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Kingston

$442+ Cheap flights from Portland, ME (PWM) to Kingston (KIN)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/9. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — KIN
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap flight deals from Portland to Kingston

Discover tips and strategies to find the most affordable flight options for your journey from Portland (PWM) to Kingston (KIN). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 11, 2025.

Round-trip from

$442
(American Airlines)
From Portland to Kingston Norman Manley
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Find flight deals from Portland to Kingston

Cheapest flights from Portland to Kingston
Explore the most affordable flight options available from Portland to Kingston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

This American Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/96:38 pmPWM - KIN
2 stops19h 28mAmerican Airlines
Sat 12/206:25 amKIN - PWM
2 stops16h 23mAmerican Airlines
Deal found 9/10$442

Cheapflights Fare Finder

 
Customize your flight search to find flights from Portland to Kingston that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 11, 2025.
Use the filters below to find and compare flights from Portland to Kingston that are best for you.

Fly from

Portland

Fly to

Kingston

Route

Depart

Return

Price

PortlandKingston

PWM - KIN

PWMKIN

Portland

Tue 12/9

6:38 pm-2:06 pm

2 stops19h 28m

Kingston Norman Manley

Sat 12/20

6:25 am-10:48 pm

2 stops16h 23m

$442

PortlandKingston

PWM - KIN

PWMKIN

Portland

Tue 2/24

6:00 am-8:00 pm

2 stops14h 00m

Kingston Norman Manley

Thu 2/26

9:00 am-9:59 pm

1 stop12h 59m

$453

PortlandKingston

PWM - KIN

PWMKIN

Portland

Mon 2/2

4:50 pm-11:55 am

2 stops19h 05m

Kingston Norman Manley

Fri 2/6

8:25 am-10:31 pm

2 stops14h 06m

$453

PortlandKingston

PWM - KIN

PWMKIN

Portland

Tue 2/24

2:29 pm-11:45 am

2 stops21h 16m

Kingston Norman Manley

Thu 2/26

1:50 pm-12:09 pm

2 stops22h 19m

$527

PortlandKingston

PWM - KIN

PWMKIN

Portland

Mon 2/2

5:30 am-8:00 pm

1 stop14h 30m

Kingston Norman Manley

Fri 2/6

9:00 am-9:59 pm

1 stop12h 59m

$638

PortlandKingston

PWM - KIN

PWMKIN

Portland

Sun 2/8

4:50 pm-11:55 am

2 stops19h 05m

Kingston Norman Manley

Sat 2/21

3:50 pm-11:39 am

2 stops19h 49m

$850

PortlandKingston

PWM - KIN

PWMKIN

Portland

Sun 2/8

5:30 am-8:00 pm

1 stop14h 30m

Kingston Norman Manley

Sat 2/21

9:00 am-11:49 pm

2 stops14h 49m

$1,149

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Best time to book a flight from Portland to Kingston

Have a flexible travel schedule? Discover the best time to fly to Kingston from Portland with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Portland to Kingston

What is the cheapest month to book a flight from Portland, Maine to Kingston?

Currently, September is the cheapest month in which you can book a flight from Portland, Maine to Kingston (average of $425). Flying from Portland, Maine to Kingston in December is currently the most expensive (average of $613). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Related info for your journey

Find useful and relevant information for your journey from Portland to Kingston. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Portland, Maine to Kingston?

    A quick flight from Portland, Maine to Kingston can take about 14h. American Airlines provides one of the quickest options available for as low as $453. The distance between Portland, Maine and Kingston is about 1815 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • Can I find deals for flights from Portland to Kingston that include hotel bookings?

    Yes. In addition to deals on Portland to Kingston flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Portland to Kingston?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Portland to Kingston.

  • Can I find deals for business class flights from Portland to Kingston?

    Yes. Cheapflights offers flight deals from Portland to Kingston by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Portland, Maine to Kingston?

    Currently, September is the cheapest month in which you can book a flight from Portland, Maine to Kingston (average of $425). Flying from Portland, Maine to Kingston in December is currently the most expensive (average of $613). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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