What airlines fly to Caribbean?

American Airlines, United Airlines and JetBlue are the top three most popular airlines that fly to Caribbean from Pittsburgh according to our data. American Airlines is the first choice among our users, with 57% of people opting to fly with this airline when traveling to Caribbean. Keep in mind that there are 8 different airlines that fly to Caribbean on a routine basis, so you have a few additional options to choose from.

What is the cheapest airline that flies from Pittsburgh to Caribbean?

American Airlines, Southwest, and United Airlines are the most popular carriers operating from Pittsburgh to Caribbean

When did momondo last update prices for flights from Pittsburgh Airport to Caribbean?

Prices for flights from Pittsburgh Airport to Caribbean refresh daily.

How many operators does momondo search for flights from Pittsburgh Airport to Caribbean?

As of November 2026, there are 8 operators available to choose from for flights from Pittsburgh Airport to Caribbean.

How old do you have to be to fly from Pittsburgh Airport to Caribbean?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Pittsburgh Airport to Caribbean.

What documentation or ID do you need to fly to Caribbean?

The required travel and health documents for your Caribbean trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Caribbean. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

$98 Cheap Flights from Pittsburgh to Caribbean in 2026/27

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Pittsburgh to Caribbean

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:28 pm - 11:29 pmPIT Pittsburgh-SJU San Juan Luis Munoz Marin Intl

28h 01m1 stop Orlando

7:00 am - 5:33 pmSJU San Juan Luis Munoz Marin Intl-PIT Pittsburgh

11h 33m1 stop Orlando

$260Frontier

Sun, Dec 6 - Sat, Dec 12

8:27 pm - 12:37 pmPIT Pittsburgh-SJU San Juan Luis Munoz Marin Intl

15h 10m1 stop Fort Lauderdale

6:00 am - 1:13 pmSJU San Juan Luis Munoz Marin Intl-PIT Pittsburgh

8h 13m1 stop Fort Lauderdale

$275Multiple Airlines

Mon, Feb 1 - Sat, Feb 6

6:09 pm - 2:41 pmPIT Pittsburgh-SJU San Juan Luis Munoz Marin Intl

19h 32m1 stop Orlando

3:55 am - 5:14 pmSJU San Juan Luis Munoz Marin Intl-PIT Pittsburgh

14h 19m1 stop Orlando

$276Frontier

Sat, Jan 16 - Fri, Jan 22

8:27 pm - 12:37 pmPIT Pittsburgh-SJU San Juan Luis Munoz Marin Intl

15h 10m1 stop Fort Lauderdale

3:48 pm - 8:24 amSJU San Juan Luis Munoz Marin Intl-PIT Pittsburgh

17h 36m2 stops Atlanta Hartsfield-Jackson Raleigh-Durham

$280Multiple Airlines

Mon, Jan 18 - Wed, Jan 20

6:05 am - 2:15 pmPIT Pittsburgh-SXM Simpson Bay Princess Juliana

7h 10m1 stop Orlando

3:15 pm - 11:55 pmSXM Simpson Bay Princess Juliana-PIT Pittsburgh

9h 40m2 stops Orlando Baltimore/Washington

$285Southwest

Tue, Dec 8 - Fri, Dec 11

6:05 am - 2:15 pmPIT Pittsburgh-SXM Simpson Bay Princess Juliana

7h 10m1 stop Orlando

4:40 pm - 11:55 pmSXM Simpson Bay Princess Juliana-PIT Pittsburgh

8h 15m1 stop Baltimore/Washington

$285Southwest

Tue, Dec 8 - Fri, Dec 11

7:24 pm - 4:31 pmPIT Pittsburgh-SXM Simpson Bay Princess Juliana

20h 07m2 stops Charlotte Douglas Miami

3:26 pm - 10:20 amSXM Simpson Bay Princess Juliana-PIT Pittsburgh

19h 54m2 stops Miami Charlotte Douglas

$290American Airlines

Sat, Nov 14 - Wed, Nov 18

6:20 am - 3:11 pmPIT Pittsburgh-SXM Simpson Bay Princess Juliana

7h 51m1 stop New York John F Kennedy Intl

4:35 pm - 11:42 pmSXM Simpson Bay Princess Juliana-PIT Pittsburgh

8h 07m1 stop New York John F Kennedy Intl

$293JetBlue

Sun, Dec 6 - Thu, Dec 17

7:15 pm - 2:23 pmPIT Pittsburgh-SXM Simpson Bay Princess Juliana

18h 08m2 stops Charlotte Douglas Miami

5:29 pm - 10:58 amSXM Simpson Bay Princess Juliana-PIT Pittsburgh

18h 29m2 stops Miami Philadelphia

$297American Airlines

Sat, Jan 2 - Fri, Jan 8

6:20 am - 3:11 pmPIT Pittsburgh-SXM Simpson Bay Princess Juliana

7h 51m1 stop New York John F Kennedy Intl

4:32 pm - 11:56 pmSXM Simpson Bay Princess Juliana-PIT Pittsburgh

8h 24m1 stop New York John F Kennedy Intl

$297JetBlue

Tue, Dec 8 - Fri, Dec 11

Cheap last minute flights

Enter your travel dates to find the best prices.

6:27 pm - 10:15 amPIT Pittsburgh-SJU San Juan Luis Munoz Marin Intl

14h 48m1 stop Orlando

7:26 pm - 5:32 pmSJU San Juan Luis Munoz Marin Intl-PIT Pittsburgh

23h 06m1 stop Orlando

$342Frontier

Thu, Nov 5 - Mon, Nov 9

6:27 pm - 2:46 amPIT Pittsburgh-SJU San Juan Luis Munoz Marin Intl

7h 19m1 stop Orlando

7:23 am - 5:32 pmSJU San Juan Luis Munoz Marin Intl-PIT Pittsburgh

11h 09m1 stop Orlando

$342Frontier

Sat, Nov 7 - Wed, Nov 11

6:11 am - 11:13 amPIT Pittsburgh-NAS Nassau Intl

5h 02m1 stop Miami

2:44 pm - 11:40 pmNAS Nassau Intl-PIT Pittsburgh

8h 56m1 stop Miami

$344American Airlines

Sun, Nov 8 - Thu, Nov 12

6:05 am - 11:18 amPIT Pittsburgh-NAS Nassau Intl

5h 13m1 stop Charlotte Douglas

12:13 pm - 8:49 pmNAS Nassau Intl-PIT Pittsburgh

8h 36m2 stops Miami Philadelphia

$349American Airlines

Sun, Nov 8 - Thu, Nov 12

6:27 pm - 2:46 amPIT Pittsburgh-SJU San Juan Luis Munoz Marin Intl

7h 19m1 stop Orlando

8:45 am - 11:06 pmSJU San Juan Luis Munoz Marin Intl-PIT Pittsburgh

39h 21m2 stops Fort Lauderdale Nashville Intl

$361Multiple Airlines

Sat, Nov 7 - Wed, Nov 11

7:20 pm - 4:25 pmPIT Pittsburgh-AUA Oranjestad Reina Beatrix

20h 05m1 stop Toronto Pearson Intl

5:25 pm - 6:36 pmAUA Oranjestad Reina Beatrix-PIT Pittsburgh

26h 11m1 stop Toronto Pearson Intl

$419Air Canada

Sun, Nov 8 - Sat, Nov 14

7:20 pm - 4:25 pmPIT Pittsburgh-AUA Oranjestad Reina Beatrix

20h 05m1 stop Toronto Pearson Intl

5:25 pm - 6:36 pmAUA Oranjestad Reina Beatrix-PIT Pittsburgh

26h 11m1 stop Toronto Pearson Intl

$419Air Canada

Thu, Nov 5 - Fri, Nov 13

5:50 am - 11:50 amPIT Pittsburgh-NAS Nassau Intl

6h 00m1 stop Atlanta Hartsfield-Jackson

3:15 pm - 12:46 amNAS Nassau Intl-PIT Pittsburgh

9h 31m1 stop Atlanta Hartsfield-Jackson

$436Delta

Wed, Nov 4 - Sat, Nov 14

5:50 am - 11:50 amPIT Pittsburgh-NAS Nassau Intl

6h 00m1 stop Atlanta Hartsfield-Jackson

3:15 pm - 12:46 amNAS Nassau Intl-PIT Pittsburgh

9h 31m1 stop Atlanta Hartsfield-Jackson

$472Delta

Wed, Nov 4 - Sat, Nov 14

6:27 pm - 10:15 amPIT Pittsburgh-SJU San Juan Luis Munoz Marin Intl

14h 48m1 stop Orlando

12:50 pm - 8:14 pmSJU San Juan Luis Munoz Marin Intl-PIT Pittsburgh

32h 24m2 stops Tampa Raleigh-Durham

$477Multiple Airlines

Sun, Nov 8 - Sun, Nov 15

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Delta flights from Pittsburgh to Caribbean

Our best Delta deals on Pittsburgh to Caribbean flight tickets

Delta

Jan 14

PIT5:15 pmPittsburgh

6h 43m

1 stop

SJU12:58 amSan Juan Luis Munoz Marin Intl

Jan 22

SJU6:30 amSan Juan Luis Munoz Marin Intl

10h 09m

1 stop

PIT3:39 pmPittsburgh

$359

Delta

Jan 30

PIT7:00 amPittsburgh

6h 53m

1 stop

STT2:53 pmSaint Thomas Island Cyril E King

Feb 3

STT4:03 pmSaint Thomas Island Cyril E King

9h 43m

1 stop

PIT12:46 amPittsburgh

$383

Delta

Feb 18

PIT6:00 amPittsburgh

9h 15m

1 stop

STT4:15 pmSaint Thomas Island Cyril E King

Feb 25

STT4:15 pmSaint Thomas Island Cyril E King

9h 25m

1 stop

PIT12:40 amPittsburgh

$410

Frontier flights from Pittsburgh to Caribbean

Our best Frontier deals on Pittsburgh to Caribbean flight tickets

Frontier

Nov 11

PIT6:27 pmPittsburgh

7h 19m

1 stop

SJU2:46 amSan Juan Luis Munoz Marin Intl

Nov 12

SJU7:23 amSan Juan Luis Munoz Marin Intl

11h 09m

1 stop

PIT5:32 pmPittsburgh

$154

Frontier

Dec 6

PIT6:28 pmPittsburgh

28h 01m

1 stop

SJU11:29 pmSan Juan Luis Munoz Marin Intl

Dec 12

SJU7:00 amSan Juan Luis Munoz Marin Intl

11h 33m

1 stop

PIT5:33 pmPittsburgh

$260

Frontier

Jan 16

PIT6:09 pmPittsburgh

19h 32m

1 stop

SJU2:41 pmSan Juan Luis Munoz Marin Intl

Jan 22

SJU3:55 amSan Juan Luis Munoz Marin Intl

14h 19m

1 stop

PIT5:14 pmPittsburgh

$276

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PittsburghSan Juan

PIT Pittsburgh - SJU San Juan Luis Munoz Marin Intl

PITSJU

Pittsburgh

Sun 12/6

6:28 pm-11:29 pm

1 stop28h 01m

San Juan Luis Munoz Marin Intl

Sat 12/12

7:00 am-5:33 pm

1 stop11h 33m

$260

PittsburghSan Juan

PIT Pittsburgh - SJU San Juan Luis Munoz Marin Intl

PITSJU

Pittsburgh

Mon 2/1

8:27 pm-12:37 pm

1 stop15h 10m

San Juan Luis Munoz Marin Intl

Sat 2/6

6:00 am-1:13 pm

1 stop8h 13m

$275

PittsburghSan Juan

PIT Pittsburgh - SJU San Juan Luis Munoz Marin Intl

PITSJU

Pittsburgh

Sat 1/16

6:09 pm-2:41 pm

1 stop19h 32m

San Juan Luis Munoz Marin Intl

Fri 1/22

3:55 am-5:14 pm

1 stop14h 19m

$276

PittsburghSan Juan

PIT Pittsburgh - SJU San Juan Luis Munoz Marin Intl

PITSJU

Pittsburgh

Mon 1/18

8:27 pm-12:37 pm

1 stop15h 10m

San Juan Luis Munoz Marin Intl

Wed 1/20

3:48 pm-8:24 am

2 stops17h 36m

$280

PittsburghSimpson Bay

PIT Pittsburgh - SXM Simpson Bay Princess Juliana

PITSXM

Pittsburgh

Tue 12/8

6:05 am-2:15 pm

1 stop7h 10m

Simpson Bay Princess Juliana

Fri 12/11

3:15 pm-11:55 pm

2 stops9h 40m

$285

Quickest round-trip

PittsburghSimpson Bay

PIT Pittsburgh - SXM Simpson Bay Princess Juliana

PITSXM

Pittsburgh

Tue 12/8

6:05 am-2:15 pm

1 stop7h 10m

Simpson Bay Princess Juliana

Fri 12/11

4:40 pm-11:55 pm

1 stop8h 15m

$285

PittsburghSimpson Bay

PIT Pittsburgh - SXM Simpson Bay Princess Juliana

PITSXM

Pittsburgh

Sat 11/14

7:24 pm-4:31 pm

2 stops20h 07m

Simpson Bay Princess Juliana

Wed 11/18

3:26 pm-10:20 am

2 stops19h 54m

$290

PittsburghSimpson Bay

PIT Pittsburgh - SXM Simpson Bay Princess Juliana

PITSXM

Pittsburgh

Sun 12/6

6:20 am-3:11 pm

1 stop7h 51m

Simpson Bay Princess Juliana

Thu 12/17

4:35 pm-11:42 pm

1 stop8h 07m

$293

PittsburghSimpson Bay

PIT Pittsburgh - SXM Simpson Bay Princess Juliana

PITSXM

Pittsburgh

Sat 1/2

7:15 pm-2:23 pm

2 stops18h 08m

Simpson Bay Princess Juliana

Fri 1/8

5:29 pm-10:58 am

2 stops18h 29m

$297

PittsburghSimpson Bay

PIT Pittsburgh - SXM Simpson Bay Princess Juliana

PITSXM

Pittsburgh

Tue 12/8

6:20 am-3:11 pm

1 stop7h 51m

Simpson Bay Princess Juliana

Fri 12/11

4:32 pm-11:56 pm

1 stop8h 24m

$297

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Pittsburgh to Caribbean

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

What is the cheapest month to fly to Caribbean?

In general, January is the cheapest month to fly from Pittsburgh to Caribbean. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $407. If you don’t want to visit Caribbean in January, then you should wait until April to fly from Pittsburgh, when ticket prices are also cheap, with an average price of $453.

What is the cheapest Pittsburgh to Caribbean flight route?

Fly from Pittsburgh to Punta Cana for the best Pittsburgh - Caribbean flight prices

How far in advance should I book a flight from Pittsburgh to Caribbean?

You are more likely to see cheaper flights to Caribbean from Pittsburgh when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean for around $406 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean from Pittsburgh for as low as $338 on momondo.

What cabin class options are available on Pittsburgh to Caribbean flights?

There are 2 cabin classes available to choose from on Pittsburgh to Caribbean flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Pittsburgh to Caribbean flights?

You could potentially save up to 36% on your flight if you consider stops on a Pittsburgh to Caribbean flight.

Cheap Pittsburgh to Caribbean flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Pittsburgh to Caribbean

Best Price Found	$98
Fastest flight time	4h 00m
Direct flights	Mon, Wed, Fri and Sun
Airports in Caribbean	197 airports

The best one-way flight to Caribbean from Pittsburgh in the past 72 hours is $98. The best round-trip flight deal from Pittsburgh to Caribbean found on momondo in the last 72 hours is $260.

The fastest flight from Pittsburgh to Caribbean takes 4h 00m

Direct flights go from Pittsburgh to Caribbean on Monday, Wednesday, Friday and Sunday. There are no airlines offering direct flights.

There are 197 airports in Caribbean. From Pittsburgh there are direct flights to Punta Cana (PUJ).

Search flight deals

Frequently asked questions about flying from Pittsburgh to Caribbean

When did momondo last update prices for flights from Pittsburgh Airport to Caribbean?
Prices for flights from Pittsburgh Airport to Caribbean refresh daily.
How many operators does momondo search for flights from Pittsburgh Airport to Caribbean?
As of November 2026, there are 8 operators available to choose from for flights from Pittsburgh Airport to Caribbean.
How old do you have to be to fly from Pittsburgh Airport to Caribbean?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Pittsburgh Airport to Caribbean.
What documentation or ID do you need to fly to Caribbean?
The required travel and health documents for your Caribbean trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Caribbean. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Pittsburgh to Caribbean?
Based on momondo bookings for flights between Pittsburgh and Caribbean, the leading plane model is Airbus A220-300, making up 55.36% of the total bookings. Other popular models include Boeing 737-800 with 25.00%, Airbus A321-100/200 with 7.14%, and Boeing 737 with 5.36%.

Best airlines flying from Pittsburgh to Caribbean

Compare and see reviews for airlines that fly from Pittsburgh to Caribbean with momondo

Airline	Rating	Free Cancellation	Price
Frontier	PriceFrom $135	Free Cancellation	Rating 5.5 2,512 reviews	Search Frontier flights
Delta	PriceFrom $156	Free Cancellation	Rating 7.8 8,699 reviews	Search Delta flights
JetBlue	PriceFrom $211	Free Cancellation	Rating 7.1 3,070 reviews	Search JetBlue flights
United Airlines	PriceFrom $218	Free Cancellation	Rating 7.3 10,464 reviews	Search United Airlines flights
American Airlines	PriceFrom $221	Free Cancellation	Rating 7.0 12,214 reviews	Search American Airlines flights
Southwest	PriceFrom $275	Free Cancellation	Rating 8.0 4,222 reviews	Search Southwest flights
Breeze Airways	PriceFrom $382	Free Cancellation	Rating 8.2 324 reviews	Search Breeze Airways flights
Air Canada	PriceFrom $404	Free Cancellation	Rating 7.1 11,844 reviews	Search Air Canada flights

Why use momondo?

Why should I use momondo to find a flight deal from Pittsburgh to Caribbean?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Pittsburgh to Caribbean. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Pittsburgh to Caribbean with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Pittsburgh to Caribbean flights to just show those with flexible booking policies.

How can momondo help me find flights from Pittsburgh to Caribbean?

momondo provides multiple filters to help you find the best flight to Caribbean from Pittsburgh. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Pittsburgh to Caribbean right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Caribbean from Pittsburgh. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.