$74 Find Cheap Flights from Portland to Kentucky - Compare and Save

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 8/31. 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.
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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$281
Lexington
Lexington1 stop$319
Nashville
Nashville1 stop$279
Louisville
Louisville1 stop$281
Lexington
Lexington1 stop$319
Nashville
Nashville1 stop$279

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

Mon, Aug 31 - Mon, Sep 7
Breeze Airways Logo
7:00 am - 9:29 amPWM  Portland-CVG Cincinnati Cinci./N. Kentucky
2h 29mnonstop
Breeze Airways Logo
8:22 pm - 10:38 pmCVG  Cincinnati Cinci./N. Kentucky-PWM Portland
2h 16mnonstop
$143Breeze Airways
Fri, Oct 2 - Mon, Oct 5
Breeze Airways Logo
7:00 am - 9:33 amPWM  Portland-CVG Cincinnati Cinci./N. Kentucky
2h 33mnonstop
Breeze Airways Logo
9:11 pm - 11:24 pmCVG  Cincinnati Cinci./N. Kentucky-PWM Portland
2h 13mnonstop
$153Breeze Airways
Tue, Sep 1 - Mon, Sep 7
Multiple Airlines Logo
8:00 am - 1:25 pmPWM  Portland-CVG Cincinnati Cinci./N. Kentucky
29h 25m2 stops Charleston Orlando
Multiple Airlines Logo
8:22 pm - 10:38 pmCVG  Cincinnati Cinci./N. Kentucky-PWM Portland
2h 16mnonstop
$189Multiple Airlines
Fri, Aug 28 - Sun, Aug 30
Multiple Airlines Logo
7:00 am - 9:29 amPWM  Portland-CVG Cincinnati Cinci./N. Kentucky
2h 29mnonstop
Multiple Airlines Logo
2:24 pm - 5:49 pmCVG  Cincinnati Cinci./N. Kentucky-PWM Portland
27h 25m1 stop Charleston
$199Multiple Airlines
Wed, Sep 9 - Mon, Sep 14
Delta Logo
6:30 am - 11:04 amPWM  Portland-TYS Knoxville McGhee Tyson
4h 34m1 stop New York LaGuardia
Delta Logo
5:15 pm - 11:17 pmTYS  Knoxville McGhee Tyson-PWM Portland
6h 02m1 stop New York LaGuardia
$292Delta
Wed, Oct 7 - Tue, Oct 13
Delta Logo
1:52 pm - 9:09 pmPWM  Portland-TYS Knoxville McGhee Tyson
7h 17m1 stop New York LaGuardia
Delta Logo
6:23 pm - 11:35 pmTYS  Knoxville McGhee Tyson-PWM Portland
5h 12m1 stop Atlanta Hartsfield-Jackson
$299Delta
Thu, Aug 27 - Mon, Aug 31
American Airlines Logo
6:02 am - 10:45 amPWM  Portland-TYS Knoxville McGhee Tyson
4h 43m1 stop Washington, D.C. Reagan-National
American Airlines Logo
5:15 am - 12:40 pmTYS  Knoxville McGhee Tyson-PWM Portland
7h 25m1 stop Charlotte Douglas
$299American Airlines
Thu, Aug 27 - Wed, Sep 2
American Airlines Logo
1:25 pm - 8:59 pmPWM  Portland-TYS Knoxville McGhee Tyson
7h 34m1 stop Charlotte Douglas
American Airlines Logo
8:10 am - 12:40 pmTYS  Knoxville McGhee Tyson-PWM Portland
4h 30m1 stop Charlotte Douglas
$299American Airlines
Thu, Aug 27 - Wed, Sep 2
United Airlines Logo
3:45 pm - 11:59 pmPWM  Portland-TYS Knoxville McGhee Tyson
8h 14m2 stops Newark Washington, D.C. Dulles Intl
United Airlines Logo
1:53 pm - 9:23 pmTYS  Knoxville McGhee Tyson-PWM Portland
7h 30m1 stop Chicago O'Hare Intl
$304United Airlines
Thu, Aug 27 - Wed, Sep 2
United Airlines Logo
3:45 pm - 11:59 pmPWM  Portland-TYS Knoxville McGhee Tyson
8h 14m2 stops Newark Washington, D.C. Dulles Intl
United Airlines Logo
7:00 am - 2:38 pmTYS  Knoxville McGhee Tyson-PWM Portland
7h 38m2 stops Chicago O'Hare Intl Washington, D.C. Dulles Intl
$309United 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 September.

Flight prices are below average for this route right now.

Flights to Kentucky from Portland, Maine usually cost between $406 and $738 in September.
The lowest price found in the past 5 days was $281 on Breeze Airways (Sep 10-Sep 12).

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 February, when tickets cost $340 (return) on average. On the other hand, the most expensive months are April and January, when the average cost of round-trip tickets is $727 and $482 respectively.

Good to know

Low season

January

Cheapest flight

$74
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly and prices are also 5% 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 $215 one-way - $416 round-trip

Reviews of the top 4 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.
8.0
SouthwestOverall score based on 4216 reviews
8.1Boarding
8.0Comfort
8.6Crew
7.5Entertainment
7.0Food
Airline reviews

Flight time kept changing and so did the gate. It was very frustrating

2.0 MediocreAnonymous, Aug 2026
Read more Southwest reviews

Flight time kept changing and so did the gate. It was very frustrating

Exceptional. The gate crew responded quickly and got me onto this earlier flight as the final passenger, saving me more than four hours of wait time for my reserved flight.

The flight was delayed due to earlier issues at other airports. The crew was excellent & made it a good trip.

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

Eveeyrime I fly they are begging for bags due to cabin overhead space. What they should so ia take the bags that are clearly too big to fit wheels first on their side. And those of us who give up the bag should really get their bags first. When boarding, nobody wants stupid jokes about how hot it is on board. Give us some cool air. Im usually sick from the heat by the time we take off.

No wifi, seems to be very common with Southwest currently. Everything else was normal.

Poor customer service, no accommodation for passengers when the flight was delayed over 5 hours.

The seats were a bit cramped and worn, but otherwise okay.

Boarded the plane in Portland and sat on the tarmac for four hours before being given clearance to take off. Apparently a "scratch" was detected on the preflight inspection. This delay resulted in me missing my connection in Baltimore. I therefore had to stay overnight and then catch an early flight this morning, which resulted in my missing a mandatory class. I would like a refund / voucher to cover the cost of the missed flight. And additional voucher for the time spent on the plane in Portland would also be appreciated.

Since the flight wasn’t full, we had some extra room. Crew was great

Both of my flights to and from JFK experienced significant delays. Most notably, my first flight was delayed by six hours due to crew members being affected by delays on a previous flight. While I understand that disruptions can occur, Delta’s staffing and operational planning should include sufficient contingency measures to handle situations like this rather than placing the full burden of those delays on customers. Additionally, the $12 meal voucher offered as compensation was inadequate, particularly given the high cost of food and beverages at the airport. Considering the length of the delay and the substantial inconvenience caused, I believe more meaningful compensation would have been appropriate.

Although I know the Airlines cannot control the situation when there’s a ground stoppage, it would’ve been nicer if we would have had more up-to-date information clarity around the delays. Additionally, I think the delays also took a toll on the Cabin crew, particularly the lead flight attendant in first class. She was not very friendly when we boarded the plane for many of the passengers. Number one she refused to hang a garment bag in the front closet for a first class passenger, she was unwilling to dispose of an empty bottle in the trash as I was boarding (despite drinking a bottle of water herself and needing to disregard), and she was very combative with a passenger, who needed to access something from his bag that was Gate checked. Frankly, it was really unfortunate as I’ve never seen a flight attendant behave that way directly to the passengers, particularly when none of us had done anything wrong.

overall the crew onboarding and providing service during our flight was great; they were friendly and helpful. I said ok to the entertainment because there was none, but the crew explained why which was very helpful. I am a diabetic and the type of snacks are not diabetic friendly (full of carbs and sugar). However, I am always prepared because I know the catering is for the larger population.

While it wasn't the crew's fault, it was a frustrating flight. We sat on the runway for 2+ hours. Both of the flight attendants were excellent and did a great job checking on the passengers. The pilot did keep us informed about the wait. I appreciate the crew apologizing for LaGuardia airport's backup.

the flight got cancelled - few hours before the departure time - no time to change

This a short easy flight. No food or drink but that was not an issue since we were only in the air for 35 minutes.

The meal tray was not usable it was completely uneven

My experience with Delta started with my luggage being found ripped open with items missing. The baggage office told me to bring the bag, and I wanted them to see how I found it. The agent refused, so I carried my bag into the office myself. The agent was nice enough to fix the zipper and gave me a red card with a number to call. I followed the steps; first one department, then the baggage department took over. This took more than two hours on the phone. The return flight was okay. The flight lead was checking her meals and then asked if we wanted anything before departure. However, throughout the flight, I had to ask for things because she was reading her book;which I have no issue with if she had been more attentive. At the end of the flight, the pilot appeared annoyed with the flight lead for not following his instructions regarding a meal he had requested; a chicken sandwichand said, "I asked for that for the flight." On the positive side, my work event in Vegas went well, and now I'm home relaxing.

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

Flight was 2.5 late. Maybe not United’s fault but late none the less. We were late as well on the first leg. WiFi quit working with an hour left.

Old 757 with poor entertainment system. United no longer partners with United for free text and email. O'Hara an absolute disaster! Limited gates clauses two hour delay. Unfortunately this appears to be the norm.

The flight to America was freezing. The overnight flight back to the UK was boiling hot and the cabin stank of toilet or occasionally perfume, even though I was several rows back from either bathroom. Food was tiny portions. Two small pieces of tough and dry beef in random gravy with pretend mashed potato raking up most of it. Very little veg. Salad was ok. Wooden cutlery broke within minutes of using. Lots of old films for entertainment. Some new ones. Generally a bit rubbish.

It was a good experience, unfortunately my checked baggages were come late and not arrived on time.

Very stressful to locate United Airline boarding area, delayed flight, changing boarding area again to another location with all tiredness 😩. But flying was fine.

It was hot and not as comfortable as the flight to Chicago. Must have been a different plane that needs to be worked on or replaced.

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