$94 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 10/9. 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$317
Lexington
Lexington1 stop$309
Nashville
Nashville1 stop$211
Louisville
Louisville1 stop$317
Lexington
Lexington1 stop$309
Nashville
Nashville1 stop$211

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, Aug 21 - Mon, Aug 24
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
$157Breeze Airways
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
Thu, Aug 27 - Mon, Aug 31
Delta Logo
6:05 am - 1:34 pm
PWM
-
TYS
7h 29m
1 stop
Delta Logo
4:38 pm - 11:13 pm
TYS
-
PWM
6h 35m
1 stop
$275Delta
Wed, Sep 9 - Mon, Sep 14
United Airlines Logo
3:43 pm - 11:59 pm
PWM
-
TYS
8h 16m
2 stops
United Airlines Logo
7:20 pm - 11:59 pm
TYS
-
PWM
4h 39m
1 stop
$280United Airlines
Mon, Oct 19 - Sat, Oct 24
Delta Logo
1:52 pm - 9:10 pm
PWM
-
TYS
7h 18m
1 stop
Delta Logo
6:00 am - 1:04 pm
TYS
-
PWM
7h 04m
1 stop
$285Delta
Thu, Aug 20 - Mon, Aug 24
United Airlines Logo
6:00 am - 2:37 pm
PWM
-
TYS
8h 37m
2 stops
United Airlines Logo
5:45 am - 10:04 am
TYS
-
PWM
4h 19m
1 stop
$302United Airlines
Sat, Sep 12 - Wed, Sep 16
American Airlines Logo
5:18 pm - 9:04 pm
PWM
-
BNA
4h 46m
1 stop
American Airlines Logo
4:37 pm - 11:59 pm
BNA
-
PWM
6h 22m
1 stop
$311American Airlines
Thu, Aug 20 - Mon, Aug 24
Southwest Logo
7:40 am - 5:10 pm
PWM
-
TYS
9h 30m
2 stops
Southwest Logo
12:40 pm - 10:25 pm
TYS
-
PWM
9h 45m
2 stops
$312Southwest
Wed, Sep 30 - Tue, Oct 6
Southwest Logo
5:45 am - 7:00 pm
PWM
-
TYS
13h 15m
2 stops
Southwest Logo
1:00 pm - 10:35 pm
TYS
-
PWM
9h 35m
2 stops
$313Southwest
Tue, Aug 18 - Mon, Aug 24
American Airlines Logo
8:50 am - 2:51 pm
PWM
-
SDF
6h 01m
1 stop
American Airlines Logo
6:18 pm - 11:37 pm
SDF
-
PWM
5h 19m
1 stop
$355American 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 August.

Flight prices are below average for this route right now.

Flights to Kentucky from Portland, Maine usually cost between $403 and $650 in August.
The lowest price found in the past 5 days was $317 on Delta (Aug 13-Aug 17).

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

$94
Best time to beat the crowds with an average 10% 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 $213 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 4236 reviews
7.0Food
8.1Boarding
8.6Crew
7.5Entertainment
8.0Comfort
Airline reviews

Friendly crew kept coming by to make sure all was ok, provide additional refreshments, etc.

10.0 ExcellentTamara, Jul 2026
MCO - DEN
Read more Southwest reviews

Friendly crew kept coming by to make sure all was ok, provide additional refreshments, etc.

It was good. Last flight was delayed but I always say that is in God's plan

Red eye from San Diego. Temperature of the cabin was way too warm and the air duct flowed very little air.

Overall good, just screaming kids in the area the whole flight.

My experience will Southwest was good. I wish there was more entertainment and the boarding process was slow at time but other than that my experience was great definitely will be flying with SouthWest again.

Flight was delayed by 2 hours, meaning that a flight to Dwnver which should have arrived at 11pm came into the airport at 1 am. Made for a very long day.

I think Southwest is the number one airline that anyone can fly I have flown for the first time Frontier and what a joke and their customer service United was a very strange experience I'm only sticking to Southwest from here on out for sure

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

It was good delayed again but once on board the flight crew were very good the entertainment and wifi worked on this plane and we were offered snacks and drinks

The boarding agent guy in Lexington on 7/23 that boarded the flights to Atlanta is very rude for working in customer service. I know there were delays but he was dismissive rude and arrogant. Most native Kentucky residents are nice and very cordial he needs to eat a big ole piece of humble pie. I watched him be rude to several people and as much as he could of filled up a delayed flight to save you money and he was so rude to people it was ridiculous. Next no water or snacks on short flights is awful 1st you delay a flight then do not even offer water on the flight.. No thanks I like delta better but I travel ever week and to be treated like this might as well fly American at least they offer water and have better rewards.

Flight was delayed multiple time and for more than 1 hr. My onward flight from BOS to MCI was also delayed. These delays have caused me so much inconvenience and Delta does nothing to ensure flights take off on time. No one knew why the inbound flight was delayed and what was the issue.

The second half of terminal C at Hartsfield was 80 something degrees. I was sweating just sitting at the gate.

Boarding was quick and i made my connection early due to early arrival time

First The flight got delayed because one of the crew members was late and we couldn’t board until she arrived. Then we all boarded and got held in the tarmac for another 30 min.

Flight from Savannah arrived very late and we did not take off till 2 hours after scheduled departure!

No food or drink, Not much conversation with crew. They didn't come through to check on people. There were no charging stations or wifi to watch movies. It was like being on a bus in the air.

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

The international portion was good. Food and beverage options were good. The sustainable wooden eatery was less than desirable. Your Star Alliance partner ANA provided real silverware. I'm 6'3" & 198 lbs and felt cramped in the exit row. How can that be? Flight attendant all had a pleasant disposition which is always good.

Flight was late to take off Plane broke down Had to move everyone to another plane Told we weren’t going to LGA but Newark Also told we would be taken to NY But United lied and we ended up at Newark at 2 in the morning Horrible experience. And the experience of trying to get compensation from United is just as bad. They could not care less about their passengers Never again!

Flight was late, the only reason I almost missed my flight was that my connection was also late.

Flight be on time would be a good start. Then train your flight attendants to be attentive and friendly. This time they completely forgot my row for the measly snack! United, do better!

I would have preferred a flight voucher and to hop on a different flight. Delayed over 6 hours.

Our flight gor canceled and there was no one to help us but told us to scan the qr code and fill the forms on-line. Very poor service especially we are tourists traveling to Washington DC for the 1st time.

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