$167 Find Cheap Flights from Portland to Jamaica - Compare and Save

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Cheap Flights from Portland to Jamaica

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Montego Bay
Montego Bay2 stops$409
Kingston
Kingston2 stops$727
Montego Bay
Montego Bay2 stops$409
Kingston
Kingston2 stops$727
Booking Insights

Price, demand and travel trends for Portland to Jamaica flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

What are the cheapest fares from Portland to Jamaica right now?

The cheapest fares from Portland to Jamaica on KAYAK in the last week were to Montego Bay Sangster Intl (MBJ) from $409 round-trip, and to Kingston Norman Manley (KIN) from $727 round-trip.

What’s the cheapest month to fly from Portland to Jamaica?

October is the cheapest time of year to fly, with average fares of $394. Prices are highest in February, when average flight costs increase to around $1,008.

Which airport in Jamaica is the cheapest to fly to from Portland?

Based on KAYAK data from the past 12 months, the cheapest airports to fly into Jamaica are:

• Montego Bay Sangster Intl (MBJ) from $636
• Kingston Norman Manley (KIN) from $698

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

Saturday tends to be the cheapest day to fly from Portland to Jamaica, while Sunday is the most expensive. Fares run about 56% higher that day, based on the past 12 months of KAYAK data.

What's the cheapest time of day to fly from Portland to Jamaica?

Data from the past 12 months shows it's cheapest to fly to Jamaica during the evening with average prices of $623. The morning is the most expensive time to fly, with average prices of $654.

Key details for Portland to Jamaica flights

Low season

February

Cheapest flight

$167
Beat the crowds with an average 37% drop in travelers.
The most popular month to fly with an average 58% increase in travelers.
One-way flight from Portland to Montego Bay

Your Portland to Jamaica flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • Is now a good time to book a flight from Portland to Jamaica?

    Yes. Fares from Portland to Jamaica are low right now. As a rule of thumb, a round-trip under $528 (cheaper than most fares this year) is a good deal, so if you spot one at or below that, it's a good time to book.

  • How much should I budget for a flight from Portland to Jamaica?

    Over the past 12 months, round-trip fares from Portland to Jamaica have ranged from $528 to $723.

  • What airlines fly nonstop from Portland to Jamaica?

    Based on the flight schedule for the next 3 months, no airline regularly operates nonstop flights from Portland to Jamaica. One-stop options include:

    • Delta
    • Southwest
    • American Airlines

  • Which cabin classes are available on flights from Portland to Jamaica?

    On flights from Portland to Jamaica you can book Economy Class or First Class.

  • What are some popular landmarks in Jamaica?

    KAYAK travelers' favorite landmarks in Jamaica include:

    • Doctor's Cave Bathing Club
    • Cornwall Beach
    • Fort Montego Craft Market
    • AquaSol Theme Park

Your guide to booking Portland to Jamaica flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your travel dates are flexible, book your trip for October when flights are typically cheapest and avoid February when prices are at their highest.
  • Flying on Saturday is usually the cheapest. Flights on Sunday cost about 56% more on average, so being flexible with your travel dates could help you save.
  • If you're looking to save, Montego Bay Sangster Intl (MBJ) is the cheapest airport to fly into from Portland. If you have onward travel, don't forget to factor in the cost of your journey by train, bus or domestic flight.
  • Start your trip in Montego Bay, which is the most popular destination in Jamaica. From there, it's easy to continue on to other popular destinations such as Negril, Ocho Rios and Kingston.

Reviews of the top airlines flying 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.
7.3
United AirlinesOverall score based on 10392 reviews
7.3Comfort
7.7Boarding
6.7Food
7.1Entertainment
8.1Crew
Airline reviews

I purchased a Polaris ticket. The plane did not have the lie flat seats - I was not notified. I actually can not believe they traded a dif plane and did not notify me or refund monies

2.0 MediocreGina, Oct 2026
Read more United Airlines reviews

I purchased a Polaris ticket. The plane did not have the lie flat seats - I was not notified. I actually can not believe they traded a dif plane and did not notify me or refund monies

One of my checked luggage was damaged. Cracked on the top by the handle.

⭐ Absolutely AWFUL Experience with United Airlines! If I could give United Airlines ZERO stars, I would. The seats have practically NO legroom, making the flight feel like being crammed into a tin can with nowhere to move. Comfort? Forget about it! And the fees? Absolutely ridiculous! They seem to charge you for EVERYTHING. You pay for your ticket, then get hit with extra charges for things that should be part of a decent flying experience. What’s next, charging passengers for breathing? Flying with United feels less like being a valued customer and more like being a walking wallet. The seats are uncomfortable, the legroom is pathetic, and the constant nickel-and-diming is infuriating. For the price you pay, you would think they could at least provide a little space to stretch your legs and a travel experience that doesn’t leave you feeling ripped off. Do yourself a favor and look at other airlines before booking with United. I certainly won’t be rushing to fly with them again. Absolutely disappointing from start to finish!

Flight was very smooth from Boston. But when we got to Houston, the gate was not open and we waited on the runway for over 30 min!!

Everything was OK except the meals, that was overpriced chicken meat.

Seat would not recline, and charger did not work. Person in front of me reclined before we took off and left it reclined when they got off the plane. Nobody ever told them to put their seat in upright position....which meant I was somewhat trapped in my window seat when deplaning. Another passenger had to go to their seat and un-recline so I could get out.

Both my flight where delayed Had 25min to make it to my transfer flight

I just got back from a trip with 3 flights each way. The flights were good and we were happy with out experience. There was one steward on our first flight that was harsh and grump with passengers. It did not leave a good impression. All of the other flight crews were great on the other five flights.

Why is it that United flights from Newark are constantly delayed? Newark is a United hub!!!!!

They changed my flight 5 hours before it took off and changed my connecting airport messing up my entire 1st day in Japan.

Good flight, excellent personnel; poor comfort, small seats, big cost.

No flight delays. No need to rebook to make connections. Enjoyed second leg of flight on Iberia.

Very Good in general. Serving attitude are very good. Just a suggestion: There 2 things can be improved: 1. The flight attendants can lower the voices when they talked in the serving station. Sometimes they talked loud and we could hear clearly what they said about the passengers. 2. Please don’t throw the utensils and plates it’s too loud and noisy. They broke the glasses and plates sometimes at the business class. These all could be done in a gentle way. Just some small observations. Thanks.

Flight was delayed a couple of times. Which is annoying, but manageable.

Both directions of our trip were befuddled by massive delays, one of which led to our connecting flight being grounded mid air due to storms that we’d have missed if we were on time. The other our originating flight was delayed repeatedly until it arrived at our connecting airport later than our final leg was even supposed to have arrived. American cannot seem to manage rebooking s for a family party… both directions we had to come up with a plan to get to Boston stay overnight only one night each direction was covered by the airline -and take a bus to or from our destination. Missed an entire leg of our trip, hotel cancellation fees, expensive stay in Boston and bus ticket expenses are unlikely to be comped and the meal vouchers are worthless.

My flight was 4 hours delayed on departure at 6a causing me to miss my connection at DCA. I had to scramble to find a seat home on a later flight and instead of an exit seat, I was in row 30 on a flight getting me home 5 hours later than planned. The AA team on the ground did a fine job. AA continues to run the airline like the passengers are cargo.

The plane was probably full boarding was easy. We were able to check our carry-on luggage for free. It was a return flight through Philly to LA. Never saw a stewardess do a demonstration of emergency Procedures. I think my flight was pretty full

Nothing exceptional. No drink of any type, even in first class was provided for the hour and half trip.

Flight was delayed after boarding and no idea when it would take off. Crew in Portland did arrange for transport to Boston for a different set of flights to my destination.

Seats are so close together. Middle seats should be discounted.

More options for your flight from Portland to Jamaica

Complete your trip to Jamaica with a hotel stay or car rental