What is the cheapest airline that flies from Portland to Caribbean Islands?

United Airlines, Southwest, and Delta are the most popular carriers operating from Portland to Caribbean Islands

What airlines fly to Caribbean Islands?

American Airlines, United Airlines and Delta are the top three most popular airlines that fly to Caribbean Islands from Portland according to our data. American Airlines is the first choice among our users, with 55% of people opting to fly with this airline when traveling to Caribbean Islands. Keep in mind that there are 5 different airlines that fly to Caribbean Islands on a routine basis, so you have a few additional options to choose from.

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

Prices for flights from Portland Airport to Caribbean Islands are updated daily.

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

The number of operators available for flights from Portland Airport to Caribbean Islands is 6 as of July 2026.

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

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 Portland Airport to Caribbean Islands.

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

The travel and health documents you'll need for your trip to Caribbean Islands may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Caribbean Islands. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$192 Cheap Flights from Portland to Caribbean Islands in 2026

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Portland to Caribbean Islands

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

11:34 pm - 3:52 pm

PDX

STT

13h 18m

2 stops

3:43 pm - 11:34 am

STT

PDX

22h 51m

2 stops

$420American Airlines

Thu, Aug 20 - Fri, Aug 28

5:50 am - 9:05 pm

PDX

SJU

12h 15m

2 stops

5:15 am - 3:00 pm

SJU

PDX

12h 45m

2 stops

$431Southwest

Tue, Sep 22 - Wed, Sep 23

5:15 pm - 12:25 pm

PDX

MBJ

16h 10m

2 stops

6:00 pm - 9:16 am

MBJ

PDX

18h 16m

2 stops

$437Delta

Mon, Nov 2 - Tue, Nov 10

7:10 am - 8:38 pm

PDX

SJU

10h 28m

1 stop

1:00 am - 3:56 pm

SJU

PDX

17h 56m

2 stops

$461United Airlines

Tue, Sep 22 - Tue, Sep 22

7:00 am - 9:00 pm

PDX

SJU

10h 00m

1 stop

8:25 am - 3:23 pm

SJU

PDX

10h 58m

1 stop

$466United Airlines

Mon, Nov 9 - Tue, Nov 17

10:55 pm - 1:34 pm

PDX

STT

11h 39m

1 stop

2:52 pm - 9:47 pm

STT

PDX

9h 55m

1 stop

$542Delta

Fri, Sep 4 - Fri, Sep 11

11:27 pm - 1:59 pm

PDX

STT

11h 32m

1 stop

2:49 pm - 10:29 pm

STT

PDX

34h 40m

2 stops

$583JetBlue

Thu, Aug 20 - Fri, Aug 28

7:45 pm - 5:30 pm

PDX

NAS

18h 45m

2 stops

6:30 pm - 7:06 pm

NAS

PDX

27h 36m

2 stops

$610Air Canada

Sun, Oct 4 - Sat, Oct 10

2:15 pm - 1:59 pm

PDX

STT

20h 44m

1 stop

2:49 pm - 1:01 pm

STT

PDX

25h 12m

2 stops

$618JetBlue

Thu, Aug 20 - Fri, Aug 28

3:30 pm - 3:25 pm

PDX

BGI

20h 55m

2 stops

4:00 pm - 2:41 pm

BGI

PDX

26h 41m

2 stops

$648Air Canada

Sat, Oct 17 - Sun, Nov 1

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American Airlines flights from Portland to Caribbean Islands

Our best American Airlines deals on Portland to Caribbean Islands flight tickets

American Airlines

Aug 20

PDX11:34 pmPortland

13h 18m

2 stops

STT3:52 pmSaint Thomas Island Cyril E King

Aug 28

STT3:43 pmSaint Thomas Island Cyril E King

22h 51m

2 stops

PDX11:34 amPortland

$420

American Airlines

Nov 2

PDX10:45 pmPortland

8h 21m

1 stop

MBJ10:06 amMontego Bay Sangster Intl

Nov 11

MBJ10:56 amMontego Bay Sangster Intl

15h 55m

1 stop

PDX11:51 pmPortland

$432

American Airlines

Aug 12

PDX11:34 pmPortland

20h 41m

1 stop

SJU11:15 pmSan Juan Luis Munoz Marin Intl

Aug 20

SJU12:55 amSan Juan Luis Munoz Marin Intl

13h 39m

1 stop

PDX11:34 amPortland

$471

United Airlines flights from Portland to Caribbean Islands

Our best United Airlines deals on Portland to Caribbean Islands flight tickets

United Airlines

Sep 22

PDX7:10 amPortland

10h 28m

1 stop

SJU8:38 pmSan Juan Luis Munoz Marin Intl

Sep 22

SJU1:00 amSan Juan Luis Munoz Marin Intl

17h 56m

2 stops

PDX3:56 pmPortland

$461

United Airlines

Oct 18

PDX10:33 pmPortland

11h 10m

1 stop

MBJ11:43 amMontego Bay Sangster Intl

Oct 24

MBJ2:40 pmMontego Bay Sangster Intl

20h 59m

2 stops

PDX9:39 amPortland

$469

United Airlines

Oct 8

PDX5:00 amPortland

9h 38m

1 stop

SJU5:38 pmSan Juan Luis Munoz Marin Intl

Oct 19

SJU2:00 pmSan Juan Luis Munoz Marin Intl

13h 59m

2 stops

PDX12:59 amPortland

$487

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PortlandSaint Thomas Island

PDX - STT

PDXSTT

Portland

Thu 8/20

11:34 pm-3:52 pm

2 stops13h 18m

Saint Thomas Island Cyril E King

Fri 8/28

3:43 pm-11:34 am

2 stops22h 51m

$420

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 9/22

5:50 am-9:05 pm

2 stops12h 15m

San Juan Luis Munoz Marin Intl

Wed 9/23

5:15 am-3:00 pm

2 stops12h 45m

$431

PortlandMontego Bay

PDX - MBJ

PDXMBJ

Portland

Mon 11/2

5:15 pm-12:25 pm

2 stops16h 10m

Montego Bay Sangster Intl

Tue 11/10

6:00 pm-9:16 am

2 stops18h 16m

$437

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 9/22

7:10 am-8:38 pm

1 stop10h 28m

San Juan Luis Munoz Marin Intl

Tue 9/22

1:00 am-3:56 pm

2 stops17h 56m

$461

Quickest round-trip

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 11/9

7:00 am-9:00 pm

1 stop10h 00m

San Juan Luis Munoz Marin Intl

Tue 11/17

8:25 am-3:23 pm

1 stop10h 58m

$466

PortlandSaint Thomas Island

PDX - STT

PDXSTT

Portland

Fri 9/4

10:55 pm-1:34 pm

1 stop11h 39m

Saint Thomas Island Cyril E King

Fri 9/11

2:52 pm-9:47 pm

1 stop9h 55m

$542

PortlandSaint Thomas Island

PDX - STT

PDXSTT

Portland

Thu 8/20

11:27 pm-1:59 pm

1 stop11h 32m

Saint Thomas Island Cyril E King

Fri 8/28

2:49 pm-10:29 pm

2 stops34h 40m

$583

PortlandNassau

PDX - NAS

PDXNAS

Portland

Sun 10/4

7:45 pm-5:30 pm

2 stops18h 45m

Nassau Intl

Sat 10/10

6:30 pm-7:06 pm

2 stops27h 36m

$610

PortlandSaint Thomas Island

PDX - STT

PDXSTT

Portland

Thu 8/20

2:15 pm-1:59 pm

1 stop20h 44m

Saint Thomas Island Cyril E King

Fri 8/28

2:49 pm-1:01 pm

2 stops25h 12m

$618

PortlandBridgetown

PDX - BGI

PDXBGI

Portland

Sat 10/17

3:30 pm-3:25 pm

2 stops20h 55m

Bridgetown Grantley Adams Intl

Sun 11/1

4:00 pm-2:41 pm

2 stops26h 41m

$648

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 Portland to Caribbean Islands

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 Islands?

The month of August is, on average, the cheapest month to fly to Caribbean Islands from Portland, with most prices found around $191. The month of March is another great option to travel to Caribbean Islands, with average flight prices from Portland averaging around $191.

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

You are more likely to see cheaper flights to Caribbean Islands from Portland when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean Islands for around $586 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean Islands from Portland for as low as $527 on momondo.

Can stopping save me money on Portland to Caribbean Islands flights?

No. A direct flight is the cheapest option for a flight between Portland to Caribbean Islands.

Cheap Portland to Caribbean Islands flight deals and tips

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

Fastest flight time	9h 18m
Direct flights	None

The fastest flight from Portland to Caribbean Islands takes 9h 18m

There are no direct flights from Portland to Caribbean Islands. There are no popular flight routes from Portland to Caribbean Islands.

Search flight deals

Frequently asked questions about flying from Portland to Caribbean Islands

When did momondo last update prices for flights from Portland Airport to Caribbean Islands?
Prices for flights from Portland Airport to Caribbean Islands are updated daily.
How many operators does momondo search for flights from Portland Airport to Caribbean Islands?
The number of operators available for flights from Portland Airport to Caribbean Islands is 6 as of July 2026.
How old do you have to be to fly from Portland Airport to Caribbean Islands?
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 Portland Airport to Caribbean Islands.
What documentation or ID do you need to fly to Caribbean Islands?
The travel and health documents you'll need for your trip to Caribbean Islands may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Caribbean Islands. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Portland to Caribbean Islands?
momondo data reveals that the most frequently booked plane model on the route from Portland to Caribbean Islands is Boeing 737-800 Passenger/BBJ2 (winglets), representing 20.08% of all bookings. The subsequent popular models are Boeing 737 MAX 8 at 12.07%, Boeing 737-800 at 8.80%, and Airbus A321neo at 8.37%.

Best airlines flying from Portland to Caribbean Islands

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

Airline	Rating	Free Cancellation	Price
Delta	PriceFrom $190	Free Cancellation	Rating 7.8 8,452 reviews	Search Delta flights
United Airlines	PriceFrom $247	Free Cancellation	Rating 7.4 9,909 reviews	Search United Airlines flights
JetBlue	PriceFrom $261	Free Cancellation	Rating 7.1 3,009 reviews	Search JetBlue flights
American Airlines	PriceFrom $392	Free Cancellation	Rating 7.1 11,765 reviews	Search American Airlines flights
Southwest	PriceFrom $408	Free Cancellation	Rating 7.9 4,246 reviews	Search Southwest flights

Why use momondo?

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

It is quick and easy to find Portland to Caribbean Islands flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Caribbean Islands that suits you.

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

All flight searches from Portland to Caribbean Islands on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Portland to Caribbean Islands?

momondo helps you find the best flight between Portland and Caribbean Islands by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

If you are not ready to book a flight from Portland to Caribbean Islands now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Caribbean Islands and let you know when they change.