$172 Find Cheap Flights from Portland to Jamaica

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Portland to Jamaica departing on 7/9. 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 Portland to Jamaica

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Montego Bay
Montego Bay1 stop$392
Kingston
Kingston2 stops$687
Montego Bay
Montego Bay1 stop$392
Kingston
Kingston2 stops$687

Book Cheap Portland to Jamaica Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Portland to Jamaica 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 Portland to Jamaica

Sun, Aug 16 - Sat, Aug 29
American Airlines Logo
11:20 pm - 1:17 pm
PDX
-
MBJ
11h 57m
1 stop
American Airlines Logo
2:20 pm - 11:56 pm
MBJ
-
PDX
11h 36m
1 stop
$392American Airlines
Sun, Aug 16 - Sat, Aug 29
American Airlines Logo
11:20 pm - 1:28 pm
PDX
-
MBJ
12h 08m
2 stops
American Airlines Logo
2:20 pm - 11:56 pm
MBJ
-
PDX
11h 36m
1 stop
$397American Airlines
Tue, Jul 28 - Sun, Aug 9
United Airlines Logo
11:30 pm - 3:10 pm
PDX
-
MBJ
13h 40m
1 stop
United Airlines Logo
2:40 pm - 10:48 pm
MBJ
-
PDX
10h 08m
1 stop
$448United Airlines
Tue, Jul 28 - Sun, Aug 9
United Airlines Logo
10:40 pm - 3:10 pm
PDX
-
MBJ
14h 30m
2 stops
United Airlines Logo
2:40 pm - 10:48 pm
MBJ
-
PDX
10h 08m
1 stop
$453United Airlines
Tue, Jul 21 - Wed, Jul 29
United Airlines Logo
11:40 pm - 3:10 pm
PDX
-
MBJ
13h 30m
2 stops
United Airlines Logo
4:12 pm - 9:34 am
MBJ
-
PDX
19h 22m
2 stops
$489United Airlines
Tue, May 12 - Fri, May 15
United Airlines Logo
7:45 pm - 1:30 pm
PDX
-
MBJ
15h 45m
2 stops
United Airlines Logo
2:40 pm - 10:59 pm
MBJ
-
PDX
10h 19m
1 stop
$496United Airlines
Mon, Aug 24 - Thu, Sep 3
Air Canada Logo
7:45 pm - 1:55 pm
PDX
-
KIN
40h 10m
2 stops
Air Canada Logo
11:35 am - 9:31 am
KIN
-
PDX
23h 56m
2 stops
$687Air Canada
Sun, Sep 20 - Wed, Sep 30
Air Canada Logo
7:45 pm - 1:55 pm
PDX
-
KIN
16h 10m
2 stops
Air Canada Logo
3:05 pm - 9:31 am
KIN
-
PDX
20h 26m
2 stops
$700Air Canada
Fri, Sep 4 - Wed, Sep 9
Multiple Airlines Logo
2:30 pm - 2:30 pm
PDX
-
KIN
22h 00m
2 stops
Multiple Airlines Logo
3:05 pm - 7:06 pm
KIN
-
PDX
30h 01m
2 stops
$736Multiple Airlines
Fri, Sep 4 - Wed, Sep 9
Multiple Airlines Logo
2:30 pm - 2:30 pm
PDX
-
KIN
22h 00m
2 stops
Multiple Airlines Logo
3:05 pm - 7:06 pm
KIN
-
PDX
30h 01m
2 stops
$741Multiple Airlines
Booking Insights

KAYAK's insights & trends for Portland to Jamaica flights

Get data-powered insights and trends into flights from Portland to Jamaica to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Portland to Jamaica?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Portland to Jamaica, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Portland to Jamaica is March, when tickets cost $224 (return) on average. On the other hand, the most expensive months are January and August, when the average cost of round-trip tickets is $638 and $638 respectively.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Portland to Jamaica, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Portland to Jamaica, you should book around 3 weeks before departure, which saves you about 64% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 23 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$172
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly and prices are also 5% lower on average.
Flight from Portland to Montego Bay

FAQs - booking Jamaica flights

  • How does KAYAK find such low prices on flights from Portland to Jamaica?

    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 Portland to Jamaica.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Portland to Jamaica?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Portland to Jamaica 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 Portland to Jamaica?

    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 from Portland to Jamaica with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Portland to Jamaica?

    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 from Portland to Jamaica 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 Portland to Jamaica

 
Need help choosing which airline to fly with from Portland to Jamaica? 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 4314 reviews
8.0Comfort
7.0Food
8.6Crew
8.1Boarding
7.5Entertainment
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.

The flight was operated by Latam. The aircraft had a technical issue and the flight was delayed for the next day. They grounded other passengers to get their airplane assigned to my flight. Most of he ground staff don't speak English (Orlando Airport), but were very polite.The crew on the other hand could speak English and Portuguese. On board service was good.

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.

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.

WiFi didn’t work. Flight delayed 3 hours Crew members were illiterate Seat lean back did not work.

Flight was delayed, we could have been notified earlier and in a consistent manner. App was not refreshing for another passenger to get the latest flight status. We could have stayed and waited at the hotel instead of waiting at the airport had we known the flight was going to delayed for more than 5 hours. The toilet is too tight, and needs to be cleaned more frequently (every hour). The entertainment screen froze, the touch screen not responding to touch. We were upgraded to comfort, it is more comfortable than regular economy seats.

Some crew were unfriendly or in some cases just straight up rude.

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.

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

United Airline crews were very friendly and very attentive. 12 hours flight was gone like in a shorter one.

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

Food was surprisingly delicious. Space in the seat is horrible when the seating front is reclined. Movie offerings were terrible. Crew was friendly and helpful.

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

I would like a refund for the extra cost the seat I paid for. An oversized person sat next to me and I couldn’t fit on my seat and had to move to another seat.

Boarding gate at LAX was too crowded—two gates next to one another

The flight was delayed about an hour for a maintenance specialist to approve the maintenance repair

This flight was delayed but it worked in my favor because my Atlanta to Dallas flight was delayed.

This was a hard flight. 3 delays out of OKC (1 on the Tarmac). Delay in Atlanta coming to Dallas. total travel time was the equivalent of driving from OKC to Atlanta.

Like: flights are on time, good boarding process Can improve: planes are old, improve entertainment and make space more comfortable

Had to wait for a gate for a long time, then waited on the run way for a long time before leaving. The actual flights part was good.

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Flying in the United States with the major airlines has become so underwhelming. A 2-3hr flight in most other parts of the world with the major carriers of the area comes with newer, CLEANER aircraft and significantly better in flight service in terms of both staff attitude and a actual meal service.

Everything you need to know for your flight from Portland to Jamaica

Information on your arrival and departure airports