$89 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$365
Nashville
Nashville1 stop$201
Louisville
Louisville1 stop$317
Lexington
Lexington1 stop$365
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
$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
Mon, Aug 17 - Wed, Aug 26
JetBlue Logo
6:00 am - 10:02 am
PWM
-
BNA
5h 02m
1 stop
JetBlue Logo
6:00 pm - 12:25 am
BNA
-
PWM
5h 25m
1 stop
$201JetBlue
Sat, Sep 5 - Tue, Sep 8
JetBlue Logo
6:40 am - 5:07 pm
PWM
-
BNA
11h 27m
1 stop
JetBlue Logo
6:00 pm - 12:10 am
BNA
-
PWM
5h 10m
1 stop
$243JetBlue
Wed, Jul 22 - Wed, Jul 29
Delta Logo
6:00 am - 1:16 pm
PWM
-
TYS
7h 16m
1 stop
Delta Logo
3:54 pm - 11:14 pm
TYS
-
PWM
7h 20m
1 stop
$275Delta
Wed, Aug 19 - Wed, Aug 26
Delta Logo
2:53 pm - 10:05 pm
PWM
-
BNA
8h 12m
1 stop
Delta Logo
7:05 am - 2:13 pm
BNA
-
PWM
6h 08m
1 stop
$277Delta
Wed, Aug 19 - Mon, Aug 24
United Airlines Logo
5:15 am - 12:35 pm
PWM
-
BNA
8h 20m
2 stops
United Airlines Logo
6:42 pm - 11:59 pm
BNA
-
PWM
4h 17m
1 stop
$282United Airlines
Thu, Aug 27 - Mon, Aug 31
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
$291American Airlines
Tue, Sep 22 - Fri, Sep 25
American Airlines Logo
5:30 am - 9:45 am
PWM
-
BNA
5h 15m
1 stop
American Airlines Logo
6:10 am - 3:51 pm
BNA
-
PWM
8h 41m
1 stop
$300American Airlines
Sat, Sep 5 - Sat, Sep 12
United Airlines Logo
5:15 am - 10:37 am
PWM
-
TYS
5h 22m
1 stop
United Airlines Logo
5:45 am - 1:55 pm
TYS
-
PWM
8h 10m
2 stops
$302United 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 October.

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$89
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 8453 reviews
8.1Boarding
8.5Crew
7.8Comfort
7.2Food
7.8Entertainment
Airline reviews

Our flight was delayed by over 4 hours due to a maintenance issue. They announced a new plane was on the way. We were given a $12 food voucher ( airport food is quite expensive You can’t even by a water and a small snack for 12:00. 4 hours later we boarded and landed in Atlanta at 10:20 ish pm. Of course we missed our connection and we were given a hotel voucher and another food voucher ! We didn’t make it home until 11:00 the next day ! Unacceptable

2.0 MediocreAnonymous, Jul 2026
MCI - ATL
Read more Delta reviews

Our flight was delayed by over 4 hours due to a maintenance issue. They announced a new plane was on the way. We were given a $12 food voucher ( airport food is quite expensive You can’t even by a water and a small snack for 12:00. 4 hours later we boarded and landed in Atlanta at 10:20 ish pm. Of course we missed our connection and we were given a hotel voucher and another food voucher ! We didn’t make it home until 11:00 the next day ! Unacceptable

Everything about this flight was good except for the very end when I reached my destination. Everyone from the tune to the wheelchair escorts were great with the case were great but I miss you with people at the check in this at the very end. I need help from the chicken desk because I forgot my pillow on the plane The female worker at the chicken desk said that they found my pillow and she was going to retrieve it for me. She left a 30 minutes without any update and her so she saw me walking back and forth waiting for her and they didn't even bother calling her or radioing her for any updates. They were busy because they were behind schedule and they were overwhelmed but thanks because at least glanced me and try to give me an update just a quick radio check or phone call. I don't care about the pillow but if you tell me to wait, I waited for at least half an hour before I said something and I just left because they wouldn't bother talking to me so I could, so everything's going in the review. I took pictures of the two men that were left working at the check-in counter. The totally ignored me despite the signals I've been giving them. I don't see any offers in the kayak review to add pictures or screenshots so I'm going to post another review I don't know their name but I'm pretty sure Delta will find other names when they see the review. Google with pictures. There was another guy at the chicken counter bring an orange workers vest who finally left after telling me that the girl that was retrieving my pillow is working the gates now. That would have been if they just told me that's what happened. But I had no update. Make me wait for nothing. Thank you Delta airlines!

We had a great experience with Delta. They helped us from the start at the kiosk all the way to our final destination, including help reassigning and upgrading our seats free of charge at the gates, escorts with the wheelchair for my brother and even getting our luggage at baggage claim for us. I also had special help because I forgot my pillow on the plane. The wheelchair escort contacted for associates at the check-in desk all the way back to the plane and retrieved my pillow for me.

Crew was real good, flight was smooth and came in early.

The CRJ-900 was clean but the overhead air vents were broken in our First Class row, making the cabin very hot until about 30 mins into the flight. The flight attendants were both extremely apologetic and accommodating though so that is why I rated the flight as very good. They checked on us many times and truly showed they cared. The snacks for an hour and a half flight could be better. Would be nice if there was a small plated meal over convenient store snacks. WiFi also was not working. And it would be nice if Delta had adjustable headrests on these planes.

New high end luggage ruined/zippers broken, items missing. All happened on return flight from msp to mso. Do better! Not store bought luggage but high end personalized ogio custom embroidered luggage. Total slap in the face ontop of an extra luggage fee that took me 3 hrs on chat to resolve.

It was as good as it could be. Flying is not a pleasant experience these days.

The plane was old and thus the seats were not good. No cushion left whatsoever, and it all was a bit worn out.

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 flight was delayed by a hour and I wish they had communicated it sooner. No issues on the plane, it did take a while for food to come.

Know that the movies that you are going to be offered are the oldest be rated movies they could possibly get. They may have one or two new movies that they keep advertising but when you’re flying 15 hours, there is nothing to see past the first new movie.

Great staff. Clean plane, but we were delayed for more than an hour due to maintenance issues and had to board another plane.

I was exhausted from a long day. The flight was smooth. The first flight during my 3 week travel that took off on time.

1 flight cancelled Had to fly out of different city Flight at new departure city was delayed 3 hours causing us to miss connecting flights. By the time we did make it to Prague our luggage did not. Had to wait day and a half for luggage to be delivered. Customer service was not good. Agents did not arrive at gate until 5-10 minutes before boarding

Awful. Delayed flights, missed connection to Toronto. Hotel vouchers were for already booked hotels x3. Giant waste of my 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