got put in the middle seat and none of my preferences were used.

Spanish speaker flight attendants were incredibly rude. A male flight attendant named Allen, grabbed my bag out of the overhead bin and moved it without my permission. When I asked what he was doing, he informed me that the overhead bins were public space? It would be easy to ignore this comment, as you don’t know the whole story, but the flight attendants were militant and rude. Delta, you can do better!

In ATL they have two sets of departure screens. Follow what is on your airline's departure board - the ATL Airport Authority departure board had completely incorrect details about the gate assignment for my flight, which would have made me miss boarding.

Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous

The flight was very good and the staff was very friendly and helpful!

The only thing I would say is we tried to get on a standby earlier flight, but with our fair we couldn’t. That seems senseless to leave with open seats..

Very easy to use and convenient, you can perform any action within the same portal

In a world of delays, Delta was on time both ways! Boarding was fast and efficient. Staff was friendly. AND wifi worked.

My business class seat was inoperable and unable to recline for 10 hour flight.

Flew steerage class. Short on leg room unless you pay more. No window unless you pay more. Etc. United is trying to squeeze every cent from you. It doesn’t make for any loyalty.

Booked through Kayak Business, had a seat in middle and towards back due to booking rate, not comfortable.

Was great in general, try to respect time and excuses when slight changes have been made, appreciated!

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

Flight crew was super friendly and helpful. Food was frequent and honestly pretty good. Plenty of on-board entertainment. Economy seats are super cramped for such a long flight, but the crew allowed people to get up and stretch, and kids could wander with their parents, so we all made it work. Overall a very good experience.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Outstanding service, efficient & friendly crew, flight was safe, comfortable & on time

Outstanding service, great food, friendly & efficient crew, safe & comfortable flight

Staff were not attentive, wifi did not work, cut my head in the bathroom due to the position of the soap on the sink, had blood running down my face, told staff, they had no expression no sympathy, didn't even say "sorry", they said "oh we will have a look at that" about 10 mins later the purser brought me a bandaid, still no sorry.... Shocking

Boarding was quick and efficient. The flight crew were friendly. There were limited food options available on the flight. The pocket guide said there would be salad and sandwich sections available on flights over 3.5 hours. The only food available were snack boxes. And those were limited as well. My flight was over 5 hours. The entertainment system worked well. I had both extra legroom seats and regular coach seats. The seats were not very comfortable. The entertainment controls in the armrest made it difficult to rest my arm without changing the channel on my neighbors TV. Overall, my experience was mediocre.

Purchased through 3rd party vendor which made everything difficult. Unable to check in online. Unable to get flight updates easily, tsa precheck information didn’t carry through, longer time to check in in person. Entertainment looked good but had to purchase conventional headphones to view.

Boarding was fast, easy, and we landed early. The entertainment system was very buggy and kept resetting throughout the flight.

Not having an assigned seat until boarding and then having to check my bag.

Boarding was done extremely poorly, with huge crowds gate loiterers blocking people from boarding, multiple lines of people trying to merge into one line. One of the male flight attendants who was doing drink service was not happy about having to let a passenger back to their seat and was unnecessarily sassy about it. I thought he was pretty entitled and not a great ambassador for JetBlue

Flight emergency landed in Chicago due to “Odor” in back of plane . Had to buy ANOTHER TICKET to get to Boston cash out of my own pocket . Then they would notchange my return flight time without a 400. Charge!!!! Insulting.

I purchased ticket so our daughter ( a minor) can sit next to her mother. No help at gate after kayak insisted that this could be done. She ended sitting by herself

Flight was as expected. But it was delayed an hour. Also, my luggage got damaged. So that sucked especially since the damage made navigating the airport difficult. Walking to get ground transportation is sooo far away now and my checked bag was difficult to carry.

we were an hour delayed after boarding and given no reason. Headsets cost money. Also there were openrows with no one setting in them but we were told we were not allowed to swtich.

Flight was smooth, amenities (entertainment options and power outlets) were good, sears decent)

Left early arrived early..right amount of talking from pilots..of course had to love the biscuit and water!

As we approached Denver, we encountered quite a bit of turbulence. I know this can sometimes be the case as I frequently fly this route but not on American. My gripe: Usually a pilot or co-pilot alerts passengers to the possibility of turbulance ahead of time. This did not occur nor did he communiucate during what was a pretty rough ride.

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

When I booked my flight a month ago - I selected a seat. That seat was NOT the one I ended up with when I checked into my flight the day before. This is the second time this has occurred. So, I checked my next flight on Wednesday and Thursday and no seat was assigned. Poor, very poor customer service.

Cleared standby and gave up my seat. Terrible policy and boarding experience

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

Flight boarded from Gate 159B, the farthest gate in the LAX Bradley Terminal. While the flight operated on time, the first class cabin attendant made no recognition of my being an Advantage Executive Platinum member.

British Airways is an excellent airline. Comfort, food and airline personnel.

We changed our flight because of weather. Unfortunately we were on hold for over an hour, but since we were 5 people who all booked individually, we felt more comfortable doing it with an agent. It all worked out in the end.

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