$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 9/4. 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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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 72 hours
Louisville
Louisville1 stop$249
Lexington
Lexington2 stops$495
Nashville
Nashville1 stop$201
Louisville
Louisville1 stop$249
Lexington
Lexington2 stops$495
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, Oct 2 - Mon, Oct 5
Breeze Airways Logo
7:00 am - 9:33 am
PWM
-
CVG
2h 33mnonstop
Breeze Airways Logo
9:11 pm - 11:24 pm
CVG
-
PWM
2h 13mnonstop
$163Breeze 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
$173Breeze Airways
Tue, Aug 18 - Wed, Aug 19
JetBlue Logo
1:25 pm - 5:08 pm
PWM
-
BNA
4h 43m
1 stop
JetBlue Logo
6:00 pm - 12:25 am
BNA
-
PWM
5h 25m
1 stop
$201JetBlue
Thu, Aug 27 - Mon, Aug 31
Delta Logo
6:05 am - 1:34 pm
PWM
-
TYS
7h 29m
1 stop
Delta Logo
6:00 am - 10:21 am
TYS
-
PWM
4h 21m
1 stop
$229Delta
Tue, Sep 1 - Tue, Sep 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
$229JetBlue
Wed, Aug 12 - Wed, Aug 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
Wed, Aug 5 - Mon, Aug 10
United Airlines Logo
5:15 am - 10:42 am
PWM
-
TYS
5h 27m
1 stop
United Airlines Logo
7:19 pm - 11:51 pm
TYS
-
PWM
4h 32m
1 stop
$270United Airlines
Wed, Aug 12 - Tue, Aug 18
American Airlines Logo
6:02 am - 11:24 am
PWM
-
BNA
6h 22m
1 stop
American Airlines Logo
6:40 am - 12:40 pm
BNA
-
PWM
5h 00m
1 stop
$272American Airlines
Sat, Sep 5 - Sat, Sep 12
United Airlines Logo
6:00 am - 4:58 pm
PWM
-
TYS
10h 58m
2 stops
United Airlines Logo
7:20 pm - 11:59 pm
TYS
-
PWM
4h 39m
1 stop
$280United Airlines
Fri, Aug 28 - Wed, Sep 2
American Airlines Logo
6:02 am - 10:40 am
PWM
-
SDF
4h 38m
1 stop
American Airlines Logo
7:31 am - 2:24 pm
SDF
-
PWM
6h 53m
1 stop
$282American 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.

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 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 $213 one-way - $531 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 8465 reviews
8.1Boarding
7.8Comfort
7.8Entertainment
8.5Crew
7.2Food
Airline reviews

My flight home from Knoxville, TN, included a layover in Atlanta. I boarded the aircraft in Zone 5 and although there was limited overhead space, I was able to put my 'backpack' style roller-bag above my seat. Unfortunately, due to continued bad weather, we had to deplane. There were many people who would have missed their connection, so they rebooked. When we were re-boarding, the gate agent welcomed zone 5 and then made an announcement: All roller-bags for zone 5 passengers and higher will need to be gate checked. I promptly pushed the telescoping handle in and held my bag like a backpack. I was able to bring it on board, which was a relief. Upon entering the aircraft it became apparent that there was easily 40% open overhead space. There were audible signs of angry passengers who felt duped into checking their bags when in fact there were noticeably LESS passengers on the aircraft and TONS of overhead space. I'm not sure what kinds of parameters are used to determine when to cut off roller-bags from being brought on board, but it seemed deceptive and underhanded to have so many people get stuck checking their bags when clearly there was ample room for at least one more zone.

4.0 OkayErnest, Jul 2026
TYS - ATL
Read more Delta reviews

My flight home from Knoxville, TN, included a layover in Atlanta. I boarded the aircraft in Zone 5 and although there was limited overhead space, I was able to put my 'backpack' style roller-bag above my seat. Unfortunately, due to continued bad weather, we had to deplane. There were many people who would have missed their connection, so they rebooked. When we were re-boarding, the gate agent welcomed zone 5 and then made an announcement: All roller-bags for zone 5 passengers and higher will need to be gate checked. I promptly pushed the telescoping handle in and held my bag like a backpack. I was able to bring it on board, which was a relief. Upon entering the aircraft it became apparent that there was easily 40% open overhead space. There were audible signs of angry passengers who felt duped into checking their bags when in fact there were noticeably LESS passengers on the aircraft and TONS of overhead space. I'm not sure what kinds of parameters are used to determine when to cut off roller-bags from being brought on board, but it seemed deceptive and underhanded to have so many people get stuck checking their bags when clearly there was ample room for at least one more zone.

Flight was delayed and then "they did not have time to load food". No snack or drink at all for 1.5 how flight. Somebody wasn't prepared.

No Internet, no backseat screen, no nothing. I bought a Delta ticket and ended up on American Airlines. How did that happen?

It is usually very pleasant. Good service for the price, international flights are even better

We never made it on this flight because we missed our connection due to o delayed flight from Jackson.

We had a terrible experience. The flight was delayed several hours, so we missed our connection. We were told to wait at the airport. At around 11:00 pm, the flight was cancelled. There were no available seats out of Jackson for the next two days. Fortunately, we had the foresight to rebook on United for the next day. However, we had to spend a long day at the airport and an overnight at a mediocre hotel. It was a miserable way to spend part of our vacation. We also sacrificed our $450 deposit on our California hotel because we could not get there.

delta wifi wouldn’t work boarding was not in sequence flight crew spent most of their time on the phone with the lights off pretending no one wanted or needed anything

Friendly flight attendant Quick checking for baggage drop Quick TSA lines

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

Have not had a flight out or returning to Norfolk that has not required maintenance, and a gate delay. Properly staff the crew so maintenance can be performed without last minute emergencies on each flight and there is enough staff to have gates prepared for inbound flights. Staff to ensure the safety and on time service vs. profit.

Always pretty good as far as I see it. Staff was friendly and process was quick to get on and off.

Our flight was great with an unexpected upgrade. However, four days into our travel we are still without a piece of luggage. The bag tracker has not been accurate, the airline is not communicating with me or the luggage delivery service and no one is willing to take responsibility or guarantee any kind of support or reimbursement. Unfortunately, we do not have the option to easily shop to replace items as we are currently on a cruise. I have been very disappointed by United Airlines response.

There could have been better food options in economy on the long 7hr trip from IAH to AM.

The seats on this flight weren’t as comfortable as we had expected. Even leaned back these seats left us feeling crappy in our backs. Also we had to use our own tablets for movies, but nothing in the seats in front of us to hold the tablets up.

It was a short, comfortable flight. It did leave an hour late due to the pilot having to be replaced (family emergency) but that didn’t inconvenience myself & my friend. The situation was explained, eventually.

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