HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Kentucky

$119+ 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 3/24. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SDF
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Portland to Kentucky with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap 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 January 29, 2026.

This Southwest deal was found by Cheapflights users on 1/28. 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 2/243:30 pm
PWM
-
BNA
1 stop5h 00m
Southwest
Sat 2/285:05 am
BNA
-
PWM
1 stop8h 40m
Southwest
Deal found 1/28$237
This American Airlines deal was found by Cheapflights users on 1/27. 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 2/115:20 am
PWM
-
BNA
2 stops10h 19m
American Airlines
Sun 2/155:05 am
BNA
-
PWM
1 stop5h 29m
American Airlines
Deal found 1/27$242
This American Airlines deal was found by Cheapflights users on 1/28. 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 3/46:00 am
PWM
-
BNA
2 stops9h 47m
American Airlines
Tue 3/1010:45 am
BNA
-
PWM
2 stops6h 19m
American Airlines
Deal found 1/28$247
This Delta deal was found by Cheapflights users on 1/27. 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.
Sat 2/2112:45 pm
PWM
-
BNA
1 stop5h 06m
Delta
Mon 2/235:00 pm
BNA
-
PWM
1 stop6h 18m
Delta
Deal found 1/27$258
This United Airlines deal was found by Cheapflights users on 1/28. 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 6/35:20 am
PWM
-
BNA
1 stop5h 06m
United Airlines
Mon 6/812:52 pm
BNA
-
PWM
1 stop8h 06m
United Airlines
Deal found 1/28$259
This United Airlines deal was found by Cheapflights users on 1/28. 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 4/16:04 am
PWM
-
BNA
1 stop7h 24m
United Airlines
Mon 4/62:49 pm
BNA
-
PWM
1 stop5h 51m
United Airlines
Deal found 1/28$261
This Southwest deal was found by Cheapflights users on 1/27. 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 2/265:30 am
PWM
-
BNA
2 stops6h 30m
Southwest
Sat 2/287:05 am
BNA
-
PWM
1 stop6h 40m
Southwest
Deal found 1/27$263
This United Airlines deal was found by Cheapflights users on 1/27. 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.
Thu 3/56:00 am
PWM
-
BNA
2 stops10h 51m
United Airlines
Mon 3/92:42 pm
BNA
-
PWM
1 stop5h 29m
United Airlines
Deal found 1/27$266
This Delta deal was found by Cheapflights users on 1/28. 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.
Thu 4/25:23 am
PWM
-
BNA
1 stop5h 54m
Delta
Mon 4/64:34 pm
BNA
-
PWM
1 stop5h 48m
Delta
Deal found 1/28$268
This United Airlines deal was found by Cheapflights users on 1/28. 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 5/84:45 pm
PWM
-
BNA
1 stop6h 07m
United Airlines
Mon 5/116:00 am
BNA
-
PWM
1 stop7h 14m
United Airlines
Deal found 1/28$270
This American Airlines deal was found by Cheapflights users on 1/27. 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 3/26:36 pm
PWM
-
BNA
1 stop4h 56m
American Airlines
Wed 3/43:45 pm
BNA
-
PWM
2 stops7h 05m
American Airlines
Deal found 1/27$273
This United Airlines deal was found by Cheapflights users on 1/27. 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 4/46:04 am
PWM
-
BNA
1 stop7h 24m
United Airlines
Mon 4/62:49 pm
BNA
-
PWM
1 stop5h 51m
United Airlines
Deal found 1/27$276

Find flight deals from Portland to Kentucky

Keep the following information in mind while searching for Portland to Kentucky flight deals. Data was last updated January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$237
(Delta)

One-way from

$119
(Delta)

Popular in

August

Cheapest in

June
Provider with most accurate pricing for Portland-Louisville Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-Louisville Intl flights.
Search Deals
From Portland to Kentucky
Search Deals
One-way flight from Portland to Kentucky
Search Deals
Highest demand for flights based on searches. 17% potential increase in price ($93 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($28 potential savings vs. average RT price).
Search Deals

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 January 29, 2026.
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 3/5

5:31 am-12:44 pm

1 stop8h 13m

Nashville Intl

Mon 3/9

4:37 pm-11:12 pm

1 stop5h 35m

$237

PortlandNashville

PWM - BNA

PWMBNA

Portland

Tue 2/24

3:30 pm-7:30 pm

1 stop5h 00m

Nashville Intl

Sat 2/28

5:05 am-2:45 pm

1 stop8h 40m

$237

PortlandNashville

PWM - BNA

PWMBNA

Portland

Wed 4/1

6:04 am-10:36 am

1 stop5h 32m

Nashville Intl

Wed 4/8

2:49 pm-9:40 pm

1 stop5h 51m

$237

PortlandNashville

PWM - BNA

PWMBNA

Portland

Sat 3/7

2:35 pm-8:25 pm

1 stop6h 50m

Nashville Intl

Mon 3/9

4:37 pm-11:12 pm

1 stop5h 35m

$237

PortlandNashville

PWM - BNA

PWMBNA

Portland

Wed 3/4

3:05 pm-10:32 pm

1 stop8h 27m

Nashville Intl

Tue 3/10

9:00 am-3:14 pm

1 stop5h 14m

$237

PortlandNashville

PWM - BNA

PWMBNA

Portland

Wed 4/1

6:00 am-1:30 pm

2 stops8h 30m

Nashville Intl

Wed 4/8

3:40 pm-11:22 pm

1 stop6h 42m

$242

PortlandNashville

PWM - BNA

PWMBNA

Portland

Mon 3/2

3:55 pm-9:45 pm

1 stop6h 50m

Nashville Intl

Thu 3/5

6:45 am-2:15 pm

1 stop6h 30m

$258

PortlandNashville

PWM - BNA

PWMBNA

Portland

Tue 5/12

2:35 pm-8:46 pm

1 stop7h 11m

Nashville Intl

Tue 5/19

5:25 am-12:18 pm

1 stop5h 53m

$258

PortlandNashville

PWM - BNA

PWMBNA

Portland

Sun 4/5

5:23 am-10:17 am

1 stop5h 54m

Nashville Intl

Sun 4/12

6:00 am-12:09 pm

1 stop5h 09m

$258

PortlandNashville

PWM - BNA

PWMBNA

Portland

Wed 6/3

5:20 am-9:26 am

1 stop5h 06m

Nashville Intl

Mon 6/8

12:52 pm-9:58 pm

1 stop8h 06m

$259

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 60 results
1
2
3
...
6

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 November is currently the most expensive (average of $273). 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 January 29, 2026.
Read through reviews of airlines operating flights from Portland to Kentucky, such as Delta and American Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,128 reviews

Entertainment

7.8

Crew

8.5

Comfort

7.9

Overall

7.9

Boarding

8.1

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,128 reviews
Delta
7.9
Good
8,128 reviews

Entertainment

7.8

Crew

8.5

Comfort

7.9

Overall

7.9

Boarding

8.1

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,205 reviews
Delta
7.9
Good
8,128 reviews

Entertainment

7.8

Crew

8.5

Comfort

7.9

Overall

7.9

Boarding

8.1

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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 5h. Fly via Delta, Southwest, or United Airlines 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 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 November is currently the most expensive (average of $273). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Portland to Kentucky

See prices for flight routes from nearby airports that may be better suited for you.
Boston to Fort Lauderdale flights
Boston to Tampa flights
Boston to Miami flights
Boston to Orlando flights
Boston to San Francisco flights
Boston to West Palm Beach flights
Boston to Los Angeles flights
Boston to Las Vegas flights
Boston to Dallas/Fort Worth flights
Boston to Fort Myers flights
Boston to Sky Harbor Intl flights
Boston to Sarasota flights
Boston to Atlanta flights
Boston to Denver flights
Boston to Seattle flights
Boston to Nashville flights
Boston to Baltimore flights
Boston to New Orleans flights
Boston to Salt Lake City flights
Boston to Hobby flights
Boston to Charleston flights
Boston to O'Hare Intl flights
Boston to Austin flights
Boston to Reagan-National flights
Boston to Dulles Intl flights
Boston to San Jose flights
Boston to San Diego flights
Boston to George Bush Intcntl flights
Boston to Jacksonville flights
Boston to Savannah flights
Boston to Raleigh flights
Boston to John F Kennedy Intl flights
Boston to Charlotte flights
Boston to Key West flights
Boston to Philadelphia flights
Boston to Newark flights
Portland to Orlando flights
Boston to Ontario flights
Boston to LaGuardia flights
Boston to Oakland flights
Boston to Pittsburgh flights
Boston to Myrtle Beach flights
Boston to Minneapolis flights
Boston to Detroit flights
Boston to Honolulu flights
Boston to Love Field flights
Boston to Cincinnati flights
Boston to Midway flights
Boston to Indianapolis flights
Boston to Daytona Beach flights

Top 2 airlines flying from Portland to Kentucky

Discover the top 2 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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$248Average$376FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$248Average$379FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.