$92 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 9/14. 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$362
Lexington
Lexington1 stop$329
Nashville
Nashville1 stop$201
Louisville
Louisville1 stop$362
Lexington
Lexington1 stop$329
Nashville
Nashville1 stop$201

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

Fri, Sep 11 - Mon, Sep 14
Breeze Airways Logo
6:00 am - 8:33 am
PWM
-
CVG
2h 33mnonstop
Breeze Airways Logo
9:11 pm - 11:24 pm
CVG
-
PWM
2h 13mnonstop
$158Breeze Airways
Fri, Aug 14 - Fri, Aug 21
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
Mon, Aug 24 - Sun, Aug 30
Multiple Airlines Logo
7:00 am - 9:29 am
PWM
-
CVG
2h 29mnonstop
Multiple Airlines Logo
2:24 pm - 5:49 pm
CVG
-
PWM
27h 25m
1 stop
$199Multiple Airlines
Mon, Aug 24 - Sun, Aug 30
Multiple Airlines Logo
7:00 am - 9:29 am
PWM
-
CVG
2h 29mnonstop
Multiple Airlines Logo
12:26 pm - 9:12 am
CVG
-
PWM
20h 46m
2 stops
$252Multiple Airlines
Wed, Aug 5 - Sat, Aug 8
United Airlines Logo
6:00 am - 12:29 pm
PWM
-
BNA
7h 29m
1 stop
United Airlines Logo
12:49 pm - 9:41 pm
BNA
-
PWM
7h 52m
1 stop
$277United Airlines
Wed, Aug 5 - Sat, Aug 8
United Airlines Logo
5:15 am - 9:29 am
PWM
-
BNA
5h 14m
1 stop
United Airlines Logo
12:49 pm - 11:30 pm
BNA
-
PWM
9h 41m
2 stops
$282United Airlines
Thu, Aug 27 - Mon, Aug 31
American Airlines Logo
5:30 am - 10:43 am
PWM
-
TYS
5h 13m
1 stop
American Airlines Logo
6:57 am - 2:21 pm
TYS
-
PWM
7h 24m
1 stop
$291American Airlines
Tue, Jul 14 - Tue, Jul 21
Delta Logo
11:01 am - 4:38 pm
PWM
-
TYS
5h 37m
1 stop
Delta Logo
5:35 pm - 11:30 pm
TYS
-
PWM
5h 55m
1 stop
$295Delta
Tue, Sep 22 - Fri, Sep 25
American Airlines Logo
5:30 am - 9:45 am
PWM
-
BNA
5h 15m
1 stop
American Airlines Logo
6:10 am - 3:51 pm
BNA
-
PWM
8h 41m
1 stop
$300American Airlines
Fri, Aug 7 - Wed, Aug 12
Delta Logo
6:05 am - 1:01 pm
PWM
-
TRI
6h 56m
1 stop
Delta Logo
3:46 pm - 11:13 pm
TRI
-
PWM
7h 27m
1 stop
$309Delta
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 September.

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$92
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly and prices are also 8% 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.

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 $204 one-way - $417 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.
7.8
DeltaOverall score based on 8455 reviews
8.5Crew
8.1Boarding
7.8Entertainment
7.8Comfort
7.2Food
Airline reviews

It was as good as it could be. Flying is not a pleasant experience these days.

8.0 ExcellentMark, Jun 2026
LAX - ORD
Read more Delta reviews

It was as good as it could be. Flying is not a pleasant experience these days.

The plane was old and thus the seats were not good. No cushion left whatsoever, and it all was a bit worn out.

I was in Comfort and we didn’t get any drinks, chips or anything! First Class got full service on the flight and Comfort got nothing. Seat was horrible and uncomfortable

My flight was delayed by 4 hours in 30 minute increments. The gate agents were amazing but the communication was not. We were told that there was a maintenance issue but they didn't know what it was. That didn't inspire confidence. Then they said they found it and it was fixed and the pilot just needed to sign off. Then the pilot needed to talk to the other pilot from the arriving flight and we'd be fine. Then we were waiting for the pilot to call back. Then the maintenance issue wasn't fixed. Then they decided we were getting a new plane (why didn't they decide this earlier??). Fine. But then they announced we were changing gates AND terminals. And we were boarding in 20 minutes. So we all had to run to the new terminal gate. We could have taken off at that time, but we then had to wait for all the people who rebooked on a different flight to book this flight again. That took 30+ minutes because there was only one gate agent. When everyone ditched this flight, I saw it as an opportunity to upgrade to comfort. Delta, the greedy jerks they are, charged me $121. After their delay, their fault, their issues, couldn't even discount an upgrade. They only handed out $12 meal vouchers for the delay. I can't even get a snack from starbucks for that.

The crew was very inconsiderate and rude. My flight was scheduled to depart at 6:00am. I received a call from the crew at 5:40am, asking if I was going to make the flight because I was the only one that hasn't boarded yet and boarding ends at 5:50am. I let them know that I will be at the gate in a few minutes, before the 5:50am cutoff. When I arrived at the gate at 5:45am the gate was closed. Departing early on last minute notice without having all passengers on board is inconsiderate and unprofessional.

FA was a bit strange and dodgy not very characteristic of Delta

Not really a “Delta” problem but worth mentioning: Boarding was a difficult process. TSA seemed understaffed and Pre-Check took longer than regular TSA. The supervisor was frazzled and yelled at travelers. Once through TSA, we had to put our carry-ons through another x-ray machine. Then queue up to board with both boarding pass and ID. Then, when we got to the stairs on the tarmac, we had to show our boarding pass again. Maybe this is just normal for Kona since the terminal is outdoors (but still a “secured” area).

flight was delayed 4+ hours. there was really no understanding of why? weather? the last hour of delay was post boarding. pilot seat was broken. was that the real reason? nonetheless, long day of inconveniences.

Lady Pilot was perfect in every way wheels up to wheels down communication, professionalism, excellent on time departure and on time arrival, excellent communication! Fantastic job with Superb attitude!!

Delta did an awful job w logistics at DTW. Missed connection. We were there an hour early. SUCKED

Great staff. Clean plane, but we were delayed for more than an hour due to maintenance issues and had to board another plane.

I was exhausted from a long day. The flight was smooth. The first flight during my 3 week travel that took off on time.

1 flight cancelled Had to fly out of different city Flight at new departure city was delayed 3 hours causing us to miss connecting flights. By the time we did make it to Prague our luggage did not. Had to wait day and a half for luggage to be delivered. Customer service was not good. Agents did not arrive at gate until 5-10 minutes before boarding

Awful. Delayed flights, missed connection to Toronto. Hotel vouchers were for already booked hotels x3. Giant waste of my time

Horrible I am at almost 2,000,000 miles on United. This was probably the worst flight ever. An hour and a half before takeoff I get a message that they’re changing the plane and I no longer have a seat in Polaris business Supposedly, there was a problem with the plane, but then there was no other plane Finally, they decided to bring a plane from Newark to Washington Dulles Of course the original flight was at 10:45 PM so by the time the plane got there it was 12:30 AM. It had not been cleaned. It had not been catered. They don’t really have people available to do those things when it’s not pre-programmed at 1 o’clock in the morning. The crew had to be changed And the new plane held 28 fewer people than the scheduled plane There is no way you can hate United Airlines enough The people at the gate were actually just fine, but it was management who was completely useless And did they send extra help to the people at the gate? Did they send supervisors? Of course not. Just don’t take United find somebody else or buy a boat

Great experience. Boarding was fast, staff were very nice and funny, everything at the seat worked well.

Both my flight where delayed Had 25min to make it to my transfer flight

Short flight, but no drink/snack service. The flights both going and coming were delayed.

I just got back from a trip with 3 flights each way. The flights were good and we were happy with out experience. There was one steward on our first flight that was harsh and grump with passengers. It did not leave a good impression. All of the other flight crews were great on the other five flights.

They changed my flight 5 hours before it took off and changed my connecting airport messing up my entire 1st day in Japan.

The gate got changed several times and the flight was delayed over an hour. Awful experience

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

No Snacks or Entertainment. The flight was short, snacks should still be given.

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

My Internet did not work for Outlook email or basically anything. I paid for one hour of in-flight usage and it was terrible. I spent a lot of time on different sites and browsers with no luck and a lot of frustration. Other than that, the flight was on time, crew was nice, service was fine. Seat was OK even though I paid for the extra 6 inches. I cannot imagine how tight the seats in the back must be.

The plane was probably full boarding was easy. We were able to check our carry-on luggage for free. It was a return flight through Philly to LA. Never saw a stewardess do a demonstration of emergency Procedures. I think my flight was pretty full

Everything was fine. Flight boarded and departed on time. Seating was spacious enough for my carryon to fit under the seat in front of me. No complaints at all. Flight even arrived early.

Boston ticket agent Cheryl Porter is WONDERFUL. Our Iberia flight to Barcelona was cancelled the morning we were scheduled to leave and Cheryl was our super hero - she found us seats on a flight to London and on to Barcelona. Truly a “can-do” attitude which we appreciated so much after the Iberia ticket agents told us there was “absolutely nothing they could do”. (As did the customer service agents at Iberia’s call center) Ms Porter is truly a wonderful person who genuinely cares about travelers!

Flight was delayed after boarding and no idea when it would take off. Crew in Portland did arrange for transport to Boston for a different set of flights to my destination.

Seats are so close together. Middle seats should be discounted.

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

Information on your arrival and departure airports