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$99+ 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 12/4. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — PWM
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
1 adult, Economy
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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 November 3, 2025.

This Delta deal was found by Cheapflights users on 11/1. 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.
Fri 12/54:27 pmBNA - PWM
1 stop4h 56mDelta
Sun 12/76:08 amPWM - BNA
1 stop6h 34mDelta
Deal found 11/1$237
This American Airlines deal was found by Cheapflights users on 11/1. 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 12/53:29 pmBNA - PWM
2 stops7h 08mAmerican Airlines
Sun 12/75:34 amPWM - BNA
1 stop7h 32mAmerican Airlines
Deal found 11/1$242
This Delta deal was found by Cheapflights users on 11/1. 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.
Fri 11/145:52 pmBNA - PWM
1 stop5h 02mDelta
Mon 11/174:53 pmPWM - BNA
1 stop5h 18mDelta
Deal found 11/1$262
This American Airlines deal was found by Cheapflights users on 11/1. 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 11/146:26 amBNA - PWM
1 stop4h 20mAmerican Airlines
Mon 11/173:52 pmPWM - BNA
2 stops7h 49mAmerican Airlines
Deal found 11/1$267
This Delta deal was found by Cheapflights users on 11/2. 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.
Fri 12/125:39 pmTYS - PWM
1 stop4h 44mDelta
Mon 12/156:00 amPWM - TYS
1 stop6h 10mDelta
Deal found 11/2$279
This American Airlines deal was found by Cheapflights users on 11/1. 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 11/212:37 pmBNA - PWM
1 stop6h 56mAmerican Airlines
Sun 11/235:43 amPWM - BNA
1 stop7h 21mAmerican Airlines
Deal found 11/1$283
This American Airlines deal was found by Cheapflights users on 11/2. 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 12/126:00 amTYS - PWM
1 stop5h 37mAmerican Airlines
Mon 12/155:34 amPWM - TYS
2 stops9h 40mAmerican Airlines
Deal found 11/2$284
This Delta deal was found by Cheapflights users on 11/2. 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 12/25:25 pmTYS - PWM
1 stop5h 56mDelta
Tue 12/96:00 amPWM - TYS
1 stop6h 10mDelta
Deal found 11/2$304
This Southwest deal was found by Cheapflights users on 11/2. 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.
Sun 11/165:10 amBNA - PWM
1 stop5h 00mSouthwest
Sun 11/235:25 pmPWM - BNA
1 stop5h 25mSouthwest
Deal found 11/2$308
This American Airlines deal was found by Cheapflights users on 11/2. 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 12/117:38 amTYS - PWM
1 stop4h 33mAmerican Airlines
Tue 12/1612:23 pmPWM - TYS
2 stops8h 59mAmerican Airlines
Deal found 11/2$314
This United Airlines deal was found by Cheapflights users on 11/1. 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 11/1712:50 pmBNA - PWM
1 stop8h 00mUnited Airlines
Fri 11/215:30 amPWM - BNA
1 stop4h 57mUnited Airlines
Deal found 11/1$317
This Kiwi.com deal was found by Cheapflights users on 10/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/158:30 amCVG - PWM
1 stop25h 39mMultiple Airlines
Wed 11/196:18 pmPWM - CVG
2 stops16h 03mMultiple Airlines
Deal found 10/31$326

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 November 3, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$237
(Delta)

One-way from

$99
(Kiwi.com)

Popular in

March

Cheapest in

August

Average price

$522
Provider with most accurate pricing for Louisville Intl-Portland flight deals.
Search Deals
Provider most trusted by Cheapflights users for Louisville Intl-Portland flights.
Search Deals
From Kentucky to Portland
Search Deals
One-way flight from Kentucky to Portland
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($18 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

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 November 3, 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

Fri 12/5

4:27 pm-10:23 pm

1 stop4h 56m

Portland

Sun 12/7

6:08 am-11:42 am

1 stop6h 34m

$237

NashvillePortland

BNA - PWM

BNAPWM

Nashville Intl

Fri 12/5

3:29 pm-11:37 pm

2 stops7h 08m

Portland

Sun 12/7

5:34 am-12:06 pm

1 stop7h 32m

$242

LexingtonPortland

LEX - PWM

LEXPWM

Lexington Blue Grass

Wed 3/25

3:45 pm-9:59 pm

1 stop6h 14m

Portland

Sat 3/28

4:50 pm-9:39 pm

1 stop4h 49m

$249

NashvillePortland

BNA - PWM

BNAPWM

Nashville Intl

Fri 11/14

5:52 pm-11:54 pm

1 stop5h 02m

Portland

Mon 11/17

4:53 pm-9:11 pm

1 stop5h 18m

$262

NashvillePortland

BNA - PWM

BNAPWM

Nashville Intl

Fri 11/14

6:26 am-11:46 am

1 stop4h 20m

Portland

Mon 11/17

3:52 pm-10:41 pm

2 stops7h 49m

$267

KnoxvillePortland

TYS - PWM

TYSPWM

Knoxville McGhee Tyson

Fri 12/12

6:00 am-11:37 am

1 stop5h 37m

Portland

Mon 12/15

5:34 am-10:50 am

1 stop5h 16m

$279

KnoxvillePortland

TYS - PWM

TYSPWM

Knoxville McGhee Tyson

Wed 3/25

5:00 pm-11:05 pm

1 stop6h 05m

Portland

Sat 3/28

4:50 pm-9:32 pm

1 stop4h 42m

$279

NashvillePortland

BNA - PWM

BNAPWM

Nashville Intl

Fri 11/21

2:37 pm-10:33 pm

1 stop6h 56m

Portland

Sun 11/23

5:43 am-12:04 pm

1 stop7h 21m

$283

KnoxvillePortland

TYS - PWM

TYSPWM

Knoxville McGhee Tyson

Tue 12/2

5:25 pm-11:21 pm

1 stop5h 56m

Portland

Tue 12/9

6:00 am-12:10 pm

1 stop6h 10m

$304

NashvillePortland

BNA - PWM

BNAPWM

Nashville Intl

Sun 11/16

5:10 am-11:10 am

1 stop5h 00m

Portland

Sun 11/23

5:25 pm-9:50 pm

1 stop5h 25m

$308

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Showing 1-10 of 56 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 December is currently the most expensive (average of $249). 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 November 3, 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 4h 56m. Fly via Delta or American 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 $119 on United Airlines. Other airlines that offer cheap prices include Delta from $119 and Southwest from $157 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 Cincinnati Cinci./N. Kentucky - Portland, Nashville Intl - Portland or Louisville Intl - 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 December is currently the most expensive (average of $249). 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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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 November 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$236Average$384FlexibilityNo cancel feeOn-time71%
DeltaCheapest$248Average$398FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$296Average$411FlexibilityNo cancel feeOn-time63%

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