$84 Find Cheap Flights from Portland to Kentucky

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Portland to Kentucky departing on 9/11. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Kentucky

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Portland to Kentucky, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Portland to Kentucky, as well as popular online travel agencies
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Cheap Flights from Portland to Kentucky

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Louisville
Louisville1 stop$263
Lexington
Lexington1 stop$400
Nashville
Nashville1 stop$187
Louisville
Louisville1 stop$263
Lexington
Lexington1 stop$400
Nashville
Nashville1 stop$187

Book Cheap Portland to Kentucky Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Portland to Kentucky that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Portland to Kentucky

Tue, May 12 - Tue, May 19
Delta Logo
2:38 pm - 9:45 pm
PWM
-
BNA
8h 07m
1 stop
Delta Logo
5:00 pm - 11:18 pm
BNA
-
PWM
5h 18m
1 stop
$187Delta
Tue, May 12 - Tue, May 19
Delta Logo
2:38 pm - 9:45 pm
PWM
-
BNA
8h 07m
1 stop
Delta Logo
5:00 pm - 11:18 pm
BNA
-
PWM
5h 18m
1 stop
$197Delta
Thu, Jun 4 - Tue, Jun 9
Southwest Logo
5:20 pm - 11:55 pm
PWM
-
BNA
7h 35m
2 stops
Southwest Logo
3:30 pm - 9:30 pm
BNA
-
PWM
5h 00m
1 stop
$202Southwest
Thu, Jun 4 - Tue, Jun 9
Southwest Logo
3:10 pm - 9:45 pm
PWM
-
BNA
7h 35m
2 stops
Southwest Logo
1:30 pm - 9:30 pm
BNA
-
PWM
7h 00m
2 stops
$207Southwest
Tue, Jun 30 - Sat, Jul 4
American Airlines Logo
6:00 am - 12:19 pm
PWM
-
BNA
7h 19m
1 stop
American Airlines Logo
6:16 am - 2:16 pm
BNA
-
PWM
7h 00m
1 stop
$237American Airlines
Tue, Jun 9 - Fri, Jun 12
United Airlines Logo
6:00 am - 1:49 pm
PWM
-
BNA
8h 49m
2 stops
United Airlines Logo
6:30 pm - 11:51 pm
BNA
-
PWM
4h 21m
1 stop
$242United Airlines
Tue, Apr 28 - Sat, May 2
United Airlines Logo
6:04 am - 1:14 pm
PWM
-
TYS
7h 10m
1 stop
United Airlines Logo
7:18 pm - 11:59 pm
TYS
-
PWM
4h 41m
1 stop
$245United Airlines
Wed, Apr 22 - Wed, Apr 29
American Airlines Logo
6:01 pm - 11:48 pm
PWM
-
SDF
5h 47m
1 stop
American Airlines Logo
6:00 am - 10:07 am
SDF
-
PWM
4h 07m
1 stop
$263American Airlines
Tue, Jul 7 - Fri, Jul 10
Multiple Airlines Logo
8:00 am - 1:52 pm
PWM
-
CVG
29h 52m
2 stops
Multiple Airlines Logo
8:22 pm - 10:38 pm
CVG
-
PWM
2h 16mnonstop
$309Multiple Airlines
Wed, Apr 29 - Mon, May 4
Multiple Airlines Logo
10:57 am - 1:31 pm
PWM
-
SDF
26h 34m
1 stop
Multiple Airlines Logo
7:48 pm - 4:16 pm
SDF
-
PWM
44h 28m
2 stops
$369Multiple Airlines
Booking Insights

KAYAK's insights & trends for Portland to Kentucky flights

Get data-powered insights and trends into flights from Portland to Kentucky to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Portland, Maine to Kentucky?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Portland, Maine to Kentucky departing in April.

Good to know

Low seasonJanuary
Cheapest flight$84
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly and prices are also 6% lower on average.
Flight from Portland to Cincinnati

FAQs - booking Kentucky flights

  • How does KAYAK find such low prices on flights from Portland to Kentucky?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Portland to Kentucky.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Portland to Kentucky?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Portland to Kentucky is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Portland to Kentucky?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Portland to Kentucky with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Portland to Kentucky?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Portland to Kentucky up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airlines flying from Portland to Kentucky

 
See real verified KAYAK customer reviews for airlines flying from Portland to Kentucky. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Portland to Kentucky? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
DeltaOverall score based on 8359 reviews
7.2Food
7.8Entertainment
8.1Boarding
8.5Crew
7.9Comfort
Airline reviews

The flight was delayed 90 minutes The Gate was wrong The Restroom on Aircraft was not clean There was a half used water bottle in my seat

2.0 MediocreJames, Mar 2026
BOS - LGA
Read more Delta reviews

The flight was delayed 90 minutes The Gate was wrong The Restroom on Aircraft was not clean There was a half used water bottle in my seat

Delta is always a wonderful experience. A clean plane and the crew is really friendly.

Too many people are taking up space in the overhead bins with their extra piece of luggage. Since they cannot fit their backpacks or extra luggage piece under the seat in front of them, they store it in the overheads and thus taking up room for other passengers. It wasn’t only one or two persons; more like 12 or 13 passengers.

This was the worse experience. They delayed our flight twice and we still had to find another flight to get home sooner which was alos delayed. Also, the flight attendant named Ginny on DL9890 leaving at 4:13pm on 3/23/26 was extremely rude.

I love Delta the flight attendants were personable and the flight arrived 1/2 earlier thanks expected. All a plus. The gate agent was a bit flustered but even with that I still had a good experience. Her supervisor assisted me.

Got to fly my favorite plane, the Boeing 767-400ER, to Milan. The soft blush pink mood lighting during meal service was very beautiful and gorgeous. The service was top-notch, and our flights were on time. I highly recommend Delta.

I am still at the Airport! Delayed Delayed and Delyaed

I took seat 15A in anticipation of window seat, there is no window.

The first class flight attendant was awful to everyone. Very rude; no customer service. She should not be working in first class.

Snacks and included beverages were appreciated. Boarding went smoothly. Plenty of overhead bin space. Seats get very uncomfortable after a couple of hours. After waiting 10 painful minutes for my walker, a very nice Delta guest agent pushed me in a wheelchair to the gate. It was finally delivered to me after another 15 minutes . Our checked bag was on the carousel long b4 I was able to retrieve it. Fortunately it was still there but somewhere along the way the straps we used to secure it were removed and and were not reattached. Wish I had made note of the agents name.

The flight itself was excellent but the gate attendant made me check my carryon since she said it was an inch too big. I’ve had no problems with this carryon on recent flights on Qantas, Delta, Austrian, Southwest Airlines even though the overhead bins are the same size. there were other carryons in the bins that also looked larger than mine and there was room left in the bins for more. When I picked up my carryon from baggage claim one of the wheels had broken off.

The flight changed gates multiple times and flight had to be delayed multiple times

We called Kayak for a change due to the TSA situation in Atlanta. What we got was a canceled return flight (in error) and we had to find the mistake. Not happy with Kayak who blamed it on AA.

I was in last row so that is never great bc the person in front of me leaned his seat all the way back into me.

Delayed for mechanical and no updates on what was happening and how long the delay might be.

My flight from LGA was cancelled and my rebooked flight from JFK was delayed numerous times. I will now be getting home after 2am.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

On the return flight, arriving in Denver we sat on the tarmac in Denver for over 20 minutes.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The flight attendant in business class was excellent! Professional, friendly and attentive.

Everything you need to know for your flight from Portland to Kentucky

Information on your arrival and departure airports