$268 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 3/3. 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.
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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$553
Kingston
Kingston1 stop$803
Montego Bay
Montego Bay1 stop$553
Kingston
Kingston1 stop$803

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

Mon, Feb 2 - Wed, Feb 11
Delta Logo
9:45 pm - 11:13 am
PDX
-
MBJ
10h 28m1 stop
Delta Logo
12:38 pm - 10:15 pm
MBJ
-
PDX
12h 37m1 stop
$553Delta
Mon, Feb 2 - Wed, Feb 11
Delta Logo
5:25 pm - 11:13 am
PDX
-
MBJ
14h 48m2 stops
Delta Logo
12:38 pm - 12:17 am
MBJ
-
PDX
14h 39m2 stops
$558Delta
Wed, Feb 11 - Wed, Feb 18
American Airlines Logo
2:43 pm - 1:26 pm
PDX
-
MBJ
19h 43m1 stop
American Airlines Logo
3:53 pm - 11:27 pm
MBJ
-
PDX
10h 34m1 stop
$621American Airlines
Fri, Feb 13 - Thu, Feb 19
United Airlines Logo
4:00 pm - 2:00 pm
PDX
-
MBJ
19h 00m2 stops
United Airlines Logo
3:20 pm - 12:38 pm
MBJ
-
PDX
24h 18m3 stops
$626United Airlines
Tue, Mar 3 - Wed, Mar 11
Delta Logo
9:45 pm - 3:19 pm
PDX
-
MBJ
14h 34m1 stop
Delta Logo
11:15 am - 10:09 pm
MBJ
-
PDX
12h 54m1 stop
$639Delta
Tue, Mar 3 - Fri, Mar 6
Southwest Logo
2:15 pm - 12:30 pm
PDX
-
MBJ
19h 15m2 stops
Southwest Logo
2:00 pm - 12:45 am
MBJ
-
PDX
13h 45m2 stops
$644Southwest
Tue, Mar 3 - Fri, Mar 6
American Airlines Logo
11:40 pm - 2:53 pm
PDX
-
MBJ
12h 13m1 stop
American Airlines Logo
3:53 pm - 1:15 pm
MBJ
-
PDX
24h 22m1 stop
$653American Airlines
Tue, Mar 3 - Fri, Mar 6
United Airlines Logo
11:59 pm - 2:05 pm
PDX
-
MBJ
35h 06m2 stops
United Airlines Logo
2:48 pm - 10:45 pm
MBJ
-
PDX
10h 57m1 stop
$660United Airlines
Sun, Jan 25 - Sun, Feb 1
Multiple Airlines Logo
9:50 am - 3:33 pm
PDX
-
KIN
26h 43m3 stops
Multiple Airlines Logo
8:05 am - 9:15 am
KIN
-
PDX
28h 10m2 stops
$832Multiple Airlines
Thu, Jan 8 - Sun, Feb 1
Multiple Airlines Logo
9:50 am - 1:45 pm
PDX
-
KIN
24h 55m2 stops
Multiple Airlines Logo
3:30 pm - 9:15 am
KIN
-
PDX
20h 45m2 stops
$870Multiple 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 $670 (return) on average. On the other hand, the most expensive months are October and September, when the average cost of round-trip tickets is $1,099 and $848 respectively.

What’s the cheapest day of the week to fly from Portland to Jamaica?

The average price of all round-trip flights from Portland to Jamaica clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Portland to Jamaica, look for departures on Mondays and avoid leaving on a Friday, as it's usually the priciest day. When flying back from Jamaica, Wednesday is the cheapest day to fly and Friday is the most expensive.

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 4 weeks before departure, which saves you about 49% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 23 weeks before departure.

Good to know

Low seasonAugust
Cheapest flight$269
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly and prices are also 6% 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.

  • What is the cheapest time of day to fly to Jamaica?

    The cheapest time of day to fly to Jamaica is generally in the afternoon, when round-trip flights cost $571 on average. Morning departures are around 17% cheaper than evening flights, on average. The most expensive time of day to fly to Jamaica is generally in the evening, which is peak travel time and where the average cost of a ticket is $789.

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 4252 reviews
7.5Entertainment
8.0Comfort
8.1Boarding
8.6Crew
7.0Food
Airline reviews

Haven’t flown on SW in years. Flight was on time departing and arriving. Served vegan butter onion flavored pretzels which were bad. Coke served was in a tiny paper cup. Crew was not engaging. Felt like they were going through the motions. Old plane, tight seats and no leg room.

2.0 MediocreMatthew, Dec 2025
DCA - OKC
Read more Southwest reviews

Haven’t flown on SW in years. Flight was on time departing and arriving. Served vegan butter onion flavored pretzels which were bad. Coke served was in a tiny paper cup. Crew was not engaging. Felt like they were going through the motions. Old plane, tight seats and no leg room.

Check-in, Boarding and flight were smooth. All the employees and crew was very nice and funny. They gave the kids crayons and workbooks to keep them occupied which was a big win. I’ve flown Southwest many times and that’s the first time I’ve seen that and it is a great addition.

Flight was on time. Wi-fi was a little spotty/slow. Boarding and exit were efficient.

Okay, not wonderful. Short flight. Wi-fi didn't work properly. Stuck waiting for a gate to open upon arrival for 20 or so minutes.

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

No delays and arrived to destination 30 min early. Staff was super friendly.

The gate attendants and the crew were terrible. Because of high winds, they needed to carry more fuel, so they had to get volunteers to take the next flight at 6 am the next day. They did a terrible job of it - our flight ended up taking off just under 3 hours of the scheduled time. I hope to never fly Delta again.

Did not realize internet screen was hidden between seats and no info printed!!!!

2 of the seats in row 31 the entertainment system was not working, and one seat the tray table did not go all the way down. Flight arrived early and departed on time which was great.

Very good flight crew and very nice people staff were incredible especially the gate agent

Waited at the usual crowded gate at DCA where one ends up standing up because there aren't enough seats.

The flight was delayed for about 2 hrs. Other than it, it was good.

Advertised fruit trays with cheese, but only snacks handed out!

The plant way delayed departing by 3 hours. It was an old airplane with broken seats and armrests. The bathroom made a hollering sound. A really crappy flight experience and travel day all around.

Flight delays both to Detroits and return flight . The flight to Detroit was associated with mechanical difficulty

I am extremely disappointed that delta internal pilot manuals now refer to the Gulf of Mexico as the “gulf of America”. You can bow down to the Orange turd on your own. I will never fly delta again

I boarded flight UA#1318 at Sacramento International Airport going back to Houston TX. The flight was scheduled at 5:10am. I was able to check in virtually using the United Airlines app. When I entered the airport, there was no one outside assisting with checked bags as it was for Delta Airlines. Immediately upon entering, there was a LONG, EXTREMELY LONG line to the kiosks to get boarding passes. I stand in line to get boarding passes then had to move to ANOTHER EXTREMELY LONG line to get my bags checked in. While standing in this line, we noticed an agent taking customers to 3 at a time to her station to check their bags in. Lucky for me, she called me back, checked my bags for me and I was on my way. I then encountered another long line at the TSA check and to avoid I ending up having to sign up for CLEAR to bypass it. So glad, I did.,...Both of my flights were great with no issues, butthe check in progress at Bush Airport was so much smoother. Check-in at SMF airport needs to be anaylzed and corrected. Do better United, I know you can....thanks

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Pushed back only to get deplaned due to a tire damaged by ground crew. They did at least go pretty fast. The bathrooms should be banned under the Geneva convention. No room to even sit straight on the toilet. The under-seat entertainment units block what little leg room there is.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Sat next to a one year old. She crawled all over the place and made me laugh.

Not United Airlines' fault. It's ORL airport's fault.

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

United airlines has the best customer experience from booking to arrival. I always fly United airlines. The mileage program is excellent

They did the one thing that really matters - got to Chicago early.

I liked the snacks and the flight attendants were friendly.

We were 4+ hours delayed. AA is absolutely obnoxious. They just kept pushing back the time to the point where we did not get into Vegas until after midnight when we were supposed to arrive like 845pm.

My last flight on 25 Dec, it’s Christmas Day, everyone happy and very good mood. I really enjoy traveling with Americans Airlines from Miami to Minneapolis my home town after long flight from lhe to Doha then Miami. Thank you again to make my travels comfortable and relaxed. Best regards

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

I requested a low sodium meal. Reason being, I take medicine for high blood pressure and I wear compression socks on long flights to help with leg swelling. Having less sodium in meals really helps me feel better on long flights. I received my initial low sodium meal after takeoff. Just before landing, the crew came through with the meal cart and offered me what was being served. I said no thank you and then noticed my low sodium meal in the meal cart, with my name and seat assignment on it. I motioned to the crew member, but he grabbed the meal cart and proceeded to move to the rear of the aircraft. He didn’t see me or other passengers who had attempted to get this attention. He was more concerned about completing meal service since we were due to land in under 45 minutes. I pressed the call light five times from my seat to receive help, but no crew member responded to me. So, I didn’t receive a second meal, one that I requested (the low sodium option). This led me to have a migraine from only eating one meal on an 11-hour flight. This is why I’m not a fan of flying US-based airlines overseas. The crew members continue to show the absolute worst customer service experience. I would not recommend flying American for overseas flights.

WiFi didn’t work the entire flight. Very disappointing. Minimal food and options - sadly the state of current affairs. All other aspects of the flight were fine.

Great flight - friendly and attentive team! Seats in coach were comfy, but a little cramped - but that is the case with all airlines ;)

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

I don’t know who decides what food to serve on these flights but I would be so embarrassed if I served this to anyone and call it food…

For whatever reason, the flight was not catered -we were told it would be a 45 minute delay waiting for catering - so no food. There were opened candy and peanuts in the seatback pocket. Flight landed early in DFW but due to the assigned gate not being available, we sat on the ground for 30 minutes waiting for the gate to open - making the flight actually arrive at the gate late.

Not great. Booked Extra seats and got nothing extra at all. It’s basically a big budget airline.

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

Information on your arrival and departure airports