What is the cheapest airline that flies from Portland to Kentucky?

Breeze Airways, Delta, and United Airlines are the most popular carriers operating from Portland to Kentucky

What airlines fly to Kentucky?

American Airlines, Delta and Southwest are the top three most popular airlines that fly to Kentucky from Portland, Maine according to our data. American Airlines is the first choice among our users, with 50% of people opting to fly with this airline when traveling to Kentucky. Keep in mind that there are 5 different airlines that fly to Kentucky on a routine basis, so you have a few additional options to choose from.

When did momondo last update prices for flights from Portland Airport to Kentucky?

Prices for flights from Portland Airport to Kentucky are updated daily.

How many operators does momondo search for flights from Portland Airport to Kentucky?

There are 4 operators available for flights from Portland Airport to Kentucky as of November 2026.

How old do you have to be to fly from Portland Airport to Kentucky?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Portland Airport to Kentucky.

What documentation or ID do you need to fly to Kentucky?

The required travel and health documents for your Kentucky trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Kentucky. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

$168 Cheap Flights from Portland, Maine to Kentucky in 2026/27

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Portland, Maine to Kentucky

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

10:54 am - 6:17 pmPWM Portland-SDF Louisville Intl

7h 23m1 stop Sarasota Bradenton Intl

4:04 pm - 4:20 pmSDF Louisville Intl-PWM Portland

24h 16m2 stops Orlando Sanford Intl Charleston

$335Multiple Airlines

Thu, Jan 28 - Sun, Jan 31

10:54 am - 6:17 pmPWM Portland-SDF Louisville Intl

7h 23m1 stop Sarasota Bradenton Intl

4:04 pm - 9:08 amSDF Louisville Intl-PWM Portland

17h 04m1 stop Orlando Sanford Intl

$354Multiple Airlines

Thu, Jan 28 - Sun, Jan 31

7:10 am - 12:14 pmPWM Portland-SDF Louisville Intl

5h 04m1 stop Newark

2:25 pm - 7:14 pmSDF Louisville Intl-PWM Portland

4h 49m1 stop Washington, D.C. Dulles Intl

$368United Airlines

Sat, Feb 13 - Wed, Feb 17

6:00 am - 11:47 amPWM Portland-LEX Lexington Blue Grass

5h 47m1 stop Atlanta Hartsfield-Jackson

3:34 pm - 11:33 pmLEX Lexington Blue Grass-PWM Portland

7h 59m1 stop Atlanta Hartsfield-Jackson

$369Delta

Wed, Dec 2 - Wed, Dec 9

5:12 pm - 11:10 pmPWM Portland-LEX Lexington Blue Grass

5h 58m1 stop New York LaGuardia

5:54 pm - 11:35 pmLEX Lexington Blue Grass-PWM Portland

5h 41m1 stop Atlanta Hartsfield-Jackson

$369Delta

Fri, Feb 12 - Sun, Feb 14

7:10 am - 12:14 pmPWM Portland-SDF Louisville Intl

5h 04m1 stop Newark

7:17 am - 2:32 pmSDF Louisville Intl-PWM Portland

7h 15m2 stops Chicago O'Hare Intl Washington, D.C. Dulles Intl

$373United Airlines

Sat, Feb 13 - Wed, Feb 17

5:10 pm - 12:25 amPWM Portland-SDF Louisville Intl

7h 15m1 stop Baltimore/Washington

3:30 pm - 9:50 pmSDF Louisville Intl-PWM Portland

6h 20m1 stop Baltimore/Washington

$412Southwest

Mon, Jan 4 - Thu, Jan 7

5:10 pm - 12:25 amPWM Portland-SDF Louisville Intl

7h 15m1 stop Baltimore/Washington

7:05 am - 2:50 pmSDF Louisville Intl-PWM Portland

7h 45m2 stops Orlando Baltimore/Washington

$417Southwest

Mon, Jan 4 - Thu, Jan 7

6:00 am - 12:28 pmPWM Portland-LEX Lexington Blue Grass

6h 28m1 stop Philadelphia

4:27 pm - 11:27 pmLEX Lexington Blue Grass-PWM Portland

7h 00m1 stop Chicago O'Hare Intl

$433American Airlines

Thu, Apr 22 - Mon, Apr 26

1:38 pm - 11:34 pmPWM Portland-LEX Lexington Blue Grass

9h 56m2 stops Washington, D.C. Reagan-National Chicago O'Hare Intl

5:17 am - 11:45 amLEX Lexington Blue Grass-PWM Portland

6h 28m1 stop Chicago O'Hare Intl

$435American Airlines

Sat, Feb 13 - Wed, Feb 17

Cheap last minute flights

Enter your travel dates to find the best prices.

5:18 pm - 11:03 pmPWM Portland-LEX Lexington Blue Grass

5h 45m1 stop New York LaGuardia

3:38 pm - 11:31 pmLEX Lexington Blue Grass-PWM Portland

7h 53m1 stop Atlanta Hartsfield-Jackson

$494Delta

Wed, Nov 18 - Sun, Nov 22

11:39 am - 11:58 pmPWM Portland-LEX Lexington Blue Grass

12h 19m2 stops New York LaGuardia Atlanta Hartsfield-Jackson

6:00 am - 1:01 pmLEX Lexington Blue Grass-PWM Portland

7h 01m1 stop Atlanta Hartsfield-Jackson

$499Delta

Wed, Nov 18 - Sun, Nov 22

12:13 pm - 11:48 pmPWM Portland-LEX Lexington Blue Grass

11h 35m2 stops Washington, D.C. Reagan-National Chicago O'Hare Intl

5:15 am - 3:35 pmLEX Lexington Blue Grass-PWM Portland

10h 20m2 stops Chicago O'Hare Intl Washington, D.C. Reagan-National

$504American Airlines

Wed, Nov 18 - Sun, Nov 22

3:04 pm - 7:57 pmPWM Portland-SDF Louisville Intl

4h 53m1 stop Washington, D.C. Reagan-National

11:42 am - 6:00 pmSDF Louisville Intl-PWM Portland

6h 18m1 stop Philadelphia

$685American Airlines

Sat, Nov 14 - Thu, Nov 19

10:50 am - 6:32 pmPWM Portland-SDF Louisville Intl

7h 42m2 stops Newark Chicago O'Hare Intl

9:55 am - 2:27 pmSDF Louisville Intl-PWM Portland

4h 32m1 stop Washington, D.C. Dulles Intl

$736United Airlines

Sat, Nov 14 - Thu, Nov 19

5:08 pm - 10:30 pmPWM Portland-SDF Louisville Intl

5h 22m1 stop Chicago O'Hare Intl

6:00 am - 2:27 pmSDF Louisville Intl-PWM Portland

8h 27m2 stops Newark Washington, D.C. Dulles Intl

$736United Airlines

Sat, Nov 14 - Thu, Nov 19

2:05 pm - 7:30 pmPWM Portland-SDF Louisville Intl

5h 25m1 stop Washington, D.C. Dulles Intl

7:00 am - 2:27 pmSDF Louisville Intl-PWM Portland

7h 27m2 stops Chicago O'Hare Intl Washington, D.C. Dulles Intl

$736United Airlines

Sat, Nov 14 - Thu, Nov 19

5:30 am - 1:37 pmPWM Portland-SDF Louisville Intl

8h 07m2 stops Washington, D.C. Dulles Intl Chicago O'Hare Intl

6:00 am - 2:27 pmSDF Louisville Intl-PWM Portland

8h 27m2 stops Newark Washington, D.C. Dulles Intl

$741United Airlines

Sat, Nov 14 - Thu, Nov 19

4:50 pm - 9:18 pmPWM Portland-LEX Lexington Blue Grass

4h 28m1 stop Detroit Metropolitan Wayne County

6:00 am - 1:01 pmLEX Lexington Blue Grass-PWM Portland

7h 01m1 stop Atlanta Hartsfield-Jackson

$870Delta

Mon, Nov 16 - Wed, Nov 18

4:03 pm - 11:58 pmPWM Portland-LEX Lexington Blue Grass

7h 55m2 stops New York John F Kennedy Intl Atlanta Hartsfield-Jackson

7:35 am - 11:58 amLEX Lexington Blue Grass-PWM Portland

4h 23m1 stop Detroit Metropolitan Wayne County

$875Delta

Mon, Nov 16 - Wed, Nov 18

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United Airlines flights from Portland, Maine to Kentucky

Our best United Airlines deals on Portland, Maine to Kentucky flight tickets

United Airlines

Feb 13

PWM7:10 amPortland

5h 04m

1 stop

SDF12:14 pmLouisville Intl

Feb 17

SDF2:25 pmLouisville Intl

4h 49m

1 stop

PWM7:14 pmPortland

$368

United Airlines

Feb 13

PWM7:10 amPortland

5h 04m

1 stop

SDF12:14 pmLouisville Intl

Feb 17

SDF7:17 amLouisville Intl

7h 15m

2 stops

PWM2:32 pmPortland

$373

United Airlines

Dec 2

PWM6:00 amPortland

7h 23m

1 stop

SDF1:23 pmLouisville Intl

Dec 5

SDF2:05 pmLouisville Intl

5h 20m

1 stop

PWM7:25 pmPortland

$447

Southwest flights from Portland, Maine to Kentucky

Our best Southwest deals on Portland, Maine to Kentucky flight tickets

Southwest

Jan 4

PWM5:10 pmPortland

7h 15m

1 stop

SDF12:25 amLouisville Intl

Jan 7

SDF3:30 pmLouisville Intl

6h 20m

1 stop

PWM9:50 pmPortland

$412

Southwest

Jan 4

PWM5:10 pmPortland

7h 15m

1 stop

SDF12:25 amLouisville Intl

Jan 7

SDF7:05 amLouisville Intl

7h 45m

2 stops

PWM2:50 pmPortland

$417

Southwest

Jan 28

PWM12:55 pmPortland

7h 25m

2 stops

SDF8:20 pmLouisville Intl

Jan 31

SDF3:05 pmLouisville Intl

8h 45m

2 stops

PWM11:50 pmPortland

$422

momondo Fare Finder

Use the filters below to find and compare flights from Portland, Maine to Kentucky that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PortlandLouisville

PWM Portland - SDF Louisville Intl

PWMSDF

Portland

Thu 1/28

10:54 am-6:17 pm

1 stop7h 23m

Louisville Intl

Sun 1/31

4:04 pm-4:20 pm

2 stops24h 16m

$335

PortlandLouisville

PWM Portland - SDF Louisville Intl

PWMSDF

Portland

Thu 1/28

10:54 am-6:17 pm

1 stop7h 23m

Louisville Intl

Sun 1/31

4:04 pm-9:08 am

1 stop17h 04m

$354

Quickest round-trip

PortlandLouisville

PWM Portland - SDF Louisville Intl

PWMSDF

Portland

Sat 2/13

7:10 am-12:14 pm

1 stop5h 04m

Louisville Intl

Wed 2/17

2:25 pm-7:14 pm

1 stop4h 49m

$368

PortlandLexington

PWM Portland - LEX Lexington Blue Grass

PWMLEX

Portland

Wed 12/2

6:00 am-11:47 am

1 stop5h 47m

Lexington Blue Grass

Wed 12/9

3:34 pm-11:33 pm

1 stop7h 59m

$369

PortlandLexington

PWM Portland - LEX Lexington Blue Grass

PWMLEX

Portland

Fri 2/12

5:12 pm-11:10 pm

1 stop5h 58m

Lexington Blue Grass

Sun 2/14

5:54 pm-11:35 pm

1 stop5h 41m

$369

PortlandLouisville

PWM Portland - SDF Louisville Intl

PWMSDF

Portland

Sat 2/13

7:10 am-12:14 pm

1 stop5h 04m

Louisville Intl

Wed 2/17

7:17 am-2:32 pm

2 stops7h 15m

$373

PortlandLouisville

PWM Portland - SDF Louisville Intl

PWMSDF

Portland

Mon 1/4

5:10 pm-12:25 am

1 stop7h 15m

Louisville Intl

Thu 1/7

3:30 pm-9:50 pm

1 stop6h 20m

$412

PortlandLouisville

PWM Portland - SDF Louisville Intl

PWMSDF

Portland

Mon 1/4

5:10 pm-12:25 am

1 stop7h 15m

Louisville Intl

Thu 1/7

7:05 am-2:50 pm

2 stops7h 45m

$417

PortlandLexington

PWM Portland - LEX Lexington Blue Grass

PWMLEX

Portland

Thu 4/22

6:00 am-12:28 pm

1 stop6h 28m

Lexington Blue Grass

Mon 4/26

4:27 pm-11:27 pm

1 stop7h 00m

$433

PortlandLexington

PWM Portland - LEX Lexington Blue Grass

PWMLEX

Portland

Sat 2/13

1:38 pm-11:34 pm

2 stops9h 56m

Lexington Blue Grass

Wed 2/17

5:17 am-11:45 am

1 stop6h 28m

$435

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Portland, Maine to Kentucky

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

What is the cheapest month to fly to Kentucky?

If you’re not able to fly to Kentucky in March, then September is your next best option. Flight prices from Portland, Maine to Kentucky during September average around $406.

Cheap Portland, Maine to Kentucky flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Portland, Maine to Kentucky

Best Price Found	$168
Fastest flight time	2h 55m
Direct flights	None

The best one-way flight to Kentucky from Portland, Maine in the past 72 hours is $168. The best round-trip flight deal from Portland, Maine to Kentucky found on momondo in the last 72 hours is $335.

The fastest flight from Portland, Maine to Kentucky takes 2h 55m

There are no direct flights from Portland, Maine to Kentucky. There are no popular flight routes from Portland, Maine to Kentucky.

Search flight deals

Frequently asked questions about flying from Portland, Maine to Kentucky

When did momondo last update prices for flights from Portland Airport to Kentucky?
Prices for flights from Portland Airport to Kentucky are updated daily.
How many operators does momondo search for flights from Portland Airport to Kentucky?
There are 4 operators available for flights from Portland Airport to Kentucky as of November 2026.
How old do you have to be to fly from Portland Airport to Kentucky?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Portland Airport to Kentucky.
What documentation or ID do you need to fly to Kentucky?
The required travel and health documents for your Kentucky trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Kentucky. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Best airlines flying from Portland, Maine to Kentucky

Compare and see reviews for airlines that fly from Portland, Maine to Kentucky with momondo

Airline	Rating	Free Cancellation	Price
American Airlines	PriceFrom $288	Free Cancellation	Rating 7.0 12,226 reviews	Search American Airlines flights
Southwest	PriceFrom $288	Free Cancellation	Rating 8.0 4,218 reviews	Search Southwest flights
Delta	PriceFrom $289	Free Cancellation	Rating 7.8 8,709 reviews	Search Delta flights
United Airlines	PriceFrom $306	Free Cancellation	Rating 7.3 10,480 reviews	Search United Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Portland to Kentucky?

It is quick and easy to find Portland to Kentucky flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Kentucky that suits you.

Can I find flights from Portland to Kentucky with flexible booking policies on momondo?

Flights from Portland to Kentucky with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Portland to Kentucky?

momondo provides multiple filters to help you find the best flight to Kentucky from Portland. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Portland to Kentucky right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Portland to Kentucky now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Kentucky and let you know when they change.