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$107+ 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 1/8. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — PWM
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap 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 December 18, 2025.

This American Airlines deal was found by Cheapflights users on 12/16. 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.
Wed 12/3111:17 amCVG - PWM
1 stop5h 22mAmerican Airlines
Mon 1/55:45 amPWM - CVG
1 stop4h 44mAmerican Airlines
Deal found 12/16$365
This American Airlines deal was found by Cheapflights users on 12/16. 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 12/255:15 amBNA - PWM
1 stop5h 05mAmerican Airlines
Mon 12/295:48 amPWM - BNA
1 stop4h 54mAmerican Airlines
Deal found 12/16$395
This American Airlines deal was found by Cheapflights users on 12/16. 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.
Wed 12/3111:17 amCVG - PWM
1 stop5h 22mAmerican Airlines
Sun 1/45:45 amPWM - CVG
1 stop4h 44mAmerican Airlines
Deal found 12/16$395
This American Airlines deal was found by Cheapflights users on 12/15. 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.
Fri 12/196:38 pmBNA - PWM
1 stop4h 04mAmerican Airlines
Sat 12/205:20 pmPWM - BNA
1 stop5h 30mAmerican Airlines
Deal found 12/15$435
This United Airlines deal was found by Cheapflights users on 12/18. 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.
Wed 12/313:44 pmSDF - PWM
1 stop7h 38mUnited Airlines
Mon 1/54:10 pmPWM - SDF
1 stop6h 20mUnited Airlines
Deal found 12/18$438
This United Airlines deal was found by Cheapflights users on 12/18. 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.
Wed 12/317:40 pmCVG - PWM
1 stop4h 19mUnited Airlines
Mon 1/55:30 amPWM - CVG
2 stops7h 47mUnited Airlines
Deal found 12/18$443
This Delta deal was found by Cheapflights users on 12/16. 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.
Wed 12/244:49 pmSDF - PWM
1 stop5h 54mDelta
Fri 12/265:45 amPWM - SDF
1 stop5h 41mDelta
Deal found 12/16$483
This American Airlines deal was found by Cheapflights users on 12/17. 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 12/235:42 amTYS - PWM
1 stop6h 29mAmerican Airlines
Tue 1/65:00 amPWM - TYS
1 stop5h 49mAmerican Airlines
Deal found 12/17$487
This United Airlines deal was found by Cheapflights users on 12/17. 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 12/236:45 amTYS - PWM
1 stop7h 29mUnited Airlines
Tue 1/611:12 amPWM - TYS
2 stops9h 40mUnited Airlines
Deal found 12/17$492
This American Airlines deal was found by Cheapflights users on 12/16. 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.
Wed 12/318:45 amBNA - PWM
2 stops6h 54mAmerican Airlines
Sun 1/45:48 amPWM - BNA
1 stop4h 54mAmerican Airlines
Deal found 12/16$513
This United Airlines deal was found by Cheapflights users on 12/16. 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.
Wed 12/247:40 pmCVG - PWM
1 stop4h 19mUnited Airlines
Fri 12/267:30 pmPWM - CVG
1 stop4h 29mUnited Airlines
Deal found 12/16$518
This Southwest deal was found by Cheapflights users on 12/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/192:25 pmBNA - PWM
2 stops8h 40mSouthwest
Sat 12/203:05 pmPWM - BNA
2 stops9h 40mSouthwest
Deal found 12/15$555

Find flight deals from Kentucky to Portland

Keep the following information in mind while searching for Kentucky to Portland flight deals. Data was last updated December 18, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$237
(Delta)

One-way from

$107
(Kiwi.com)

Popular in

January

Cheapest in

February

Average price

$377
Provider with most accurate pricing for Louisville Intl-Boston Logan Intl flight deals.
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Provider most trusted by Cheapflights users for Louisville Intl-Boston Logan Intl flights.
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From Kentucky to Portland
Search Deals
One-way flight from Kentucky to Portland
Search Deals
Highest demand for flights based on searches. 1% potential increase in price ($5 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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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 December 18, 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

Thu 1/15

6:50 am-1:45 pm

1 stop5h 55m

Portland

Sat 1/17

1:13 pm-6:24 pm

1 stop6h 11m

$237

NashvillePortland

BNA - PWM

BNAPWM

Nashville Intl

Thu 1/15

6:00 am-12:05 pm

1 stop5h 05m

Portland

Sat 1/17

12:45 pm-7:59 pm

2 stops8h 14m

$242

LexingtonPortland

LEX - PWM

LEXPWM

Lexington Blue Grass

Tue 1/13

4:35 pm-10:07 pm

1 stop5h 32m

Portland

Sat 1/17

12:45 pm-5:47 pm

1 stop5h 02m

$243

LexingtonPortland

LEX - PWM

LEXPWM

Lexington Blue Grass

Tue 1/13

6:55 am-11:20 am

1 stop4h 25m

Portland

Sat 1/17

1:13 pm-9:41 pm

2 stops8h 28m

$248

KnoxvillePortland

TYS - PWM

TYSPWM

Knoxville McGhee Tyson

Tue 2/3

11:55 am-5:16 pm

1 stop5h 21m

Portland

Wed 2/4

12:43 pm-8:22 pm

1 stop7h 39m

$279

NashvillePortland

BNA - PWM

BNAPWM

Nashville Intl

Thu 1/1

2:23 pm-10:51 pm

1 stop7h 28m

Portland

Mon 1/5

5:20 pm-10:32 pm

1 stop6h 12m

$282

KnoxvillePortland

TYS - PWM

TYSPWM

Knoxville McGhee Tyson

Tue 2/3

7:54 am-4:37 pm

2 stops8h 43m

Portland

Wed 2/4

5:07 pm-9:44 pm

1 stop4h 37m

$284

LouisvillePortland

SDF - PWM

SDFPWM

Louisville Intl

Wed 1/14

3:37 pm-10:27 pm

1 stop6h 50m

Portland

Sun 1/18

5:30 am-11:37 am

1 stop6h 07m

$290

KnoxvillePortland

TYS - PWM

TYSPWM

Knoxville McGhee Tyson

Tue 1/6

4:00 pm-10:07 pm

1 stop6h 07m

Portland

Sat 1/10

7:00 am-11:42 am

1 stop4h 42m

$304

KnoxvillePortland

TYS - PWM

TYSPWM

Knoxville McGhee Tyson

Tue 1/6

6:10 am-11:20 am

1 stop5h 10m

Portland

Sat 1/10

6:00 am-12:09 pm

1 stop6h 09m

$304

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 54 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, September is the cheapest month in which you can book a flight from Kentucky to Portland, Maine (average of $139). Flying from Kentucky to Portland, Maine in May is currently the most expensive (average of $248). 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 December 18, 2025.

When flying from Kentucky to Portland, Maine, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 22% versus a flight in the morning.

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 5h 05m. Fly via Delta, American Airlines, 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 most popular routes from Kentucky to Portland, Maine?

    When deciding which route to take from Kentucky to Portland, Maine consider Nashville Intl - Portland, Lexington Blue Grass - 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, September is the cheapest month in which you can book a flight from Kentucky to Portland, Maine (average of $139). Flying from Kentucky to Portland, Maine in May is currently the most expensive (average of $248). 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
North Conway
Brunswick
Auburn
Conway

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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 3 airlines flying from Kentucky to Portland

Discover the top 3 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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$236Average$396FlexibilityNo cancel feeOn-time71%
DeltaCheapest$248Average$405FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$296Average$446FlexibilityNo cancel feeOn-time63%

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