$93 Find Cheap Flights from Caribbean to Pittsburgh - Compare and Save

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Cheap Flights from Caribbean to Pittsburgh

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Caribbean to Pittsburgh

Tue, Oct 20 - Fri, Oct 23
American Airlines Logo
2:18 pm - 11:35 pmSJU  San Juan Luis Munoz Marin Intl-PIT Pittsburgh
9h 17m2 stops Miami Philadelphia
American Airlines Logo
8:18 pm - 11:20 amPIT  Pittsburgh-SJU San Juan Luis Munoz Marin Intl
15h 02m1 stop Charlotte Douglas
$186American Airlines
Tue, Oct 6 - Tue, Oct 13
American Airlines Logo
6:30 am - 11:35 pmSJU  San Juan Luis Munoz Marin Intl-PIT Pittsburgh
17h 05m1 stop Miami
American Airlines Logo
6:00 am - 1:37 pmPIT  Pittsburgh-SJU San Juan Luis Munoz Marin Intl
7h 37m1 stop Philadelphia
$186American Airlines
Thu, Oct 15 - Mon, Oct 19
Frontier Logo
6:42 pm - 6:56 pmSJU  San Juan Luis Munoz Marin Intl-PIT Pittsburgh
24h 14m1 stop Orlando
Frontier Logo
7:51 pm - 5:37 pmPIT  Pittsburgh-SJU San Juan Luis Munoz Marin Intl
21h 46m1 stop Orlando
$202Frontier
Wed, Oct 28 - Mon, Nov 2
Frontier Logo
7:23 am - 5:32 pmSJU  San Juan Luis Munoz Marin Intl-PIT Pittsburgh
10h 09m1 stop Orlando
Frontier Logo
6:27 pm - 10:15 amPIT  Pittsburgh-SJU San Juan Luis Munoz Marin Intl
14h 48m1 stop Orlando
$202Frontier
Fri, Oct 30 - Tue, Nov 3
United Airlines Logo
7:05 am - 6:19 pmSJU  San Juan Luis Munoz Marin Intl-PIT Pittsburgh
11h 14m2 stops Washington, D.C. Dulles Intl Chicago O'Hare Intl
United Airlines Logo
3:15 pm - 10:22 pmPIT  Pittsburgh-SJU San Juan Luis Munoz Marin Intl
6h 07m1 stop Washington, D.C. Dulles Intl
$260United Airlines
Sat, Sep 19 - Tue, Sep 29
United Airlines Logo
4:55 pm - 11:30 pmSJU  San Juan Luis Munoz Marin Intl-PIT Pittsburgh
6h 35m1 stop Washington, D.C. Dulles Intl
United Airlines Logo
6:30 am - 8:38 pmPIT  Pittsburgh-SJU San Juan Luis Munoz Marin Intl
14h 08m2 stops Newark Houston George Bush Intcntl
$315United Airlines
Thu, Oct 29 - Fri, Nov 6
Southwest Logo
5:35 pm - 11:35 pmSJU  San Juan Luis Munoz Marin Intl-PIT Pittsburgh
6h 00m1 stop Baltimore/Washington
Southwest Logo
1:30 pm - 12:55 amPIT  Pittsburgh-SJU San Juan Luis Munoz Marin Intl
10h 25m2 stops Nashville Intl Orlando
$331Southwest
Sun, Sep 20 - Sun, Oct 4
Southwest Logo
5:30 am - 12:20 pmSJU  San Juan Luis Munoz Marin Intl-PIT Pittsburgh
6h 50m1 stop Baltimore/Washington
Southwest Logo
5:45 pm - 12:15 amPIT  Pittsburgh-SJU San Juan Luis Munoz Marin Intl
6h 30m1 stop Baltimore/Washington
$343Southwest
Tue, Dec 22 - Sun, Dec 27
Delta Logo
4:50 pm - 10:50 pmSJU  San Juan Luis Munoz Marin Intl-PIT Pittsburgh
7h 00m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:05 am - 2:35 pmPIT  Pittsburgh-SJU San Juan Luis Munoz Marin Intl
7h 30m1 stop Detroit Metropolitan Wayne County
$799Delta
Wed, Nov 4 - Sun, Nov 8
Delta Logo
2:15 pm - 10:59 pmSJU  San Juan Luis Munoz Marin Intl-PIT Pittsburgh
9h 44m2 stops New York John F Kennedy Intl Detroit Metropolitan Wayne County
Delta Logo
12:20 pm - 11:18 pmPIT  Pittsburgh-SJU San Juan Luis Munoz Marin Intl
9h 58m2 stops New York John F Kennedy Intl Atlanta Hartsfield-Jackson
$3,691Delta
Useful Info

Good to know

Low season

April

Cheapest flight

$93
Best time to beat the crowds with an average 67% drop in price.
Most popular time to fly with an average 221% 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 4195 reviews
8.0Comfort
7.5Entertainment
8.6Crew
7.0Food
8.1Boarding
Airline reviews

Delayed and once landed waited very long for the luggage

6.0 GoodIngeborg, Sep 2026
Read more Southwest reviews

Delayed and once landed waited very long for the luggage

Nice managed … it was a smaller plane, so the seating wasn’t as comfortable.

The Southwest airline was ok. A big thank you to Kayak team (David), who worked with me on Sunday afternoon to rebook my travel from Burbank, CA, to CVG. My original flight on Sunday was delayed, so I had to cancel Sunday flight and rebook my travel to Monday. Could not have done it without help from David from Kayak team. Ante Soda GE Aerospace

Very poor service with connecting flight. I missed the connection because of a delayed flight and significant delay in getting my bags in order to make the connection. The ground staff where unhelpful and rude!

Seated at front bulkhead for a smidge extra leg room away from home and on flight back home. Away crew was very proactive about assuring our carryons had space close behind us (because no seat in front of us our personal items had to be in a small bin overhead). They actively required passengers place overhead luggage on its side so more items could fit in bins. Home crew made no such efforts. I had to struggle back rows to get overhead bags upon landing, no crew help then either, and some disgruntled passengers as I and others retrieved our bags. There was a system that worked pretty well. The home bound crew just didn't feel like working.

Southwest has inacted unfriendly customer policies like other airlines. Watch the fine print very carefully if you are having to alter flight arrangements. Rules are now complicated and very stilted to travelers sacrificing travel funds (unlike before where the simple, straight forward flight change policy was worth the extra premium for ticket price.) On the positive side, SW Flight crews are still wonderfully helpful.

The flight was delayed due to earlier issues at other airports. The crew was excellent & made it a good trip.

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.

Very aggressive at the boarding area of only allowing one person passed a line/ sign

We were delayed so pilots can rest and had no WiFi the whole trip. First class seats are small compared to other planes

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.

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

Did not like the check in guy quibbling over a couple pounds at the luggage weigh in

Just having a little bit more legroom would've been nice.

This is related to my second leg of the flight, from Washington DC to SFO. I understand things happen, but I got home at 3 am for a 12:59 am landing. I live 10 min from the airport. Bridge breaks when a few rows of the plane are off? Maintenance didn’t catch that?

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.

It was delayed 5 hours due weather and your app should be rebuilt or disabled. I could not change my original flight on delta so I did it through the delta app. Then rebooked on American once delta cancelled all flights from LGA to PIT on 8/27. American Airlines was fine once the flight took off 5 hours later. I wish my company would find a better provider than kayak.

There was no service on the flight even though there was no turbulence or any other issues on the flight. Nobody greeted at the entry or leaving the airplane, staff crew looked annoyed and not helpful at all.

There was a 6 hours delay in our departure. And yet, no compensation was offered. A company should be responsible for such a delay.

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

Traveling to a place near Pittsburgh?

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