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

American Airlines, Delta, and Frontier are the most popular carriers operating from Oregon to Caribbean

How long is the flight from Oregon to Caribbean?

If you’re flying from a popular airport in Oregon, such as Medford or Redmond, and flying into Caribbean, then you can expect flight times to average 2h 01m and 2h 11m, respectively.

What airlines fly to Caribbean?

American Airlines, United Airlines and Delta are the top three most popular airlines that fly to Caribbean from Oregon according to our data. American Airlines is the first choice among our users, with 51% of people opting to fly with this airline when traveling to Caribbean. Keep in mind that there are 5 different airlines that fly to Caribbean on a routine basis, so you have a few additional options to choose from.

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

Prices for flights from Oregon to Caribbean refresh daily.

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

The number of operators available for flights from Oregon to Caribbean is 5 as of May 2026.

How old do you have to be to fly from Oregon 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 Oregon to Caribbean.

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

The travel and health documents you'll need for your trip to Caribbean 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. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$233 Cheap Flights from Oregon to Caribbean in 2026

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Find the cheapest flights from Oregon to Caribbean

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

10:45 pm - 10:15 am

PDX

MBJ

8h 30m

1 stop

1:55 pm - 11:51 pm

MBJ

PDX

12h 56m

1 stop

$392American Airlines

Mon, Nov 2 - Tue, Nov 10

11:20 pm - 1:34 pm

PDX

MBJ

12h 14m

2 stops

5:13 pm - 10:51 am

MBJ

PDX

19h 38m

2 stops

$397American Airlines

Fri, Aug 21 - Fri, Aug 28

11:59 pm - 1:30 pm

PDX

MBJ

11h 31m

1 stop

4:12 pm - 9:34 am

MBJ

PDX

19h 22m

2 stops

$412United Airlines

Sat, Aug 1 - Thu, Aug 6

5:10 pm - 12:25 pm

PDX

MBJ

16h 15m

2 stops

6:00 pm - 9:31 am

MBJ

PDX

18h 31m

2 stops

$427Delta

Mon, Nov 2 - Tue, Nov 10

5:15 am - 4:50 pm

PDX

MBJ

8h 35m

1 stop

1:25 pm - 9:21 am

MBJ

PDX

22h 56m

1 stop

$465United Airlines

Sat, Nov 14 - Sun, Nov 22

6:04 am - 10:00 pm

PDX

SJU

12h 56m

1 stop

4:18 pm - 11:47 pm

SJU

PDX

10h 29m

1 stop

$466Delta

Sat, Sep 26 - Sat, Oct 31

10:45 pm - 2:30 pm

PDX

SJU

12h 45m

1 stop

6:00 am - 4:35 pm

SJU

PDX

13h 35m

2 stops

$498Southwest

Thu, Aug 13 - Mon, Aug 17

6:00 pm - 10:30 am

PDX

SJU

13h 30m

2 stops

8:55 pm - 11:40 am

SJU

PDX

17h 45m

2 stops

$516Southwest

Fri, Jul 31 - Thu, Aug 6

3:15 pm - 5:45 pm

PDX

PUJ

23h 30m

2 stops

12:35 pm - 9:26 am

PUJ

PDX

24h 51m

2 stops

$598Air Canada

Sun, Oct 25 - Sun, Nov 1

7:45 pm - 3:20 pm

PDX

PUJ

40h 35m

2 stops

5:05 pm - 9:26 am

PUJ

PDX

43h 21m

2 stops

$603Air Canada

Fri, Oct 16 - Sat, Oct 24

JetBlue flights from Oregon to Caribbean

Our best JetBlue deals on Oregon to Caribbean flight tickets

JetBlue

May 29

PDX2:30 pmPortland

18h 34m

1 stop

SJU12:04 pmSan Juan Luis Munoz Marin Intl

Jun 4

SJU5:01 amSan Juan Luis Munoz Marin Intl

11h 09m

1 stop

PDX1:10 pmPortland

$601

JetBlue

Jun 1

PDX2:30 pmPortland

20h 52m

1 stop

SDQ2:22 pmSanto Domingo Las Americas

Jun 8

SDQ3:10 amSanto Domingo Las Americas

12h 57m

1 stop

PDX1:07 pmPortland

$635

JetBlue

Jul 13

PDX11:27 pmPortland

11h 36m

1 stop

STT2:03 pmSaint Thomas Island Cyril E King

Jul 21

STT2:58 pmSaint Thomas Island Cyril E King

25h 06m

2 stops

PDX1:04 pmPortland

$648

Southwest flights from Oregon to Caribbean

Our best Southwest deals on Oregon to Caribbean flight tickets

Southwest

Aug 13

PDX10:45 pmPortland

12h 45m

1 stop

SJU2:30 pmSan Juan Luis Munoz Marin Intl

Aug 17

SJU6:00 amSan Juan Luis Munoz Marin Intl

13h 35m

2 stops

PDX4:35 pmPortland

$498

Southwest

Jul 31

PDX6:00 pmPortland

13h 30m

2 stops

SJU10:30 amSan Juan Luis Munoz Marin Intl

Aug 6

SJU8:55 pmSan Juan Luis Munoz Marin Intl

17h 45m

2 stops

PDX11:40 amPortland

$516

Southwest

Jul 31

PDX11:30 pmPortland

11h 15m

1 stop

SJU1:45 pmSan Juan Luis Munoz Marin Intl

Aug 6

SJU5:30 amSan Juan Luis Munoz Marin Intl

12h 30m

1 stop

PDX3:00 pmPortland

$536

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

PortlandMontego Bay

PDX - MBJ

PDXMBJ

Portland

Mon 11/2

10:45 pm-10:15 am

1 stop8h 30m

Montego Bay Sangster Intl

Tue 11/10

1:55 pm-11:51 pm

1 stop12h 56m

$392

PortlandMontego Bay

PDX - MBJ

PDXMBJ

Portland

Fri 8/21

11:20 pm-1:34 pm

2 stops12h 14m

Montego Bay Sangster Intl

Fri 8/28

5:13 pm-10:51 am

2 stops19h 38m

$397

PortlandMontego Bay

PDX - MBJ

PDXMBJ

Portland

Sat 8/1

11:59 pm-1:30 pm

1 stop11h 31m

Montego Bay Sangster Intl

Thu 8/6

4:12 pm-9:34 am

2 stops19h 22m

$412

PortlandMontego Bay

PDX - MBJ

PDXMBJ

Portland

Mon 11/2

5:10 pm-12:25 pm

2 stops16h 15m

Montego Bay Sangster Intl

Tue 11/10

6:00 pm-9:31 am

2 stops18h 31m

$427

PortlandMontego Bay

PDX - MBJ

PDXMBJ

Portland

Sat 11/14

5:15 am-4:50 pm

1 stop8h 35m

Montego Bay Sangster Intl

Sun 11/22

1:25 pm-9:21 am

1 stop22h 56m

$465

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sat 9/26

6:04 am-10:00 pm

1 stop12h 56m

San Juan Luis Munoz Marin Intl

Sat 10/31

4:18 pm-11:47 pm

1 stop10h 29m

$466

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Thu 8/13

10:45 pm-2:30 pm

1 stop12h 45m

San Juan Luis Munoz Marin Intl

Mon 8/17

6:00 am-4:35 pm

2 stops13h 35m

$498

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Fri 7/31

6:00 pm-10:30 am

2 stops13h 30m

San Juan Luis Munoz Marin Intl

Thu 8/6

8:55 pm-11:40 am

2 stops17h 45m

$516

PortlandPunta Cana

PDX - PUJ

PDXPUJ

Portland

Sun 10/25

3:15 pm-5:45 pm

2 stops23h 30m

Punta Cana

Sun 11/1

12:35 pm-9:26 am

2 stops24h 51m

$598

PortlandPunta Cana

PDX - PUJ

PDXPUJ

Portland

Fri 10/16

7:45 pm-3:20 pm

2 stops40h 35m

Punta Cana

Sat 10/24

5:05 pm-9:26 am

2 stops43h 21m

$603

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 Oregon 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

Other information

What is the cheapest month to fly to Caribbean?

In general, July is the cheapest month to fly from Oregon to Caribbean. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $184. If you don’t want to visit Caribbean in July, then you should wait until August to fly from Oregon, when ticket prices are also cheap, with an average price of $185.

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

You are more likely to see cheaper flights to Caribbean from Oregon when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean for around $585 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean from Oregon for as low as $507 on momondo.

Can stopping save me money on Oregon to Caribbean flights?

You could potentially save up to 2% on your flight if you consider stops on a Oregon to Caribbean flight.

Cheap Oregon to Caribbean flight deals and tips

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

Fastest flight time	7h 40m
Direct flights	None

The fastest flight from Oregon to Caribbean takes 7h 40m

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

Search flight deals

Frequently asked questions about flying from Oregon to Caribbean

When did momondo last update prices for flights from Oregon to Caribbean?
Prices for flights from Oregon to Caribbean refresh daily.
How many operators does momondo search for flights from Oregon to Caribbean?
The number of operators available for flights from Oregon to Caribbean is 5 as of May 2026.
How old do you have to be to fly from Oregon 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 Oregon to Caribbean.
What documentation or ID do you need to fly to Caribbean?
The travel and health documents you'll need for your trip to Caribbean 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. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Best airlines flying from Oregon to Caribbean

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

Airline	Rating	Free Cancellation	Price
Delta	PriceFrom $190	Free Cancellation	Rating 7.9 8,452 reviews	Search Delta flights
United Airlines	PriceFrom $247	Free Cancellation	Rating 7.4 9,732 reviews	Search United Airlines flights
JetBlue	PriceFrom $261	Free Cancellation	Rating 7.2 2,982 reviews	Search JetBlue flights
American Airlines	PriceFrom $396	Free Cancellation	Rating 7.1 11,645 reviews	Search American Airlines flights
Southwest	PriceFrom $408	Free Cancellation	Rating 7.9 4,284 reviews	Search Southwest flights

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Caribbean from Oregon.

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

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

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

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

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

Yes. momondo can track prices for Oregon to Caribbean flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.