$104 Find Cheap Flights from Portland to Kentucky - Compare and Save

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1 adult, Economy, 0 bags

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Cheap Flights from Portland to Kentucky

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Sort by: Cheapest
Cincinnati
2h 33mNonstop
from $182per person
Knoxville
4h 10m2 stops
from $303per person
Nashville
2h 40mNonstop
from $325per person
Louisville
4h 31m2 stops
from $345per person
Lexington
4h 03m2 stops
from $367per person
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?

Flight prices are typical for this route right now.

Flights to Kentucky from Portland, Maine usually cost between $306 and $472 in October.
The lowest price found in the past 5 days was $325 on United Airlines (Oct 3-Oct 10).

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

The cheapest month for flights from Portland to Kentucky is November, when tickets cost $376 (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

$104
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly and prices are also 2% 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 $234 one-way - $473 round-trip

Reviews of the top 3 airlines serving from Portland to Kentucky

 
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 8554 reviews
7.8Entertainment
7.8Comfort
8.5Crew
7.2Food
8.1Boarding
Airline reviews

Audio Visual Equipment lacking content and features. No connection ability for noise cancellation pods

8.0 ExcellentFrances, Sep 2026
Read more Delta reviews

Audio Visual Equipment lacking content and features. No connection ability for noise cancellation pods

DL482 did not wait for about 10 of us including a mother and 3 children when we were in the same terminal on DL486, where we were switching from waiting for a jet bridge fix, to moving to a neighboring gate. I understand taxiing delays are ok either but man. We only needed 5 more minutes. DL482 did not adjust from their times at all. This was my first time with Delta.

DL486 could not get to the gate due to jet bridge malfunction. We moved gates. The connecting flight of LAX to MCO was not communicated with. Even though we were in the same terminal, DL482 left without about 10 of us, including a mother and her 3 children. I got to the gate at 7:34 am which is past the 7:20 am last call for a 7:35 am departure. Had they waited 5 minutes, all of us would have made it on board.

Both legs on the way were smaller planes, each had a mechanical issue causing a delay

Delta exceeded my expectations! I am beyond satisfied. Thank you!

Flight was on time! That's the most important thing for me.

Delayed flight. Dirty seats, dirty seat belts with food stuck on it from previous passengers maybe. No one cleaned the seats or flight.

The flight was delayed and knowing I was going to miss my connection, nothing was done proactively to try and get me rebooked. It was an act of congress to do so. This is not on the crew, but on the experience itself

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

Did not like the check in guy quibbling over a couple pounds at the luggage weigh in

Just having a little bit more legroom would've been nice.

This is related to my second leg of the flight, from Washington DC to SFO. I understand things happen, but I got home at 3 am for a 12:59 am landing. I live 10 min from the airport. Bridge breaks when a few rows of the plane are off? Maintenance didn’t catch that?

Boarding, time to take off, in flight offerings, and staff were all great. I recommend using UA for this short flight.

This was an auto-rebook due to being delayed from an earlier UA connecting flight. The boarding was fine, but they sat me in a middle seat when my original booking was a window seat. Overall, the flight was fine as it still got me to my final destination.

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.

Our flight was delayed to Louisville. What made this worse was they did not have another flight attendant to service the flight. This caused an even longer delay. Then when a flight attendant did show up, she chose to "swap" flights with another flight attendant. Therefore, we had to wait longer for the other flight attendant to come to our flight. This is information that the gate attendant should not have shared. Processes and execution at American are broken. Passengers are feeling it. Fixing this starts at the top of the organization.

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.

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.

More options for your flight from Portland to Kentucky

Complete your trip to Kentucky with a hotel stay or car rental