$229 Find Cheap Flights from Portland to Jamaica

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Portland to Jamaica departing on 3/1. 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 Bay2 stops$337
Kingston
Kingston2 stops$421
Montego Bay
Montego Bay2 stops$337
Kingston
Kingston2 stops$421

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, Mar 1 - Tue, Mar 17
American Airlines Logo
5:40 pm - 12:21 pm
PWM
-
MBJ
18h 41m2 stops
American Airlines Logo
1:14 pm - 11:37 pm
MBJ
-
PWM
9h 23m1 stop
$337American Airlines
Thu, Feb 19 - Thu, Feb 26
American Airlines Logo
7:10 am - 12:21 pm
PWM
-
MBJ
29h 11m1 stop
American Airlines Logo
3:26 pm - 10:50 pm
MBJ
-
PWM
7h 24m1 stop
$339American Airlines
Thu, Feb 19 - Thu, Feb 26
Delta Logo
6:00 am - 3:19 pm
PWM
-
MBJ
9h 19m2 stops
Delta Logo
2:19 pm - 12:18 am
MBJ
-
PWM
9h 59m2 stops
$357Delta
Mon, Jan 19 - Sat, Jan 24
Delta Logo
5:30 am - 12:54 pm
PWM
-
MBJ
7h 24m1 stop
Delta Logo
2:00 pm - 11:59 pm
MBJ
-
PWM
9h 59m1 stop
$399Delta
Mon, Jan 19 - Sat, Jan 24
American Airlines Logo
7:00 am - 1:34 pm
PWM
-
MBJ
6h 34m1 stop
American Airlines Logo
4:22 pm - 12:06 pm
MBJ
-
PWM
19h 44m2 stops
$404American Airlines
Wed, Feb 18 - Wed, Feb 25
Delta Logo
6:30 am - 8:00 pm
PWM
-
KIN
13h 30m2 stops
Delta Logo
9:00 am - 11:20 pm
KIN
-
PWM
14h 20m2 stops
$421Delta
Tue, May 26 - Tue, Jun 2
JetBlue Logo
2:18 pm - 11:47 pm
PWM
-
KIN
10h 29m1 stop
JetBlue Logo
9:09 am - 11:36 pm
KIN
-
PWM
13h 27m1 stop
$488JetBlue
Mon, Feb 23 - Thu, Feb 26
United Airlines Logo
6:00 am - 2:00 pm
PWM
-
MBJ
8h 00m1 stop
United Airlines Logo
3:20 pm - 11:20 pm
MBJ
-
PWM
8h 00m1 stop
$504United Airlines
Sat, May 23 - Mon, Jun 1
JetBlue Logo
2:18 pm - 11:47 pm
PWM
-
KIN
10h 29m1 stop
JetBlue Logo
11:28 am - 11:36 pm
KIN
-
PWM
11h 08m1 stop
$513JetBlue
Mon, Feb 23 - Thu, Feb 26
United Airlines Logo
6:00 am - 2:00 pm
PWM
-
MBJ
8h 00m1 stop
United Airlines Logo
3:20 pm - 9:09 pm
MBJ
-
PWM
29h 49m2 stops
$526United 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.

Which airlines fly non-stop between Portland and Jamaica?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for round-trip flights from Portland to Jamaica.

There are 4 airlines that fly nonstop from Portland to Jamaica. They are: American Airlines, Southwest, Delta and United Airlines. The cheapest price of all airlines flying this route was found with Delta at $404 for a round-trip flight to Montego Bay (MBJ). On average, Delta offers the best prices for nonstop flights between Portland and Jamaica.

Which airlines provide the cheapest flights from Portland to Jamaica?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Portland to Jamaica were found on American Airlines ($337) and Delta ($357).

Good to know

Low seasonMay
Cheapest flight$337
Best time to beat the crowds with an average 24% drop in price.
Most popular time to fly with an average 91% increase 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 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 4249 reviews
8.1Boarding
8.0Comfort
7.0Food
8.6Crew
7.5Entertainment
Airline reviews

The flight crew was extremely rude and especially not helpful when our flight was delayed.

2.0 MediocreMatthew, Jan 2026
DAL - SAN
Read more Southwest reviews

The flight crew was extremely rude and especially not helpful when our flight was delayed.

Pretty seamless, just a tad bit late in taking off and landing.

Flight was fine other than there was a gate change that I was not notified of. By chance I happened to check my phone and saw the change, otherwise, we would have missed our connecting flight.

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.

Flight was late from Newark to Atlanta, I asked flight attendant to please let my family of 3 out first when we landed to Atlanta because we were late for our connecting flight to Quito. She didn't and we were late for 5 minutes we couldn't board the plane and spend hours trying to get another flight with customer service for the next day.

I really liked the legroom. I am 6’4”.a at For some reason our seats were not together and using the app to fix it didn’t work. Passengers were nice enough to move for us but you should absolutely ensure a parent sits with their child.

Late delayed flight delays boarding and delays leaving and delays on arrival too. Cramped plane no room no food.

DTW line is too long. The flights from DTW to BWI are always delayed for unknown reasons.

Delta canceled our flight and we had to scramble to find another airline to get home. Phoenix is not a delta hub so they didn’t have another plane. It would have been a red eye though Salt Lake City. Getting in at 5am. No bueno.

This flight was no comparison to our prior flight. I'm thinking it all has to do with the age of the aircraft.

This flight was a first class choice and left much to be desired. Seat backs on seats were falling apart and torn. Seats actually didn't come to a "full & upright position". Pull out table was sprung. Not any significant leg room. All in all we were on an obviously older plane and felt overcharged for what we received as first class.

A 12 hour flight during the day with one real meal service - are you kidding? Also the breakfast was one of the worst and not what was listed

Flight was delayed several times. At one point, they "pulled back" 15 minutes from the delayed boarding and sent a text saying we would board sooner than previously advised. The flight then was delayed again. And when we boarded, there was an unspecified technical issue which had us waiting in the plane for about an hour.

Delta is a good airline. I've never had an issue with Delta. I'll continue to fly with them until they show me that I shouldn't.

It was great with United overall except for two things. 1) It was a 5-hour flight and we were with kids, so we were asking for extra snacks. They were extremely reticent to dole them out even though there wasn't any meal and the kids were starting to hit their limit towards the end. 2) Baggage didn't arrive until 80 minutes after we landed.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

The staff was hospitable and professional. The seat had a bit of wear. The winner shade was stuck 1/4 open. I received the best of both worlds. The morning sun was able to come in and blind the screen i was trying to use while at the same time it was too low to look out and enjoy the view. Rather embarrassing for a 1st class ticket.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

I’m so sorry, I can’t remember her name, I believe it was Dimpti. She was stellar, also a mature Asian flight attendant, lots of flowers in her hair, just as amazing! But literally the crew was AWESOME . Only downside is there weren’t any charging outlets. Maybe I needed to ask a flight attendant , but it would’ve been nice to have one easily accessible.

The flight was delayed by two de-icings. The seatbelt did not work correctly. It did not stay tight.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

Aircraft was noisy, old and never dimmed the lights on a night flight even on business class! I flew 17 times on United and probably another 40 on other airlines United USA /Europe flights were the worst to include luggage delayed once going to europe and once coming back

Check how old the airframe is, some older ones have inoperable seat back entertainment or power.

The economy seats are very cramped and the food was bizarre. However, I did like the greek yogurt option for breakfast.

While I didn’t watch much tv I would have liked a few more options of TV series from Apple TV or hbo max ..

Everything about the flight was lovely. My only suggestion would be to offer a few more options of tv series from Apple TV or HBO.

Nothing to write home about, average flight experience. Seats were spacious enough, crew friendly enough. Loved the AA entertainment/wifi service.

Kayak was among the missing. There was not the usual advice regarding next gate after arriving in Dallas. No communication after the reminder to check in before the Moline flight. What happened?

They should have allowed for extra time to de-ice the plane before boarding passengers. This delayed us about 10-15 mins after we boarded. Overall experience was fine. Crew was friendly and on top of everything. We didn’t have any issues during the flight.

Experience was good. We were delayed in leaving by 15 mins because the flight was waiting on a family that was late in getting to the gate. Food and drink options were as expected. I highly recommend checking in ahead of time using the airline’s app so that it’s quicker to get your luggage tags as soon as you arrive at the terminal. No more waiting in long lines!

Overall experience was great. Flights were almost on time in departing and we arrived at our destination as scheduled. No issues with amenities or flight crew. Everything went well as as expected. Will fly again with American Airlines in the future!

We never made it due to delays on both ends. Gate attendant said it was mechanical but the system said otherwise, so no compensation. That’s not right.

Our flight from Eagle to Vail was delayed to the point we missed our connection to Savannah. Now we’re a family of 4 in a hotel room with luggage, no toiletries, no clean clothes. Gate attendant said the delay was mechanical but it was put in the system as something else so no compensation. That’s just wrong.

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

Information on your arrival and departure airports