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$119+ 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 2/25. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — PWM
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
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 January 29, 2026.

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.
Tue 2/178:54 am
BNA
-
PWM
1 stop7h 13m
American Airlines
Tue 2/246:00 am
PWM
-
BNA
1 stop7h 45m
American Airlines
Deal found 1/27$237
This Delta deal was found by Cheapflights users on 1/26. 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.
Sun 4/56:35 am
SDF
-
PWM
1 stop4h 29m
Delta
Tue 4/146:00 am
PWM
-
SDF
1 stop7h 31m
Delta
Deal found 1/26$265
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.
Thu 5/284:36 pm
LEX
-
PWM
1 stop6h 04m
American Airlines
Wed 6/311:01 am
PWM
-
LEX
1 stop4h 39m
American Airlines
Deal found 1/27$269
This American Airlines deal was found by Cheapflights users on 1/29. 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 3/48:54 am
BNA
-
PWM
1 stop7h 13m
American Airlines
Tue 3/1712:44 pm
PWM
-
BNA
2 stops8h 39m
American Airlines
Deal found 1/29$270
This Delta deal was found by Cheapflights users on 1/26. 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.
Mon 4/62:17 pm
SDF
-
PWM
2 stops9h 05m
Delta
Wed 4/85:23 am
PWM
-
SDF
1 stop6h 35m
Delta
Deal found 1/26$270
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 2/256:00 am
BNA
-
PWM
2 stops7h 23m
United Airlines
Tue 3/36:00 am
PWM
-
BNA
2 stops10h 34m
United Airlines
Deal found 1/28$271
This Delta deal was found by Cheapflights users on 1/26. 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.
Mon 4/62:17 pm
SDF
-
PWM
2 stops9h 05m
Delta
Tue 4/146:00 am
PWM
-
SDF
2 stops10h 42m
Delta
Deal found 1/26$276
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.
Sat 3/144:59 pm
BNA
-
PWM
1 stop5h 23m
Delta
Sat 3/214:48 pm
PWM
-
BNA
1 stop5h 22m
Delta
Deal found 1/28$278
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.
Sat 9/196:30 pm
TYS
-
PWM
1 stop4h 54m
American Airlines
Sat 9/267:20 pm
PWM
-
TYS
1 stop4h 50m
American Airlines
Deal found 1/27$279
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.
Wed 4/13:53 pm
TRI
-
PWM
1 stop7h 29m
Delta
Wed 4/85:23 am
PWM
-
TRI
1 stop7h 37m
Delta
Deal found 1/28$279
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.
Tue 2/246:43 am
LEX
-
PWM
1 stop4h 35m
Delta
Mon 3/95:48 pm
PWM
-
LEX
1 stop5h 18m
Delta
Deal found 1/28$279
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 3/48:54 am
BNA
-
PWM
1 stop7h 13m
American Airlines
Sun 3/85:40 pm
PWM
-
BNA
1 stop5h 48m
American Airlines
Deal found 1/27$283

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$237
(American Airlines)

One-way from

$119
(Delta)

Popular in

December

Cheapest in

January

Average price

$283
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. 11% potential increase in price ($54 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 29, 2026.
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 5/28

12:52 pm-9:58 pm

1 stop8h 06m

Portland

Sun 5/31

5:20 am-9:26 am

1 stop5h 06m

$237

NashvillePortland

BNA - PWM

BNAPWM

Nashville Intl

Tue 2/17

8:54 am-5:07 pm

1 stop7h 13m

Portland

Tue 2/24

6:00 am-12:45 pm

1 stop7h 45m

$237

NashvillePortland

BNA - PWM

BNAPWM

Nashville Intl

Wed 2/25

6:00 am-3:14 pm

1 stop8h 14m

Portland

Tue 3/3

3:05 pm-10:32 pm

1 stop8h 27m

$237

NashvillePortland

BNA - PWM

BNAPWM

Nashville Intl

Mon 6/15

8:30 am-2:29 pm

1 stop4h 59m

Portland

Sat 6/20

5:20 am-9:26 am

1 stop5h 06m

$237

NashvillePortland

BNA - PWM

BNAPWM

Nashville Intl

Tue 5/12

7:25 am-1:27 pm

1 stop5h 02m

Portland

Tue 5/19

4:45 pm-9:52 pm

1 stop6h 07m

$237

NashvillePortland

BNA - PWM

BNAPWM

Nashville Intl

Sun 7/5

11:15 am-5:12 pm

1 stop4h 57m

Portland

Thu 7/9

6:00 am-10:14 am

1 stop5h 14m

$237

LouisvillePortland

SDF - PWM

SDFPWM

Louisville Intl

Fri 4/10

5:35 pm-11:22 pm

1 stop5h 47m

Portland

Tue 4/14

6:00 am-1:31 pm

1 stop7h 31m

$265

LouisvillePortland

SDF - PWM

SDFPWM

Louisville Intl

Tue 4/7

5:04 pm-11:12 pm

1 stop6h 08m

Portland

Tue 4/14

6:00 am-10:48 am

1 stop4h 48m

$265

LouisvillePortland

SDF - PWM

SDFPWM

Louisville Intl

Mon 4/6

5:04 pm-11:12 pm

1 stop6h 08m

Portland

Wed 4/8

5:23 am-11:58 am

1 stop6h 35m

$265

LouisvillePortland

SDF - PWM

SDFPWM

Louisville Intl

Sun 4/5

6:35 am-11:04 am

1 stop4h 29m

Portland

Tue 4/14

6:00 am-1:31 pm

1 stop7h 31m

$265

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

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, 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.

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 47m. Fly via United Airlines, American Airlines, or Delta to get the fastest option. The distance from Kentucky to Portland, Maine is about 887 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, Cincinnati Cinci./N. Kentucky - 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 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

Browse thousands of different options on Cheapflights for your next trip

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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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$236Average$394FlexibilityNo cancel feeOn-time71%
DeltaCheapest$248Average$403FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$283Average$599FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$296Average$436FlexibilityNo cancel feeOn-time63%

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