$77 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 9/30. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Portland to Kentucky

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Louisville
Louisville1 stop$335
Lexington
Lexington1 stop$365
Nashville
Nashville1 stop$170
Louisville
Louisville1 stop$335
Lexington
Lexington1 stop$365
Nashville
Nashville1 stop$170

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

Wed, Aug 26 - Wed, Sep 2
Southwest Logo
7:45 am - 2:00 pm
PWM
-
BNA
7h 15m
1 stop
Southwest Logo
2:15 pm - 9:10 pm
BNA
-
PWM
5h 55m
1 stop
$170Southwest
Sat, Sep 12 - Mon, Sep 14
American Airlines Logo
7:00 am - 12:33 pm
PWM
-
BNA
6h 33m
1 stop
American Airlines Logo
4:42 pm - 11:59 pm
BNA
-
PWM
6h 17m
1 stop
$173American Airlines
Fri, Jul 3 - Mon, Jul 6
Breeze Airways Logo
7:00 am - 9:29 am
PWM
-
CVG
2h 29mnonstop
Breeze Airways Logo
8:22 pm - 10:38 pm
CVG
-
PWM
2h 16mnonstop
$173Breeze Airways
Fri, Jul 3 - Mon, Jul 6
Breeze Airways Logo
7:00 am - 9:29 am
PWM
-
CVG
2h 29mnonstop
Breeze Airways Logo
8:22 pm - 10:38 pm
CVG
-
PWM
2h 16mnonstop
$178Breeze Airways
Tue, Aug 25 - Sat, Sep 5
Delta Logo
6:30 am - 12:00 pm
PWM
-
BNA
6h 30m
1 stop
Delta Logo
12:42 pm - 9:31 pm
BNA
-
PWM
7h 49m
1 stop
$197Delta
Fri, Aug 28 - Sat, Sep 5
Delta Logo
6:30 am - 12:00 pm
PWM
-
BNA
6h 30m
1 stop
Delta Logo
12:42 pm - 9:31 pm
BNA
-
PWM
7h 49m
1 stop
$200Delta
Fri, Jul 24 - Fri, Jul 31
Multiple Airlines Logo
7:00 am - 9:29 am
PWM
-
CVG
2h 29mnonstop
Multiple Airlines Logo
9:30 pm - 10:27 am
CVG
-
PWM
12h 57m
1 stop
$247Multiple Airlines
Mon, Jul 27 - Thu, Jul 30
Multiple Airlines Logo
7:00 am - 9:29 am
PWM
-
CVG
2h 29mnonstop
Multiple Airlines Logo
6:29 pm - 9:12 am
CVG
-
PWM
14h 43m
1 stop
$249Multiple Airlines
Wed, Aug 26 - Sat, Aug 29
United Airlines Logo
7:35 pm - 11:59 pm
PWM
-
TYS
4h 24m
1 stop
United Airlines Logo
1:35 pm - 7:17 pm
TYS
-
PWM
5h 42m
1 stop
$328United Airlines
Thu, Jun 11 - Mon, Jun 15
United Airlines Logo
5:00 pm - 11:59 pm
PWM
-
LEX
6h 59m
1 stop
United Airlines Logo
1:55 pm - 9:51 pm
LEX
-
PWM
7h 56m
1 stop
$396United 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 June.

What is the cheapest month to fly from Portland to Kentucky?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Portland to Kentucky, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Portland to Kentucky is December, when tickets cost $153 (return) on average. On the other hand, the most expensive months are January and April, when the average cost of round-trip tickets is $482 and $446 respectively.

Good to know

Low seasonJanuary
Cheapest flight$77
Best time to beat the crowds with an average 6% drop in price.
Flight from Portland to Nashville

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.

Top tips for finding cheap flights to Kentucky

  • Looking for a cheap flight? 25% of our users found tickets from Portland to the following destinations at these prices or less: Nashville $229 one-way - $459 round-trip

Reviews of the top 3 airlines serving 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 8416 reviews
8.1Boarding
7.8Entertainment
7.2Food
7.8Comfort
8.5Crew
Airline reviews

No service flight that took 5 hrs and a stop at an unscheduled airport. Crew and pilots did their jobs

6.0 GoodAnonymous, May 2026
ATL - ECP
Read more Delta reviews

No service flight that took 5 hrs and a stop at an unscheduled airport. Crew and pilots did their jobs

Clean planes and not take my comfort class seat away.

Weather caused a long delay, but the efficiency and updates from the pilot were helpful. We were able to make our connection fortunately.

Planes were clean, no water or snacks on either flight.

Free & relatively fast Wi-Fi. Would've liked a wider drink selection.

I continue to be satisfied with Delta’s excellent service out of LGA. The digit id works well and gets me through security in no time. Whenever possible, I choose Delta.

Was revoked with Jet Blue due to delay from Kenya Air

Enjoyed it very much. Especially liked the free WiFi that Delta offers.

Smooth flight. Left on time, and got in 15 minutes early. Onboard video was great

For some reason, TSA Atlanta didn’t have my bag on the flight on time and they don’t have to provide Delta a reason for that.

It was a short flight so I was expecting too much

Horrifying Almost 2 million miles. Bring your own food and drink. One coffee or drink every three hours. Have to order meals on app more than 24 hours ahead Tiny and dirty bathrooms

Flight was delayed but more than 90 minutes. This caused me to miss my available windows for pick-up by a friend. I had to pay $125 for an uber back home from the airport which was an added expense that I had not budgeted for my trip. Staff was friendly.

Seat pitch is horrible especially on the 15 hour flight. Gate crew at SFO was Outstanding. The flight crew was also great.

Had a one hour delay due to mechanical issue. I didn’t think I’d be able to make my connecting flight, but they waited for me and greeted me when I arrived to help things run smooth.

6 1/2 hours from Tampa to SFO on a Boeing 737. Cramped. No Service. No real food. One pass for coffee at the beginning and a second pass THREE hours later. And check-in in Tampa was nasty even by United standards. And I am at almost TWO million miles on United. It's a non-stop. But terrible service.

MY FAMILY'S LUGGAGE WAS LOST FROM ROME TO BARI. I WAS THE ONLY ONE THAT RECEIVED MY LUGGAGE FROM ROME TO BARI. AFTER DEPLANING IN BARI, WE WASTED A LOT OF TIME AT BAG CLAIMS LOST AND FOUND REPORTING THE CLAIM AND PLEADING FOR THE BAGS TO BE DELIVERED THE NEXT DAY. WE WERE TOLD THAT IT TAKES 3 DAYS MINIMUM TO DELIVER. MY DAUGHTER AND MY GIRLFRIEND NEEDED THEIR PERSONAL THINGS AND WE WERE STAYING 3 HOURS AWAY FROM THE BARI AIRPORT. WE HAD TO DRIVE 3 HOURS TO THE AIRPORT TO COLLECT OUR LOST LUGGAGE THE NEXT DAY. WE ARE NOT HAPPY WITH THE EXPERIENCE

We had a delay, but thankfully I made it to my connection. Overall it went smooth

The flight had a delay but I made it to my connection. Flight was smooth overall

As I wrote earlier, poor planning and/or communication. At least twice, we were told that we would be boarding in less than ten minutes, only to have the flight again delayed at least another hour.

Movies on my phone are great. It would be nice to have a gluten free snack option.

It was what i expected. I like the movies you can access from your phone. It would be nice if there was a gluten free snack offered. But I did bring my own snack knowing there would not be a gluten free option

The flight was peaceful, just s slight turbulence, pilots and crews were all nice and made a great job! Arrived safely in the Philippines. Thank you ya’ll!

Ontario airport boarding was very easy to park and access, is clean and TSA took 10 minutes total. Check-in was a breeze and cruise was very nice.

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

The flight attendants were very friendly, efficient, and helpful. The plane was ahead of schedule, and it all went very smoothly. Thank you.

They lost my baggage and I am still struggling to the information and update

We got delayed getting out of DFW for broken overhead bins. Once the flight got underway the captain kept the seatbelt sign lit the entire flight despite little perceptible turbulence, preventing use of the rest rooms and any sort of refreshment service in the main cabin.

Flight delays for communication overall not a good experience uncomfortable on the plane. Person in front of me reclined his seat, putting them inches from my lap.

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

Information on your arrival and departure airports