$289 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 6/20. 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$697
Montego Bay
Montego Bay1 stop$392
Kingston
Kingston2 stops$697

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

Fri, Aug 21 - Fri, Aug 28
American Airlines Logo
5:18 am - 4:08 pm
PDX
-
MBJ
8h 50m
1 stop
American Airlines Logo
2:12 pm - 11:59 pm
MBJ
-
PDX
11h 47m
1 stop
$392American Airlines
Fri, Aug 21 - Fri, Aug 28
American Airlines Logo
11:34 pm - 1:16 pm
PDX
-
MBJ
11h 42m
1 stop
American Airlines Logo
2:52 pm - 10:54 am
MBJ
-
PDX
22h 02m
2 stops
$397American Airlines
Tue, Oct 13 - Tue, Oct 20
Delta Logo
10:05 pm - 11:25 am
PDX
-
MBJ
11h 20m
1 stop
Delta Logo
1:32 pm - 10:26 pm
MBJ
-
PDX
10h 54m
1 stop
$422Delta
Mon, Nov 2 - Tue, Nov 10
Delta Logo
10:05 pm - 12:25 pm
PDX
-
MBJ
11h 20m
1 stop
Delta Logo
6:00 pm - 9:16 am
MBJ
-
PDX
18h 16m
2 stops
$427Delta
Thu, Sep 17 - Thu, Sep 24
Delta Logo
10:00 pm - 11:25 am
PDX
-
MBJ
11h 25m
1 stop
Delta Logo
1:25 pm - 9:45 pm
MBJ
-
PDX
10h 20m
1 stop
$432Delta
Fri, Sep 18 - Tue, Sep 22
Southwest Logo
10:45 pm - 12:25 pm
PDX
-
MBJ
11h 40m
1 stop
Southwest Logo
11:50 am - 10:15 pm
MBJ
-
PDX
12h 25m
2 stops
$459Southwest
Sun, Nov 1 - Sat, Nov 7
United Airlines Logo
10:56 pm - 2:29 pm
PDX
-
MBJ
12h 33m
1 stop
United Airlines Logo
1:40 pm - 10:38 pm
MBJ
-
PDX
11h 58m
1 stop
$469United Airlines
Sat, Oct 17 - Sun, Oct 25
United Airlines Logo
5:00 am - 3:45 pm
PDX
-
MBJ
8h 45m
1 stop
United Airlines Logo
1:48 pm - 12:02 am
MBJ
-
PDX
12h 14m
1 stop
$471United Airlines
Mon, Aug 24 - Wed, Sep 2
JetBlue Logo
11:27 pm - 9:20 pm
PDX
-
KIN
19h 53m
2 stops
JetBlue Logo
9:45 pm - 1:04 pm
KIN
-
PDX
17h 19m
2 stops
$697JetBlue
Fri, Jul 3 - Sat, Jul 11
JetBlue Logo
2:20 pm - 3:25 pm
PDX
-
KIN
23h 05m
2 stops
JetBlue Logo
9:45 pm - 10:48 pm
KIN
-
PDX
27h 03m
2 stops
$821JetBlue
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 $540 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 58% 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$289
Best time to beat the crowds with an average 16% drop in price.
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 3 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.
7.9
DeltaOverall score based on 8396 reviews
7.8Entertainment
8.5Crew
8.1Boarding
7.2Food
7.8Comfort
Airline reviews

Long story short, it was one of the better flight experiences I've had in some time when compared with other airlines.

10.0 ExcellentJulian, Jun 2026
LAX - AUS
Read more Delta reviews

Long story short, it was one of the better flight experiences I've had in some time when compared with other airlines.

Flight was great! This flight from Atlanta was even better than when I paid for Comfort from SNA to Atlanta.

Connection flights should be spaced out farther because too close I missed my connection.

Definitely a southern flavor. Cordiality was evident even though no drinks or snacks were served.

On time! There were plenty of airport employees who were able to keep us moving in the right direction. The crew on the plane were professional.

Left /arrived on time. Decent seat space. Like the wifi/plugs and entertainment. Windows and tray table were kinda gross. Attendants didn't start snack service til 40mins before landing. Two rows before us, captain came on to say there's turbulence and recalled staff to seats. So, no drink/snack. Later, attendants didn't stop to see if we had trash nor even look our way. Felt invisible! Almost all pilot announcements were not only unintelligible, but so quiet. We had no idea what she said.

Average seat comfort, a drink and chips were provided, early boarding because we checked a carryon at the gate was nice. Ticket pricing shenanigans, including fees to pick a seat, check a bag, and get food onboard - evidence the industry is reinvigorating last century’s strategies- destroys the experience before one ever arrives at the airport. It’s difficult to recognize any value or sustain loyalty in the end-to-end process making air travel more drudgery than pleasure.

Gate agent was unhelpful for handicapped boarding. Flight attendant seemed untrained.

No service flight that took 5 hrs and a stop at an unscheduled airport. Crew and pilots did their jobs

Clean planes and not take my comfort class seat away.

Smooth travel. Immediate update prior flight delay so I can arrange myself properly without too rush.

Everything was the best it could be. Crew found me with pre- ordered food. Excellent experience!

Improve the food offerings and cabin seating. My wife would prefer to fly another airline, even with a connection for a more comfortable trip. A 737-8 should not be scheduled for a 6 hour segment, which turned into 7.5 hours due to the origin ground delay.

Packed flight, which makes it tough on crew and boarding staff (and the customers of course). But this was great boarding, clear instructions, etc. Traveling on the weekends are always fraught with danger as you have families and less frequent flyers thus more confusion. But this flight went as planned.

Destroyed my suitcase. Tired of talking about it. Cancelling my unite mileage plus account.

Read the fine print. This was my flight home. I booked my flight for the quickest way home. Had a carry-on and a personal item. Same as my outbound flight. Apparently I needed to pre-pay extra for my carry-on. When I checked in, I was told that I had to check it. I said I’ll pay for it, and was told that this wasn’t an option anymore. They said I still had to pay $50 to check my carry-on. I told them I’ll pay whatever to just carry it in as intended. I was not allowed, so eventually I paid $50 to check my carry-on under a plane that was half full, with overhead compartments that were even less full. My white carry-on suitcase was practically destroyed getting from Idaho falls to Denver to Orange County. The low price air fair was a bait and switch. Got me to the gate, made me pay extra, then didn’t even allow me to pay for a carry on. Not to mention that I paid the $8 for WiFi that didn’t work. All to get my suitcase destroyed. I don’t think I’m going to even keep my Untied mileage plus membership and card. Apparently, membership does not have its privileges for this one.

The flight was delayed, they didn’t even have water for the toilets or for drinks

Even through the flight was delayed due to storms near IAH The flight was great! The crew was so hospitable and professional

I flew from Santa Fe to Denver to catch a flight to London and the transfer of my luggage on arrival at Denver to the London flight worked perfectly. The crew on the ground and on board for the London flight were so friendly and efficient.

Boarded early; and arrived home 40 mins early. After a long flight, it’s nice to be back home early. These flights have no amenities; no snacks. So need to bring your own

Our flight from JFK to Madrid was delayed. We had to go from one side of the Madrid airport (Terminal 4s to the far end of terminal 4 - Gate K98) to our gate in less than 30 minutes. Put passport control and security/baggage check and that’s very hard unless you’re Usain Bolt. I called Iberia Airlines and the telephone customer service told me that I was going to have to pay to re-book. Luckily the help desk in the airport (who was dealing with dozens of people from the same JFK-Madrid flight) did not charge us extra to reschedule to a flight 8 hours later. They also gave us a voucher for breakfast and lunch. Glad the actual person at the airport had some actual sense.

As always, most AA flights that we fly are almost ALWAYS delayed and that too multiple times. Very frustrating

Boarding was smooth and seamless and the flight was without incident.

For an long range economy flight I feel more space and more meal options need to be offered for flights over 5 hours

Our flight was repeatedly delayed for maintenance problems: scheduled for 9.30am, eventually delayed to 7pm! Very very inconvenient! AA should have provided a substitute plane much earlier.. On the other hand, Customer Service crew in Charlotte helped us to reach NY (LGA) by late afternoon. Thank you Patricia!! The actual flight was quick and very comfortable. As always a. excellent, professional crew. [no food on a a short hop).

Take-off delayed an hour because of a missing flight officer, so,arrived in Charlotte lates causing many passengers to miss connections. Otherwise a very good flight, safe and comfortable, with an excellent professional crew.

Little time between flight from Dallas to flight to Gainesville. We chose this one, 43 minutes between, because the price for a connection with at least an hour between, was so much higher. Had to ask passengers on the Dallas flight to please allow us to deplane ahead of them. The economy passengers allowed this. We had to walk very fast to the next gate, 35 gates away. Thankfully all in the same terminal. Getting to the small Gainesville plane was a little confusing as you enter an area that is boarding many small planes at the same time. We stood in the wrong line for about 15 seconds before realizing it was not our Gainesville flight. Since I had boarded at this gate in the past, I knew to check the signs carefully so we weren’t lost. The first class seat experience was wonderful. I really enjoyed the upgrade. We were offered an alcohol drink as soon as we sat down. I got something different but it was a great gesture especially since we really had to hurry to make the flight. We had packed expecting we might miss this connection, but made it. Our luggage didn’t miss the flight. American Airlines delivered our bags to our home the next day. That was very convenient!

The plane was large, not full, but one with 3 seats near each window and 4 in a row in the middle of the plane. There were screens on the backs of the seats for entertainment and information. To use the entertainment one needs ear plugs that physically plug into the screen. My husband had some he let me use as I only had blue tooth type. The stewards gave out some headphones to some, but when my neighbor asked for some, the steward said no. So maybe they ran out? Idk. Bring the old kind of headphones or earbuds if you want entertainment in case this is the type of entertainment offered. We had a very tight connection in Miami. 43 minutes. The other economy passengers allowed us to get ahead of them because I asked if we could since we were near boarding time for our next flight and 35 gates away. They were extremely kind. First class wasn’t going to allow us to pass through. We did make the next flight. Our baggage didn’t, but they were delivered to us the next day and we were prepared with essentials in our carry on packs.

Food is what you expect on a plane. Nothing gluten free. But that is expected. Drinks, apple juice, was fine. Seat, what I expected. Fine.

The check in agents in PHL and gate agents had to have been the rudest women that I have ever encountered; the agent weighing the bags at check in screamed continuously at all of the guests as did the woman at the gate.I have Executive Platinum status with AA and fly a lot with AA but these ladies were the absolute worst I had the displeasure to encounter!

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

Information on your arrival and departure airports