$79 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 9/21. 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

Save 20% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

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$249
Lexington
Lexington1 stop$324
Nashville
Nashville1 stop$201
Louisville
Louisville1 stop$249
Lexington
Lexington1 stop$324
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

ven, ago 14 - ven, ago 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
$163Breeze Airways
ven, ago 14 - ven, ago 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
$173Breeze Airways
mar, set 1 - mar, set 8
JetBlue Logo
1:20 pm - 5:07 pm
PWM
-
BNA
4h 47m
1 stop
JetBlue Logo
6:00 pm - 12:10 am
BNA
-
PWM
5h 10m
1 stop
$201JetBlue
mer, ago 5 - lun, ago 10
Delta Logo
6:30 am - 10:58 am
PWM
-
TYS
4h 28m
1 stop
Delta Logo
6:00 am - 10:21 am
TYS
-
PWM
4h 21m
1 stop
$229Delta
lun, ago 17 - sab, ago 29
JetBlue Logo
6:00 am - 10:02 am
PWM
-
BNA
5h 02m
1 stop
JetBlue Logo
5:58 pm - 12:25 am
BNA
-
PWM
5h 27m
1 stop
$229JetBlue
mar, ago 18 - lun, ago 24
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
$245American Airlines
mer, ago 12 - mer, ago 19
Delta Logo
6:30 am - 1:27 pm
PWM
-
SDF
6h 57m
1 stop
Delta Logo
5:59 pm - 11:30 pm
SDF
-
PWM
5h 31m
1 stop
$249Delta
sab, nov 14 - lun, nov 16
United Airlines Logo
6:00 am - 5:02 pm
PWM
-
TYS
11h 02m
2 stops
United Airlines Logo
7:20 pm - 11:59 pm
TYS
-
PWM
4h 39m
1 stop
$262United Airlines
sab, set 26 - lun, set 28
American Airlines Logo
10:44 am - 6:29 pm
PWM
-
BNA
8h 45m
1 stop
American Airlines Logo
6:10 am - 4:39 pm
BNA
-
PWM
9h 29m
1 stop
$269American Airlines
gio, ago 6 - lun, ago 10
United Airlines Logo
5:15 am - 9:29 am
PWM
-
BNA
5h 14m
1 stop
United Airlines Logo
1:35 pm - 11:30 pm
BNA
-
PWM
8h 55m
2 stops
$276United 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.

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$79
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly and prices are also 9% 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.

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 8465 reviews
8.1Boarding
7.2Food
7.8Entertainment
7.8Comfort
8.5Crew
Airline reviews

Internet didn’t work for this leg either. The seat was fine but didn’t have seatback screen, which I knew when I booked it. The biggest letdown is Deltas new policy on beverage/snack service not being served for flights less than 350 miles. I know this is a cost cutting measure, but how much does it really cost to give a drink and a snack for inflated airfare? I really am surprised that with Delta Comfort they don’t provide beverage/snack service given these seats cost extra to purchase. Really need to reconsider this, even if it’s for the Delta Comfort and above.

6.0 GoodLane, Jul 2026
ATL - MEM
Read more Delta reviews

Internet didn’t work for this leg either. The seat was fine but didn’t have seatback screen, which I knew when I booked it. The biggest letdown is Deltas new policy on beverage/snack service not being served for flights less than 350 miles. I know this is a cost cutting measure, but how much does it really cost to give a drink and a snack for inflated airfare? I really am surprised that with Delta Comfort they don’t provide beverage/snack service given these seats cost extra to purchase. Really need to reconsider this, even if it’s for the Delta Comfort and above.

I am a die hard Delta flyer, but they missed it on this flight. It was on their very dated 717-200 aircraft, which I knew when I booked it so I knew it wouldn’t have seatback screens. However, the internet was awful and it wouldn’t even send texts a lot of the time, much less even connect to the delta app. It was also very hot while in the air, which never happens. What was even more disappointing is that the crew only gave me cheezits and a beverage, even though I was in Delta Comfort. The main cabin fare gets these items. I didn’t get any kind of improved snacks and that was unacceptable. The crew wasn’t very visible at all either. If this was my first delta flight, it would be my last. I am just going to assume it was a one-off flight.

Flight attendant was very poor in taking care or showing attention. I slept up front for a few and missed the snacks. She saw me many times, went by me many times and never once asked if I needed anything. The whole 2 hours flight. And this is to a Diamond member in first.

No entertainment on flight, no food service, could not connect to WiFi

The team was wonderful. The entertainment screens were not working, so they recommended that we use the plane wifi to watch entertainment on our phones and none of the Delta entertainment links worked. Extremely frustrating process.

The flight was mostly smooth and direct (although it was 2 hours late). The glow of the flight attendant’s phone was annoying as I tried to sleep on this midnight flight.

The plane was not clean. Vomit was removed from seat-back pocket right in front of me. The flight attendants were rude to one another. 3 children were seated together with their parents across the aisle. The children fought physically with one slamming another’s head into the plane wall at one point. The parents were aware, but took no action to intervene. Delays occurred in Atlanta after boarding before takeoff, in the air, and in Detroit after landing (no ground crew assigned). Flight attendants offered no support for connecting flights. There were weather conditions on each end of the flight, but I didn’t mark down my ratings for these.

MSY had lots of coffee/breakfast options for morning flights. Bathrooms were clean. Lots of filling stations for water bottles. Delta flight was on time. The plane was clean. The staff was friendly and efficient.

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

It was great. All the crew were professional and nice.

Flight was delayed 14 hours due to DC air show and weather. Missed connection to MUC.

UA594 was delayed multiple times. I ended up getting picked up so I can make it in time for work 6AM on Monday, 7/6/2026

My original flight was cancelled and that affected my trip and my plans and I got no compensation and customer service was hard to reach as well

Boarded from a very small gate at LAX. Staff at gate had us line up, then waited 25 minutes to board without a word of explanation. Plane arrived on time then waited 20 minutes for a plane to vacate our gate. Majority of bags arrived after 15 minutes but it took an hour for a small number of remaining bags to be off-loaded despite my “priority” bag tag.

It's fine but Newark to Nashville was too long

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