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Kentucky

$79+ Cheap flights from Portland, ME (PWM) to Kentucky

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 3/29. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SDF
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
1 adult, Economy
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Cheap flight deals from Portland to Kentucky

Keep the following information in mind while searching for Portland to Kentucky 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
(Southwest)

One-way from

$119
(Delta)

Popular in

August

Cheapest in

June

Average price

$382
Provider with most accurate pricing for Portland-Louisville Intl flight deals.
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Provider most trusted by Cheapflights users for Portland-Louisville Intl flights.
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From Portland to Kentucky
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One-way flight from Portland to Kentucky
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Highest demand for flights based on searches. 17% potential increase in price ($91 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($25 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Find flight deals from Portland to Kentucky

Cheapest flights from Portland to Kentucky
Explore the most affordable flight options available from Portland to Kentucky. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 3, 2025.

This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/113:30 pmPWM - BNA
1 stop6h 35mSouthwest
Mon 12/153:55 pmBNA - PWM
1 stop5h 20mSouthwest
Deal found 10/31$237
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 12/115:34 amPWM - BNA
2 stops9h 18mAmerican Airlines
Sun 12/146:26 amBNA - PWM
1 stop4h 11mAmerican Airlines
Deal found 11/2$242
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 12/55:17 pmPWM - BNA
2 stops7h 39mAmerican Airlines
Sun 12/77:16 amBNA - PWM
2 stops7h 11mAmerican Airlines
Deal found 11/2$247
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/115:30 amPWM - BNA
1 stop6h 00mSouthwest
Sat 11/159:30 amBNA - PWM
1 stop4h 10mSouthwest
Deal found 11/1$257
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/289:40 amPWM - BNA
1 stop7h 04mUnited Airlines
Fri 12/52:35 pmBNA - PWM
1 stop7h 34mUnited Airlines
Deal found 10/31$261
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/122:30 pmPWM - BNA
1 stop8h 16mDelta
Wed 11/195:15 amBNA - PWM
1 stop6h 15mDelta
Deal found 10/31$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.
Mon 11/175:37 pmPWM - LEX
1 stop6h 01mAmerican Airlines
Sat 11/226:08 pmLEX - PWM
1 stop4h 25mAmerican Airlines
Deal found 11/1$264
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.
Wed 11/126:00 amPWM - BNA
2 stops7h 57mAmerican Airlines
Mon 11/175:59 pmBNA - PWM
1 stop5h 00mAmerican Airlines
Deal found 11/2$267
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.
Wed 11/126:00 amPWM - BNA
2 stops7h 57mAmerican Airlines
Wed 11/197:05 amBNA - PWM
2 stops8h 36mAmerican Airlines
Deal found 11/2$272
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 12/55:17 pmPWM - TYS
1 stop4h 19mAmerican Airlines
Mon 12/86:00 amTYS - PWM
1 stop5h 37mAmerican Airlines
Deal found 11/2$279
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 11/2112:26 pmPWM - BNA
1 stop7h 33mAmerican Airlines
Sat 11/222:37 pmBNA - PWM
1 stop6h 56mAmerican Airlines
Deal found 11/2$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.
Thu 12/45:46 amPWM - TYS
2 stops8h 41mAmerican Airlines
Mon 12/86:00 amTYS - PWM
1 stop5h 37mAmerican Airlines
Deal found 11/2$284

Cheapflights Fare Finder

 
Customize your flight search to find flights from Portland to Kentucky 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 Portland to Kentucky that are best for you.

Fly from

Portland

Fly to

Kentucky

Route

Depart

Return

Price

PortlandNashville

PWM - BNA

PWMBNA

Portland

Thu 12/11

7:11 am-1:52 pm

1 stop7h 41m

Nashville Intl

Sun 12/14

6:26 am-11:37 am

1 stop4h 11m

$237

PortlandNashville

PWM - BNA

PWMBNA

Portland

Wed 1/7

12:45 pm-7:30 pm

1 stop7h 45m

Nashville Intl

Wed 1/14

7:35 am-2:55 pm

1 stop6h 20m

$237

PortlandNashville

PWM - BNA

PWMBNA

Portland

Fri 12/5

2:34 pm-9:46 pm

1 stop8h 12m

Nashville Intl

Sun 12/7

6:00 am-12:13 pm

1 stop5h 13m

$237

PortlandNashville

PWM - BNA

PWMBNA

Portland

Tue 3/10

2:35 pm-8:46 pm

1 stop7h 11m

Nashville Intl

Wed 3/11

5:26 pm-11:49 pm

1 stop5h 23m

$237

PortlandNashville

PWM - BNA

PWMBNA

Portland

Fri 12/5

5:17 pm-11:56 pm

2 stops7h 39m

Nashville Intl

Sun 12/7

7:16 am-3:27 pm

2 stops7h 11m

$247

PortlandNashville

PWM - BNA

PWMBNA

Portland

Sun 11/23

6:00 am-10:02 am

1 stop5h 02m

Nashville Intl

Wed 11/26

4:42 pm-10:19 pm

1 stop4h 37m

$262

PortlandNashville

PWM - BNA

PWMBNA

Portland

Wed 11/19

4:40 pm-9:00 pm

1 stop5h 20m

Nashville Intl

Wed 11/26

4:42 pm-10:19 pm

1 stop4h 37m

$262

PortlandLexington

PWM - LEX

PWMLEX

Portland

Tue 11/18

5:37 pm-11:38 pm

1 stop6h 01m

Lexington Blue Grass

Sat 11/22

6:08 pm-10:33 pm

1 stop4h 25m

$264

PortlandKnoxville

PWM - TYS

PWMTYS

Portland

Fri 12/5

5:17 pm-9:36 pm

1 stop4h 19m

Knoxville McGhee Tyson

Mon 12/8

6:00 am-11:37 am

1 stop5h 37m

$279

PortlandKnoxville

PWM - TYS

PWMTYS

Portland

Tue 3/31

6:00 am-11:12 am

1 stop5h 12m

Knoxville McGhee Tyson

Sat 4/4

7:30 am-11:57 am

1 stop4h 27m

$279

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 Portland to Kentucky

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

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

Currently, September is the cheapest month in which you can book a flight from Portland, Maine to Kentucky (average of $187). Flying from Portland, Maine to Kentucky in March is currently the most expensive (average of $252). 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.

Reviews of airlines servicing Kentucky

Get insights into the airlines that provide service to Kentucky. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Kentucky. Reviews last updated November 3, 2025.
Read through reviews of airlines operating flights from Portland to Kentucky, such as Southwest, Delta, and United Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,240 reviews

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,240 reviews
Southwest
8.0
Very good
4,240 reviews

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
7.9
Good
8,001 reviews
Southwest
8.0
Very good
4,240 reviews

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,997 reviews
Southwest
8.0
Very good
4,240 reviews

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,034 reviews
Southwest
8.0
Very good
4,240 reviews

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Portland to Kentucky. 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 from for flights from Portland to Kentucky?

    Most people fly from Portland (PWM) if they book a flight from Portland to Kentucky. Portland is conveniently located just 2.9 mi from Portland’s city center.

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

    There are many flights that can get you from Portland, Maine to Kentucky in 7h 41m. Fly via American Airlines, Southwest, or Delta to get the fastest option. The distance between Portland, Maine and Kentucky 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 Portland, Maine to Kentucky one-way?

    For one-way options, check prices for JetBlue. According to our data, you can fly for as low as $116. Users have also found prices from $119 and $119 on Delta and United Airlines, respectively.

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

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

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

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

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

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

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

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

    Currently, September is the cheapest month in which you can book a flight from Portland, Maine to Kentucky (average of $187). Flying from Portland, Maine to Kentucky in March is currently the most expensive (average of $252). 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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Alternative routes for Portland to Kentucky

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

Discover the top 4 airlines that operate flights from Portland to Kentucky. 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
DeltaCheapest$248Average$414FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$248Average$383FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$376Average$457FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$387Average$532FlexibilityNo cancel feeOn-time63%

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