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$75+ Cheap flights from Kentucky to Portland, ME (PWM)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/18. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — PWM
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Kentucky to Portland

Keep the following information in mind while searching for Kentucky to Portland flight deals. Data was last updated September 15, 2025.

Round-trip from

$159
(American Airlines)

One-way from

$75
(Southwest)

Popular in

March

Cheapest in

August

Average price

$436
From Kentucky to Portland
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One-way flight from Kentucky to Portland
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Highest demand for flights based on searches. 2% potential increase in price ($10 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Kentucky to Portland

Cheapest flights from Kentucky to Portland
Explore the most affordable flight options available from Kentucky to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This American Airlines deal was found by Cheapflights users on 9/14. 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.
Sat 10/254:00 pmBNA - PWM
1 stop5h 45mAmerican Airlines
Tue 10/283:38 pmPWM - BNA
1 stop7h 47mAmerican Airlines
Deal found 9/14$159
This Southwest deal was found by Cheapflights users on 9/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/183:30 pmBNA - PWM
1 stop5h 55mSouthwest
Sat 10/255:50 amPWM - BNA
1 stop5h 30mSouthwest
Deal found 9/12$162
This United Airlines deal was found by Cheapflights users on 9/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2612:50 pmBNA - PWM
1 stop7h 54mUnited Airlines
Thu 10/25:45 amPWM - BNA
1 stop4h 31mUnited Airlines
Deal found 9/12$217
This United Airlines deal was found by Cheapflights users on 9/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/296:27 pmBNA - PWM
1 stop4h 32mUnited Airlines
Fri 10/35:45 amPWM - BNA
2 stops7h 50mUnited Airlines
Deal found 9/14$222
This United Airlines deal was found by Cheapflights users on 9/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/116:27 pmBNA - PWM
1 stop4h 32mUnited Airlines
Tue 10/218:00 amPWM - BNA
1 stop5h 53mUnited Airlines
Deal found 9/13$231
This United Airlines deal was found by Cheapflights users on 9/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2312:42 pmBNA - PWM
1 stop4h 44mUnited Airlines
Sat 9/276:14 amPWM - BNA
1 stop5h 17mUnited Airlines
Deal found 9/13$237
This American Airlines deal was found by Cheapflights users on 9/13. 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 9/239:48 amBNA - PWM
2 stops6h 51mAmerican Airlines
Sat 9/276:00 amPWM - BNA
2 stops7h 58mAmerican Airlines
Deal found 9/13$247
This JetBlue deal was found by Cheapflights users on 9/13. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/181:35 pmBNA - PWM
1 stop8h 29mJetBlue
Sun 10/267:01 amPWM - BNA
1 stop6h 14mJetBlue
Deal found 9/13$249
This American Airlines deal was found by Cheapflights users on 9/15. 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 10/283:52 pmLEX - PWM
1 stop6h 18mAmerican Airlines
Sat 11/85:37 pmPWM - LEX
1 stop6h 01mAmerican Airlines
Deal found 9/15$249
This Delta deal was found by Cheapflights users on 9/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/283:46 pmLEX - PWM
1 stop6h 33mDelta
Sat 11/84:48 pmPWM - LEX
2 stops7h 17mDelta
Deal found 9/15$254
This American Airlines deal was found by Cheapflights users on 9/14. 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.
Thu 12/117:10 amCVG - PWM
1 stop9h 18mAmerican Airlines
Tue 12/1612:23 pmPWM - CVG
1 stop9h 16mAmerican Airlines
Deal found 9/14$279
This American Airlines deal was found by Cheapflights users on 9/14. 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.
Mon 10/206:14 pmTYS - PWM
1 stop4h 34mAmerican Airlines
Sat 10/257:44 amPWM - TYS
1 stop6h 04mAmerican Airlines
Deal found 9/14$294

Cheapflights Fare Finder

 
Customize your flight search to find flights from Kentucky to Portland 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 15, 2025.
Use the filters below to find and compare flights from Kentucky to Portland that are best for you.

Fly from

Kentucky

Fly to

Portland

Route

Depart

Return

Price

NashvillePortland

BNA - PWM

BNAPWM

Nashville Intl

Tue 9/30

6:05 pm-12:34 am

1 stop5h 29m

Portland

Sat 10/4

6:00 am-11:53 am

1 stop6h 53m

$217

NashvillePortland

BNA - PWM

BNAPWM

Nashville Intl

Wed 11/5

5:54 pm-12:05 am

1 stop5h 11m

Portland

Sun 11/9

6:00 am-11:39 am

1 stop6h 39m

$217

NashvillePortland

BNA - PWM

BNAPWM

Nashville Intl

Mon 9/29

6:00 pm-12:11 am

1 stop5h 11m

Portland

Fri 10/3

1:35 pm-8:34 pm

1 stop7h 59m

$217

NashvillePortland

BNA - PWM

BNAPWM

Nashville Intl

Sat 10/18

4:35 pm-8:05 pm

Nonstop2h 30m

Portland

Sat 10/25

5:50 am-10:20 am

1 stop5h 30m

$219

NashvillePortland

BNA - PWM

BNAPWM

Nashville Intl

Mon 9/29

6:27 pm-11:59 pm

1 stop4h 32m

Portland

Fri 10/3

5:45 am-12:35 pm

2 stops7h 50m

$222

NashvillePortland

BNA - PWM

BNAPWM

Nashville Intl

Sat 10/11

6:27 pm-11:59 pm

1 stop4h 32m

Portland

Tue 10/21

8:00 am-12:53 pm

1 stop5h 53m

$231

NashvillePortland

BNA - PWM

BNAPWM

Nashville Intl

Sat 10/18

1:35 pm-11:04 pm

1 stop8h 29m

Portland

Sun 10/26

7:01 am-12:15 pm

1 stop6h 14m

$249

NashvillePortland

BNA - PWM

BNAPWM

Nashville Intl

Sat 10/4

6:27 pm-11:59 pm

1 stop4h 32m

Portland

Tue 10/7

10:40 am-6:52 pm

2 stops9h 12m

$255

NashvillePortland

BNA - PWM

BNAPWM

Nashville Intl

Fri 9/26

12:50 pm-9:44 pm

1 stop7h 54m

Portland

Mon 9/29

5:45 am-9:16 am

1 stop4h 31m

$257

NashvillePortland

BNA - PWM

BNAPWM

Nashville Intl

Wed 11/26

5:15 am-12:30 pm

1 stop6h 15m

Portland

Mon 12/1

4:53 pm-9:06 pm

1 stop5h 13m

$268

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 60 results
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Best time to book a flight from Kentucky to Portland

Have a flexible travel schedule? Discover the best time to fly to Portland from Kentucky 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 Kentucky to Portland

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

Currently, January is the cheapest month in which you can book a flight from Kentucky to Portland, Maine (average of $296). Flying from Kentucky to Portland, Maine in July is currently the most expensive (average of $394). 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.

What is the cheapest time of day to fly from KY to PWM?

Find hourly flight availability from Kentucky to Portland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 15, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Kentucky to Portland, Maine as you normally would.

Related info for your journey

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

  • What airport do you fly into for flights to Portland from Kentucky?

    Located just 2.9 mi from the city center, Portland (PWM) is the airport most travelers will use when flying to Portland from Kentucky.

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

    There are many flights that can get you from Kentucky to Portland, Maine in 2h 30m. Fly via Delta, Southwest, or United Airlines to get the fastest option. The distance from Kentucky to Portland, Maine is about 1009 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Kentucky to Portland, Maine one-way?

    One-way options have recently been found by users for as low as $76 on United Airlines. Other airlines that offer cheap prices include Delta from $145 and Southwest from $154 one-way.

  • What are the most popular routes from Kentucky to Portland, Maine?

    When deciding which route to take from Kentucky to Portland, Maine consider Nashville Intl - Portland, Knoxville McGhee Tyson - Portland or Cincinnati Cinci./N. Kentucky - Portland as they are the most popular.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Kentucky to Portland 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 Kentucky to Portland, Maine?

    Currently, January is the cheapest month in which you can book a flight from Kentucky to Portland, Maine (average of $296). Flying from Kentucky to Portland, Maine in July is currently the most expensive (average of $394). 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

Traveling to a place near Portland?

Book flights to Portland if you plan to visit one of these locations
Brunswick
North Conway
Auburn
Conway
Lewiston

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Alternative routes for Kentucky to Portland

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Kentucky to Portland

Discover the top 4 airlines that operate flights from Kentucky to Portland. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$248Average$379FlexibilityNo cancel feeOn-time71%
DeltaCheapest$248Average$380FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$283Average$626FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$296Average$422FlexibilityNo cancel feeOn-time63%

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